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 "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 inc ...

and

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

(AAS) medication which was developed by

Organon The ''Organon'' ( grc, Ὄργανον, 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. The si ...

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 oral ...

and

injectable An injection (often and usually referred to as a "shot" in US English, a "jab" in UK English, or a "jag" in Scottish English and Scots) is the act of administering a liquid, especially a drug, into a person's body using a needle (usually a hypo ...

(as

methandriol dipropionate Methandriol dipropionate (MADP), also known as methylandrostenediol dipropionate and sold under the brand names Arbolic, Durabolic, Or-Bolic, Probolik, and Protabolin among others, is a synthetic, injected anabolic-androgenic steroid (AAS) and a ...

methandriol propionate Methandriol propionate (brand name Metilbisexovis), or methylandrostenediol propionate, also known as 17α-methylandrost-5-ene-3β,17β-diol 3β-propionate, is a synthetic, injected anabolic-androgenic steroid (AAS) and a 17α-alkylated derivat ...

, or

methandriol bisenanthoyl acetate Methandriol bisenanthoyl acetate (brand name Notandron-Depot), or methylandrostenediol bisenanthoyl acetate, also known as 17α-methylandrost-5-ene-3β,17β-diol 3β,17β-di(3-oxononanoate), is a synthetic, injected anabolic–androgenic steroid ...

) formulations. It is an orally active 17α-alkylated AAS 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. F ...

of the

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, es ...

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 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 a re ...

in women. It has been reported to be almost as

virilizing 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 ...

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 suspension In chemistry, a suspension is a Mixture#Homogeneous and heterogeneous mixtures, heterogeneous mixture of a fluid that contains solid particles sufficiently large for sedimentation. The particles may be macroscopic, visible to the naked eye, usual ...

s for use by

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 ...

Chemistry

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

synthetic Synthetic things are composed of multiple parts, often with the implication that they are artificial. In particular, 'synthetic' may refer to: Science * Synthetic chemical or compound, produced by the process of chemical synthesis * Synthetic o ...

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 Pharmacology ...

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 a ...

and a 17α-alkylated

5-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 ...

(androst-5-ene-3β,17β-diol). A number 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 ar ...

s of methandriol exist, including

(methylandrostenediol 3β,17β-dipropionate),

(methylandrostenediol 3β-propionate),

(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, injected anabolic–androgenic steroid (AAS) and a 17α-alkylated derivative of 5-androstenediol ...

(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 In chemistry, a structural isomer (or constitutional isomer in the IUPAC nomenclature) of a compound is another compound whose molecule has the same number of atoms of each element, but with logically distinct bonds between them. The term metam ...

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 Ethandrostate, also known as ethinylandrostenediol 3β-cyclohexanepropionate, is a synthetic steroidal estrogen and ester of ethinylandrostenediol (17α-ethynyl-5-androstenediol) which was developed and studied in people with certain cancers like ...

(ethynylandrostanediol 3β-cyclohexylpropionate).

History

Methandriol was first synthesized in 1935 along with

and

mestanolone Mestanolone, also known as methylandrostanolone and sold under the brand names Androstalone and Ermalone among others, is an androgen and anabolic steroid (AAS) medication which is mostly no longer used. It is still available for use in Japan ...

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, at the junction of the East and South China Seas in the northwestern Pacific Ocean, with the People's Republic of China (PRC) to the northwest, Japan to the nort ...

and for veterinary use (as

) only in

Australia Australia, officially the Commonwealth of Australia, is a Sovereign state, sovereign country comprising the mainland of the Australia (continent), Australian continent, the island of Tasmania, and numerous List of islands of Australia, sma ...

References

External links

Methandriol (methandriol, methandriol dipropionate) - William Llewellyn's Anabolic.org
{{Androgen receptor modulators Abandoned drugs Androgens and anabolic steroids Androstanes Diols Hepatotoxins World Anti-Doping Agency prohibited substances