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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
Molecular Formula C21H32N2O
Molecular Weight 328.4916
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 7 / 7
E/Z Centers 0
Optical Activity UNSPECIFIED

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
17-Epimerization of 17 alpha-methyl anabolic steroids in humans: metabolism and synthesis of 17 alpha-hydroxy-17 beta-methyl steroids.
1992 Nov
Multi-laboratory study of the analysis and kinetics of stanozolol and its metabolites in treated calves.
1998 Dec
Anabolic-androgenic steroids induce apoptotic cell death in adult rat ventricular myocytes.
2001 Apr
Anabolic steroid abuse and cardiac sudden death: a pathologic study.
2001 Feb
N-isobutyloxycarbonylation for improved detection of 3'-hydroxystanozolol and its 17-epimer in doping control.
2001 Mar
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
Molecular cloning and functional characterization of the canine androgen receptor.
2001 Oct
Effects of withdrawal from anabolic androgenic steroids on aggression in adult male rats.
2002 Apr 1
Hair analysis of seven bodybuilders for anabolic steroids, ephedrine, and clenbuterol.
2002 Jan
[Turner syndrome].
2002 Jan
'Skin popping' ulceration in an HIV patient. Successful treatment with antiretroviral drugs and stanozolol.
2002 Jul
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
Sports medicine update.
2002 Oct
[Cold-induced urticaria].
2002 Sep
Species, sex and inter-individual differences in DNA repair induced by nine sex steroids in primary cultures of rat and human hepatocytes.
2003 Apr 20
Effects of prolonged stanozolol treatment on antioxidant enzyme activities, oxidative stress markers, and heat shock protein HSP72 levels in rat liver.
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
Improvement in steroid screening for doping control with special emphasis on stanozolol.
2003 Jan 24
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
Two related cases of primary complement deficiency.
2003 Nov
Effects of pubertal anabolic-androgenic steroid (AAS) administration on reproductive and aggressive behaviors in male rats.
2003 Oct
Validation of a GC-MS screening method for anabolizing agents in solid nutritional supplements.
2004 Apr
Screening of free 17-alkyl-substituted anabolic steroids in human urine by liquid chromatography-electrospray ionization tandem mass spectrometry.
2004 Feb
[Clinical report on treatment of 7 patients with refractory anemia by using cyclosporin A].
2004 Oct
[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
First synthesis of a pentadeuterated 3'-hydroxystanozolol--an internal standard in doping analysis.
2005 Feb
Validation of a GC-MS screening method for anabolizing agents in aqueous nutritional supplements.
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
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
Successful treatment of primary refractory anemia with a combination regimen of all-trans retinoic acid, calcitriol, and androgen.
2006 Aug
Quantitative detection of doping substances by a localised surface plasmon sensor.
2006 Jan 15
Screening for anabolic steroids in doping analysis by liquid chromatography/electrospray ion trap mass spectrometry.
2006 May
Androgen receptor gene mutations in androgen insensitivity syndrome cause distinct patterns of reduced activation of androgen-responsive promoter constructs.
2006 Sep
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
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
Clinical study on effect of Astragalus Injection and its immuno-regulation action in treating chronic aplastic anemia.
2007 Jun
[Clinical experiment of cytokines induced killer cells for treatment of benzene poisoning].
2007 Sep
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:27:01 GMT 2023
Edited
by admin
on Fri Dec 15 16:27:01 GMT 2023
Record UNII
4R1VB9P8V3
Record Status Validated (UNII)
Record Version
  • Download
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
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 522.2150
Created by admin on Fri Dec 15 16:27:01 GMT 2023 , Edited by admin on Fri Dec 15 16:27:01 GMT 2023
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
Created by admin on Fri Dec 15 16:27:01 GMT 2023 , Edited by admin on Fri Dec 15 16:27:01 GMT 2023
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
Created by admin on Fri Dec 15 16:27:01 GMT 2023 , Edited by admin on Fri Dec 15 16:27:01 GMT 2023
Code System Code Type Description
DRUG CENTRAL
2477
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
EPA CompTox
DTXSID3044128
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
302-96-5
Created by admin on Fri Dec 15 16:27:01 GMT 2023 , Edited by admin on Fri Dec 15 16:27:01 GMT 2023
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
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
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
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
MERCK INDEX
m10191
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 Merck Index
DRUG BANK
DB06718
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
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
Related Record Type Details
Structure of 3'-HYDROXYSTANOZOLOL
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METABOLITE -> PARENT
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Structure of 16.ALPHA.-HYDROXYSTANOZOLOL
METABOLITE -> PARENT
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Structure of 3-HYDROXYSTANOZOLOL GLUCURONIDE
METABOLITE INACTIVE -> PARENT
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Structure of STANOZOLOL
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