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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H32N2O
Molecular Weight 328.4916
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of STANOZOLOL

SMILES

C[C@]1(O)CC[C@H]2[C@@H]3CC[C@H]4CC5=C(C[C@]4(C)[C@H]3CC[C@]12C)C=NN5

InChI

InChIKey=LKAJKIOFIWVMDJ-IYRCEVNGSA-N
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

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including: http://www.rxlist.com/winstrol-drug/side-effects-interactions.htm | http://en.pharmacodia.com/web/drug/1_7820.html

Stanozolol is a synthetic anabolic steroid derived from dihydrotestosterone. It is indicated prophylactically to decrease the frequency and severity of attacks of angioedema. In rare cases, serious and even fatal cases of liver problems have developed during treatment with stanozolol. Anabolic steroids may increase sensitivity to anticoagulants; therefore, dosage of an anticoagulant may have to be decreased in order to maintain the prothrombin time at the desired therapeutic level.

CNS Activity

Originator

Clinton, R.O. et al.
1
Sources: DOI: 10.1021/ja01515a060

Approval Year

1962
70
Targets

Targets

Primary TargetPharmacologyConditionPotency
Low-affinity glucocorticoid-binding protein
1
Target ID: Low-affinity glucocorticoid-binding protein
Binding Agent
1076
 30.0 nM [Ki]
Stanosolol binding protein
1
Target ID: Stanosolol binding protein
Binding Agent
1076
 30.0 nM [Kd]
Agonist
2752
 4.5 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Approved
8583
WINSTROL

Approved Use

WINSTROL (anabolic steroids) is indicated prophylactically to decrease the frequency and severity of attacks of angioedema.

Launch Date

1962
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
9 h
REVIEW
https://books.google.com/books?id=w4ZUJAdleTsC&pg=PA358#v=onepage&q&f=false#page=358
single, oral
 STANOZOLOL plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:9249
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:9249
ChemicalBook
CB0247357
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB0247357
eMolecules
31228973
https://www.emolecules.com/cgi-bin/more?vid=31228973
eMolecules
594442
https://www.emolecules.com/cgi-bin/more?vid=594442
MolPort
MolPort-003-959-588
https://www.molport.com/shop/molecule-link/MolPort-003-959-588
ZINC
ZINC000004097376
http://zinc15.docking.org/substances/ZINC000004097376
PubMed

PubMed

TitleDatePubMed
The detection of danazol and its significance in doping analysis.
1992 Jan-Feb
Anabolic-androgenic steroids induce apoptotic cell death in adult rat ventricular myocytes.
2001 Apr
Confirmatory analysis of residues of stanozolol and its major metabolite in bovine urine by liquid chromatography-tandem mass spectrometry.
2001 Aug 10
Anabolic steroid abuse and cardiac sudden death: a pathologic study.
2001 Feb
Stanozolol in chronic urticaria: a double blind, placebo controlled trial.
2001 Jun
Phenotypic variation in a family with partial androgen insensitivity syndrome explained by differences in 5alpha dihydrotestosterone availability.
2001 Mar
Effects of acute stanozolol treatment on puberty in female rats.
2001 May
Masseteric hypertrophy associated with administration of anabolic steroids and unilateral mastication: a case report.
2001 Nov
Aggression in male rats receiving anabolic androgenic steroids: effects of social and environmental provocation.
2001 Nov
Low dose cyclosporine-a therapy in severe aplastic anaemia.
2001 Oct
Molecular cloning and functional characterization of the canine androgen receptor.
2001 Oct
Physical provocation potentiates aggression in male rats receiving anabolic androgenic steroids.
2002 Feb
[Turner syndrome].
2002 Jan
'Skin popping' ulceration in an HIV patient. Successful treatment with antiretroviral drugs and stanozolol.
2002 Jul
Hepatatis in growth promoter treated cows.
2002 Nov
[Cold-induced urticaria].
2002 Sep
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.
2003 Dec
Torpid ulcer on the achilles tendon: conservative treatment with stanozolol and pinch grafting.
2003 Feb
Chronic administration of anabolic steroids disrupts pubertal onset and estrous cyclicity in rats.
2003 Feb
Effects of stanozolol on bone mineral density and bone biomechanical properties of osteoporotic rats.
2003 Nov
Long-term effects of pubertal anabolic-androgenic steroid exposure on reproductive and aggressive behaviors in male rats.
2004 Aug
Anabolic androgenic steroids and aggression: studies using animal models.
2004 Dec
Androgens in childhood acquired aplastic anaemia in Chandigarh, India.
2004 Jul
Nonhealing ulcer secondary to factor V Leiden mutation and cryofibrinogenemia.
2004 Nov
Detection of stanozolol and its metabolites in equine urine by liquid chromatography-electrospray ionization ion trap mass spectrometry.
2004 Nov 5
[Clinical report on treatment of 7 patients with refractory anemia by using cyclosporin A].
2004 Oct
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.
2005
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.
2005 Feb 25
Validation of a GC-MS screening method for anabolizing agents in aqueous nutritional supplements.
2005 Jan
Effects of chronic anabolic steroid treatment on tonic and reflex cardiovascular control in male rats.
2005 Jan
[Clinical efficacy and T-lymphocyte subset, serum interferon-gamma (IFN-gamma), tumor necrosis factor-alpha (TNF-alpha), interleukin-2(IL-2) levels on treatment of chronic aplastic anemia patients by shenfu injection combined with stanozol and cyclosporin A].
2005 Mar
Successful treatment of primary refractory anemia with a combination regimen of all-trans retinoic acid, calcitriol, and androgen.
2006 Aug
[Plasmapheresis in the treatment of cholestasis-induced pruritus].
2006 Feb 20
Clinical observation on treatment of chronic aplastic anemia by Shengxuening and cyclosporin A.
2006 Jun
Synchronous bilateral ductal carcinoma in situ of the male breast associated with gynecomastia in a 30-year-old patient following repeated injections of stanozolol.
2006 May
Screening for anabolic steroids in doping analysis by liquid chromatography/electrospray ion trap mass spectrometry.
2006 May
[Prevalence of the use of anabolic agents among strength training apprentices in Porto Alegre, RS].
2007 Feb
High amounts of 17-methylated anabolic-androgenic steroids in effervescent tablets on the dietary supplement market.
2007 Feb
Lupus nephritis remission, albeit with positive anti-doping test.
2007 Jan
Clinical study on effect of Astragalus Injection and its immuno-regulation action in treating chronic aplastic anemia.
2007 Jun
Determination of synthetic hormones in animal urine by high-performance liquid chromatography/mass spectrometry.
2007 Mar-Apr
Natural selection and adaptive evolution of leptin in the ochotona family driven by the cold environmental stress.
2008 Jan 23
Patents

Patents

EP1891940 A1
1

Sample Use Guides

In Vivo Use Guide
It is recommended that the patient be started on 2 mg, three times a day. After a favorable initial response is obtained in terms of prevention of episodes of edematous attacks, the proper continuing dosage should be determined by decreasing the dosage at intervals of one to three months to a maintenance dosage of 2 mg a day.
Route of Administration: Oral
In Vitro Use Guide
To assess whether Stanozolol is capable of activating the Androgen receptor (AR), a cell-based transactivation system was employed consisting of the full-length recombinant rat AR and a reporter plasmid which contains an androgen response elemement.The calculated EC50 value for the stanozolol is 52 pM.
Name Type Language
STANOZOLOL
EP   GREEN BOOK   HSDB   INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP   VANDF   WHO-DD  
INN   USAN  
Official Name English
STANOZOLOL CIII
USP-RS  
Preferred Name English
WIN 14833
Code English
17-METHYL-5.ALPHA.-ANDROSTANO(3,2-C)PYRAZOL-17.BETA.-OL
Common Name English
STANOZOLOL [GREEN BOOK]
Common Name English
17.BETA.-HYDROXY-17.ALPHA.-METHYL-5.ALPHA.-ANDROSTANO(3,2-C)PYRAZOLE
Common Name English
17-METHYL-2'H-5.ALPHA.-ANDROST-2-ENO(3,2-C)PYRAZOL-17.BETA.-OL
Common Name English
stanozolol [INN]
Common Name English
STANOZOLOL [MI]
Common Name English
CYCLOPENTA(7,8)PHENANTHRO(2,3-C)PYRAZOL-1-OL, 1,2,3,3A,3B,4,5,5A,6,8,10,10A,10B,11,12,12A-HEXADECAHYDRO-1,10A,12A-TRIMETHYL-
Common Name English
STANOZOLOL [JAN]
Common Name English
STANOZOLOL [USP MONOGRAPH]
Common Name English
STANOZOLOL [ORANGE BOOK]
Common Name English
STANOZOLOL [MART.]
Common Name English
ANDROSTANAZOLE
Common Name English
STANOZOLOL [EP MONOGRAPH]
Common Name English
ANDROSTANAZOL
Common Name English
STANOZOLOL [HSDB]
Common Name English
STANOZOLOL [USAN]
Common Name English
STANOZOLOL CIII [USP-RS]
Common Name English
WINSTROL
Brand Name English
STANOZOLOL [VANDF]
Common Name English
2'H-ANDROST-2-ENO(3,2-C)PYRAZOL-17-OL, 17-METHYL-, (5.ALPHA.,17.BETA.)
Common Name English
NSC-233046
Code English
NSC-43193
Code English
WIN-14833
Code English
1'H-ANDROSTANO(3,2-C)PYRAZOL-17-OL, 17-METHYL-, (5.ALPHA.,17.BETA.)-
Common Name English
Stanozolol [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C243
Created by admin on Mon Mar 31 18:28:19 GMT 2025 , Edited by admin on Mon Mar 31 18:28:19 GMT 2025
WHO-VATC QA14AA02
Created by admin on Mon Mar 31 18:28:19 GMT 2025 , Edited by admin on Mon Mar 31 18:28:19 GMT 2025
WIKIPEDIA Designer-drugs-Stanozolol
Created by admin on Mon Mar 31 18:28:19 GMT 2025 , Edited by admin on Mon Mar 31 18:28:19 GMT 2025
CFR 21 CFR 520.2150
Created by admin on Mon Mar 31 18:28:19 GMT 2025 , Edited by admin on Mon Mar 31 18:28:19 GMT 2025
CFR 21 CFR 522.2150
Created by admin on Mon Mar 31 18:28:19 GMT 2025 , Edited by admin on Mon Mar 31 18:28:19 GMT 2025
LIVERTOX 898
Created by admin on Mon Mar 31 18:28:19 GMT 2025 , Edited by admin on Mon Mar 31 18:28:19 GMT 2025
WHO-ATC A14AA02
Created by admin on Mon Mar 31 18:28:19 GMT 2025 , Edited by admin on Mon Mar 31 18:28:19 GMT 2025
DEA NO. 4000
Created by admin on Mon Mar 31 18:28:19 GMT 2025 , Edited by admin on Mon Mar 31 18:28:19 GMT 2025
NCI_THESAURUS C2360
Created by admin on Mon Mar 31 18:28:19 GMT 2025 , Edited by admin on Mon Mar 31 18:28:19 GMT 2025
Code System Code Type Description
DRUG CENTRAL
2477
Created by admin on Mon Mar 31 18:28:19 GMT 2025 , Edited by admin on Mon Mar 31 18:28:19 GMT 2025
PRIMARY
EPA CompTox
DTXSID3044128
Created by admin on Mon Mar 31 18:28:19 GMT 2025 , Edited by admin on Mon Mar 31 18:28:19 GMT 2025
PRIMARY
CAS
302-96-5
Created by admin on Mon Mar 31 18:28:19 GMT 2025 , Edited by admin on Mon Mar 31 18:28:19 GMT 2025
ALTERNATIVE
CAS
875293-72-4
Created by admin on Mon Mar 31 18:28:19 GMT 2025 , Edited by admin on Mon Mar 31 18:28:19 GMT 2025
SUPERSEDED
MESH
D013197
Created by admin on Mon Mar 31 18:28:19 GMT 2025 , Edited by admin on Mon Mar 31 18:28:19 GMT 2025
PRIMARY
INN
958
Created by admin on Mon Mar 31 18:28:19 GMT 2025 , Edited by admin on Mon Mar 31 18:28:19 GMT 2025
PRIMARY
PUBCHEM
25249
Created by admin on Mon Mar 31 18:28:19 GMT 2025 , Edited by admin on Mon Mar 31 18:28:19 GMT 2025
PRIMARY
HSDB
3185
Created by admin on Mon Mar 31 18:28:19 GMT 2025 , Edited by admin on Mon Mar 31 18:28:19 GMT 2025
PRIMARY
CAS
69353-49-7
Created by admin on Mon Mar 31 18:28:19 GMT 2025 , Edited by admin on Mon Mar 31 18:28:19 GMT 2025
SUPERSEDED
EVMPD
SUB10641MIG
Created by admin on Mon Mar 31 18:28:19 GMT 2025 , Edited by admin on Mon Mar 31 18:28:19 GMT 2025
PRIMARY
NCI_THESAURUS
C842
Created by admin on Mon Mar 31 18:28:19 GMT 2025 , Edited by admin on Mon Mar 31 18:28:19 GMT 2025
PRIMARY
CHEBI
9249
Created by admin on Mon Mar 31 18:28:19 GMT 2025 , Edited by admin on Mon Mar 31 18:28:19 GMT 2025
PRIMARY
CAS
10418-03-8
Created by admin on Mon Mar 31 18:28:19 GMT 2025 , Edited by admin on Mon Mar 31 18:28:19 GMT 2025
PRIMARY
ECHA (EC/EINECS)
233-894-8
Created by admin on Mon Mar 31 18:28:19 GMT 2025 , Edited by admin on Mon Mar 31 18:28:19 GMT 2025
PRIMARY
CAS
17966-55-1
Created by admin on Mon Mar 31 18:28:19 GMT 2025 , Edited by admin on Mon Mar 31 18:28:19 GMT 2025
SUPERSEDED
FDA UNII
4R1VB9P8V3
Created by admin on Mon Mar 31 18:28:19 GMT 2025 , Edited by admin on Mon Mar 31 18:28:19 GMT 2025
PRIMARY
ChEMBL
CHEMBL2079587
Created by admin on Mon Mar 31 18:28:19 GMT 2025 , Edited by admin on Mon Mar 31 18:28:19 GMT 2025
PRIMARY
WIKIPEDIA
STANOZOLOL
Created by admin on Mon Mar 31 18:28:19 GMT 2025 , Edited by admin on Mon Mar 31 18:28:19 GMT 2025
PRIMARY
SMS_ID
100000083853
Created by admin on Mon Mar 31 18:28:19 GMT 2025 , Edited by admin on Mon Mar 31 18:28:19 GMT 2025
PRIMARY
RXCUI
10032
Created by admin on Mon Mar 31 18:28:19 GMT 2025 , Edited by admin on Mon Mar 31 18:28:19 GMT 2025
PRIMARY RxNorm
NSC
233046
Created by admin on Mon Mar 31 18:28:19 GMT 2025 , Edited by admin on Mon Mar 31 18:28:19 GMT 2025
PRIMARY
RS_ITEM_NUM
1620005
Created by admin on Mon Mar 31 18:28:19 GMT 2025 , Edited by admin on Mon Mar 31 18:28:19 GMT 2025
PRIMARY
MERCK INDEX
m10191
Created by admin on Mon Mar 31 18:28:19 GMT 2025 , Edited by admin on Mon Mar 31 18:28:19 GMT 2025
PRIMARY Merck Index
DRUG BANK
DB06718
Created by admin on Mon Mar 31 18:28:19 GMT 2025 , Edited by admin on Mon Mar 31 18:28:19 GMT 2025
PRIMARY
NSC
43193
Created by admin on Mon Mar 31 18:28:19 GMT 2025 , Edited by admin on Mon Mar 31 18:28:19 GMT 2025
PRIMARY
ACTIVE MOIETY
Structure of STANOZOLOL
METABOLITE (PARENT)
Structure of 3'-HYDROXYSTANOZOLOL
METABOLITE INACTIVE (PARENT)
Structure of 3-HYDROXYSTANOZOLOL GLUCURONIDE
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
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