Methandriol (brand names Anabol, Crestabolic, Cytobolin, Diandren, Durabolic, Madiol, Mestenediol, Methabolic, Methydiol, Sterabolic, Stenediol), also known as methylandrostenediol, is 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 ...

and

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) medication which was developed by

Organon The ''Organon'' (, meaning "instrument, tool, organ") is the standard collection of Aristotle's six works on logical analysis and dialectic. The name ''Organon'' was given by Aristotle's followers, the Peripatetics, who maintained against the ...

and is used in both

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 ...

and injectable (as methandriol dipropionate, methandriol propionate, or methandriol bisenanthoyl acetate) formulations. It is an orally active 17α-alkylated AAS 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 ...

of the

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 prohormone An androgen prohormone, or proandrogen, is a prohormone (or prodrug) of an anabolic-androgenic steroid (AAS). They can be prohormones of testosterone or of synthetic compound, synthetic AAS, for example, nandrolone (19-nortestosterone). Dehydroepia ...

androstenediol Androstenediol, or 5-androstenediol (abbreviated as A5 or Δ5-diol), also known as androst-5-ene-3β,17β-diol, is an endogenous weak androgen and estrogen steroid hormone and intermediate in the biosynthesis of testosterone from dehydroepiand ...

Medical uses

Methandriol has been used in the treatment of

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 ...

in women. It has been reported to be almost as virilizing as comparable doses of

testosterone propionate Testosterone propionate, sold under the brand name Testoviron among others, is an androgen and anabolic steroid (AAS) medication which is used mainly in the treatment of low testosterone levels in men. It has also been used to treat breast cance ...

and

methyltestosterone Methyltestosterone, sold under the brand names Android, Metandren, and Testred among others, is an androgen and anabolic steroid (AAS) medication which is used in the treatment of low testosterone levels in men, delayed puberty in boys, at low ...

in women.

Available forms

Methandriol (brand name Androteston M, Notandron, Protandren) was previously marketed as 25 mL and 50 mg/mL aqueous suspensions for use by

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 ...

Chemistry

Methandriol, also known as 17α-methyl-5-androstenediol or as 17α-methylandrost-5-ene-3β,17β-diol, is a

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 ...

androstane Androstane is a C19 steroidal hydrocarbon with a gonane core. Androstane can exist as either of two isomers, known as 5α-androstane and 5β-androstane. File:androstane.png, 5α-Androstane File:androstane 5beta.png, 5β-Androstane Pharmacolog ...

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 17α-alkylated

of 5-androstenediol (androst-5-ene-3β,17β-diol). A number 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 of methandriol exist, including methandriol dipropionate (methylandrostenediol 3β,17β-dipropionate), methandriol propionate (methylandrostenediol 3β-propionate), methandriol bisenanthoyl acetate (methylandrostenediol 3β,17β-dioxononanoate), and

methandriol diacetate Methandriol diacetate, or methylandrostenediol diacetate, also known as 17α-methylandrost-5-ene-3β,17β-diol 3β,17β-diacetate, is a synthetic compound, synthetic, injection (medicine), injected anabolic–androgenic steroid (AAS) and a 17α-a ...

(methylandrostenediol 3β,17β-diacetate; never marketed). Methandriol is closely related to

(17α-methyltestosterone or 17α-methylandrost-4-ene-17β-ol-3-one). An analogue of methandriol is its positional isomer methyl-4-androstenediol (17α-methylandrost-4-ene-3β,17β-diol). Another analogue of methandriol is ethynylandrostanediol (17α-ethynyl-5α-androstane-3β,17β-diol) as well as its

ethandrostate (ethynylandrostanediol 3β-cyclohexylpropionate).

History

Methandriol was first synthesized in 1935 along with

and mestanolone.

Society and culture

Generic names

Methandriol is the generic name of methylandrostenediol and its .

Availability

Methandriol remains marketed for clinical use only in

Taiwan Taiwan, officially the Republic of China (ROC), is a country in East Asia. The main geography of Taiwan, island of Taiwan, also known as ''Formosa'', lies between the East China Sea, East and South China Seas in the northwestern Pacific Ocea ...

and for veterinary use (as methandriol dipropionate) only in

Australia Australia, officially the Commonwealth of Australia, is a country comprising mainland Australia, the mainland of the Australia (continent), Australian continent, the island of Tasmania and list of islands of Australia, numerous smaller isl ...

References

External links

Methandriol (methandriol, methandriol dipropionate) - William Llewellyn's Anabolic.org
{{Androgen receptor modulators Abandoned drugs Anabolic–androgenic steroids Androstanes Diols Hepatotoxins