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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-05-22 15:12:34 UTC
Update Date2021-09-14 15:40:23 UTC
HMDB IDHMDB0003116
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 ).
Structure
Data?1582752263
Synonyms
ValueSource
AndrostanazoleChEBI
EstanozololChEBI
StanozololumChEBI
StrombaChEBI
StrombajectChEBI
WinstrolChEBI
(5a,17b)-17-Methyl-2'H-androst-2-eno[3,2-c]pyrazol-17-olHMDB
1,2,3,3a,3b,4,5,5a,6,7,10,10a,10b,11,12,12a-hexadecahydro-1,10a,12a-Trimethyl-cyclopenta[7,8]phenanthro[2,3-c]pyrazol-1-olHMDB
17-Methyl-5a-androstano[3,2-c]pyrazol-17b-olHMDB
17-Methyl-pyrazolo[4',3':2,3]-5a-androstan-17b-olHMDB
17a-Methyl-17b-hydroxy-5a-androstano(3,2-c)pyrazoleHMDB
17b-Hydroxy-17-methyl-5a-androstano[3,2-c]pyrazoleHMDB
17b-Hydroxy-17a-methyl-5a-androstano[3,2-c]pyrazoleHMDB
2'H-5a-Androst-2-eno[3,2-c]pyrazol-17b-ol, 17-methyl- (8ci)HMDB
AnabolHMDB
AndrostanazolHMDB, MeSH
AndrostanazolestanazolHMDB
Cyclopenta[7,8]phenanthro[2,3-c]pyrazole, 2'H-androst-2-eno[3,2-c]pyrazol-17-ol deriv.HMDB
EstazolHMDB
StanazololHMDB, MeSH
TevabolinHMDB
Win 14833HMDB
WinstroidHMDB
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[11.7.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁸]icosa-4,7-dien-17-ol
Traditional Namestanozolol
CAS Registry Number10418-03-8
SMILES
[H][C@@]12CC[C@](C)(O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])CC3=NNC=C3C[C@]12C
InChI Identifier
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
InChI KeyLKAJKIOFIWVMDJ-IYRCEVNGSA-N
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
Substituents
  • 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
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
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
DeepCCS[M+H]+CBM188.130932474
Predicted Molecular Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+179.41331661259
DarkChem[M-H]-176.1331661259

Predicted Kovats Retention Indices

Derivatized

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 polarhttps://arxiv.org/abs/1905.12712
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 polarhttps://arxiv.org/abs/1905.12712
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 polarhttps://arxiv.org/abs/1905.12712
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 polarhttps://arxiv.org/abs/1905.12712
Spectra

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
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
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  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 ]
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  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 ]
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  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 ]
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  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 ]
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  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 ]
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