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(Top) 1 Medical uses 1.1 Available forms 2 Chemistry 3 History 4 Society and culture 4.1 Generic names 4.2 Availability 5 References 6 External links

Methandriol

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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)^[1]
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
CompTox Dashboard (EPA)	DTXSID50878534
ECHA InfoCard	100.007.548
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 (asmethandriol 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]

Medical uses[edit]

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[edit]

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[edit]

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 derivativeof5-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]

Ananalogue 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[edit]

Methandriol was first synthesized in 1935 along with methyltestosterone and mestanolone.^[5]^[12]^[13]

v

t

e
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 (IMTooltip intramuscular injectionorSCTooltip subcutaneous injection)	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[edit]

Generic names[edit]

Methandriol is the generic name of methylandrostenediol and its INNTooltip International Nonproprietary Name.^[2]^[3]

Availability[edit]

Methandriol remains marketed for clinical use only in Taiwan and for veterinary use (asmethandriol dipropionate) only in Australia.^[14]

References[edit]

^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-15.

^ ^a ^b ^c ^d ^e ^f Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 794–. ISBN 978-1-4757-2085-3.

^ ^a ^b ^c ^d ^e ^f Morton IK, Hall JM (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 177–. ISBN 978-94-011-4439-1.

^ Thomas JA, Keenan EJ (6 December 2012). Principles of Endocrine Pharmacology. Springer Science & Business Media. pp. 125–. ISBN 978-1-4684-5036-1.

^ ^a ^b Henderson E, Weinberg M (June 1951). "Methylandrostenediol". The Journal of Clinical Endocrinology and Metabolism. 11 (6): 641–652. doi:10.1210/jcem-11-6-641. PMID 14841252.

^ Homburger F, Kasdon SC, Fishman WH (May 1950). "Methylandrostenediol: a non-virilizing derivative of testosterone in metastatic cancer of the breast". Proceedings of the Society for Experimental Biology and Medicine. 74 (1): 162–164. doi:10.3181/00379727-74-17840. PMID 15430420. S2CID 209361921.

^ Kasdon SC, Fishman WH, Dart RM, Bonner CD, Homburger F (April 1952). "Methylandrostenediol in palliative treatment of breast cancer". Journal of the American Medical Association. 148 (14): 1212–1216. doi:10.1001/jama.1952.02930140044014. PMID 14907362.

^ Segaloff A, Gordon D, Horwitt BN, Schlosser JV, Murison PJ (March 1952). "Hormonal therapy in cancer of the breast. II. Effect of methylandrostenediol on clinical course and hormonal excretion". Cancer. 5 (2): 271–274. doi:10.1002/1097-0142(195203)5:2<271::AID-CNCR2820050212>3.0.CO;2-W. PMID 14905410. S2CID 39681958.

^ Harold Gardiner-Hill (1958). Modern Trends in Endocrinology. Butterworth. p. 235. Foss (1956), using methylandrostenediol in doses of 100 milligrams daily in the treatment of patients with inoperable carcinoma of the breast, found it almost as virilizing as testosterone propionate or methyltestosterone in comparable doses.

^ Heinrich Kahr (8 March 2013). Konservative Therapie der Frauenkrankheiten: Anzeigen, Grenzen und Methoden Einschliesslich der Rezeptur. Springer-Verlag. pp. 21–. ISBN 978-3-7091-5694-0.

^ ^a ^b Bernstein S, Stolar S, Heller M (1957). "Notes - Synthesis of 17α-Methyl-4-androstene-3β,17,β-diol". The Journal of Organic Chemistry. 22 (4): 472–473. doi:10.1021/jo01355a626. ISSN 0022-3263.

^ Schänzer W (July 1996). "Metabolism of anabolic androgenic steroids". Clinical Chemistry. 42 (7): 1001–1020. doi:10.1093/clinchem/42.7.1001. PMID 8674183.

^ Ruzicka L, Goldberg MW, Rosenberg HR (1935). "Sexualhormone X. Herstellung des 17-Methyl-testosterons und anderer Androsten- und Androstanderivate. Zusammenhänge zwischen chemischer Konstitution und männlicher Hormonwirkung". Helvetica Chimica Acta. 18 (1): 1487–1498. doi:10.1002/hlca.193501801203. ISSN 0018-019X.

^ "List of Androgens and anabolic steroids". Drugs.com.