U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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

[H][C@@]12CC[C@](C)(O)[C@@]1(C)CC[C@@]3([H])[C@@]2([H])CC[C@@]4([H])CC5=C(C[C@]34C)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
69
Targets

Targets

Primary TargetPharmacologyConditionPotency
Low-affinity glucocorticoid-binding protein
1
Target ID: Low-affinity glucocorticoid-binding protein
Binding Agent
1064
 30.0 nM [Ki]
Stanosolol binding protein
1
Target ID: Stanosolol binding protein
Binding Agent
1064
 30.0 nM [Kd]
Agonist
2678
 4.5 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Approved
8429
WINSTROL

Approved Use

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

Launch Date

1962
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
2.26 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/22489613
0.55 mg/kg single, intramuscular
dose: 0.55 mg/kg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
STANOZOLOL plasma
Equus caballus
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
0.81 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/22489613
0.55 mg/kg single, intramuscular
dose: 0.55 mg/kg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
STANOZOLOL plasma
Equus caballus
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
3.16 day
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/22489613
0.55 mg/kg single, intramuscular
dose: 0.55 mg/kg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
STANOZOLOL plasma
Equus caballus
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
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
MolPort
MolPort-003-959-588
https://www.molport.com/shop/molecule-link/MolPort-003-959-588
ZINC
ZINC000004097376
http://zinc15.docking.org/substances/ZINC000004097376
eMolecules
31228973
https://www.emolecules.com/cgi-bin/more?vid=31228973
eMolecules
594442
https://www.emolecules.com/cgi-bin/more?vid=594442
PubMed

PubMed

TitleDatePubMed
The detection of danazol and its significance in doping analysis.
1992 Jan-Feb
Aggression in male rats receiving anabolic androgenic steroids: effects of social and environmental provocation.
2001 Nov
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
Sources of variability in genetic association studies: insights from the analysis of hepatic lipase (LIPC).
2002 May
Anabolic steroids, testosterone-precursors and virilizing androgens induce distinct activation profiles of androgen responsive promoter constructs.
2002 Nov
Hepatatis in growth promoter treated cows.
2002 Nov
Effects of prolonged stanozolol treatment on antioxidant enzyme activities, oxidative stress markers, and heat shock protein HSP72 levels in rat liver.
2003 Dec
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
Cryofibrinogenaemia complicated by amyloidosis: a new association.
2003 Jun
Effects of stanozolol on bone mineral density and bone biomechanical properties of osteoporotic rats.
2003 Nov
The anti-doping hot-line, a means to capture the abuse of doping agents in the Swedish society and a new service function in clinical pharmacology.
2003 Nov
Long-term effects of pubertal anabolic-androgenic steroid exposure on reproductive and aggressive behaviors in male rats.
2004 Aug
Screening of free 17-alkyl-substituted anabolic steroids in human urine by liquid chromatography-electrospray ionization tandem mass spectrometry.
2004 Feb
Oxandrolone treatment of childhood hereditary angioedema.
2004 Mar
Detection of stanozolol and its metabolites in equine urine by liquid chromatography-electrospray ionization ion trap mass spectrometry.
2004 Nov 5
[Management of male sterility in patients taking anabolic steroids].
2005 Apr
Anabolic-androgenic steroid interaction with rat androgen receptor in vivo and in vitro: a comparative study.
2005 Apr
[Influence of Shenmai injection on blood serum tumor necrosis factor and bone marrow CD34+ cell's apoptosis of chronic aplastic anemia patient].
2005 Aug
Analysis of anabolic steroids in the horse: development of a generic ELISA for the screening of 17alpha-alkyl anabolic steroid metabolites.
2005 Aug
Detection, quantification and confirmation of anabolic steroids in equine plasma by liquid chromatography and tandem mass spectrometry.
2005 Dec 27
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
Effects of chronic anabolic steroid treatment on tonic and reflex cardiovascular control in male rats.
2005 Jan
Intracerebroventricular self-administration of commonly abused anabolic-androgenic steroids in male hamsters (Mesocricetus auratus): nandrolone, drostanolone, oxymetholone, and stanozolol.
2005 Jun
Anabolic steroid-induced rhabdomyolysis.
2005 Jun
[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
Hepatocellular adenomas associated with anabolic androgenic steroid abuse in bodybuilders: a report of two cases and a review of the literature.
2005 May
Acquired angioedema secondary to hormone replacement therapy.
2005 Oct
A fast liquid chromatographic/mass spectrometric screening method for the simultaneous detection of synthetic glucocorticoids, some stimulants, anti-oestrogen drugs and synthetic anabolic steroids.
2006
Quantitative detection of doping substances by a localised surface plasmon sensor.
2006 Jan 15
Immunosuppressive therapy for acquired severe aplastic anemia (SAA): a prospective comparison of four different regimens.
2006 Jul
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
Anabolic steroid and gonadotropin releasing hormone analog combined treatment increased pubertal height gain and adult height in two children who entered puberty with short stature.
2006 Sep
Androgen receptor gene mutations in androgen insensitivity syndrome cause distinct patterns of reduced activation of androgen-responsive promoter constructs.
2006 Sep
[Incomplete androgen insensitivity].
2006 Sep 17
Angioedema: clinical and etiological aspects.
2007
Pharmacokinetics of boldenone and stanozolol and the results of quantification of anabolic and androgenic steroids in race horses and nonrace horses.
2007 Apr
Nanomolar concentrations of anabolic-androgenic steroids amplify excitotoxic neuronal death in mixed mouse cortical cultures.
2007 Aug 24
Guidelines for evaluation and management of urticaria in adults and children.
2007 Dec
Effects of anabolic androgenic steroids on the development and expression of running wheel activity and circadian rhythms in male rats.
2007 Dec 5
[Prevalence of the use of anabolic agents among strength training apprentices in Porto Alegre, RS].
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
Screening and confirmation criteria for hormone residue analysis using liquid chromatography accurate mass time-of-flight, Fourier transform ion cyclotron resonance and orbitrap mass spectrometry techniques.
2007 Mar 14
Current anti-doping policy: a critical appraisal.
2007 Mar 29
Determination of synthetic hormones in animal urine by high-performance liquid chromatography/mass spectrometry.
2007 Mar-Apr
[Clinical experiment of cytokines induced killer cells for treatment of benzene poisoning].
2007 Sep
Hereditary angioedema: Safety of long-term stanozolol therapy.
2007 Sep
Simultaneous immunochemical detection of stanozolol and the main human metabolite, 3'-hydroxy-stanozolol, in urine and serum samples.
2008 May 15
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
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 CIII
USP-RS  
Common Name English
Stanozolol [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C243
Created by admin on Fri Dec 15 16:27:01 GMT 2023 , Edited by admin on Fri Dec 15 16:27:01 GMT 2023
WHO-VATC QA14AA02
Created by admin on Fri Dec 15 16:27:01 GMT 2023 , Edited by admin on Fri Dec 15 16:27:01 GMT 2023
WIKIPEDIA Designer-drugs-Stanozolol
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CFR 21 CFR 520.2150
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CFR 21 CFR 522.2150
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LIVERTOX 898
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WHO-ATC A14AA02
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DEA NO. 4000
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NCI_THESAURUS C2360
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Code System Code Type Description
DRUG CENTRAL
2477
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PRIMARY
EPA CompTox
DTXSID3044128
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PRIMARY
CAS
302-96-5
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ALTERNATIVE
CAS
875293-72-4
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SUPERSEDED
MESH
D013197
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PRIMARY
INN
958
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PRIMARY
PUBCHEM
25249
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PRIMARY
HSDB
3185
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PRIMARY
CAS
69353-49-7
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SUPERSEDED
EVMPD
SUB10641MIG
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PRIMARY
NCI_THESAURUS
C842
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PRIMARY
CHEBI
9249
Created by admin on Fri Dec 15 16:27:01 GMT 2023 , Edited by admin on Fri Dec 15 16:27:01 GMT 2023
PRIMARY
CAS
10418-03-8
Created by admin on Fri Dec 15 16:27:01 GMT 2023 , Edited by admin on Fri Dec 15 16:27:01 GMT 2023
PRIMARY
ECHA (EC/EINECS)
233-894-8
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PRIMARY
CAS
17966-55-1
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SUPERSEDED
FDA UNII
4R1VB9P8V3
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PRIMARY
ChEMBL
CHEMBL2079587
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PRIMARY
WIKIPEDIA
STANOZOLOL
Created by admin on Fri Dec 15 16:27:01 GMT 2023 , Edited by admin on Fri Dec 15 16:27:01 GMT 2023
PRIMARY
SMS_ID
100000083853
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PRIMARY
RXCUI
10032
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PRIMARY RxNorm
NSC
233046
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PRIMARY
RS_ITEM_NUM
1620005
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PRIMARY
MERCK INDEX
m10191
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PRIMARY Merck Index
DRUG BANK
DB06718
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PRIMARY
NSC
43193
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PRIMARY
ACTIVE MOIETY
Structure of STANOZOLOL
METABOLITE (PARENT)
Structure of 3'-HYDROXYSTANOZOLOL
METABOLITE INACTIVE (PARENT)
Structure of 3-HYDROXYSTANOZOLOL GLUCURONIDE
NIH
NCATS
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ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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