Stanozolol

Not to be confused with Stanolone, Stanozide, or Winstan.
Stanozolol
Clinical data
Trade namesWinstrol, Stromba, others[1]
Other namesAndrostanazol; 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.comMultum Consumer Information
Pregnancy
category
  • X
Routes of
administration		By mouth, intramuscular injection (veterinary)[2]
Drug classAndrogen; Anabolic steroid
ATC code
Legal status
Legal status
Pharmacokinetic data
BioavailabilityHigh[4]
MetabolismLiver[6]
Elimination half-lifeOral: 9 hours[5]
IMTooltip Intramuscular injection: 24 hours (aq. susp.)[5][2]
Duration of actionIM: >1 week[6]
ExcretionUrine: 84%[citation needed]
Identifiers
  • (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
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.030.801 Edit this at Wikidata
Chemical and physical data
FormulaC21H32N2O
Molar mass328.500 g·mol−1
3D model (JSmol)
  • [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=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 checkY
  • Key:LKAJKIOFIWVMDJ-IYRCEVNGSA-N checkY
  (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 Winthrop Laboratories (Sterling Drug) 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 USA.[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 injectable 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]

  1. ^ a b c d "Stanozolol - Drugs.com".
  2. ^ a b Cite error: The named reference ThiemeHemmersbach2009 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.
  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.e3–4. 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.
  5. ^ 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.
  6. ^ a b Hsu WH (25 April 2013). Handbook of Veterinary Pharmacology. John Wiley & Sons. pp. 404–. ISBN 978-1-118-71416-4.
  7. ^ Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 961–. ISBN 978-3-88763-075-1.
  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.
  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.