| 词条 | Bolandiol |
| 释义 |
| Verifiedfields = | Watchedfields = | verifiedrevid = | IUPAC_name = (3S,8R,9S,10R,13S,14S,17S)-13-methyl-1,2,3,6,7,8,9,10,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,17-diol | image = Bolandiol.svg | width = 250 | tradename = | pregnancy_AU = | pregnancy_US = | pregnancy_category = | legal_AU = | legal_CA = | legal_UK = | legal_US = | legal_status = | routes_of_administration = | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion = | CAS_number_Ref = | CAS_number = 19793-20-5 | CAS_supplemental = | ATC_prefix = | ATC_suffix = | PubChem = 9835303 | DrugBank_Ref = | DrugBank = | ChemSpiderID_Ref = | ChemSpiderID = 8011024 | UNII = | ChEMBL = 2106664 | C=18 | H=28 | O=2 | molecular_weight = | smiles = O[C@@H]4/C=C2\\[C@@H]([C@H]1CC[C@@]3([C@@H](O)CC[C@H]3[C@@H]1CC2)C)CC4 | StdInChI_Ref = | StdInChI = 1S/C18H28O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h10,12-17,19-20H,2-9H2,1H3/t12-,13-,14+,15+,16-,17-,18-/m0/s1 | StdInChIKey_Ref = | StdInChIKey = CMXKUJNZWYTFJN-XFUVECHXSA-N | synonyms = 19-Norandrostenediol; 19-Nor-4-androstene-3β,17β-diol; Estr-4-ene-3β,17β-diol; 3β-Dihydronandrolone }}Bolandiol (INN), also known as 19-nor-4-androstenediol, estr-4-en-3β,17β-diol, or 3β-dihydronandrolone, is an anabolic-androgenic steroid (AAS) that was never marketed.[1] A dipropionate ester, bolandiol dipropionate (brand names Anabiol, Storinal; former developmental code name SC-7525), has been marketed.[1][2] Bolandiol (and its dipropionate ester) is unique among AAS in that it reportedly also possesses estrogenic and progestogenic activity.[3][4] Bolandiol is on the World Anti-Doping Agency's list of prohibited substances,[5] and is therefore banned from use in most major sports. It is a potential metabolic precursor to nandrolone.[6] However, several clinical studies have concluded that bolandiol does not alter strength, body composition, or exercise performance.[7][8] See also
References1. ^1 {{cite book|author=J. Elks|title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA899|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=899–}} {{Androgens and antiandrogens}}{{Androgen receptor modulators}}{{Estrogen receptor modulators}}{{Progesterone receptor modulators}}2. ^{{cite book|author1=Thomas E. Hyde|author2=Marianne S. Gengenbach|title=Conservative Management of Sports Injuries|url=https://books.google.com/books?id=uzPwfNYyjjUC&pg=PA1100|year=2007|publisher=Jones & Bartlett Learning|isbn=978-0-7637-3252-3|pages=1100–}} 3. ^{{cite book|title=Hormones: Advances in Research and Application: 2011 Edition|url=https://books.google.com/books?id=zhzrlLrsI4AC&pg=PT59|date=9 January 2012|publisher=ScholarlyEditions|isbn=978-1-4649-2242-8|pages=59–}} 4. ^{{Cite journal |pmid = 19941958 |year = 2010 |last1 = Attardi |first1 = BJ |last2 = Page |first2 = ST |last3 = Hild |first3 = SA |last4 = Coss |first4 = CC |last5 = Matsumoto |first5 = AM |title = Mechanism of action of bolandiol (19-nortestosterone-3beta,17beta-diol), a unique anabolic steroid with androgenic, estrogenic, and progestational activities |volume = 118 |issue = 3 |pages = 151–61 |doi = 10.1016/j.jsbmb.2009.11.008 |pmc = 2831543 |journal = The Journal of Steroid Biochemistry and Molecular Biology}} 5. ^{{cite web | url=http://www.wada-ama.org/Documents/World_Anti-Doping_Program/WADP-Prohibited-list/2012/WADA_Prohibited_List_2012_EN.pdf | title=The World Anti-Doping Code: The 2012 Prohibited List | publisher=World Anti-Doping Agency | accessdate=2012-07-17 | deadurl=yes | archiveurl=https://web.archive.org/web/20120513020202/http://www.wada-ama.org/Documents/World_Anti-Doping_Program/WADP-Prohibited-list/2012/WADA_Prohibited_List_2012_EN.pdf | archivedate=2012-05-13 | df= }} 6. ^{{Cite journal | title = Human nutritional supplements in the horse: comparative effects of 19-norandrostenedione and 19-norandrostenediol on the 19-norsteroid profile and consequences for doping control |author1=Dehennin, L. |author2=Bonnaire, Y. |author3=Plou, Ph. | journal = Journal of Chromatography B | year = 2002 | volume = 766 | issue = 2 | pages = 257–263 | doi = 10.1016/S0378-4347(01)00506-0}} 7. ^{{Cite journal |pmid = 11417430 |year = 2001 |last1 = Van Gammeren |first1 = D |last2 = Falk |first2 = D |last3 = Antonio |first3 = J |title = The effects of supplementation with 19-nor-4-androstene-3,17-dione and 19-nor-4-androstene-3,17-diol on body composition and athletic performance in previously weight-trained male athletes |volume = 84 |issue = 5 |pages = 426–31 |journal = European journal of applied physiology |doi=10.1007/s004210100395}} 8. ^{{Cite journal |pmid = 12297208 |year = 2002 |last1 = Van Gammeren |first1 = D |last2 = Falk |first2 = D |last3 = Antonio |first3 = J |title = Effects of norandrostenedione and norandrostenediol in resistance-trained men |volume = 18 |issue = 9 |pages = 734–7 |journal = Nutrition |doi=10.1016/s0899-9007(02)00834-1}} 6 : Androgens and anabolic steroids|Estranes|Estrogens|Prodrugs|Progestogens|World Anti-Doping Agency prohibited substances |
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