Chemistry:Methandriol

Short description: Chemical compound

Methandriol

Clinical data
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
Legal status
Legal status	BR: Class C5 (Anabolic steroids)
Identifiers
IUPAC name (3S,8S,9R,10R,13S,14R,17S)-10,13,17-trimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene-3,17-diol
CAS Number	521-10-8 Y
PubChem CID	229021
ChemSpider	199375 N
UNII	5730Z864KG
Chemical and physical data
Formula	C20H32O2
Molar mass	304.474 g·mol−1
3D model (JSmol)	Interactive image
SMILES C[C@]12CC[C@@H](CC1=CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@]4(C)O)C)O
InChI InChI=1S/C20H32O2/c1-18-9-6-14(21)12-13(18)4-5-15-16(18)7-10-19(2)17(15)8-11-20(19,3)22/h4,14-17,21-22H,5-12H2,1-3H3/t14-,15+,16-,17-,18-,19-,20-/m0/s1 N Key:WRWBCPJQPDHXTJ-DTMQFJJTSA-N N
NY (what is this?)  (verify)

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. It is an orally active 17α-alkylated AAS and a derivative of the endogenous androgen prohormone androstenediol.

Medical uses

Methandriol has been used in the treatment of breast cancer in women. It has been reported to be almost as virilizing as comparable doses of testosterone propionate and methyltestosterone 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.

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). 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). Methandriol is closely related to methyltestosterone (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 ester ethandrostate (ethynylandrostanediol 3β-cyclohexylpropionate).

History

Methandriol was first synthesized in 1935 along with methyltestosterone and mestanolone.

Androgen/anabolic steroid dosages for breast cancer

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.

Availability

Methandriol remains marketed for clinical use only in Taiwan and for veterinary use (as methandriol dipropionate) only in Australia .

External links

• Methandriol (methandriol, methandriol dipropionate) - William Llewellyn's Anabolic.org

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| name = Androgens and antiandrogens
| title = Androgens and antiandrogens
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| group1 = Androgens
(incl. AAS)

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AR agonists

Testosterone derivatives: Androstenediol dipropionate Boldenone undecylenate Clostebol Clostebol acetate Clostebol caproate Clostebol propionate Cloxotestosterone acetate Prasterone (dehydroepiandrosterone, DHEA) Prasterone enanthate (DHEA enanthate) Prasterone sulfate (DHEA sulfate) Quinbolone Testosterone# Testosterone esters (e.g., testosterone cypionate, testosterone enanthate]], testosterone propionate]], testosterone undecanoate]], testosterone ester mixture]]s (Deposterona, Omnadren, Sustanon, Testoviron Depot)) Dihydrotestosterone derivatives: Androstanolone (stanolone, dihydrotestosterone, DHT) Androstanolone esters Bolazine capronate Drostanolone propionate (dromostanolone propionate) Epitiostanol Mepitiostane Mesterolone Metenolone acetate (methenolone acetate) Metenolone enanthate (methenolone enanthate) Stenbolone acetate 19-Nortestosterone derivatives: Bolandiol dipropionate Nandrolone esters (e.g., nandrolone decanoate, nandrolone phenylpropionate) Norclostebol Norclostebol acetate Oxabolone cipionate (oxabolone cypionate) Trenbolone acetate Trenbolone hexahydrobenzylcarbonate (trenbolone cyclohexylmethylcarbonate) 17α-Alkylated testosterone derivatives: Bolasterone Calusterone Chlorodehydromethyltestosterone (CDMT) Fluoxymesterone Formebolone Metandienone (methandienone, methandrostenolone) Methandriol (methylandrostenediol) Methandriol bisenanthoyl acetate Methandriol dipropionate Methandriol propionate Methyltestosterone Methyltestosterone 3-hexyl ether Oxymesterone Penmesterol Tiomesterone (thiomesterone) 17α-Alkylated dihydrotestosterone derivatives: Androisoxazole Furazabol Mebolazine (dimethazine) Mestanolone Oxandrolone Oxymetholone Stanozolol 17α-Alkylated 19-nortestosterone derivatives: Ethylestrenol Mibolerone Norethandrolone Normethandrone (methylestrenolone, normethisterone) Propetandrol (propethandrol) 17α-Vinyltestosterone derivatives: Norvinisterone (vinylnortestosterone) 17α-Ethynyltestosterone derivatives: Danazol Gestrinone Progestins (e.g., ethisterone (ethynyltestosterone), levonorgestrel, norgestrel, norethisterone (norethindrone), [[Chemistry:Lynestrlynestrenol, Norgestrienone|norgestrienone]]) Tibolone Progesterone derivatives: Medroxyprogesterone acetate

Progonadotropins

Antiestrogens (e.g., tamoxifen, Chemistry:Clomifene

| group2 = Antiandrogens
| list2 = {{Navbox|child
| groupstyle = text-align:center;
| groupwidth = 9em;

  | group1 = AR antagonists
  | list1 =

• Steroidal: Abiraterone acetate
• Canrenone
• Chlormadinone acetate
• Cyproterone acetate
• Delmadinone acetate
• Dienogest
• Drospirenone
• Medrogestone
• Megestrol acetate
• Nomegestrol acetate
• Osaterone acetate
• Oxendolone
• Potassium canrenoate
• Spironolactone

• Nonsteroidal: Apalutamide
• Bicalutamide
• Cimetidine
• Darolutamide
• Enzalutamide
• Flutamide
• Ketoconazole
• Nilutamide
• Seviteronel^†
• Topilutamide (fluridil)

  | group2 = Steroidogenesis
inhibitors

| list2 =

5α-Reductase	Alfatradiol Dutasteride Epristeride Finasteride Saw palmetto extract
Others	Abiraterone acetate Aminoglutethimide Bifluranol Cyproterone acetate Flutamide Ketoconazole Nilutamide Seviteronel† Spironolactone

  | group3 = Antigonadotropins
  | list3 =

• D₂ receptor antagonists (prolactin releasers) (e.g., domperidone, metoclopramide, risperidone, haloperidol, chlorpromazine, sulpiride)
• Estrogens (e.g., bifluranol, [[diethylstilbestrol, estradiol, estradiol esters, ethinylestradiol, ethinylestradiol sulfonate, paroxypropione)
• GnRH agonists (e.g., leuprorelin)
• GnRH antagonists (e.g., cetrorelix)
• Progestogens (incl., chlormadinone acetate, [[cyproterone acetate, hydroxyprogesterone caproate, gestonorone caproate, [[Chemistry:Medroxyprogesterone medroxyprogesterone acetate, Chemistry:Megestrol acetate|megestrol acetate]])

  | group4 = Others
  | list4 =

• Androstenedione immunogens: Androvax (androstenedione albumin)
• Ovandrotone albumin (Fecundin)

}}

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• ^#WHO-EM
• ^‡Withdrawn from market
• Clinical trials:
  • ^†Phase III
  • ^§Never to phase III

See also

Androgen receptor modulators

Estrogens and antiestrogens

Progestogens and antiprogestogens

List of androgens/anabolic steroids

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