| 词条 | 4-Androstenediol |
| 释义 |
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 477221112 | IUPAC_name = (3S,8R,9S,10R,13S,14S,17S)-10,13-dimethyl-2,3,6,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,17-diol | image = 4-Androstenediol.svg | width = 250px | image2 = 4-Androstenediol3D.png | width2 = 250px | tradename = | pregnancy_AU = | pregnancy_US = | pregnancy_category = | legal_AU = | legal_CA = | legal_UK = | legal_US = | legal_status = | routes_of_administration = Oral | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion = | CAS_number_Ref = {{cascite|changed|??}} | CAS_number = 1156-92-9 | CAS_supplemental = | ATC_prefix = | ATC_suffix = | ATC_supplemental = | PubChem = 136297 | IUPHAR_ligand = | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = DB01526 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 120071 | UNII = | KEGG = | ChEBI = | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 195836 | C=19 | H=30 | O=2 | molecular_weight = 290.44 g/mol | SMILES = C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CCC4=C[C@H](CC[C@]34C)O | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h11,13-17,20-21H,3-10H2,1-2H3/t13-,14-,15-,16-,17-,18-,19-/m0/s1 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = BTTWKVFKBPAFDK-LOVVWNRFSA-N | synonyms = Androst-4-ene-3β,17β-diol }} 4-Androstenediol, also known as androst-4-ene-3β,17β-diol, is an androstenediol that is converted to testosterone. The conversion rate is about 15.76%, almost triple that of 4-androstenedione, due to utilization of a different enzymatic pathway. There is also some conversion into estrogen, since testosterone is the metabolic precursor of the estrogens. 4-Androstenediol is closer to testosterone structurally than 5-androstenediol, and has androgenic effects, acting as a weak partial agonist of the androgen receptor.[1] However, due to its lower intrinsic activity in comparison, in the presence of full agonists like testosterone or dihydrotestosterone (DHT), 4-androstenediol has antagonistic actions, behaving more like an antiandrogen.[1] 4-Androstenediol is very weakly estrogenic. It has approximately 0.5% and 0.6% of the affinity of estradiol at the ERα and ERβ, respectively.[2] Medical and commercial usePatrick Arnold holds a 1999 patent on "Use of 4-androstenediol to increase testosterone levels in humans".[3]References1. ^1 {{cite journal | vauthors = Chen F, Knecht K, Leu C | title = Partial agonist/antagonist properties of androstenedione and 4-androsten-3beta,17beta-diol | journal = The Journal of Steroid Biochemistry and Molecular Biology | volume = 91 | issue = 4-5 | pages = 247–57 | date = August 2004 | pmid = 15336702 | doi = 10.1016/j.jsbmb.2004.04.009 | url = http://linkinghub.elsevier.com/retrieve/pii/S0960-0760(04)00288-2 | display-authors = etal | deadurl = no | archiveurl = https://web.archive.org/web/20180513140650/https://linkinghub.elsevier.com/retrieve/pii/S0960-0760(04)00288-2 | archivedate = 2018-05-13 | df = }} {{Androgen receptor modulators}}{{Estrogen receptor modulators}}{{DEFAULTSORT:Androstenediol, 4-}}{{steroid-stub}}{{genito-urinary-drug-stub}}2. ^{{cite journal | vauthors = Kuiper GG, Carlsson B, Grandien K, Enmark E, Häggblad J, Nilsson S, Gustafsson JA | title = Comparison of the ligand binding specificity and transcript tissue distribution of estrogen receptors alpha and beta | journal = Endocrinology | volume = 138 | issue = 3 | pages = 863–70 | year = 1997 | pmid = 9048584 | doi = 10.1210/endo.138.3.4979 | url = }} 3. ^{{cite web |url=http://www.patentstorm.us/patents/5880117/description.html |title=Archived copy |accessdate=2011-03-18 |deadurl=yes |archiveurl=https://web.archive.org/web/20110318185140/http://www.patentstorm.us/patents/5880117/description.html |archivedate=2011-03-18 |df= }} 5 : Androgens and anabolic steroids|Androstanes|Estrogens|Prodrugs|World Anti-Doping Agency prohibited substances |
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