Methandriol
Chemical compound
From Wikipedia, the free encyclopedia
Methandriol (brand names Anabol, Crestabolic, Cytobolin, Diandren, Durabolic, Madiol, Mestenediol, Methabolic, Methydiol, Sterabolic, Stenediol), also known as methylandrostenediol, is an androgen and anabolic steroid (AAS) medication which was developed by Organon and is used in both oral and injectable (as methandriol dipropionate, methandriol propionate, or methandriol bisenanthoyl acetate) formulations.[2][3][4] It is an orally active 17α-alkylated AAS and a derivative of the endogenous androgen prohormone androstenediol.[2][3]
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| Clinical data | |
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| Trade names | Crestabolic, Cytobolin, Diandren, Madiol, Stenediol, Mestenediol |
| Other names | Metandriol; Methylandrostenediol; Methyl-5-androstenediol; Methylandrostenediole; 17α-Methylandrost-5-ene-3β,17β-diol |
| Routes of administration | By mouth |
| Drug class | Androgen; Anabolic steroid |
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| Identifiers | |
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| ECHA InfoCard | 100.007.548 |
| Chemical and physical data | |
| Formula | C20H32O2 |
| Molar mass | 304.474 g·mol−1 |
| 3D model (JSmol) | |
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Medical uses
Methandriol has been used in the treatment of breast cancer in women.[5][6][7][8] It has been reported to be almost as virilizing as comparable doses of testosterone propionate and methyltestosterone in women.[9]
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.[10]
Chemistry
Methandriol, also known as 17α-methyl-5-androstenediol or as 17α-methylandrost-5-ene-3β,17β-diol, is a synthetic androstane steroid and a 17α-alkylated derivative of 5-androstenediol (androst-5-ene-3β,17β-diol).[2][3] A number of esters 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 (methylandrostenediol 3β,17β-diacetate; never marketed).[2][3] Methandriol is closely related to methyltestosterone (17α-methyltestosterone or 17α-methylandrost-4-ene-17β-ol-3-one).[2][3]
An analogue of methandriol is its positional isomer methyl-4-androstenediol (17α-methylandrost-4-ene-3β,17β-diol).[11] Another analogue of methandriol is ethynylandrostanediol (17α-ethynyl-5α-androstane-3β,17β-diol) as well as its ester ethandrostate (ethynylandrostanediol 3β-cyclohexylpropionate).[11]
History
Methandriol was first synthesized in 1935 along with methyltestosterone and mestanolone.[5][12][13]
| Route | Medication | Form | Dosage | |
|---|---|---|---|---|
| Oral | Methyltestosterone | Tablet | 30–200 mg/day | |
| Fluoxymesterone | Tablet | 10–40 mg 3x/day | ||
| Calusterone | Tablet | 40–80 mg 4x/day | ||
| Normethandrone | Tablet | 40 mg/day | ||
| Buccal | Methyltestosterone | Tablet | 25–100 mg/day | |
| Injection (IM or SC) | Testosterone propionate | Oil solution | 50–100 mg 3x/week | |
| Testosterone enanthate | Oil solution | 200–400 mg 1x/2–4 weeks | ||
| Testosterone cypionate | Oil solution | 200–400 mg 1x/2–4 weeks | ||
| Mixed testosterone esters | Oil solution | 250 mg 1x/week | ||
| Methandriol | Aqueous suspension | 100 mg 3x/week | ||
| Androstanolone (DHT) | Aqueous suspension | 300 mg 3x/week | ||
| Drostanolone propionate | Oil solution | 100 mg 1–3x/week | ||
| Metenolone enanthate | Oil solution | 400 mg 3x/week | ||
| Nandrolone decanoate | Oil solution | 50–100 mg 1x/1–3 weeks | ||
| Nandrolone phenylpropionate | Oil solution | 50–100 mg/week | ||
| Note: Dosages are not necessarily equivalent. Sources: See template. | ||||
Society and culture
Generic names
Methandriol is the generic name of methylandrostenediol and its INN.[2][3]
Availability
Methandriol remains marketed for clinical use only in Taiwan and for veterinary use (as methandriol dipropionate) only in Australia.[14]