| Revision as of 19:08, 11 August 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'ChemSpiderID_Ref', 'DrugBank_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEBI_Ref') per [[Misplaced Pages:WikiProject Chemicals/Chembox validati← Previous edit | Latest revision as of 05:25, 14 January 2025 edit undoArthurfragoso (talk | contribs)Extended confirmed users, Template editors4,591 edits dark mode fix | ||
| (72 intermediate revisions by 35 users not shown) | |||
| Line 1: | Line 1: | ||
| {{short description|Chemical compound}} | |||
| {{unreferenced|date=June 2011}} | |||
| {{Infobox drug | |||
| {{chembox | |||
| | Verifiedfields = changed | |||
| | Watchedfields = changed | |||
| | verifiedrevid = 444312123 | |||
| | IUPAC_name = (3''S'',8''S'',9''R'',10''R'',13''S'',14''R'',17''S'')-10,13,17-trimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopentaphenanthrene-3,17-diol | |||
| | image = Methandriol.svg | |||
| | image_class = skin-invert-image | |||
| | width = 225px | |||
| <!--Clinical data--> | |||
| | tradename = Crestabolic, Cytobolin, Diandren, Madiol, Stenediol, Mestenediol | |||
| | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | |||
| | pregnancy_US = <!-- A / B / C / D / X --> | |||
| | pregnancy_category = | |||
| | legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> | |||
| | legal_BR = C5 | |||
| | legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-15 |publisher=] |language=pt-BR |publication-date=2023-04-04}}</ref> | |||
| | legal_CA = | |||
| | legal_UK = | |||
| | legal_US = | |||
| | legal_status = | |||
| | routes_of_administration = ] | |||
| | class = ]; ] | |||
| <!--Pharmacokinetic data--> | |||
| | bioavailability = | |||
| | protein_bound = | |||
| | metabolism = | |||
| | elimination_half-life = | |||
| | excretion = | |||
| <!-- Identifiers --> | |||
| | CAS_number_Ref = {{cascite|correct|??}} | |||
| | CAS_number = 521-10-8 | |||
| | CAS_supplemental = | |||
| | ATC_prefix = | |||
| | ATC_suffix = | |||
| | ATC_supplemental = | |||
| | PubChem = 229021 | |||
| | IUPHAR_ligand = | |||
| | DrugBank_Ref = | |||
| | DrugBank = | |||
| | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | |||
| | ChemSpiderID = 199375 | |||
| | UNII_Ref = {{fdacite|correct|FDA}} | | UNII_Ref = {{fdacite|correct|FDA}} | ||
| | UNII = 5730Z864KG | | UNII = 5730Z864KG | ||
| | KEGG = | |||
| | verifiedrevid = 437148756 | |||
| | ChEBI = | |||
| |ImageFile=methandriol.png | |||
| | ChEMBL = | |||
| |ImageSize=200px | |||
| | synonyms = Metandriol; Methylandrostenediol; Methyl-5-androstenediol; Methylandrostenediole; 17α-Methylandrost-5-ene-3β,17β-diol | |||
| |IUPACName=(3''S'',8''S'',9''R'',10''R'',13''S'',14''R'',17''S'')-10,13,17-trimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopentaphenanthrene-3,17-diol | |||
| |OtherNames= | |||
| <!--Chemical data--> | |||
| |Section1={{Chembox Identifiers | |||
| | C=20 | H=32 | O=2 | |||
| | CASNo=521-10-8 | |||
| | SMILES = C12CC(CC1=CC32CC4(3CC4(C)O)C)O | |||
| | PubChem=11869527 | |||
| | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | |||
| | SMILES=C12CC(CC1=CC32CC4(3CC4(C)O)C) | |||
| | StdInChI = 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 | |||
| }} | |||
| | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | |||
| |Section2={{Chembox Properties | |||
| | StdInChIKey = WRWBCPJQPDHXTJ-DTMQFJJTSA-N | |||
| | Formula=C<sub>20</sub>H<sub>32</sub>O<sub>2</sub> | |||
| | MolarMass=304.47 g/mol | |||
| | Appearance= | |||
| | Density= | |||
| | MeltingPt= | |||
| | BoilingPt= | |||
| | Solubility= | |||
| }} | |||
| |Section3={{Chembox Hazards | |||
| | MainHazards= | |||
| | FlashPt= | |||
| | Autoignition= | |||
| }} | |||
| }} | }} | ||
| '''Methandriol''' (brand names '''Anabol''', '''Crestabolic''', '''Cytobolin''', '''Diandren''', '''Durabolic''', '''Madiol''', '''Mestenediol''', '''Methabolic''', '''Methydiol''', '''Sterabolic''', '''Stenediol'''), also known as '''methylandrostenediol''', is an ] and ] (AAS) medication which was developed by ] and is used in both ] and ] (as ], ], or ]) formulations.<ref name="Elks2014">{{cite book| vauthors = Elks J |title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA794|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=794–}}</ref><ref name="MortonHall2012">{{cite book| vauthors = Morton IK, Hall JM |title=Concise Dictionary of Pharmacological Agents: Properties and Synonyms|url=https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA177|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-94-011-4439-1|pages=177–}}</ref><ref name="ThomasKeenan2012">{{cite book| vauthors = Thomas JA, Keenan EJ |title=Principles of Endocrine Pharmacology|url=https://books.google.com/books?id=mTagBQAAQBAJ&pg=PA125|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-1-4684-5036-1|pages=125–}}</ref> It is an ] ] and a ] of the ] ] ].<ref name="Elks2014" /><ref name="MortonHall2012" /> | |||
| ==Medical uses== | |||
| Methandriol has been used in the treatment of ] in women.<ref name="HendersonWeinberg1951">{{cite journal | vauthors = Henderson E, Weinberg M | title = Methylandrostenediol | journal = The Journal of Clinical Endocrinology and Metabolism | volume = 11 | issue = 6 | pages = 641–652 | date = June 1951 | pmid = 14841252 | doi = 10.1210/jcem-11-6-641 }}</ref><ref name="HomburgerKasdon1950">{{cite journal | vauthors = Homburger F, Kasdon SC, Fishman WH | title = Methylandrostenediol: a non-virilizing derivative of testosterone in metastatic cancer of the breast | journal = Proceedings of the Society for Experimental Biology and Medicine | volume = 74 | issue = 1 | pages = 162–164 | date = May 1950 | pmid = 15430420 | doi = 10.3181/00379727-74-17840 | s2cid = 209361921 }}</ref><ref name="Kasdon1952">{{cite journal | vauthors = Kasdon SC, Fishman WH, Dart RM, Bonner CD, Homburger F | title = Methylandrostenediol in palliative treatment of breast cancer | journal = Journal of the American Medical Association | volume = 148 | issue = 14 | pages = 1212–1216 | date = April 1952 | pmid = 14907362 | doi = 10.1001/jama.1952.02930140044014 }}</ref><ref name="SegaloffGordon1952">{{cite journal | vauthors = Segaloff A, Gordon D, Horwitt BN, Schlosser JV, Murison PJ | title = Hormonal therapy in cancer of the breast. II. Effect of methylandrostenediol on clinical course and hormonal excretion | journal = Cancer | volume = 5 | issue = 2 | pages = 271–274 | date = March 1952 | pmid = 14905410 | doi = 10.1002/1097-0142(195203)5:2<271::AID-CNCR2820050212>3.0.CO;2-W | s2cid = 39681958 | doi-access = }}</ref> It has been reported to be almost as ] as comparable doses of ] and ] in women.<ref name="Gardiner-Hill1958">{{cite book|author=Harold Gardiner-Hill|title=Modern Trends in Endocrinology|url=https://archive.org/details/in.ernet.dli.2015.548948|year=1958|publisher=Butterworth|page=235|quote=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.}}</ref> | |||
| ===Available forms=== | |||
| Methandriol (brand name Androteston M, Notandron, Protandren) was previously marketed as 25 mL and 50 mg/mL ]s for use by ].<ref name="Kahr2013">{{cite book|author=Heinrich Kahr|title=Konservative Therapie der Frauenkrankheiten: Anzeigen, Grenzen und Methoden Einschliesslich der Rezeptur|url=https://books.google.com/books?id=Hte1BgAAQBAJ&pg=PA21|date=8 March 2013|publisher=Springer-Verlag|isbn=978-3-7091-5694-0|pages=21–}}</ref> | |||
| ==Chemistry== | |||
| {{See also|List of androgens/anabolic steroids#Testosterone derivatives}} | |||
| Methandriol, also known as 17α-methyl-5-androstenediol or as 17α-methylandrost-5-ene-3β,17β-diol, is a ] ] ] and a ] ] of ] (androst-5-ene-3β,17β-diol).<ref name="Elks2014" /><ref name="MortonHall2012" /> A number of ]s of methandriol exist, including ] (methylandrostenediol 3β,17β-dipropionate), ] (methylandrostenediol 3β-propionate), ] (methylandrostenediol 3β,17β-dioxononanoate), and ] (methylandrostenediol 3β,17β-diacetate; never marketed).<ref name="Elks2014" /><ref name="MortonHall2012" /> Methandriol is closely related to ] (17α-methyltestosterone or 17α-methylandrost-4-ene-17β-ol-3-one).<ref name="Elks2014" /><ref name="MortonHall2012" /> | |||
| An ] of methandriol is its ] ] (17α-methylandrost-4-ene-3β,17β-diol).<ref name="BernsteinStolar1957">{{cite journal| vauthors = Bernstein S, Stolar S, Heller M |title=Notes - Synthesis of 17α-Methyl-4-androstene-3β,17,β-diol|journal=The Journal of Organic Chemistry|volume=22|issue=4|year=1957|pages=472–473|issn=0022-3263|doi=10.1021/jo01355a626}}</ref> Another analogue of methandriol is ] (17α-ethynyl-5α-androstane-3β,17β-diol) as well as its ] ] (ethynylandrostanediol 3β-cyclohexylpropionate).<ref name="BernsteinStolar1957" /> | |||
| ==History== | |||
| Methandriol was first ] in 1935 along with ] and ].<ref name="HendersonWeinberg1951" /><ref name="pmid8674183">{{cite journal | vauthors = Schänzer W | title = Metabolism of anabolic androgenic steroids | journal = Clinical Chemistry | volume = 42 | issue = 7 | pages = 1001–1020 | date = July 1996 | pmid = 8674183 | doi = 10.1093/clinchem/42.7.1001 | doi-access = free }}</ref><ref name="RuzickaGoldberg1935">{{cite journal| vauthors = Ruzicka L, Goldberg MW, Rosenberg HR |title=Sexualhormone X. Herstellung des 17-Methyl-testosterons und anderer Androsten- und Androstanderivate. Zusammenhänge zwischen chemischer Konstitution und männlicher Hormonwirkung|journal=Helvetica Chimica Acta|volume=18|issue=1|year=1935|pages=1487–1498|issn=0018-019X|doi=10.1002/hlca.193501801203}}</ref> | |||
| {{Androgen/anabolic steroid dosages for breast cancer}} | |||
| ==Society and culture== | |||
| ===Generic names=== | |||
| Methandriol is the ] of methylandrostenediol and its {{abbrlink|INN|International Nonproprietary Name}}.<ref name="Elks2014" /><ref name="MortonHall2012" /> | |||
| ===Availability=== | |||
| Methandriol remains marketed for clinical use only in ] and for ] (as ]) only in ].<ref name="Drugs.com">{{Cite web|url=https://www.drugs.com/international/methandriol.html|title = List of Androgens and anabolic steroids | work = Drugs.com }}</ref> | |||
| == References == | |||
| '''Methandriol''' is an ]. | |||
| {{Reflist}} | |||
| == External links == | |||
| * | |||
| {{Androgens and antiandrogens}} | |||
| {{steroid-stub}} | |||
| {{Androgen receptor modulators}} | |||
| ] | ] | ||
| ] | |||
| ] | |||
| ] | |||
| ] | |||