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{{Short description|Chemical compound}}
{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 477221112
| IUPAC_name = (3''S'',8''R'',9''S'',10''R'',13''S'',14''S'',17''S'')-10,13-dimethyl-2,3,6,7,8,9,11,12,14,15,16,17-dodecahydro-1''H''-cyclopenta[''a'']phenanthrene-3,17-diol
| image = 4-Androstenediol.svg
| image_class = skin-invert-image
| width = 250px
| image2 = 4-Androstenediol3D.png
| image_class2 = bg-transparent
| width2 = 250px


| tradename =
| pregnancy_AU = 
| pregnancy_US = 
| pregnancy_category =
| legal_AU = 
| legal_CA =
| legal_UK =
| legal_US =
| legal_status =
| routes_of_administration = [[Oral administration|Oral]]


| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
| excretion =


| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = 1156-92-9
| CAS_supplemental =
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = G10EHA9I0D
| ATC_prefix =
| ATC_suffix =
| ATC_supplemental =
| PubChem = 136297
| IUPHAR_ligand =
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB01526
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 120071
| KEGG =
| ChEBI =
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 195836


| C=19 | H=30 | O=2
| 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 [[androgen]]ic effects, acting as a weak [[partial agonist]] of the [[androgen receptor]].<ref name="pmid15336702">{{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 | s2cid = 53267316 | display-authors = etal }}</ref> However, due to its lower [[intrinsic activity]] in comparison, in the presence of [[full agonist]]s like testosterone or [[dihydrotestosterone]] (DHT), 4-androstenediol has [[receptor antagonist|antagonistic]] actions, behaving more like an [[antiandrogen]].<ref name="pmid15336702" />

4-Androstenediol is very weakly [[estrogen]]ic. It has approximately 0.5% and 0.6% of the [[affinity (pharmacology)|affinity]] of estradiol at the [[ERα]] and [[ERβ]], respectively.<ref name="pmid9048584">{{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 | doi-access = free }}</ref>

==Medical and commercial use==
[[Patrick Arnold]] holds a 1999 patent on "Use of 4-androstenediol to increase testosterone levels in humans".<ref>{{cite web |url=http://www.patentstorm.us/patents/5880117/description.html |title=Use of 4-androstenediol to increase testosterone levels in humans |access-date=2011-03-18 |url-status=dead |archive-url=https://web.archive.org/web/20110318185140/http://www.patentstorm.us/patents/5880117/description.html |archive-date=2011-03-18 }}</ref>

==References==
{{Reflist|2}}

{{Androgen receptor modulators}}
{{Estrogen receptor modulators}}

{{DEFAULTSORT:Androstenediol, 4-}}

[[Category:Anabolic–androgenic steroids]]
[[Category:Androstanes]]
[[Category:Estrogens]]
[[Category:Androgen esters]]
{{steroid-stub}}
{{genito-urinary-drug-stub}}

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