Stanozolol

Stanozolol
Clinical data
Trade names	Winstrol, Stromba, others
Other names	Androstanazol; Androstanazole; Stanazol; WIN-14833; NSC-43193; NSC-233046; 17α-Methyl-2'H-5α-androst-2-eno[3,2-c]pyrazol-17β-ol; 17α-Methylpyrazolo[4',3':2,3]-5α-androstan-17β-ol
AHFS/Drugs.com	Multum Consumer Information
Pregnancy; category	X;
Routes of; administration	By mouth, intramuscular injection (veterinary)
Drug class	Androgen; Anabolic steroid
ATC code	A14AA02 (WHO) ;
Legal status
Legal status	BR: Class C5 (Anabolic steroids); CA: Schedule IV; US: Schedule III; In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	High
Metabolism	Liver
Elimination half-life	Oral: 9 hours; IMTooltip Intramuscular injection: 24 hours (aq. susp.)
Duration of action	IM: >1 week
Excretion	Urine: 84%
Identifiers
	IUPAC name (1S,3aS,3bR,5aS,10aS,10bS,12aS)-1,10a,12a-trimethyl-1,2,3,3a,3b,4,5,5a,6,7,10,10a,10b,11,12,12a-hexadecahydrocyclopenta[5,6]naphtho[1,2-f]indazol-1-ol;
CAS Number	10418-03-8 ;
PubChem CID	25249;
IUPHAR/BPS	10369;
DrugBank	DB06718 ;
ChemSpider	23582 ;
UNII	4R1VB9P8V3;
KEGG	D00444 ;
ChEBI	CHEBI:9249 ;
ChEMBL	ChEMBL2079587 ;
CompTox Dashboard (EPA)	DTXSID3044128 ;
ECHA InfoCard	100.030.801
Chemical and physical data
Formula	C21H32N2O
Molar mass	328.500 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES [H][C@@]35CC[C@@]2([H])[C@]1([H])CC[C@](C)(O)[C@@]1(C)CC[C@]2([H])[C@@]3(C)Cc4c[nH]nc4C5;
	InChI InChI=1S/C21H32N2O/c1-19-11-13-12-22-23-18(13)10-14(19)4-5-15-16(19)6-8-20(2)17(15)7-9-21(20,3)24/h12,14-17,24H,4-11H2,1-3H3,(H,22,23)/t14-,15+,16-,17-,19-,20-,21-/m0/s1 ; Key:LKAJKIOFIWVMDJ-IYRCEVNGSA-N ;
	(verify)

Stanozolol (abbrev. Stz), sold under many brand names, is a synthetic androgen and anabolic steroid (AAS) medication derived from dihydrotestosterone (DHT). It is used to treat hereditary angioedema.^[7]^[1]^[8] It was developed by American pharmaceutical company Sterling-Winthrop in 1962, and has been approved by the U.S. Food and Drug Administration for human use, though it is no longer marketed in the United States.^[8]^[9] It is also used in veterinary medicine.^[1]^[8] Stanozolol has mostly been discontinued, and remains available in only a few countries.^[1]^[8] It is given by mouth in humans or by injection into muscle in animals.^[8]

Unlike most AAS, stanozolol is not esterified and is sold as an aqueous suspension, or in oral tablet form.^[8] The drug has a high oral bioavailability, due to a C17α alkylation which allows the hormone to survive first-pass liver metabolism when ingested.^[10]^[8] It is because of this that stanozolol is also sold in tablet form.^[8]

Stanozolol is one of the AAS commonly used as performance-enhancing drugs and is banned from use in sports competition under the auspices of the World Anti-Doping Agency (WADA). It is an anabolic steroid that is known to have a diuretic effect. Additionally, stanozolol has been highly restricted in US horse racing.^[11]^[12]^[13]

^ ^a ^b ^c ^d "Stanozolol - Drugs.com".
^ ^a ^b Cite error: The named reference Thieme_2009 was invoked but never defined (see the help page).
^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-15.
^ Maini AA, Maxwell-Scott H, Marks DJ (February 2014). "Severe alkalosis and hypokalemia with stanozolol misuse". The American Journal of Emergency Medicine. 32 (2): 196.e3–196.e4. doi:10.1016/j.ajem.2013.09.027. PMID 24521609. This case is important as stanozolol misuse is relatively common, due to its high oral bioavailability and perceived safety profile compared with other parenteral AAS.
^ ^a ^b Ruiz P, Strain EC (2011). Lowinson and Ruiz's Substance Abuse: A Comprehensive Textbook. Lippincott Williams & Wilkins. pp. 358–. ISBN 978-1-60547-277-5.
^ ^a ^b Hsu WH (25 April 2013). Handbook of Veterinary Pharmacology. John Wiley & Sons. pp. 404–. ISBN 978-1-118-71416-4.
^ Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 961–. ISBN 978-3-88763-075-1.
^ ^a ^b ^c ^d ^e ^f ^g ^h Llewellyn W (2011). Anabolics. Molecular Nutrition Llc. pp. 726–737. ISBN 978-0-9828280-1-4.
^ "Drugs@FDA: FDA Approved Drug Products". www.accessdata.fda.gov. Retrieved 2016-02-18.
^ "stanozolol (CHEBI:9249)". www.ebi.ac.uk. Retrieved 2020-09-06.
^ "Anabolic Steroids Still an Issue in U.S. Horse Racing". The Horse. 2015-02-13. Retrieved 2020-09-06.
^ "Win, Place, and Dope". Slate. 1 May 2009.
^ Anonymous. "Model Rules Ver 9.5". ARCI.com. ARCI. Archived from the original on 2021-06-03. Retrieved 2021-03-14.

[Drugs.com-1] "Stanozolol - Drugs.com".

[Thieme_2009-2] Cite error: The named reference Thieme_2009 was invoked but never defined (see the help page).

[3] Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-15.

[Maini_2014-4] Maini AA, Maxwell-Scott H, Marks DJ (February 2014). "Severe alkalosis and hypokalemia with stanozolol misuse". The American Journal of Emergency Medicine. 32 (2): 196.e3–196.e4. doi:10.1016/j.ajem.2013.09.027. PMID 24521609. This case is important as stanozolol misuse is relatively common, due to its high oral bioavailability and perceived safety profile compared with other parenteral AAS.

[Ruiz_2011-5] Ruiz P, Strain EC (2011). Lowinson and Ruiz's Substance Abuse: A Comprehensive Textbook. Lippincott Williams & Wilkins. pp. 358–. ISBN 978-1-60547-277-5.

[Hsu_2013-6] Hsu WH (25 April 2013). Handbook of Veterinary Pharmacology. John Wiley & Sons. pp. 404–. ISBN 978-1-118-71416-4.

[IndexNominum2000-7] Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 961–. ISBN 978-3-88763-075-1.

[Llewellyn_2011-8] ^ ^a ^b ^c ^d ^e ^f ^g ^h Llewellyn W (2011). Anabolics. Molecular Nutrition Llc. pp. 726–737. ISBN 978-0-9828280-1-4.

[Drugs@FDA-9] "Drugs@FDA: FDA Approved Drug Products". www.accessdata.fda.gov. Retrieved 2016-02-18.

[10] "stanozolol (CHEBI:9249)". www.ebi.ac.uk. Retrieved 2020-09-06.

[11] "Anabolic Steroids Still an Issue in U.S. Horse Racing". The Horse. 2015-02-13. Retrieved 2020-09-06.

[12] "Win, Place, and Dope". Slate. 1 May 2009.

[13] Anonymous. "Model Rules Ver 9.5". ARCI.com. ARCI. Archived from the original on 2021-06-03. Retrieved 2021-03-14.

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