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Record Information
StatusExpected but not Quantified
Creation Date2006-05-22 15:12:34 UTC
Update Date2021-09-14 15:40:23 UTC
Secondary Accession Numbers
  • HMDB0015663
  • HMDB03116
  • HMDB15663
Metabolite Identification
Common NameStanozolol
DescriptionStanozolol is only found in individuals that have used or taken this drug. Stanozolol has is a synthetic anabolic steroid with therapeutic uses in treating hereditary angioedema. Stanozolol was first synthesized by Clinton et al. in 1959, as a heterocyclic anabolic androgenic steroid. The structure of Stanozolol differs from endogenous steroid hormones and most commercially available anabolic steroids. It most closely resembles methyl testosterone. Instead of the 3-ketogroup in methyltestosterone, there is a pyrazole ring fused to the androstane ring system. This slightly different structure has the disadvantage of making extraction and isolation of the molecule from matrices more difficult. Like most other anabolic steroids, Stanozolol has poor gas chromatographic behavior and is difficult to detect in urine, because of renal clearance and low urinary excretion. This is due to the rapid metabolization, leading to low concentration levels of the parent compound found in urine. Therefore, most research studies had focused on the detection of urinary metabolites. Androgens are drugs, derived from the natural male sex hormone testosterone, with high anabolic potential and minimized androgenic activity. It has been abused by several high profile professional athletes. Stanozolol binds to androgen receptors, such as membrane bound receptor proteins LAGS and stanozolol-binding protein (STBP). Anabolic steroids stimulate protein synthesis, resulting in an acceleration of the food conversion rate and increasing muscle growth, body mass and enhanced performance. Androgens can be used as therapeutics, because they accelerate the recovery of protein deficiency and protein-wasting disorders (e.g. osteoporosis), but they are also widely abused in doping, as well in animals as in men. (PMID: 10404632 , 10435307 , 11175645 , 11284331 , 12064656 , 12580506 , 1448813 , 14698206 , 15013688 , 15458725 , 15631866 , 15664350 , 16040239 , 16259046 , 16288903 , 1640693 , 17066372 , 17146762 , 2306548 , 2362445 , 2625454 , 2663904 , 6539197 , 9001957 , 9300863 , 9580049 ).
2'H-5a-Androst-2-eno[3,2-c]pyrazol-17b-ol, 17-methyl- (8ci)HMDB
AndrostanazolHMDB, MeSH
Cyclopenta[7,8]phenanthro[2,3-c]pyrazole, 2'H-androst-2-eno[3,2-c]pyrazol-17-ol deriv.HMDB
StanazololHMDB, MeSH
Win 14833HMDB
Winstrol depotHMDB
Winstrol VHMDB
Sanofi winthrop brand OF stanozololMeSH, HMDB
Zambon brand OF stanozololMeSH, HMDB
MethylstanazolMeSH, HMDB
Sanofi-synthelabo brand OF stanozololMeSH, HMDB
Chemical FormulaC21H32N2O
Average Molecular Weight328.4916
Monoisotopic Molecular Weight328.251463656
IUPAC Name(1S,2S,10S,13R,14S,17S,18S)-2,17,18-trimethyl-6,7-diazapentacyclo[²,¹⁰.0⁴,⁸.0¹⁴,¹⁸]icosa-4,7-dien-17-ol
Traditional Namestanozolol
CAS Registry Number10418-03-8
InChI Identifier
Chemical Taxonomy
Description Belongs to the class of organic compounds known as estrane steroids. These are steroids with a structure based on the estrane skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassEstrane steroids
Direct ParentEstrane steroids
Alternative Parents
  • Estrane-skeleton
  • Hydroxysteroid
  • 17-hydroxysteroid
  • Azole
  • Cyclic alcohol
  • Pyrazole
  • Tertiary alcohol
  • Heteroaromatic compound
  • Organoheterocyclic compound
  • Azacycle
  • Alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors

Biological location


Route of exposure

Physical Properties
Experimental Molecular Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral Properties

Experimental Collision Cross Sections

PredictorAdduct TypeData SourceCCS Value (Å2)Reference
Predicted Molecular Properties
Water Solubility0.0017 g/LALOGPS
logP10(4.33) g/LALOGPS
logP10(3.81) g/LChemAxon
logS10(-5.3) g/LALOGPS
pKa (Strongest Acidic)16.23ChemAxon
pKa (Strongest Basic)2.86ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area48.91 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity96.8 m³·mol⁻¹ChemAxon
Polarizability39.22 ųChemAxon
Number of Rings5ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference

Predicted Kovats Retention Indices


Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Stanozolol,1TMS,#1C[C@]12CC3=C[NH]N=C3C[C@@H]1CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1CC[C@]2(C)O[Si](C)(C)C3053.9Semi standard non polar
Stanozolol,1TMS,#2C[C@]12CC3=CN([Si](C)(C)C)N=C3C[C@@H]1CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1CC[C@]2(C)O3082.1Semi standard non polar
Stanozolol,1TBDMS,#1CC(C)(C)[Si](C)(C)O[C@@]1(C)CC[C@H]2[C@@H]3CC[C@H]4CC5=N[NH]C=C5C[C@]4(C)[C@H]3CC[C@@]21C3306.0Semi standard non polar
Stanozolol,1TBDMS,#2CC(C)(C)[Si](C)(C)N1C=C2C[C@@]3(C)[C@@H](CC[C@@H]4[C@@H]3CC[C@@]3(C)[C@H]4CC[C@]3(C)O)CC2=N13297.3Semi standard non polar

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Stanozolol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ika-1698000000-3f8c35eb18e311ca156b2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Stanozolol GC-MS (1 TMS) - 70eV, Positivesplash10-0079-3249000000-250fe7ac2a107a0209162017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Stanozolol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Stanozolol 35V, Positive-QTOFsplash10-004i-0009000000-092e853c1b3ea4cea4762021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stanozolol 10V, Positive-QTOFsplash10-03fr-0009000000-e44e17759e6628cd979d2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stanozolol 20V, Positive-QTOFsplash10-03dl-0092000000-fb2af0d825cd4939b25f2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stanozolol 40V, Positive-QTOFsplash10-0udj-9870000000-8e6ba7db421ffbe6d4d42016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stanozolol 10V, Negative-QTOFsplash10-004i-0009000000-f62def968e0fcaf5ad8b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stanozolol 20V, Negative-QTOFsplash10-002b-0096000000-6c72948a57cb2e8a76832016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stanozolol 40V, Negative-QTOFsplash10-03xr-6198000000-d225125a553d5bedac3e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stanozolol 10V, Negative-QTOFsplash10-004i-0009000000-507d1b76f5fbab2cd6172021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stanozolol 20V, Negative-QTOFsplash10-004i-0009000000-507d1b76f5fbab2cd6172021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stanozolol 40V, Negative-QTOFsplash10-004i-0039000000-a11542c5a5960f8c2e3a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stanozolol 10V, Positive-QTOFsplash10-004i-0019000000-e17ed5d1d401678c0a122021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stanozolol 20V, Positive-QTOFsplash10-000i-2963000000-c456325d88b698b6ee3e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Stanozolol 40V, Positive-QTOFsplash10-0udr-1790000000-56ae15e8bf663dc1ee842021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Normal Concentrations
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB06718 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB06718 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB06718
Phenol Explorer Compound IDNot Available
FooDB IDFDB023109
KNApSAcK IDNot Available
Chemspider ID23582
KEGG Compound IDC07311
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkStanozolol
METLIN IDNot Available
PubChem Compound25249
PDB IDNot Available
ChEBI ID9249
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Hungerford NL, Sortais B, Smart CG, McKinney AR, Ridley DD, Stenhouse AM, Suann CJ, Munn KJ, Sillence MN, McLeod MD: Analysis of anabolic steroids in the horse: development of a generic ELISA for the screening of 17alpha-alkyl anabolic steroid metabolites. J Steroid Biochem Mol Biol. 2005 Aug;96(3-4):317-34. [PubMed:16040239 ]
  2. de Oca Porto RM, Fernandez AR, Brito DM, Vidal TC, Diaz AL: Gas chromatography/mass spectrometry characterization of urinary metabolites of danazol after oral administration in human. J Chromatogr B Analyt Technol Biomed Life Sci. 2006 Jan 2;830(1):178-83. Epub 2005 Nov 8. [PubMed:16288903 ]
  3. Leinonen A, Kuuranne T, Kotiaho T, Kostiainen R: Screening of free 17-alkyl-substituted anabolic steroids in human urine by liquid chromatography-electrospray ionization tandem mass spectrometry. Steroids. 2004 Feb;69(2):101-9. [PubMed:15013688 ]
  4. Kintz P, Cirimele V, Sachs H, Jeanneau T, Ludes B: Testing for anabolic steroids in hair from two bodybuilders. Forensic Sci Int. 1999 May 17;101(3):209-16. [PubMed:10404632 ]
  5. De Brabander HF, De Wasch K, van Ginkel LA, Sterk SS, Blokland MH, Delahaut P, Taillieu X, Dubois M, Arts CJ, van Baak MJ, Gramberg LG, Schilt R, van Bennekom EO, Courtheyn D, Vercammen J, Witkamp RF: Multi-laboratory study of the analysis and kinetics of stanozolol and its metabolites in treated calves. Analyst. 1998 Dec;123(12):2599-604. [PubMed:10435307 ]
  6. Fineschi V, Baroldi G, Monciotti F, Paglicci Reattelli L, Turillazzi E: Anabolic steroid abuse and cardiac sudden death: a pathologic study. Arch Pathol Lab Med. 2001 Feb;125(2):253-5. [PubMed:11175645 ]
  7. Choi MH, Chung BC: N-isobutyloxycarbonylation for improved detection of 3'-hydroxystanozolol and its 17-epimer in doping control. Analyst. 2001 Mar;126(3):306-9. [PubMed:11284331 ]
  8. Dumestre-Toulet V, Cirimele V, Ludes B, Gromb S, Kintz P: Hair analysis of seven bodybuilders for anabolic steroids, ephedrine, and clenbuterol. J Forensic Sci. 2002 Jan;47(1):211-4. [PubMed:12064656 ]
  9. Huenerbein A, Sipoli Marques MA, Pereira Ados S, de Aquino Neto FR: Improvement in steroid screening for doping control with special emphasis on stanozolol. J Chromatogr A. 2003 Jan 24;985(1-2):375-86. [PubMed:12580506 ]
  10. Schanzer W, Opfermann G, Donike M: 17-Epimerization of 17 alpha-methyl anabolic steroids in humans: metabolism and synthesis of 17 alpha-hydroxy-17 beta-methyl steroids. Steroids. 1992 Nov;57(11):537-50. [PubMed:1448813 ]
  11. Betancor-Hernandez E, Perez-Machin R, Henriquez-Hernandez L, Mateos-Diaz C, Novoa-Mogollon J, Fernandez-Perez L: Photoaffinity labeling identification of thyroid hormone-regulated glucocorticoid-binding peptides in rat liver endoplasmic reticulum: an oligomeric protein with high affinity for 16beta-hydroxylated stanozolol. J Steroid Biochem Mol Biol. 2003 Dec;87(4-5):253-64. [PubMed:14698206 ]
  12. McKinney AR, Suann CJ, Dunstan AJ, Mulley SL, Ridley DD, Stenhouse AM: Detection of stanozolol and its metabolites in equine urine by liquid chromatography-electrospray ionization ion trap mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2004 Nov 5;811(1):75-83. [PubMed:15458725 ]
  13. Felzmann W, Gmeiner G, Gartner P: First synthesis of a pentadeuterated 3'-hydroxystanozolol--an internal standard in doping analysis. Steroids. 2005 Feb;70(2):103-10. Epub 2004 Dec 15. [PubMed:15631866 ]
  14. Mateus-Avois L, Mangin P, Saugy M: Use of ion trap gas chromatography-multiple mass spectrometry for the detection and confirmation of 3'hydroxystanozolol at trace levels in urine for doping control. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Feb 25;816(1-2):193-201. [PubMed:15664350 ]
  15. Thevis M, Makarov AA, Horning S, Schanzer W: Mass spectrometry of stanozolol and its analogues using electrospray ionization and collision-induced dissociation with quadrupole-linear ion trap and linear ion trap-orbitrap hybrid mass analyzers. Rapid Commun Mass Spectrom. 2005;19(22):3369-78. [PubMed:16259046 ]
  16. de Boer D, de Jong EG, Maes RA: The detection of danazol and its significance in doping analysis. J Anal Toxicol. 1992 Jan-Feb;16(1):14-8. [PubMed:1640693 ]
  17. Mazzarino M, Botre F: A fast liquid chromatographic/mass spectrometric screening method for the simultaneous detection of synthetic glucocorticoids, some stimulants, anti-oestrogen drugs and synthetic anabolic steroids. Rapid Commun Mass Spectrom. 2006;20(22):3465-76. [PubMed:17066372 ]
  18. Parr MK, Geyer H, Hoffmann B, Kohler K, Mareck U, Schanzer W: High amounts of 17-methylated anabolic-androgenic steroids in effervescent tablets on the dietary supplement market. Biomed Chromatogr. 2007 Feb;21(2):164-8. [PubMed:17146762 ]
  19. Muck WM, Henion JD: High-performance liquid chromatography/tandem mass spectrometry: its use for the identification of stanozolol and its major metabolites in human and equine urine. Biomed Environ Mass Spectrom. 1990 Jan;19(1):37-51. [PubMed:2306548 ]
  20. Schanzer W, Opfermann G, Donike M: Metabolism of stanozolol: identification and synthesis of urinary metabolites. J Steroid Biochem. 1990 Jun;36(1-2):153-74. [PubMed:2362445 ]
  21. Masse R, Ayotte C, Bi HG, Dugal R: Studies on anabolic steroids. III. Detection and characterization of stanozolol urinary metabolites in humans by gas chromatography-mass spectrometry. J Chromatogr. 1989 Dec 29;497:17-37. [PubMed:2625454 ]
  22. Masse R, Ayotte C, Dugal R: Studies on anabolic steroids. I. Integrated methodological approach to the gas chromatographic-mass spectrometric analysis of anabolic steroid metabolites in urine. J Chromatogr. 1989 Apr 7;489(1):23-50. [PubMed:2663904 ]
  23. Saartok T, Dahlberg E, Gustafsson JA: Relative binding affinity of anabolic-androgenic steroids: comparison of the binding to the androgen receptors in skeletal muscle and in prostate, as well as to sex hormone-binding globulin. Endocrinology. 1984 Jun;114(6):2100-6. [PubMed:6539197 ]
  24. Schanzer W, Delahaut P, Geyer H, Machnik M, Horning S: Long-term detection and identification of metandienone and stanozolol abuse in athletes by gas chromatography-high-resolution mass spectrometry. J Chromatogr B Biomed Appl. 1996 Dec 6;687(1):93-108. [PubMed:9001957 ]
  25. Ferchaud V, Le Bizec B, Montrade MP, Maume D, Monteau F, Andre F: Gas chromatographic-mass spectrometric identification of main metabolites of stanozolol in cattle after oral and subcutaneous administration. J Chromatogr B Biomed Sci Appl. 1997 Aug 1;695(2):269-77. [PubMed:9300863 ]
  26. Munoz-Guerra J, Carreras D, Soriano C, Rodriguez C, Rodriguez AF: Use of ion trap gas chromatography-tandem mass spectrometry for detection and confirmation of anabolic substances at trace levels in doping analysis. J Chromatogr B Biomed Sci Appl. 1997 Dec 19;704(1-2):129-41. [PubMed:9580049 ]
  27. Sloane DE, Lee CW, Sheffer AL: Hereditary angioedema: Safety of long-term stanozolol therapy. J Allergy Clin Immunol. 2007 Sep;120(3):654-8. [PubMed:17765757 ]
  28. Guilarte M, Luengo O, Nogueiras C, Labrador-Horrillo M, Munoz E, Lopez A, Cardona V: Acquired angioedema associated with hereditary angioedema due to C1 inhibitor deficiency. J Investig Allergol Clin Immunol. 2008;18(2):126-30. [PubMed:18447143 ]
  29. Thevis M, Schanzer W: Synthetic anabolic agents: steroids and nonsteroidal selective androgen receptor modulators. Handb Exp Pharmacol. 2010;(195):99-126. doi: 10.1007/978-3-540-79088-4_5. [PubMed:20020362 ]