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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

[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
Multi-laboratory study of the analysis and kinetics of stanozolol and its metabolites in treated calves.
1998 Dec
Testing for anabolic steroids in hair from two bodybuilders.
1999 May 17
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
Phenotypic variation in a family with partial androgen insensitivity syndrome explained by differences in 5alpha dihydrotestosterone availability.
2001 Mar
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
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
Hepatatis in growth promoter treated cows.
2002 Nov
Sports medicine update.
2002 Oct
[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
Effects of stanozolol on bone mineral density and bone biomechanical properties of osteoporotic rats.
2003 Nov
Two related cases of primary complement deficiency.
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
Effects of pubertal anabolic-androgenic steroid (AAS) administration on reproductive and aggressive behaviors in male rats.
2003 Oct
Oxandrolone treatment of childhood hereditary angioedema.
2004 Mar
[Clinical report on treatment of 7 patients with refractory anemia by using cyclosporin A].
2004 Oct
Anabolic-androgenic steroid interaction with rat androgen receptor in vivo and in vitro: a comparative study.
2005 Apr
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
First synthesis of a pentadeuterated 3'-hydroxystanozolol--an internal standard in doping analysis.
2005 Feb
Effects of chronic anabolic steroid treatment on tonic and reflex cardiovascular control in male rats.
2005 Jan
Anabolic steroid-induced rhabdomyolysis.
2005 Jun
Hepatocellular adenomas associated with anabolic androgenic steroid abuse in bodybuilders: a report of two cases and a review of the literature.
2005 May
Gas chromatography/mass spectrometry characterization of urinary metabolites of danazol after oral administration in human.
2006 Jan 2
Impaired vasoreactivity in bodybuilders using androgenic anabolic steroids.
2006 Jul
Clinical observation on treatment of chronic aplastic anemia by Shengxuening and cyclosporin A.
2006 Jun
Stacking anabolic androgenic steroids (AAS) during puberty in rats: a neuroendocrine and behavioral assessment.
2006 Mar
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
Nanomolar concentrations of anabolic-androgenic steroids amplify excitotoxic neuronal death in mixed mouse cortical cultures.
2007 Aug 24
Effects of anabolic androgenic steroids on the development and expression of running wheel activity and circadian rhythms in male rats.
2007 Dec 5
Clinical study on effect of Astragalus Injection and its immuno-regulation action in treating chronic aplastic anemia.
2007 Jun
Hereditary angioedema: Safety of long-term stanozolol therapy.
2007 Sep
Hereditary angioedema: a current state-of-the-art review, V: attenuated androgens for the treatment of hereditary angioedema.
2008 Jan
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
Created by admin on Fri Dec 15 16:27:01 GMT 2023 , Edited by admin on Fri Dec 15 16:27:01 GMT 2023
CFR 21 CFR 520.2150
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CFR 21 CFR 522.2150
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LIVERTOX 898
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-ATC A14AA02
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DEA NO. 4000
Created by admin on Fri Dec 15 16:27:01 GMT 2023 , Edited by admin on Fri Dec 15 16:27:01 GMT 2023
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
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
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
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
17966-55-1
Created by admin on Fri Dec 15 16:27:01 GMT 2023 , Edited by admin on Fri Dec 15 16:27:01 GMT 2023
SUPERSEDED
FDA UNII
4R1VB9P8V3
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PRIMARY
ChEMBL
CHEMBL2079587
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
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
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
RXCUI
10032
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 RxNorm
NSC
233046
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
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
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
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
HHS VULNERABILITY DISCLOSURE
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