Nandrolone, also known as 19-nortestosterone, is an

endogenous Endogeny, in biology, refers to the property of originating or developing from within an organism, tissue, or cell. For example, ''endogenous substances'', and ''endogenous processes'' are those that originate within a living system (e.g. an ...

androgen An androgen (from Greek ''andr-'', the stem of the word meaning ) is any natural or synthetic steroid hormone that regulates the development and maintenance of male characteristics in vertebrates by binding to androgen receptors. This includes ...

. It is also an

anabolic steroid Anabolic steroids, also known as anabolic-androgenic steroids (AAS), are a class of drugs that are structurally related to testosterone, the main male sex hormone, and produce effects by binding to the androgen receptor (AR). Anabolism, Anaboli ...

(AAS) which is medically used in the form of

ester In chemistry, an ester is a compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds contain a distin ...

s such as

nandrolone decanoate Nandrolone decanoate, sold under the brand names Rolon and Deca-Durabolin, among others, is an androgen and anabolic steroid (AAS) medication which is used primarily in the treatment of anemias and wasting syndromes, as well as osteoporosis in me ...

(brand name Deca-Durabolin) and

nandrolone phenylpropionate Nandrolone phenylpropionate (NPP), or nandrolone phenpropionate, sold under the brand name Durabolin among others, is an androgen and anabolic steroid (AAS) medication which has been used primarily in the treatment of breast cancer and osteoporos ...

(brand name Durabolin).

Nandrolone ester This is a list of androgen esters, including esters (as well as ethers) of natural androgens like testosterone and dihydrotestosterone (DHT) and synthetic anabolic–androgenic steroids (AAS) like nandrolone (19-nortestosterone). Esters of nat ...

s are used in the treatment of

anemia Anemia (also spelt anaemia in British English) is a blood disorder in which the blood has a reduced ability to carry oxygen. This can be due to a lower than normal number of red blood cells, a reduction in the amount of hemoglobin availabl ...

cachexia Cachexia () is a syndrome that happens when people have certain illnesses, causing muscle loss that cannot be fully reversed with improved nutrition. It is most common in diseases like cancer, Heart failure, congestive heart failure, chronic o ...

(

muscle Muscle is a soft tissue, one of the four basic types of animal tissue. There are three types of muscle tissue in vertebrates: skeletal muscle, cardiac muscle, and smooth muscle. Muscle tissue gives skeletal muscles the ability to muscle contra ...

wasting syndrome),

osteoporosis Osteoporosis is a systemic skeletal disorder characterized by low bone mass, micro-architectural deterioration of bone tissue leading to more porous bone, and consequent increase in Bone fracture, fracture risk. It is the most common reason f ...

breast cancer Breast cancer is a cancer that develops from breast tissue. Signs of breast cancer may include a Breast lump, lump in the breast, a change in breast shape, dimpling of the skin, Milk-rejection sign, milk rejection, fluid coming from the nipp ...

, and for other indications. They are now used by

oral administration Oral administration is a route of administration whereby a substance is taken through the Human mouth, mouth, swallowed, and then processed via the digestive system. This is a common route of administration for many medications. Oral administ ...

or instead are given by injection into muscle or

fat In nutrition science, nutrition, biology, and chemistry, fat usually means any ester of fatty acids, or a mixture of such chemical compound, compounds, most commonly those that occur in living beings or in food. The term often refers specif ...

Side effect In medicine, a side effect is an effect of the use of a medicinal drug or other treatment, usually adverse but sometimes beneficial, that is unintended. Herbal and traditional medicines also have side effects. A drug or procedure usually use ...

s of nandrolone esters include

symptom Signs and symptoms are diagnostic indications of an illness, injury, or condition. Signs are objective and externally observable; symptoms are a person's reported subjective experiences. A sign for example may be a higher or lower temperature ...

s of

masculinization Virilization or masculinization is the biological development of adult male characteristics in young males or females. Most of the changes of virilization are produced by androgens. Virilization is a medical term commonly used in three medical a ...

acne Acne ( ), also known as ''acne vulgaris'', is a long-term Cutaneous condition, skin condition that occurs when Keratinocyte, dead skin cells and Sebum, oil from the skin clog hair follicles. Typical features of the condition include comedo, ...

, increased hair growth, and voice changes. They are

synthetic Synthetic may refer to: Science * Synthetic biology * Synthetic chemical or compound, produced by the process of chemical synthesis * Synthetic elements, chemical elements that are not naturally found on Earth and therefore have to be created in ...

androgens and anabolic steroids and hence are

agonist An agonist is a chemical that activates a Receptor (biochemistry), receptor to produce a biological response. Receptors are Cell (biology), cellular proteins whose activation causes the cell to modify what it is currently doing. In contrast, an R ...

s of the

androgen receptor The androgen receptor (AR), also known as NR3C4 (nuclear receptor subfamily 3, group C, member 4), is a type of nuclear receptor that is activated by binding any of the androgenic hormones, including testosterone and dihydrotestosterone, in th ...

(AR), the

biological target A biological target is anything within a living organism to which some other entity (like an endogenous ligand or a drug) is directed and/or binds, resulting in a change in its behavior or function. Examples of common classes of biological targets ...

of androgens like

testosterone Testosterone is the primary male sex hormone and androgen in Male, males. In humans, testosterone plays a key role in the development of Male reproductive system, male reproductive tissues such as testicles and prostate, as well as promoting se ...

and

dihydrotestosterone Dihydrotestosterone (DHT, 5α-dihydrotestosterone, 5α-DHT, androstanolone or stanolone) is an endogenous androgen sex steroid and hormone primarily involved in the growth and repair of the prostate and the penis, as well as the production o ...

(DHT). Nandrolone has strong

anabolic Anabolism () is the set of metabolic pathways that construct macromolecules like DNA or RNA from smaller units. These reactions require energy, known also as an endergonic process. Anabolism is the building-up aspect of metabolism, whereas catab ...

effects and weak

ic effects, which give them a mild side effect profile and make them especially suitable for use in women and children. There are metabolites of Nandrolone that act as long-lasting

prodrug A prodrug is a pharmacologically inactive medication or compound that, after intake, is metabolized (i.e., converted within the body) into a pharmacologically active drug. Instead of administering a drug directly, a corresponding prodrug can be ...

s in the body, such as

5α-Dihydronandrolone 5α-Dihydronandrolone (also known as 5α-DHN, dihydronandrolone, DHN, 5α-dihydro-19-nortestosterone, or 5α-estran-17β-ol-3-one) is a natural product, naturally occurring anabolic–androgenic steroid (AAS) and a 5α-reductase, 5α-reduced chem ...

. Nandrolone esters were first described and introduced for medical use in the late 1950s. They are among the most widely used anabolic steroid worldwide. In addition to their medical use, nandrolone esters are used to improve physique and performance, and are said to be the most widely used anabolic steroid for such purposes. The drugs are

controlled substance A controlled substance is generally a drug or chemical whose manufacture, possession and use is regulated by a government, such as illicitly used drugs or prescription medications that are designated by law. Some treaties, notably the Sing ...

s in many countries and so non-medical use is generally illicit.

Medical uses

Nandrolone esters are used clinically, although increasingly rarely, for people in catabolic states with major burns, cancer, and AIDS, and an ophthalmological formulation was available to support cornea healing. The positive effects of nandrolone esters include muscle growth, appetite stimulation and increased

red blood cell Red blood cells (RBCs), referred to as erythrocytes (, with -''cyte'' translated as 'cell' in modern usage) in academia and medical publishing, also known as red cells, erythroid cells, and rarely haematids, are the most common type of blood cel ...

production, and

bone density Bone density, or bone mineral density, is the amount of bone mineral in bone tissue. The concept is of mass of mineral per volume of bone (relating to density in the physics sense), although medicine#Clinical practice, clinically it is measured by ...

. Clinical studies have shown them to be effective in treating

, and

. Nandrolone sulfate has been used in an

eye drop Eye drops or eyedrops are liquid drops applied directly to the surface of the eye usually in small amounts such as a single drop or a few drops. Eye drops usually contain saline to match the salinity of the eye. Drops containing only saline ...

formulation as an ophthalmic medication.

Non-medical uses

Nandrolone esters are used for physique- and performance-enhancing purposes by

competitive Competition is a rivalry where two or more parties strive for a common goal which cannot be shared: where one's gain is the other's loss (an example of which is a zero-sum game). Competition can arise between entities such as organisms, indi ...

athlete An athlete is most commonly a person who competes in one or more sports involving physical strength, speed, power, or endurance. Sometimes, the word "athlete" is used to refer specifically to sport of athletics competitors, i.e. including track ...

bodybuilder Bodybuilding is the practice of progressive resistance exercise to build, control, and develop one's muscles via hypertrophy. An individual who engages in this activity is referred to as a bodybuilder. It is primarily undertaken for aesthetic ...

s, and

powerlifter Powerlifting is a competitive strength sport that consists of three attempts at maximal weight on three lifts: squat, bench press, and deadlift. As in the sport of Olympic weightlifting, it involves the athlete attempting a maximal weight singl ...

Side effects

s of nandrolone esters include

among others. In women, nandrolone and

nandrolone ester This is a list of androgen esters, including esters (as well as ethers) of natural androgens like testosterone and dihydrotestosterone (DHT) and synthetic anabolic–androgenic steroids (AAS) like nandrolone (19-nortestosterone). Esters of nat ...

s have been reported to produce increased

libido In psychology, libido (; ) is psychic drive or energy, usually conceived of as sexual in nature, but sometimes conceived of as including other forms of desire. The term ''libido'' was originally developed by Sigmund Freud, the pioneering origin ...

facial A facial is a family of skin care treatments for the face, including steam, exfoliation (physical and chemical), extraction, creams, lotions, facial masks, peels, and massage. They are normally performed in beauty salons, but are also a c ...

and

body hair Body hair or androgenic hair is terminal hair that develops on the human body during and after puberty. It is different from head hair and also from less visible vellus hair, which is much finer and lighter in color. Growth of androgenic hai ...

growth Growth may refer to: Biology *Auxology, the study of all aspects of human physical growth *Bacterial growth *Cell growth *Growth hormone, a peptide hormone that stimulates growth *Human development (biology) *Plant growth *Secondary growth, growt ...

, voice changes, and

clitoral enlargement In amniotes, the clitoris ( or ; : clitorises or clitorides) is a female sex organ. In humans, it is the vulva's most erogenous area and generally the primary anatomical source of female sexual pleasure. The clitoris is a complex structu ...

. However, the masculinizing effects of nandrolone and its esters are reported to be slighter than those of

. Nandrolone has also been found to produce penile growth in prepubertal boys.

Amenorrhea Amenorrhea or amenorrhoea is the absence of a menstrual period in a female organism who has reached reproductive age. Physiological states of amenorrhoea are most commonly seen during pregnancy and lactation (breastfeeding). In humans, it is wher ...

and

menorrhagia Heavy menstrual bleeding (HMB), previously known as menorrhagia or hematomunia, is a menstrual period with excessively heavy flow. It is a type of abnormal uterine bleeding (AUB). Abnormal uterine bleeding can be caused by structural abnorm ...

have been reported as side effects of nandrolone cypionate. Nandrolone theoretically may produce

erectile dysfunction Erectile dysfunction (ED), also referred to as impotence, is a form of sexual dysfunction in males characterized by the persistent or recurring inability to achieve or maintain a Human penis, penile erection with sufficient rigidity and durat ...

as a side effect, although there is no clinical evidence to support this notion at present. Side effects of high doses of nandrolone may include

cardiovascular In vertebrates, the circulatory system is a system of organs that includes the heart, blood vessels, and blood which is circulated throughout the body. It includes the cardiovascular system, or vascular system, that consists of the heart a ...

toxicity Toxicity is the degree to which a chemical substance or a particular mixture of substances can damage an organism. Toxicity can refer to the effect on a whole organism, such as an animal, bacteria, bacterium, or plant, as well as the effect o ...

as well as

hypogonadism Hypogonadism means diminished functional activity of the human gonad, gonads—the testicles or the ovary, ovaries—that may result in diminished biosynthesis, production of sex hormones. Low androgen (e.g., testosterone) levels are referred t ...

and

infertility In biology, infertility is the inability of a male and female organism to Sexual reproduction, reproduce. It is usually not the natural state of a healthy organism that has reached sexual maturity, so children who have not undergone puberty, whi ...

. Nandrolone may not produce

scalp hair loss Pattern hair loss (also known as androgenetic alopecia (AGA)) is a hair loss condition that primarily affects the top and front of the scalp. In male-pattern hair loss (MPHL), the hair loss typically presents itself as either a receding front h ...

, although this is also theoretical.

Pharmacology

Pharmacodynamics

Nandrolone is an

of the AR, the

s like

and . Unlike testosterone and certain other anabolic steroids, nandrolone is not potentiated in androgenic tissues like the

scalp The scalp is the area of the head where head hair grows. It is made up of skin, layers of connective and fibrous tissues, and the membrane of the skull. Anatomically, the scalp is part of the epicranium, a collection of structures covering th ...

skin Skin is the layer of usually soft, flexible outer tissue covering the body of a vertebrate animal, with three main functions: protection, regulation, and sensation. Other animal coverings, such as the arthropod exoskeleton, have different ...

, and

prostate The prostate is an male accessory gland, accessory gland of the male reproductive system and a muscle-driven mechanical switch between urination and ejaculation. It is found in all male mammals. It differs between species anatomically, chemica ...

, hence deleterious effects in these tissues are lessened. This is because nandrolone is metabolized by 5α-reductase to the much weaker AR ligand

5α-dihydronandrolone 5α-Dihydronandrolone (also known as 5α-DHN, dihydronandrolone, DHN, 5α-dihydro-19-nortestosterone, or 5α-estran-17β-ol-3-one) is a natural product, naturally occurring anabolic–androgenic steroid (AAS) and a 5α-reductase, 5α-reduced chem ...

(DHN), which has both reduced

affinity Affinity may refer to: Commerce, finance and law * Affinity (law), kinship by marriage * Affinity analysis, a market research and business management technique * Affinity Credit Union, a Saskatchewan-based credit union * Affinity Equity Pa ...

for the

(AR) relative to nandrolone ''

in vitro ''In vitro'' (meaning ''in glass'', or ''in the glass'') Research, studies are performed with Cell (biology), cells or biological molecules outside their normal biological context. Colloquially called "test-tube experiments", these studies in ...

'' and weaker AR agonistic

potency Potency may refer to: * Potency (pharmacology), a measure of the activity of a drug in a biological system * Virility * Cell potency, a measure of the differentiation potential of stem cells * In homeopathic dilutions, potency is a measure of ho ...

in vivo Studies that are ''in vivo'' (Latin for "within the living"; often not italicized in English) are those in which the effects of various biological entities are tested on whole, living organisms or cells, usually animals, including humans, an ...

''. The lack of alkylation on the 17α-carbon drastically reduces the

hepatotoxic Hepatotoxicity (from ''hepatic toxicity'') implies chemical-driven liver damage. Drug-induced liver injury (DILI) is a cause of acute and chronic liver disease caused specifically by medications and the most common reason for a drug to be withdr ...

potential of nandrolone.

Estrogen Estrogen (also spelled oestrogen in British English; see spelling differences) is a category of sex hormone responsible for the development and regulation of the female reproductive system and secondary sex characteristics. There are three ...

effects resulting from reaction with

aromatase Aromatase (), also called estrogen synthetase or estrogen synthase, is an enzyme responsible for a key step in the biosynthesis of estrogens. It is CYP19A1, a member of the cytochrome P450 superfamily, which are monooxygenases that catalyze man ...

are also reduced due to lessened enzyme interaction, but effects such as

gynecomastia Gynecomastia (also spelled gynaecomastia) is the non-cancerous enlargement of one or both breasts in men due to the growth of breast tissue as a result of a hormone imbalance between estrogens and androgens. Updated by Brent Wisse (10 Novemb ...

and reduced

may still occur at sufficiently high doses. In addition to its AR agonistic activity, unlike many other anabolic steroids, nandrolone is also a potent

progestogen Progestogens, also sometimes written progestins, progestagens or gestagens, are a class of natural or synthetic steroid hormones that bind to and activate the progesterone receptors (PR). Progesterone is the major and most important progestoge ...

. It binds to the

progesterone receptor The progesterone receptor (PR), also known as NR3C3 or nuclear receptor subfamily 3, group C, member 3, is a protein found inside cells. It is activated by the steroid hormone progesterone. In humans, PR is encoded by a single ''PGR'' gene resi ...

with approximately 22% of the affinity of

progesterone Progesterone (; P4) is an endogenous steroid and progestogen sex hormone involved in the menstrual cycle, pregnancy, and embryogenesis of humans and other species. It belongs to a group of steroid hormones called the progestogens and is the ma ...

. The progestogenic activity of nandrolone serves to augment its

antigonadotropic An antigonadotropin is a drug which suppresses the activity and/or downstream effects of one or both of the gonadotropins, follicle-stimulating hormone (FSH) and luteinizing hormone (LH). This results in an inhibition of the hypothalamic-pituita ...

effects, as antigonadotropic action is a known property of progestogens.Mauvais-Jarvis, P. "Progesterone and progestins: a general overview." (1983): 1-16.

Anabolic and androgenic activity

Nandrolone has a very high ratio of anabolic to androgenic activity. In fact, many nandrolone-like anabolic steroids and even nandrolone itself are said to have among the highest ratio of anabolic to androgenic effects of all anabolic steroids. This is attributed to the fact that whereas testosterone is potentiated via conversion into

(DHT) in androgenic tissues, the opposite is true with nandrolone and similar anabolic steroids (i.e., other 19-nortestosterone derivatives). As such, nandrolone-like anabolic steroids, namely nandrolone esters, are the most frequently used anabolic steroids in clinical settings in which anabolic effects are desired; for instance, in the treatment of

AIDS The HIV, human immunodeficiency virus (HIV) is a retrovirus that attacks the immune system. Without treatment, it can lead to a spectrum of conditions including acquired immunodeficiency syndrome (AIDS). It is a Preventive healthcare, pr ...

-associated

, severe

burn A burn is an injury to skin, or other tissues, caused by heat, electricity, chemicals, friction, or ionizing radiation (such as sunburn, caused by ultraviolet radiation). Most burns are due to heat from hot fluids (called scalding), soli ...

s, and

chronic obstructive pulmonary disease Chronic obstructive pulmonary disease (COPD) is a type of progressive lung disease characterized by chronic respiratory symptoms and airflow limitation. GOLD defines COPD as a heterogeneous lung condition characterized by chronic respiratory s ...

. However, anabolic steroids with a very high ratio of anabolic to androgenic action like nandrolone still have significant androgenic effects and can produce symptoms of

hirsutism Hirsutism is excessive body hair on parts of the body where hair is normally absent or minimal. The word is from early 17th century: from Latin ''hirsutus'' meaning "hairy". It usually refers to a male pattern of hair growth in a female that ma ...

and

voice deepening A voice change or voice mutation, sometimes referred to as a voice break or voice crack, commonly refers to the deepening of the voice of men as they reach puberty. Before puberty both sexes have roughly similar vocal pitches, but during puberty ...

in women and children with extended use.

Pharmacokinetics

The

oral The word oral may refer to: Relating to the mouth * Relating to the mouth, the first portion of the alimentary canal that primarily receives food and liquid **Oral administration of medicines ** Oral examination (also known as an oral exam or ora ...

activity of nandrolone has been studied. With oral administration of nandrolone in rodents, it had about one-tenth of the

subcutaneous injection Subcutaneous administration is the insertion of medications beneath the skin either by injection or infusion. A subcutaneous injection is administered as a bolus (medicine), bolus into the subcutis, the layer of skin directly below the dermis and ...

of nandrolone. Nandrolone has very low

for human serum

sex hormone-binding globulin Sex hormone-binding globulin (SHBG) or sex steroid-binding globulin (SSBG) is a glycoprotein that binds to androgens and estrogens. When produced by the Sertoli cells in the seminiferous tubules of the testis, it is called androgen-binding prot ...

(SHBG), about 5% of that of testosterone and 1% of that of DHT. It is

metabolized Metabolism (, from ''metabolē'', "change") is the set of life-sustaining chemical reactions in organisms. The three main functions of metabolism are: the conversion of the energy in food to energy available to run cellular processes; the co ...

by the

enzyme An enzyme () is a protein that acts as a biological catalyst by accelerating chemical reactions. The molecules upon which enzymes may act are called substrate (chemistry), substrates, and the enzyme converts the substrates into different mol ...

5α-reductase, among others. Nandrolone is less susceptible to metabolism by 5α-reductase and

17β-hydroxysteroid dehydrogenase A hydroxysteroid is a molecule derived from a steroid with a hydrogen replaced with a hydroxy group. When the hydroxy group is specifically at the C3 position, hydroxysteroids are referred to as sterols, with an example being cholesterol ...

than

. This results in it being transformed less in so-called "androgenic" tissues like the

hair follicle The hair follicle is an organ found in mammalian skin. It resides in the dermal layer of the skin and is made up of 20 different cell types, each with distinct functions. The hair follicle regulates hair growth via a complex interaction betwee ...

s, and

prostate gland The prostate is an male accessory gland, accessory gland of the male reproductive system and a muscle-driven mechanical switch between urination and ejaculation. It is found in all male mammals. It differs between species anatomically, chemica ...

and in the

kidney In humans, the kidneys are two reddish-brown bean-shaped blood-filtering organ (anatomy), organs that are a multilobar, multipapillary form of mammalian kidneys, usually without signs of external lobulation. They are located on the left and rig ...

s, respectively.

Metabolite In biochemistry, a metabolite is an intermediate or end product of metabolism. The term is usually used for small molecules. Metabolites have various functions, including fuel, structure, signaling, stimulatory and inhibitory effects on enzymes, c ...

s of nandrolone include

, 19-norandrosterone, and

19-noretiocholanolone 19-Noretiocholanolone, also known as 5β-estran-3α-ol-17-one, is a metabolite of nandrolone (19-nortestosterone) and bolandione (19-norandrostenedione) that is formed by 5α-reductase. It is on the list of substances prohibited by the World An ...

, and these metabolites may be detected in

urine Urine is a liquid by-product of metabolism in humans and many other animals. In placental mammals, urine flows from the Kidney (vertebrates), kidneys through the ureters to the urinary bladder and exits the urethra through the penile meatus (mal ...

. Single

intramuscular injection Intramuscular injection, often abbreviated IM, is the medical injection, injection of a substance into a muscle. In medicine, it is one of several methods for parenteral, parenteral administration of medications. Intramuscular injection may be ...

s of 100 mg

have been found to produce an anabolic effect for 10 to 14 days and 20 to 25 days, respectively. Conversely, unesterified nandrolone has been used by intramuscular injection once daily.

Chemistry

Nandrolone, also known as 19-nortestosterone (19-NT) or as estrenolone, as well as estra-4-en-17β-ol-3-one or 19-norandrost-4-en-17β-ol-3-one, is a

naturally occurring A natural product is a natural compound or substance produced by a living organism—that is, found in nature. In the broadest sense, natural products include any substance produced by life. Natural products can also be prepared by chemical ...

estrane Estrane is a C18 steroid derivative, with a gonane core. ''Estrenes'' are estrane derivatives that contain a double bond, with an example being nandrolone. ''Estratrienes'' (estrins) are estrane derivatives that contain three double bonds, for i ...

(19-norandrostane)

steroid A steroid is an organic compound with four fused compound, fused rings (designated A, B, C, and D) arranged in a specific molecular configuration. Steroids have two principal biological functions: as important components of cell membranes t ...

and a

derivative In mathematics, the derivative is a fundamental tool that quantifies the sensitivity to change of a function's output with respect to its input. The derivative of a function of a single variable at a chosen input value, when it exists, is t ...

(androst-4-en-17β-ol-3-one). It is specifically the C19

demethyl In chemical nomenclature, nor- is a prefix to name a structural analog that can be derived from a parent compound by the removal of one carbon atom along with the accompanying hydrogen atoms. The nor-compound can be derived by removal of a , , or ...

ated ( nor) analogue of testosterone. Nandrolone is an

intermediate in the

production Production may refer to: Economics and business * Production (economics) * Production, the act of manufacturing goods * Production, in the outline of industrial organization, the act of making products (goods and services) * Production as a stat ...

estradiol Estradiol (E2), also called oestrogen, oestradiol, is an estrogen steroid hormone and the major female sex hormone. It is involved in the regulation of female reproductive cycles such as estrous and menstrual cycles. Estradiol is responsible ...

from

via

mammal A mammal () is a vertebrate animal of the Class (biology), class Mammalia (). Mammals are characterised by the presence of milk-producing mammary glands for feeding their young, a broad neocortex region of the brain, fur or hair, and three ...

s including humans and is present in the body naturally in trace amounts. It can be detected during

pregnancy Pregnancy is the time during which one or more offspring gestation, gestates inside a woman's uterus. A multiple birth, multiple pregnancy involves more than one offspring, such as with twins. Conception (biology), Conception usually occurs ...

in women. Nandrolone esters have an

such as

decanoate Capric acid, also known as decanoic acid or decylic acid, is a saturated fatty acid, medium-chain fatty acid (MCFA), and carboxylic acid. Its formula is . Salts and esters of decanoic acid are called caprates or decanoates. The term capric aci ...

or phenylpropionate attached at the C17β position.

Derivatives

Esters

A variety of esters of nandrolone have been marketed and used medically. The most commonly used esters are

and to a lesser extent

. Examples of other nandrolone esters that have been marketed and used medically include

nandrolone cyclohexylpropionate Nandrolone cyclohexylpropionate (, ) (brand names Andol, Fherbolico, Megabolin, Megabolin Retar, Pluropon, Proteron-Depot, Sanabolicum), or nandrolone cyclohexanepropionate, also known as 19-nortestosterone 17β-(3-cyclohexyl)propionate (NTHCP), ...

, nandrolone cypionate,

nandrolone hexyloxyphenylpropionate Nandrolone hexyloxyphenylpropionate (NHPP; brand names Anador, Anadur, Anadurine), also known as 19-nortestosterone 17β-(3-(4-hexyloxy)phenyl)propionate, is a synthetic compound, synthetic androgen and anabolic steroid and a nandrolone ester tha ...

nandrolone laurate Nandrolone laurate () (brand names Clinibolin, Fortadex, Laurabolin), or nandrolone dodecanoate, also known as 19-nortestosterone 17β-laurate, is a synthetic androgen and anabolic steroid and a nandrolone ester. It is used in veterinary medicine ...

, nandrolone sulfate, and

nandrolone undecanoate Nandrolone undecanoate (NU), also known as nandrolone undecylate, and sold under the brand names Dynabolon, Dynabolin, and Psychobolan, is an androgen and anabolic steroid medication and a nandrolone ester. It was developed in the 1960s, and was ...

Anabolic steroids

Nandrolone is the parent compound of a large group of anabolic steroids. Notable examples include the non-17α-alkylated

trenbolone Trenbolone is an androgen and anabolic steroid (AAS) of the nandrolone group which itself was never marketed. Trenbolone ester prodrugs, including trenbolone acetate (brand names Finajet, Finaplix, others) and trenbolone hexahydrobenzylcarbonat ...

and the 17α-alkylated ethylestrenol (ethylnandrol) and

metribolone Metribolone (developmental code R1881, also known as methyltrienolone) is a synthetic and orally active anabolic–androgenic steroid (AAS) and a 17α-alkylated nandrolone (19-nortestosterone) derivative which was never marketed for medical use ...

(R-1881), as well as the 17α-alkylated designer steroids norboletone and

tetrahydrogestrinone Tetrahydrogestrinone (THG), known by the nickname The Clear, is a synthetic and orally active anabolic–androgenic steroid (AAS) which was never marketed for medical use. It was developed by Patrick Arnold and was used by a number of high-profi ...

(THG). The following is list of derivatives of nandrolone that have been developed as anabolic steroids: ; Non-17α-alkylated derivatives * Marketed **

Bolandiol Bolandiol ( INN, also known as 19-nor-4-androstenediol, estr-4-ene-3β,17β-diol, or 3β-dihydronandrolone) is an anabolic-androgenic steroid (AAS) that was never marketed. However, a dipropionate ester derivative, bolandiol dipropionate, has ...

(19-nor-4-androstenediol) **

Norclostebol Norclostebol (; brand name Lentabol; former developmental code names SKF-6611, CP-73) is a synthetic androgen and anabolic steroid (AAS) that was derived from nandrolone. It was described in the literature in 1957. Norclostebol is also used as a ...

(4-chloro-19-NT) **

Oxabolone Oxabolone is a synthetic anabolic-androgenic steroid (AAS) of the nandrolone (19-nortestosterone) group which was never marketed. It can be formulated as the cipionate ester prodrug oxabolone cipionate, which, in contrast, has been marketed fo ...

(4-hydroxy-19-NT) **

Trenbolone Trenbolone is an androgen and anabolic steroid (AAS) of the nandrolone group which itself was never marketed. Trenbolone ester prodrugs, including trenbolone acetate (brand names Finajet, Finaplix, others) and trenbolone hexahydrobenzylcarbonat ...

(δ^9,11-19-NT) * Never marketed ** 7α-Methyl-19-nor-4-androstenedione (MENT dione, trestione) **

11β-Methyl-19-nortestosterone 11β-Methyl-19-nortestosterone (11β-MNT) is a synthetic and orally active anabolic–androgenic steroid (AAS) and a derivative of nandrolone (19-nortestosterone) which was developed by the Contraceptive Development Branch (CDB) of the National ...

(11β-MNT; 11β-methyl-19-NT) ** 19-Nor-5-androstenediol **

19-Nor-5-androstenedione 19-Nor-5-androstenedione, also known as estr-5-ene-3,17-dione, is a synthetic, orally active anabolic-androgenic steroid (AAS) and a derivative of 19-nortestosterone (nandrolone) that was never introduced for medical use. It is an androgen pro ...

** Bolandione (19-nor-4-androstenedione) **

Dienedione Dienedione, also known as estra-4,9-diene-3,17-dione, is a synthetic, orally active anabolic-androgenic steroid (AAS) of the 19-nortestosterone group that was never introduced for medical use. It is thought to be a prohormone of dienolone. The ...

(δ⁹-19-nor-4-androstenedione) **

Dienolone Dienolone (developmental code name RU-3118; online product names Trenazone, Dienazone), or nordienolone, also known as 19-nor-δ9(10)-testosterone, δ9(10)-nandrolone, or estra-4,9(10)-dien-17β-ol-3-one, is a synthetic anabolic-androgenic steroi ...

(δ⁹-19-NT) **

Dimethandrolone Dimethandrolone (DMA), also known by its developmental code name CDB-1321, is an experimental androgen/anabolic steroid (AAS) and progestogen medication which is under investigation for potential clinical use. Dimethandrolone is an AAS, and he ...

(7α,11β-dimethyl-19-NT) ** Methoxydienone (18-methyl-δ^2,5(10)- 3β-methyl ether) **

Trestolone Trestolone, also known as 7α-methyl-19-nortestosterone (MENT), is an experimental androgen/anabolic steroid (AAS) and progestogen medication which has been under development for potential use as a form of hormonal birth control for men and in ...

(MENT; 7α-methyl-19-NT) ; 17α-Alkylated derivatives * Marketed ** Ethylestrenol (ethylnandrol; 3-deketo-17α-ethyl-19-NT) **

Mibolerone Mibolerone, also known as dimethylnortestosterone (DMNT) and sold under the brand names Cheque Drops and Matenon, is a synthetic, orally active, and extremely potent anabolic–androgenic steroid (AAS) and a 17α-alkylated nandrolone (19-norte ...

(7α,17α-dimethyl-19-NT) **

Norethandrolone Norethandrolone, sold under the brand names Nilevar and Pronabol among others, is an androgen and anabolic steroid (AAS) medication which has been used to promote muscle growth and to treat severe burns, physical trauma, and aplastic anemia but ...

(17α-ethyl-19-NT) **

Normethandrone Normethandrone, also known as methylestrenolone or methylnortestosterone and sold under the brand name Metalutin among others, is a progestin and androgen/anabolic steroid (AAS) medication which is used in combination with an estrogen in the tr ...

(methylestrenolone; 17α-methyl-19-NT) **

Propetandrol Propetandrol () (brand name Solevar; former developmental code name SC-7294), or propethandrol, also known as 17α-ethyl-19-nortestosterone 3β-propionate or 17α-ethyl-19-nor-4-androstenediol 3β-propionate, as well as 17α-ethylestr-4-en-3β,17 ...

(17α-ethyl-19-NT 3β-propionate) * Never marketed **

Bolenol Bolenol (, ), also known as 17α-ethyl-19-norandrost-5-en-17β-ol (ethylnorandrostenol), is a synthetic, orally active anabolic-androgenic steroid (AAS) and a 17α-alkylated derivative of 19-nortestosterone (nandrolone) that was never marketed. ...

(3-deketo-17α-ethyl-19-nor-5-androstenediol) **

Dimethyltrienolone Dimethyltrienolone (developmental code name RU-2420) is a synthetic, orally active, and extremely potent anabolic–androgenic steroid (AAS) and 17α-alkylated 19-nortestosterone (nandrolone) derivative which was never marketed for medical u ...

(7α,17α-dimethyl-δ^9,11-19-NT) **

Ethyldienolone Ethyldienolone, also known as 17α-methyl-19-nor-δ9-testosterone, as well as 17α-methylestra-4,9-dien-17β-ol-3-one, is synthetic, orally active anabolic-androgenic steroid (AAS) and a 17α-alkylated derivative of 19-nortestosterone. It is sl ...

(17α-ethyl-δ⁹-19-NT) **

Methyldienolone Methyldienolone (developmental code name RU-3467), also known as 17α-methyl-19-nor-δ9-testosterone, as well as 17α-methylestra-4,9-dien-17β-ol-3-one, is a synthetic, orally active anabolic-androgenic steroid (AAS) and a 17α-alkylated deriv ...

(17α-methyl-δ⁹-19-NT) ** Methylhydroxynandrolone (MOHN, MHN; 4-hydroxy-17α-methyl-19-NT) **

Metribolone Metribolone (developmental code R1881, also known as methyltrienolone) is a synthetic and orally active anabolic–androgenic steroid (AAS) and a 17α-alkylated nandrolone (19-nortestosterone) derivative which was never marketed for medical use ...

(methyltrienolone, R-1881; 17α-methyl-δ^9,11-19-NT) ** Norboletone (17α-ethyl-18-methyl-19-NT) **

Tetrahydrogestrinone Tetrahydrogestrinone (THG), known by the nickname The Clear, is a synthetic and orally active anabolic–androgenic steroid (AAS) which was never marketed for medical use. It was developed by Patrick Arnold and was used by a number of high-profi ...

(THG; 17α-ethyl-18-methyl-δ^9,11-19-NT)

Progestins

Nandrolone, together with

ethisterone Ethisterone, also known as ethinyltestosterone, pregneninolone, and anhydrohydroxyprogesterone and formerly sold under the brand names Proluton C and Pranone among others, is a progestin medication which was used in the treatment of gynecologica ...

(17α-ethynyltestosterone), is also the parent compound of a large group of

progestin A progestogen, also referred to as a progestagen, gestagen, or gestogen, is a type of medication which produces effects similar to those of the natural female sex hormone progesterone in the body. A progestin is a '' synthetic'' progestogen. ...

s, the

norethisterone Norethisterone, also known as norethindrone and sold under the brand name Norlutin among others, is a progestin medication used in birth control pills, menopausal hormone therapy, and for the treatment of gynecological disorders. The medicatio ...

(17α-ethynyl-19-nortestosterone) derivatives. This family is subdivided into two groups: the

s and the

gonane Gonane (cyclopentanoperhydrophenanthrene) is a chemical compound with formula , whose structure consists of four hydrocarbon rings fused together: three cyclohexane units and one cyclopentane. It can also be viewed as the result of fusing a cyc ...

s. The estranes include

(norethindrone),

norethisterone acetate Norethisterone acetate (NETA), also known as norethindrone acetate and sold under the brand name Primolut-Nor among others, is a progestin medication which is used in birth control pills, menopausal hormone therapy, and for the treatment of gynec ...

norethisterone enanthate Norethisterone enanthate (NETE), also known as norethindrone enanthate, is a form of hormonal birth control which is used to prevent pregnancy in women. It is used both as a form of progestogen-only injectable birth control and in combined inje ...

, lynestrenol,

etynodiol diacetate Etynodiol diacetate, or ethynodiol diacetate, sold under the brand name Ovulen among others, is a progestin medication which is used in birth control pills. The medication is available only in combination with an estrogen. It is taken by mouth ...

, and

noretynodrel Noretynodrel, or norethynodrel, sold under the brand name Enovid among others, is a progestin medication which was previously used in birth control pills and in the treatment of gynecological disorders but is now no longer marketed. It was availa ...

, while the gonanes include

norgestrel Norgestrel, sold under the brand name Opill among others, is a progestin which is used in birth control pills. It is often combined with the estrogen ethinylestradiol, marketed as Ovral. It is also used in menopausal hormone therapy. It is t ...

levonorgestrel Levonorgestrel is a hormonal medication used in a number of birth control methods. It is combined with an estrogen to make combination birth control pills. As an emergency birth control, sold under the brand names Plan B One-Step and Julie, ...

desogestrel Desogestrel is a progestin medication which is used in birth control pills. It is also used in the treatment of menopausal symptoms in women. The medication is available and used alone or in combination with an estrogen. It is taken by mouth. ...

etonogestrel Etonogestrel is a medication which is used as a means of birth control for women. It is available as an implant placed under the skin of the upper arm under the brand names Nexplanon and Implanon. It is a progestin that is also used in combinat ...

gestodene Gestodene, sold under the brand names Femodene and Minulet among others, is a progestin medication which is used in birth control pills for women. It is also used in menopausal hormone therapy. The medication is available almost exclusively in c ...

norgestimate Norgestimate, sold under the brand name Ortho Tri-Cyclen among others, is a progestin medication which is used in birth control pills for women and in menopausal hormone therapy. The medication is available in combination with an estrogen and ...

dienogest Dienogest, sold under the brand name Visanne among others, is a progestin medication which is used in birth control pills and in the treatment of endometriosis. It is also used in menopausal hormone therapy and to treat heavy periods. Dienogest ...

(actually a 17α-cyanomethyl-19-nortestosterone derivative), and

norelgestromin Norelgestromin, or norelgestromine, sold under the brand names Evra and Ortho Evra among others, is a progestin medication which is used as a method of birth control for women. The medication is available in combination with an estrogen and is no ...

Synthesis

The elaboration of a method for the reduction of aromatic rings to the corresponding dihydrobenzenes under controlled conditions by A. J. Birch opened a convenient route to compounds related to the putative 19-norprogesterone. This reaction, now known as the

Birch reduction The Birch reduction or Metal-Ammonia reduction is an organic reaction that is used to convert arenes to Cyclohexa-1,4-diene, 1,4-cyclohexadienes. The reaction is named after the Australian chemist Arthur Birch (organic chemist), Arthur Birch and i ...

, is typified by the treatment of the monomethyl ether of

(1) with a solution of lithium metal in liquid ammonia in the presence of alcohol as a proton source. Initial reaction constituents of 1,4-dimetalation of the most electron deficient positions of the aromatic ring–in the case of an estrogen, the 1 and 4-positions. Rxn of the intermediate with the proton source leads to a dihydrobenzene; a special virtue of this sequence in steroids is the fact that the double bind at 2 is in effect becomes an enol ether moiety. Treatment of this product (2) with weak acid,

oxalic acid Oxalic acid is an organic acid with the systematic name ethanedioic acid and chemical formula , also written as or or . It is the simplest dicarboxylic acid. It is a white crystalline solid that forms a colorless solution in water. Its name i ...

for e.g., leads to the hydrolysis of the enol ether, producing β,γ-unconjugated ketone 3. Hydrolysis under more strenuous conditions (

mineral acids A mineral acid (or inorganic acid) is an acid derived from one or more inorganic compounds, as opposed to organic acids which are acidic, organic compounds. All mineral acids form hydrogen ions and the conjugate base when dissolved in water. Cha ...

) results in migration/conjugation of the olefin to yield nandrolone (4).

Esters

* Treatment of 4 with decanoic anhydride and

pyridine Pyridine is a basic (chemistry), basic heterocyclic compound, heterocyclic organic compound with the chemical formula . It is structurally related to benzene, with one methine group replaced by a nitrogen atom . It is a highly flammable, weak ...

affords ''nandrolone decanoate''. * Acylation of 4 with phenylpropionyl chloride yields ''nandrolone phenpropionate''.

Detection in body fluids

Nandrolone use is directly detectable in hair or indirectly detectable in urine by testing for the presence of 19-norandrosterone, a

metabolite In biochemistry, a metabolite is an intermediate or end product of metabolism. The term is usually used for small molecules. Metabolites have various functions, including fuel, structure, signaling, stimulatory and inhibitory effects on enzymes, c ...

. The

International Olympic Committee The International Olympic Committee (IOC; , CIO) is the international, non-governmental, sports governing body of the modern Olympic Games. Founded in 1894 by Pierre de Coubertin and Demetrios Vikelas, it is based i ...

has set a limit of 2.0 μg/L of 19-norandrosterone in urine as the upper limit, beyond which an

is suspected of doping. In the largest nandrolone study performed on 621 athletes at the 1998 Nagano Olympic Games, no athlete tested over 0.4 μg/L. 19-Norandrosterone was identified as a trace contaminant in commercial preparations of

androstenedione Androstenedione, or 4-androstenedione (abbreviated as A4 or Δ4-dione), also known as androst-4-ene-3,17-dione, is an endogenous weak androgen steroid hormone and intermediate in the biosynthesis of estrone and of testosterone from dehydroe ...

, which until 2004 was available without a prescription as a dietary supplement in the U.S. A number of nandrolone cases in

athletics Athletics may refer to: Sports * Sport of athletics, a collection of sporting events that involve competitive running, jumping, throwing, and walking ** Track and field, a sub-category of the above sport * Athletics (physical culture), competitio ...

occurred in 1999, which included high-profile athletes such as

Merlene Ottey Merlene Joyce Ottey (born 10 May 1960) is a Jamaican-Slovenian former track and field sprint (running), sprinter. She began her career representing Jamaica in 1978 and continued to do so for 24 years before representing Slovenia from 2002 to 20 ...

Dieter Baumann Dieter Baumann (, ; born 9 February 1965) is a German former athlete and 5000 m Olympic champion at the 1992 Summer Olympics. He also won the silver medal in the same event (5000 m) at the 1988 Summer Olympics. In 1999, Baumann test ...

, and

Linford Christie Linford Christie (born 2 April 1960) is a Jamaican-born British former Sprint (running), sprinter and athletics coach. He is the only British man to have won gold medals in the 100 metres at all four major competitions open to British athletes ...

. However, the following year the detection method for nandrolone at the time was proved to be faulty. Mark Richardson, a British Olympic relay runner who tested positive for the substance, gave a significant amount of urine samples in a controlled environment and delivered a positive test for the drug, demonstrating that false positives could occur, which led to an overhaul of his competitive ban. Heavy consumption of the essential amino acid

lysine Lysine (symbol Lys or K) is an α-amino acid that is a precursor to many proteins. Lysine contains an α-amino group (which is in the protonated form when the lysine is dissolved in water at physiological pH), an α-carboxylic acid group ( ...

(as indicated in the treatment of cold sores) has allegedly shown false positives in some and was cited by American

shotput The shot put is a track-and-field event involving "putting" (throwing) a heavy spherical ball—the ''shot''—as far as possible. For men, the sport has been a part of the modern Olympics since their revival (1896), and women's competition bega ...

ter C. J. Hunter as the reason for his positive test, though in 2004 he admitted to a federal

grand jury A grand jury is a jury empowered by law to conduct legal proceedings, investigate potential criminal conduct, and determine whether criminal charges should be brought. A grand jury may subpoena physical evidence or a person to testify. A grand ju ...

that he had injected nandrolone. A possible cause of incorrect urine test results is the presence of metabolites from other anabolic steroids, though modern

urinalysis Urinalysis, a portmanteau of the words ''urine'' and ''analysis'', is a Test panel, panel of medical tests that includes physical (macroscopic) examination of the urine, chemical evaluation using urine test strips, and #Microscopic examination, m ...

can usually determine the exact anabolic steroid used by analyzing the ratio of the two remaining nandrolone metabolites. As a result of the numerous overturned verdicts, the testing procedure was reviewed by

UK Sport UK Sport is the government agency responsible for investing money sourced from the National Lottery and the government, into Olympic and Paralympic sport in the United Kingdom. It is an executive non-departmental public body sponsored by the D ...

. In October 2007, three-time Olympic gold medalist for track and field

Marion Jones Marion Lois Jones (born October 12, 1975), also known as Marion Jones-Thompson, is an American former world champion track-and-field athlete and former professional basketball player. She won three gold medals and two bronze medals at the 2000 ...

admitted to use of the drug, and was sentenced to six months in jail for lying to a federal grand jury in 2000.

Mass spectrometry Mass spectrometry (MS) is an analytical technique that is used to measure the mass-to-charge ratio of ions. The results are presented as a ''mass spectrum'', a plot of intensity as a function of the mass-to-charge ratio. Mass spectrometry is used ...

is also used to detect small amounts of nandrolone in urine samples.

History

Nandrolone was first synthesized in 1950. It was first introduced, as nandrolone phenylpropionate, in 1959, and then as nandrolone decanoate in 1962, followed by additional esters.

Society and culture

Generic names

Nandrolone is the generic name of the drug and its , , , and . The formal generic names of nandrolone esters include

(),

nandrolone cyclotate Nandrolone cyclotate () (developmental code name RS-3268R), or nandrolone ciclotate, also known as 19-nortestosterone 17β-ciclotate, is a synthetic and injected anabolic–androgenic steroid (AAS) of the nandrolone (19-nortestosterone) group wh ...

(),

(, , , ),

(), nandrolone phenpropionate (), and

(, ).

Doping in sports

Nandrolone was probably among the first anabolic steroids to be used as a doping agent in sports in the 1960s. It has been banned at the Olympics since 1974. There are many known cases of

doping in sports In competitive sports, doping is the use of banned athletic performance-enhancing drugs (PEDs) by athletes, as a way of cheating. As stated in the World Anti-Doping Code by WADA, doping is defined as the occurrence of one or more of the anti-d ...

with nandrolone esters by

professional A professional is a member of a profession or any person who work (human activity), works in a specified professional activity. The term also describes the standards of education and training that prepare members of the profession with the partic ...

Research

Nandrolone esters have been studied in several indications. They were intensively studied for

, and increased calcium uptake and decreased bone loss, but caused virilization in about half of the women who took them and were mostly abandoned for this use when better drugs like the

bisphosphonate Bisphosphonates are a class of drugs that prevent the loss of bone density, used to treat osteoporosis and similar diseases. They are the most commonly prescribed to treat osteoporosis. Evidence shows that they reduce the risk of fracture in ...

s became available. They have also been studied in

clinical trial Clinical trials are prospective biomedical or behavioral research studies on human subject research, human participants designed to answer specific questions about biomedical or behavioral interventions, including new treatments (such as novel v ...

s for

chronic kidney failure Chronic kidney disease (CKD) is a type of long-term kidney disease, defined by the sustained presence of abnormal kidney function and/or abnormal kidney structure. To meet criteria for CKD, the abnormalities must be present for at least three mo ...

aplastic anemia Aplastic anemia (AA) is a severe hematologic condition in which the body fails to make blood cells in sufficient numbers. Normally, blood cells are produced in the bone marrow by stem cells that reside there, but patients with aplastic anemia ...

, and as

male contraceptive Male contraceptives, also known as male birth control, are methods of preventing pregnancy by interrupting the function of sperm. The main forms of male Birth control, contraception available today are condoms, vasectomy, and Coitus interruptus, w ...

Medical uses

Non-medical uses

Side effects

Pharmacology

Pharmacodynamics

Anabolic and androgenic activity

Pharmacokinetics

Chemistry

Derivatives

Esters

Anabolic steroids

Progestins

Synthesis

Esters

Detection in body fluids

History

Society and culture

Generic names

Doping in sports

Research

References

Further reading