{{Short description|Chemical compound}} {{cs1 config|name-list-style=vanc}} {{Drugbox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 477209467 | IUPAC_name = (3''R'',5''S'',8''R'',9''R'',10''S'',13''S'',14''S'')-3-Hydroxy-13-methyl-2,3,4,5,6,7,8,9,10,11,12,14,15,16-tetradecahydro-1''H''-cyclopenta[''a'']phenanthren-17-one | image = 19-Norandrosterone.svg | image_class = skin-invert-image | width = 250
<!--Clinical data--> | tradename = | 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_CA = | legal_UK = | legal_US = | legal_status = | routes_of_administration =
<!--Pharmacokinetic data--> | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion =
<!-- Identifiers --> | CAS_number_Ref = {{cascite|changed|??}} | CAS_number = 1225-01-0 | CAS_supplemental = | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 5W4XKU708V | ATC_prefix = | ATC_suffix = | ATC_supplemental = | PubChem = 9548753 | IUPHAR_ligand = | DrugBank_Ref = | DrugBank = | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 7827676 | KEGG = | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 36412 | ChEMBL =
<!--Chemical data--> | C=18 | H=28 | O=2 | SMILES = C[C@]12CC[C@@H]3[C@H]4CC[C@H](C[C@@H]4CC[C@H]3[C@@H]1CCC2=O)O | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | 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/h11-16,19H,2-10H2,1H3/t11-,12+,13-,14+,15+,16-,18-/m0/s1 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = UOUIARGWRPHDBX-CQZDKXCPSA-N | synonyms = 3α-Hydroxy-5α-estran-17-one; 5α-Estran-3α-ol-17-one }}
'''19-Norandrosterone''', also known as '''5α-estran-3α-ol-17-one''', is a metabolite of nandrolone (19-nortestosterone) and bolandione (19-norandrostenedione) that is formed by 5α-reductase. It is on the list of substances prohibited by the World Anti-Doping Agency since it is a detectable metabolite of nandrolone, an anabolic-androgenic steroid (AAS).<ref>{{cite web|url=http://www.wada-ama.org/rtecontent/document/2007_List_En.pdf |title=THE 2007 PROHIBITED LIST INTERNATIONAL STANDARD |work=The World Anti-Doping Code |publisher=World Anti-Doping Agency |access-date=2009-05-14 |archive-url=https://web.archive.org/web/20090410171528/http://www.wada-ama.org/rtecontent/document/2007_List_En.pdf |archive-date=10 April 2009 |url-status=dead }}</ref> Consumption of androstendione products contaminated with traces of bolandione may also result in testing positive for nandrolone.<ref>{{cite journal |vauthors=Catlin DH, Leder BZ, Ahrens B, Starcevic B, Hatton CK, Green GA, Finkelstein JS |title=Trace contamination of over-the-counter androstenedione and positive urine test results for a nandrolone metabolite |journal=JAMA |volume=284 |issue=20 |pages=2618–21 |year=2000 |pmid=11086369 |doi= 10.1001/jama.284.20.2618|url=http://jama.ama-assn.org/cgi/pmidlookup?view=long&pmid=11086369| access-date= 29 December 2008 <!--DASHBot-->|doi-access= |url-access=subscription }}</ref>
Traces of 19-norandrosterone may be naturally present in human urine. An experiment conducted on athletes showed that after a prolonged intense effort, the 19-norandrosterone concentration can be increased by a factor varying between 2 and 4,<ref name="pmid10080643">{{cite journal |vauthors=Le Bizec B, Monteau F, Gaudin I, André F |title=Evidence for the presence of endogenous 19-norandrosterone in human urine |journal=J. Chromatogr. B |volume=723 |issue=1–2 |pages=157–72 |date=February 1999 |pmid=10080643 |doi= 10.1016/S0378-4347(98)00541-6}}</ref> but another study failed to replicate the result.<ref>{{cite journal |vauthors=Schmitt N, Flament MM, Goubault C, Legros P, Grenier-Loustalot MF, Denjean A |title=Nandrolone excretion is not increased by exhaustive exercise in trained athletes |journal=Med Sci Sports Exerc |volume=34 |issue=9 |pages=1436–9 |date=September 2002 |pmid=12218735 |doi=10.1097/00005768-200209000-00006 |doi-access=free }}</ref> Concentration also increases in the urine of female athletes during menstruation.<ref name="pmid11717005">{{cite journal |vauthors=Van Eenoo P, Delbeke FT, de Jong FH, De Backer P |title=Endogenous origin of norandrosterone in female urine: indirect evidence for the production of 19-norsteroids as by-products in the conversion from androgen to estrogen |journal=J. Steroid Biochem. Mol. Biol. |volume=78 |issue=4 |pages=351–7 |date=October 2001 |pmid=11717005 |doi= 10.1016/S0960-0760(01)00112-1|s2cid=19065089 }}</ref> The consumption of edible parts of a non-castrated pig, containing 19-nortestosterone, has been shown to result in the excretion of 19-norandrosterone in the following hours, so athletes should prudently avoid meals composed of pig offal in the hours preceding doping tests.<ref name="pmid16799098">{{cite journal |author=Ayotte C |title=Significance of 19-norandrosterone in athletes' urine samples |journal=Br J Sports Med |volume=40 |issue= Suppl 1|pages=i25–9 |date=July 2006 |pmid=16799098 |doi=10.1136/bjsm.2006.028027 |pmc=2657496}}</ref> Consumption of boar meat, liver, kidneys and heart also increased 19-norandrosterone output.<ref name="pmid10861987">{{cite journal |vauthors=Le Bizec B, Gaudin I, Monteau F, Andre F, Impens S, De Wasch K, De Brabander H |title=Consequence of boar edible tissue consumption on urinary profiles of nandrolone metabolites. I. Mass spectrometric detection and quantification of 19-norandrosterone and 19-noretiocholanolone in human urine |journal=Rapid Commun. Mass Spectrom. |volume=14 |issue=12 |pages=1058–65 |year=2000 |pmid=10861987 |doi=10.1002/1097-0231(20000630)14:12<1058::AID-RCM991>3.0.CO;2-7 }}</ref>
==See also== * Androsterone * 19-Noretiocholanolone * 5α-Dihydronandrolone * 5α-Dihydronorethisterone
==References== {{Reflist}}
==External links== * [http://strengthtraining.com/articledisplay.cfm?ArticleID=36 Testing for 19-norandrosterone] * [https://web.archive.org/web/20060928214908/http://www.uksport.gov.uk/assets/File/Generic_Template_Documents/Drug_Free_Sport/Nandrolone_Progress_Report_Feb03.pdf Doping Control Procedures]
{{Androgen receptor modulators}}
{{DEFAULTSORT:Norandrosterone, 19-}} Category:5α-Reduced steroid metabolites Category:Secondary alcohols Category:Androgens Category:Estranes Category:Human drug metabolites Category:Ketones