Methandriol

Last updated
Methandriol
Methandriol.svg
Clinical data
Trade names Crestabolic, Cytobolin, Diandren, Madiol, Stenediol, Mestenediol
Other namesMetandriol; 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
Identifiers
  • (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
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard 100.007.548 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C20H32O2
Molar mass 304.474 g·mol−1
3D model (JSmol)
  • 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=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 X mark.svgN
  • Key:WRWBCPJQPDHXTJ-DTMQFJJTSA-N X mark.svgN
 X mark.svgNYes check.svgY  (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. [2] [3] [4] It is an orally active 17α-alkylated AAS and a derivative of the endogenous androgen prohormone androstenediol. [2] [3]

Contents

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]

Androgen/anabolic steroid dosages for breast cancer
RouteMedicationFormDosage
Oral Methyltestosterone Tablet30–200 mg/day
Fluoxymesterone Tablet10–40 mg 3x/day
Calusterone Tablet40–80 mg 4x/day
Normethandrone Tablet40 mg/day
Buccal Methyltestosterone Tablet25–100 mg/day
Injection (IM Tooltip intramuscular injection or SC Tooltip subcutaneous injection) Testosterone propionate Oil solution50–100 mg 3x/week
Testosterone enanthate Oil solution200–400 mg 1x/2–4 weeks
Testosterone cypionate Oil solution200–400 mg 1x/2–4 weeks
Mixed testosterone esters Oil solution250 mg 1x/week
MethandriolAqueous suspension100 mg 3x/week
Androstanolone (DHT) Aqueous suspension300 mg 3x/week
Drostanolone propionate Oil solution100 mg 1–3x/week
Metenolone enanthate Oil solution400 mg 3x/week
Nandrolone decanoate Oil solution50–100 mg 1x/1–3 weeks
Nandrolone phenylpropionate Oil solution50–100 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 Tooltip International Nonproprietary Name. [2] [3]

Availability

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

Related Research Articles

<span class="mw-page-title-main">Androstenedione</span> Endogenous weak androgen

Androstenedione, or 4-androstenedione, also known as androst-4-ene-3,17-dione, is an endogenous weak androgen steroid hormone and intermediate in the biosynthesis of estrone and of testosterone from dehydroepiandrosterone (DHEA). It is closely related to androstenediol (androst-5-ene-3β,17β-diol).

<span class="mw-page-title-main">Methyltestosterone</span> Chemical compound

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 doses as a component of menopausal hormone therapy for menopausal symptoms like hot flashes, osteoporosis, and low sexual desire in women, and to treat breast cancer in women. It is taken by mouth or held in the cheek or under the tongue.

<span class="mw-page-title-main">Androstenediol</span> Chemical compound

Androstenediol, or 5-androstenediol, 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 dehydroepiandrosterone (DHEA). It is closely related to androstenedione (androst-4-ene-3,17-dione).

<span class="mw-page-title-main">Drostanolone propionate</span> Chemical compound

Drostanolone propionate, or dromostanolone propionate, sold under the brand names Drolban, Masteril, and Masteron among others, is an androgen and anabolic steroid (AAS) medication which was used to treat breast cancer in women but is now no longer marketed. It is given by injection into muscle.

<span class="mw-page-title-main">1-Testosterone</span> Chemical compound

1-Testosterone, also known as δ1-dihydrotestosterone (δ1-DHT), as well as dihydroboldenone, is a synthetic anabolic–androgenic steroid (AAS) and a 5α-reduced derivative of boldenone (Δ1-testosterone). It differs from testosterone by having a 1(2)-double bond instead of a 4(5)-double bond in its A ring. It was legally sold online in the United States until 2005, when it was reclassified as a Schedule III drug.

<span class="mw-page-title-main">Propetandrol</span> Chemical compound

Propetandrol, or propethandrol, also known as 17α-ethyl-19-nortestosterone 3β-propionate or 17α-ethyl-19-nor-4-androstenediol 3β-propionate, as well as 17α-ethylestr-4-en-3β,17β-diol 3β-propionate, is a synthetic and orally active anabolic–androgenic steroid (AAS) and progestogen and a 17α-alkylated derivative of 19-nortestosterone. It is an androgen ester – specifically, the 3β-propionate ester of norethandrolone (17α-ethyl-19-nortestosterone).

<span class="mw-page-title-main">Bolandiol dipropionate</span> Chemical compound

Bolandiol dipropionate (USAN), or bolandiol propionate (JAN), also known as norpropandrolate or 19-nor-4-androstenediol dipropionate, as well as estr-4-ene-3β,17β-diol 3,17-dipropionate, is a synthetic anabolic-androgenic steroid (AAS) and derivative of 19-nortestosterone (nandrolone). It is an androgen ester – specifically, the 3,17-dipropionate ester of bolandiol (19-nor-4-androstenediol).

<span class="mw-page-title-main">Ethyltestosterone</span> Synthetic anabolic steroid

Ethyltestosterone, or 17α-ethyltestosterone, also known as 17α-ethylandrost-4-en-17β-ol-3-one or 17α-pregn-4-en-17-ol-3-one, is a synthetic, orally active anabolic–androgenic steroid (AAS) of the 17α-alkylated group related to methyltestosterone which was never marketed. Like methyltestosterone, ethyltestosterone is the parent compound of many AAS. Derivatives of ethyltestosterone include norethandrolone, ethylestrenol (ethylnandrol), norboletone, ethyldienolone, tetrahydrogestrinone, bolenol (ethylnorandrostenol), and propetandrol.

<span class="mw-page-title-main">Vinyltestosterone</span> Chemical compound

Vinyltestosterone is a synthetic anabolic–androgenic steroid (AAS) that was never marketed. However, two 19-nortestosterone derivatives of vinyltestosterone, norvinisterone (17α-vinyl-19-nortestosterone) and norgesterone, have been marketed. They are used as progestins for female hormonal contraception, rather than as AAS.

<span class="mw-page-title-main">Methandriol propionate</span> Chemical compound

Methandriol propionate, 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 derivative of 5-androstenediol that is or was marketed by Vister in Italy. It is an androgen ester – specifically, the C3,17β propionate ester of methandriol (17α-methyl-5-androstenediol) – and acts as a prodrug of methandriol in the body. Methandriol propionate is administered by intramuscular injection and, relative to methandriol, has an extended duration via this route due to a depot effect afforded by its ester.

Methandriol bisenanthoyl acetate, 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 (AAS) and a 17α-alkylated derivative of 5-androstenediol. It is an androgen ester—specifically, the C3β,17β di(3-oxononanoate) ester of methandriol (17α-methyl-5-androstenediol)—and acts as a prodrug of methandriol in the body. Methandriol bisenanthoyl acetate is administered by intramuscular injection and, relative to methandriol, has an extended duration via this route due to a depot effect afforded by its ester.

<span class="mw-page-title-main">Methandriol diacetate</span> Chemical compound

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 that was never marketed. It is an androgen ester – specifically, the C3,17β diacetate ester of methandriol (17α-methyl-5-androstenediol) – and acts as a prodrug of methandriol in the body.

<span class="mw-page-title-main">Testosterone dipropionate</span> Chemical compound

Testosterone dipropionate, or testosterone 3β,17β-dipropanoate, also known as 4-androstenediol dipropionate, as well as androst-4-ene-3β,17β-diol 3β,17β-dipropanoate, is a synthetic anabolic-androgenic steroid and an androgen ester which was never marketed. It is the 3β,17β-dipropionate (dipropanoate) diester of testosterone (androst-4-en-17β-ol-3-one), or, more accurately, of 4-androstenediol (androst-4-ene-3β,17β-diol).

<span class="mw-page-title-main">Testosterone diacetate</span> Chemical compound

Testosterone diacetate, or testosterone 3β,17β-diacetate, also known as 4-androstenediol diacetate, as well as androst-4-ene-3β,17β-diol 3β,17β-diacetate, is a synthetic anabolic-androgenic steroid and an androgen ester which was never marketed. It is the 3β,17β-diacetate diester of testosterone (androst-4-en-17β-ol-3-one), or, more accurately, of 4-androstenediol (androst-4-ene-3β,17β-diol).

<span class="mw-page-title-main">Testosterone acetate butyrate</span> Chemical compound

Testosterone acetate butyrate, or testosterone 3β-acetate 17β-butanoate, also known as 4-androstenediol acetate butyrate, as well as androst-4-ene-3β,17β-diol 3β-acetate 17β-butanoate, is a synthetic anabolic-androgenic steroid and an androgen ester which was never marketed. It is the 3β-acetate, 17β-butyrate (butanoate) diester of testosterone (androst-4-en-17β-ol-3-one), or, more accurately, of 4-androstenediol (androst-4-ene-3β,17β-diol).

<span class="mw-page-title-main">Testosterone acetate propionate</span> Chemical compound

Testosterone acetate propionate, or testosterone 3β-acetate 17β-propanoate, also known as 4-androstenediol acetate propionate, as well as androst-4-ene-3β,17β-diol 3β-acetate 17β-propanoate, is a synthetic anabolic-androgenic steroid and an androgen ester which was never marketed. It is the 3β-acetate, 17β-propionate (propanoate) diester of testosterone (androst-4-en-17β-ol-3-one), or, more accurately, of 4-androstenediol (androst-4-ene-3β,17β-diol).

<span class="mw-page-title-main">Androstenediol diacetate</span> Chemical compound

Androstenediol diacetate, or 5-androstenediol 3β,17β-diacetate, also known as androst-5-ene-3β,17β-diol 3β,17β-diacetate, is a synthetic anabolic-androgenic steroid and an androgen ester – specifically, the C3β,17β diacetate diester of 5-androstenediol (androst-5-ene-3β,17β-diol) – which was never marketed. The medication has been used with success to treat breast cancer in women.

<span class="mw-page-title-main">Ethinylandrostenediol</span> Chemical compound

Ethinylandrostenediol, also known as 17α-ethynyl-5-androstenediol, is a synthetic estrogen, progestogen, and androgen which was never marketed. It is the C17α ethynyl derivative of the androgen precursor and prohormone 5-androstenediol.

References

  1. ↑ 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.
  2. 1 2 3 4 5 6 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.
  3. 1 2 3 4 5 6 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.
  4. ↑ Thomas JA, Keenan EJ (6 December 2012). Principles of Endocrine Pharmacology. Springer Science & Business Media. pp. 125–. ISBN   978-1-4684-5036-1.
  5. 1 2 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.
  6. ↑ 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.
  7. ↑ 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.
  8. ↑ 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.
  9. ↑ 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.
  10. ↑ 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.
  11. 1 2 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.
  12. ↑ Schänzer W (July 1996). "Metabolism of anabolic androgenic steroids". Clinical Chemistry. 42 (7): 1001–1020. doi: 10.1093/clinchem/42.7.1001 . PMID   8674183.
  13. ↑ 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.
  14. ↑ "List of Androgens and anabolic steroids". Drugs.com.
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