Nandrolone, also known as 19-nortestosterone, is an

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

and

anabolic steroid Anabolic steroids, also known more properly as anabolic–androgenic steroids (AAS), are steroidal androgens that include natural androgens like testosterone as well as synthetic androgens that are structurally related and have similar effects t ...

(AAS) which is used in the form of

ester In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides ...

s such as

nandrolone decanoate Nandrolone decanoate, sold under the brand name 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 menopausal wom ...

(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 na ...

s are used in the treatment of

anemia Anemia or anaemia (British English) is a blood disorder in which the blood has a reduced ability to carry oxygen due to a lower than normal number of red blood cells, or a reduction in the amount of hemoglobin. When anemia comes on slowly, ...

cachexia Cachexia () is a complex syndrome associated with an underlying illness, causing ongoing muscle loss that is not entirely reversed with nutritional supplementation. A range of diseases can cause cachexia, most commonly cancer, congestive heart fai ...

(

muscle Skeletal muscles (commonly referred to as muscles) are Organ (biology), organs of the vertebrate muscular system and typically are attached by tendons to bones of a skeleton. The muscle cells of skeletal muscles are much longer than in the other ...

wasting syndrome), osteoporosis,

breast cancer Breast cancer is cancer that develops from breast tissue. Signs of breast cancer may include a lump in the breast, a change in breast shape, dimpling of the skin, milk rejection, fluid coming from the nipple, a newly inverted nipple, or ...

, and for other indications. They are not used

by mouth Oral administration is a route of administration where a substance is taken through the mouth. Per os abbreviated to P.O. is sometimes used as a direction for medication to be taken orally. Many medications are taken orally because they are i ...

and instead are given by injection into muscle or

fat In nutrition, biology, and chemistry, fat usually means any ester of fatty acids, or a mixture of such compounds, most commonly those that occur in living beings or in food. The term often refers specifically to triglycerides (triple es ...

Side effect In medicine, a side effect is an effect, whether therapeutic or adverse, that is secondary to the one intended; although the term is predominantly employed to describe adverse effects, it can also apply to beneficial, but unintended, consequence ...

s of nandrolone esters include

symptom Signs and symptoms are the observed or detectable signs, and experienced symptoms of an illness, injury, or condition. A sign for example may be a higher or lower temperature than normal, raised or lowered blood pressure or an abnormality showi ...

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 most commonly used in three medical and biology ...

acne Acne, also known as ''acne vulgaris'', is a long-term skin condition that occurs when dead skin cells and oil from the skin clog hair follicles. Typical features of the condition include blackheads or whiteheads, pimples, oily skin, and ...

, increased hair growth, voice changes, and decreased

sexual desire Sexual desire is an emotion and motivational state characterized by an interest in sexual objects or activities, or by a drive to seek out sexual objects or to engage in sexual activities. It is an aspect of sexuality, which varies significantly ...

due to its ability to suppress endogenous testosterone synthesis while not being a sufficient androgen itself. They are synthetic androgens and anabolic steroids and hence are

agonist An agonist is a chemical that activates a receptor to produce a biological response. Receptors are cellular proteins whose activation causes the cell to modify what it is currently doing. In contrast, an antagonist blocks the action of the ago ...

s of the androgen receptor (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 sex hormone and anabolic steroid in males. In humans, testosterone plays a key role in the development of male reproductive tissues such as testes and prostate, as well as promoting secondary sexual characteris ...

and

dihydrotestosterone Dihydrotestosterone (DHT, 5α-dihydrotestosterone, 5α-DHT, androstanolone or stanolone) is an endogenous androgen sex steroid and hormone. The enzyme 5α-reductase catalyzes the formation of DHT from testosterone in certain tissues incl ...

(DHT). Nandrolone has strong

anabolic Anabolism () is the set of metabolic pathways that construct molecules from smaller units. These reactions require energy, known also as an endergonic process. Anabolism is the building-up aspect of metabolism, whereas catabolism is the breaking-d ...

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 prodrugs 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 naturally occurring anabolic–androgenic steroid (AAS) and a 5α-reduced derivative of nandrolone (19-nortes ...

. Nandrolone esters were first described and introduced for medical use in the late 1950s. They are among the most widely used AAS 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 AAS 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), also referred to as red cells, red blood corpuscles (in humans or other animals not having nucleus in red blood cells), haematids, erythroid cells or erythrocytes (from Greek ''erythros'' for "red" and ''kytos'' for "holl ...

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 clinically it is measured by proxy according to op ...

. Clinical studies have shown them to be effective in treating

, osteoporosis, and

Nandrolone sulfate Nandrolone sulfate, also known as 19-nortestosterone 17β-sulfate and used medically as the sodium salt nandrolone sodium sulfate (brand names Keratyl, Nandrol, Nandain, Colirio Ocul Nandrol), is a synthetic androgen and anabolic steroid and a na ...

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 an ...

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 (also sportsman or sportswoman) is a person who competes in one or more sports that involve physical strength, speed, or endurance. Athletes may be professionals or amateurs. Most professional athletes have particularly well-dev ...

bodybuilder Bodybuilding is the use of progressive resistance exercise to control and develop one's muscles (muscle building) by muscle hypertrophy for aesthetic purposes. It is distinct from similar activities such as powerlifting because it focuse ...

s, and

powerlifter Powerlifting is a 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 single-lift effor ...

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 na ...

s have been reported to produce increased

libido Libido (; colloquial: sex drive) is a person's overall sexual drive or desire for sexual activity. Libido is influenced by biological, psychological, and social factors. Biologically, the sex hormones and associated neurotransmitters that act ...

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 ...

and

body hair Body hair, or androgenic hair, is the terminal hair that develops on the human body during and after puberty. It is differentiated from the head hair and less visible vellus hair, which is much finer and lighter in color. The growth of andr ...

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 grow ...

, voice changes, and clitoral enlargement. 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 is the absence of a menstrual period in a woman of reproductive age. Physiological states of amenorrhoea are seen, most commonly, during pregnancy and lactation (breastfeeding). Outside the reproductive years, there is absence of mense ...

and

menorrhagia Heavy menstrual bleeding (HMB), previously known as menorrhagia or hypermenorrhea, 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 abnor ...

have been reported as side effects of

nandrolone cypionate Nandrolone cypionate (brand names Anabo, Depo-Nortestonate, Dynabol, Nortestrionate, Pluropon, Sterocrinolo), or nandrolone cipionate, also known as 19-nortestosterone 17β-cyclopentanepropionate, is a synthetic androgen and anabolic steroid and ...

. Nandrolone theoretically may produce

erectile dysfunction Erectile dysfunction (ED), also called impotence, is the type of sexual dysfunction in which the penis fails to become or stay erect during sexual activity. It is the most common sexual problem in men.Cunningham GR, Rosen RC. Overview of ma ...

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 The blood circulatory system is a system of organs that includes the heart, blood vessels, and blood which is circulated throughout the entire body of a human or other vertebrate. It includes the cardiovascular system, or vascular system, tha ...

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, bacterium, or plant, as well as the effect on a subs ...

as well as

hypogonadism Hypogonadism means diminished functional activity of the gonads—the testes or the ovaries—that may result in diminished production of sex hormones. Low androgen (e.g., testosterone) levels are referred to as hypoandrogenism and low est ...

and

infertility Infertility is the inability of a person, animal or plant to reproduce by natural means. It is usually not the natural state of a healthy adult, except notably among certain eusocial species (mostly haplodiploid insects). It is the normal st ...

. 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 ha ...

, although this is also theoretical.

Pharmacology

Pharmacodynamics

Nandrolone is an

of the AR, the

s like

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

scalp The scalp is the anatomical area bordered by the human face at the front, and by the neck at the sides and back. Structure The scalp is usually described as having five layers, which can conveniently be remembered as a mnemonic: * S: The s ...

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 cuticle, animal coverings, such as the arthropod exoskeleton, have diffe ...

, and

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

, hence deleterious effects in these tissues are lessened. This is because nandrolone is metabolized by

5α-reductase 5α-Reductases, also known as 3-oxo-5α-steroid 4-dehydrogenases, are enzymes involved in steroid metabolism. They participate in three metabolic pathways: bile acid biosynthesis, androgen and estrogen metabolism. There are three isozymes ...

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 naturally occurring anabolic–androgenic steroid (AAS) and a 5α-reduced derivative of nandrolone (19-nortes ...

(DHN), which has both reduced affinity for the androgen receptor (AR) relative to nandrolone ''

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

'' and weaker AR agonistic potency ''

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, and ...

''. 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 is a cause of acute and chronic liver disease caused specifically by medications and the most common reason for a drug to be withdrawn f ...

potential of nandrolone.

Estrogen Estrogen or oestrogen is a category of sex hormone responsible for the development and regulation of the female reproductive system and secondary sex characteristics. There are three major endogenous estrogens that have estrogenic hormonal a ...

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 ma ...

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

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

and reduced

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

progestogen Progestogens, also sometimes written 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 progestogen in the bod ...

. 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 res ...

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 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, nandrolone-like AAS like nandrolone itself and

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 hexahydrobenzylcarbo ...

are said to have among the highest ratio of anabolic to androgenic effect of all AAS. 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 AAS (i.e., other 19-nortestosterone derivatives). As such, nandrolone-like AAS, namely nandrolone esters, are the most frequently used AAS in clinical settings in which anabolic effects are desired; for instance, in the treatment of AIDS-associated

, severe

burn A burn is an injury to skin, or other tissues, caused by heat, cold, electricity, chemicals, friction, or ultraviolet radiation (like sunburn). Most burns are due to heat from hot liquids (called scalding), solids, or fire. Burns occur mainl ...

s, and

chronic obstructive pulmonary disease Chronic obstructive pulmonary disease (COPD) is a type of progressive lung disease characterized by long-term respiratory symptoms and airflow limitation. The main symptoms include shortness of breath and a cough, which may or may not produce ...

. However, AAS 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 ...

and

voice deepening A hoarse voice, also known as dysphonia or hoarseness, is when the voice involuntarily sounds breathy, raspy, or strained, or is softer in volume or lower in pitch. A hoarse voice, can be associated with a feeling of unease or scratchiness in the ...

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 potency of

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 into the subcutis, the layer of skin directly below the dermis and epidermis, co ...

of nandrolone. Nandrolone has very low affinity 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 has also been called androgen-bi ...

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

metabolized Metabolism (, from el, μεταβολή ''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 cell ...

by the

enzyme Enzymes () are proteins that act as biological catalysts by accelerating chemical reactions. The molecules upon which enzymes may act are called substrate (chemistry), substrates, and the enzyme converts the substrates into different molecule ...

, 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. See ...

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 betwe ...

s, and

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

and in the

kidney The kidneys are two reddish-brown bean-shaped organs found in vertebrates. They are located on the left and right in the retroperitoneal space, and in adult humans are about in length. They receive blood from the paired renal arteries; bloo ...

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, ...

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 Anti ...

, and these metabolites may be detected in

urine Urine is a liquid by-product of metabolism in humans and in many other animals. Urine flows from the kidneys through the ureters to the urinary bladder. Urination results in urine being excreted from the body through the urethra. Cellular ...

. Single

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

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 syn ...

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 ...

(19-norandrostane)

steroid A steroid is a biologically active organic compound with four rings arranged in a specific molecular configuration. Steroids have two principal biological functions: as important components of cell membranes that alter membrane fluidity; and ...

and a

derivative In mathematics, the derivative of a function of a real variable measures the sensitivity to change of the function value (output value) with respect to a change in its argument (input value). Derivatives are a fundamental tool of calculus. ...

(androst-4-en-17β-ol-3-one). It is specifically the C19 demethylated ( nor) analogue of testosterone. Nandrolone is an

endogenous Endogenous substances and processes are those that originate from within a living system such as an organism, tissue, or cell. In contrast, exogenous substances and processes are those that originate from outside of an organism. For example, ...

intermediate in the production of

estradiol Estradiol (E2), also spelled oestradiol, is an estrogen steroid hormone and the major female sex hormone. It is involved in the regulation of the estrous and menstrual female reproductive cycles. Estradiol is responsible for the development o ...

from

via

in mammals 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 develops ( gestates) inside a woman's uterus (womb). A multiple pregnancy involves more than one offspring, such as with twins. Pregnancy usually occurs by sexual intercourse, but ...

in women. Nandrolone esters have an

such as decanoate or

phenylpropionate Phenylpropanoic acid or hydrocinnamic acid is a carboxylic acid with the formula C9H10O2 belonging to the class of phenylpropanoids. It is a white, crystalline solid with a sweet, floral scent at room temperature. Phenylpropanoic acid has a wide v ...

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 hexyloxyphenylpropionate, nandrolone laurate,

nandrolone sulfate Nandrolone sulfate, also known as 19-nortestosterone 17β-sulfate and used medically as the sodium salt nandrolone sodium sulfate (brand names Keratyl, Nandrol, Nandain, Colirio Ocul Nandrol), is a synthetic androgen and anabolic steroid and a na ...

, and nandrolone undecanoate.

Anabolic steroids

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

and the 17α-alkylated ethylestrenol (ethylnandrol) and metribolone (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-profil ...

(THG). The following is list of derivatives of nandrolone that have been developed as AAS: ; Non-17α-alkylated derivatives * Marketed ** Bolandiol (19-nor-4-androstenediol) ** Norclostebol (4-chloro-19-NT) ** Oxabolone (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 hexahydrobenzylcarbo ...

(δ^9,11-19-NT) * Never marketed ** 7α-Methyl-19-nor-4-androstenedione (MENT dione, trestione) ** 11β-Methyl-19-nortestosterone (11β-MNT; 11β-methyl-19-NT) ** 19-Nor-5-androstenediol ** 19-Nor-5-androstenedione ** Bolandione (19-nor-4-androstenedione) ** Dienedione (δ⁹-19-nor-4-androstenedione) ** Dienolone (δ⁹-19-NT) ** Dimethandrolone (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 i ...

(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 (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 tre ...

(methylestrenolone; 17α-methyl-19-NT) ** Propetandrol (17α-ethyl-19-NT 3β-propionate) * Never marketed ** Bolenol (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 use ...

(7α,17α-dimethyl-δ^9,11-19-NT) ** Ethyldienolone (17α-ethyl-δ⁹-19-NT) ** Methyldienolone (17α-methyl-δ⁹-19-NT) ** Methylhydroxynandrolone (MOHN, MHN; 4-hydroxy-17α-methyl-19-NT) ** Metribolone (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-profil ...

(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. Pro ...

s, the

norethisterone Norethisterone, also known as norethindrone and sold under many brand names, is a progestin medication used in birth control pills, menopausal hormone therapy, and for the treatment of gynecological disorders. The medication is available in ...

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

s and the

gonane Gonane is a chemical compound with formula , whose molecule can be described as three molecules or entities of cyclohexane and one of cyclopentane, fused in a particular way. More specifically, the molecule can be described as that of cyclohe ...

s. The estranes include

(norethindrone), norethisterone acetate,

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 injec ...

, lynestrenol,

etynodiol diacetate Etynodiol diacetate, or ethynodiol diacetate, sold under the brand names Demulen and Femulen 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 tak ...

, 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 Ovral among others, is a progestin medication which is used in birth control pills and in menopausal hormone therapy. It is available both in combination with an estrogen and alone. It is taken by mouth. ...

levonorgestrel Levonorgestrel is a hormonal medication which is 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 name Plan B One-Step amon ...

desogestrel Desogestrel is a progestin medication which is used in birth control pills for women. 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 tak ...

, etonogestrel, gestodene,

norgestimate Norgestimate, sold under the brand names Ortho Tri-Cyclen and Previfem 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 ...

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.Drugs.comNorelgestromin/Ethinyl Estradiol Patch/ref> The medication i ...

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 is an organic reaction that is used to convert arenes to cyclohexadienes. The reaction is named after the Australian chemist Arthur Birch and involves the organic reduction of aromatic rings in an amine solvent (traditional ...

, 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 formula . It is the simplest dicarboxylic acid. It is a white crystalline solid that forms a colorless solution in water. Its name comes from the fact that early inve ...

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. Ch ...

) 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, weakl ...

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, ...

. The

International Olympic Committee The International Olympic Committee (IOC; french: link=no, Comité international olympique, ''CIO'') is a non-governmental sports organisation based in Lausanne, Switzerland. It is constituted in the form of an association under the Swis ...

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 Doping may refer to: * Doping, adding a dopant to something * Doping (semiconductor), intentionally introducing impurities into an extremely pure semiconductor to change its electrical properties * Aircraft dope, a lacquer that is applied to fabr ...

. 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 dehy ...

, 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), competiti ...

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 sprinter. She began her career representing Jamaica in 1978, and continued to do so for 24 years, before representing Slovenia from 2002 to 2012. She is rank ...

Dieter Baumann Dieter Baumann (, ; born 9 February 1965) is a former German athlete and winner of the 5000 m 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 tested positive for na ...

and

Linford Christie Linford Cicero Christie (born 2 April 1960) is a Jamaican-born British former sprinter. He is the only British man to have won gold medals in the 100 metres at all four major competitions open to British athletes: the Olympic Games, the Worl ...

. 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. It contains an α-amino group (which is in the protonated form under biological conditions), an α-carboxylic acid group (which is in the deprotonated &minu ...

(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. The shot put competition for men has been a part of the modern Olympics since their revival in 1896, and women's co ...

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—a group of citizens—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 ...

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

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

can usually determine the exact AAS 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 in Olympic and Paralympic sport in the United Kingdom. It is an executive non-departmental public body sponsored by the Department for Digital, Culture, Media & Sport. It was created ...

. On October 5, 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 u ...

is also used to detect small samples of nandrolone in urine samples, as it has a unique molar mass.

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 laurate'' (), ''

nandrolone phenpropionate 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 osteoporo ...

'' (), and ''

'' (, ).

Doping in sports

Nandrolone was probably among the first AAS 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 by athletic competitors as a way of cheating in sports. The term ''doping'' is widely used by organizations that regulate sporting competitions. The use of ...

with nandrolone esters by

professional A professional is a member of a profession or any person who works in a specified professional activity. The term also describes the standards of education and training that prepare members of the profession with the particular knowledge and ski ...

Research

Nandrolone esters have been studied in several indications. They were intensively studied for osteoporosis, 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 drugs used to treat osteoporosis. They are called bisphosphonates because they ...

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 kidney disease in which a gradual loss of kidney function occurs over a period of months to years. Initially generally no symptoms are seen, but later symptoms may include pedal edema, leg swelling, feelin ...

aplastic anemia Aplastic anemia is a cancer in which the body fails to make blood cells in sufficient numbers. Blood cells are produced in the bone marrow by stem cells that reside there. Aplastic anemia causes a deficiency of all blood cell types: red blood ...

, and as

male contraceptive Male contraceptives, also known as male birth control, are methods of preventing pregnancy that solely involve the male physiology. The most common kinds of male contraception include condoms, outercourse, and vasectomy. In domestic animals, cas ...

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