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

Details

Stereochemistry ABSOLUTE
Molecular Formula C21H32N2O
Molecular Weight 328.4924
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of STANOZOLOL

SMILES

C[C@@]12Cc3c[nH]nc3C[C@]2([H])CC[C@]4([H])[C@]1([H])CC[C@@]5(C)[C@@]4([H])CC[C@]5(C)O

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:: 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.

Originator

Sources: DOI: 10.1021/ja01515a060

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Low-affinity glucocorticoid-binding protein
30 nM [Ki]
Target ID: Stanosolol binding protein
30 nM [Kd]
4.5 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
WINSTROL

Approved Use

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

Launch Date

-251769600000
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
2.26 ng/mL
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
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
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
PubMed

PubMed

TitleDatePubMed
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
Confirmatory analysis of residues of stanozolol and its major metabolite in bovine urine by liquid chromatography-tandem mass spectrometry.
2001 Aug 10
Stanozolol in chronic urticaria: a double blind, placebo controlled trial.
2001 Jun
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
Physical provocation potentiates aggression in male rats receiving anabolic androgenic steroids.
2002 Feb
Hair analysis of seven bodybuilders for anabolic steroids, ephedrine, and clenbuterol.
2002 Jan
[Turner syndrome].
2002 Jan
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
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
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
Anabolic androgenic steroids and aggression: studies using animal models.
2004 Dec
Applicability of the SHBG androgen sensitivity test in the differential diagnosis of 46,XY gonadal dysgenesis, true hermaphroditism, and androgen insensitivity syndrome.
2004 May
[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
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
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
Mitochondrial function in diaphragm of emphysematous hamsters after treatment with nandrolone.
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
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
Nanomolar concentrations of anabolic-androgenic steroids amplify excitotoxic neuronal death in mixed mouse cortical cultures.
2007 Aug 24
Factors influencing aggression toward females by male rats exposed to anabolic androgenic steroids during puberty.
2007 Jan
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
Simultaneous immunochemical detection of stanozolol and the main human metabolite, 3'-hydroxy-stanozolol, in urine and serum samples.
2008 May 15
Patents

Patents

Sample Use Guides

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
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 [USP]
Common 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
STANOZOLOL [WHO-DD]
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 [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
Classification Tree Code System Code
NCI_THESAURUS C243
Created by admin on Fri Jun 25 21:17:49 UTC 2021 , Edited by admin on Fri Jun 25 21:17:49 UTC 2021
WHO-VATC QA14AA02
Created by admin on Fri Jun 25 21:17:49 UTC 2021 , Edited by admin on Fri Jun 25 21:17:49 UTC 2021
CFR 21 CFR 520.2150
Created by admin on Fri Jun 25 21:17:49 UTC 2021 , Edited by admin on Fri Jun 25 21:17:49 UTC 2021
CFR 21 CFR 522.2150
Created by admin on Fri Jun 25 21:17:49 UTC 2021 , Edited by admin on Fri Jun 25 21:17:49 UTC 2021
LIVERTOX 898
Created by admin on Fri Jun 25 21:17:49 UTC 2021 , Edited by admin on Fri Jun 25 21:17:49 UTC 2021
WHO-ATC A14AA02
Created by admin on Fri Jun 25 21:17:49 UTC 2021 , Edited by admin on Fri Jun 25 21:17:49 UTC 2021
DEA NO. 4000
Created by admin on Fri Jun 25 21:17:49 UTC 2021 , Edited by admin on Fri Jun 25 21:17:49 UTC 2021
NCI_THESAURUS C2360
Created by admin on Fri Jun 25 21:17:49 UTC 2021 , Edited by admin on Fri Jun 25 21:17:49 UTC 2021
Code System Code Type Description
DRUG CENTRAL
2477
Created by admin on Fri Jun 25 21:17:49 UTC 2021 , Edited by admin on Fri Jun 25 21:17:49 UTC 2021
PRIMARY
EPA CompTox
10418-03-8
Created by admin on Fri Jun 25 21:17:49 UTC 2021 , Edited by admin on Fri Jun 25 21:17:49 UTC 2021
PRIMARY
CAS
302-96-5
Created by admin on Fri Jun 25 21:17:49 UTC 2021 , Edited by admin on Fri Jun 25 21:17:49 UTC 2021
ALTERNATIVE
USP_CATALOG
1620005
Created by admin on Fri Jun 25 21:17:49 UTC 2021 , Edited by admin on Fri Jun 25 21:17:49 UTC 2021
PRIMARY USP-RS
CAS
875293-72-4
Created by admin on Fri Jun 25 21:17:49 UTC 2021 , Edited by admin on Fri Jun 25 21:17:49 UTC 2021
SUPERSEDED
MESH
D013197
Created by admin on Fri Jun 25 21:17:49 UTC 2021 , Edited by admin on Fri Jun 25 21:17:49 UTC 2021
PRIMARY
INN
958
Created by admin on Fri Jun 25 21:17:49 UTC 2021 , Edited by admin on Fri Jun 25 21:17:49 UTC 2021
PRIMARY
PUBCHEM
25249
Created by admin on Fri Jun 25 21:17:49 UTC 2021 , Edited by admin on Fri Jun 25 21:17:49 UTC 2021
PRIMARY
HSDB
3185
Created by admin on Fri Jun 25 21:17:49 UTC 2021 , Edited by admin on Fri Jun 25 21:17:49 UTC 2021
PRIMARY
CAS
69353-49-7
Created by admin on Fri Jun 25 21:17:49 UTC 2021 , Edited by admin on Fri Jun 25 21:17:49 UTC 2021
SUPERSEDED
EVMPD
SUB10641MIG
Created by admin on Fri Jun 25 21:17:49 UTC 2021 , Edited by admin on Fri Jun 25 21:17:49 UTC 2021
PRIMARY
NCI_THESAURUS
C842
Created by admin on Fri Jun 25 21:17:49 UTC 2021 , Edited by admin on Fri Jun 25 21:17:49 UTC 2021
PRIMARY
CAS
10418-03-8
Created by admin on Fri Jun 25 21:17:49 UTC 2021 , Edited by admin on Fri Jun 25 21:17:49 UTC 2021
PRIMARY
ECHA (EC/EINECS)
233-894-8
Created by admin on Fri Jun 25 21:17:49 UTC 2021 , Edited by admin on Fri Jun 25 21:17:49 UTC 2021
PRIMARY
CAS
17966-55-1
Created by admin on Fri Jun 25 21:17:49 UTC 2021 , Edited by admin on Fri Jun 25 21:17:49 UTC 2021
SUPERSEDED
FDA UNII
4R1VB9P8V3
Created by admin on Fri Jun 25 21:17:49 UTC 2021 , Edited by admin on Fri Jun 25 21:17:49 UTC 2021
PRIMARY
ChEMBL
CHEMBL2079587
Created by admin on Fri Jun 25 21:17:49 UTC 2021 , Edited by admin on Fri Jun 25 21:17:49 UTC 2021
PRIMARY
WIKIPEDIA
STANOZOLOL
Created by admin on Fri Jun 25 21:17:49 UTC 2021 , Edited by admin on Fri Jun 25 21:17:49 UTC 2021
PRIMARY
RXCUI
10032
Created by admin on Fri Jun 25 21:17:49 UTC 2021 , Edited by admin on Fri Jun 25 21:17:49 UTC 2021
PRIMARY RxNorm
MERCK INDEX
M10191
Created by admin on Fri Jun 25 21:17:49 UTC 2021 , Edited by admin on Fri Jun 25 21:17:49 UTC 2021
PRIMARY Merck Index
DRUG BANK
DB06718
Created by admin on Fri Jun 25 21:17:49 UTC 2021 , Edited by admin on Fri Jun 25 21:17:49 UTC 2021
PRIMARY