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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
Anabolic steroids, testosterone-precursors and virilizing androgens induce distinct activation profiles of androgen responsive promoter constructs.
2002 Nov
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
Torpid ulcer on the achilles tendon: conservative treatment with stanozolol and pinch grafting.
2003 Feb
Improvement in steroid screening for doping control with special emphasis on stanozolol.
2003 Jan 24
Effects of stanozolol on bone mineral density and bone biomechanical properties of osteoporotic rats.
2003 Nov
Effects of pubertal anabolic-androgenic steroid (AAS) administration on reproductive and aggressive behaviors in male rats.
2003 Oct
Anabolic androgenic steroids and aggression: studies using animal models.
2004 Dec
Nonhealing ulcer secondary to factor V Leiden mutation and cryofibrinogenemia.
2004 Nov
[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
[Management of male sterility in patients taking anabolic steroids].
2005 Apr
First synthesis of a pentadeuterated 3'-hydroxystanozolol--an internal standard in doping analysis.
2005 Feb
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
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
Acquired angioedema secondary to hormone replacement therapy.
2005 Oct
Mitochondrial function in diaphragm of emphysematous hamsters after treatment with nandrolone.
2006
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
[Plasmapheresis in the treatment of cholestasis-induced pruritus].
2006 Feb 20
Immunosuppressive therapy for acquired severe aplastic anemia (SAA): a prospective comparison of four different regimens.
2006 Jul
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
[Turner syndrome].
2006 Jun 28
[Cholestatic injury by stanozolol intake].
2006 Mar
Stacking anabolic androgenic steroids (AAS) during puberty in rats: a neuroendocrine and behavioral assessment.
2006 Mar
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
Physical provocation of pubertal anabolic androgenic steroid exposed male rats elicits aggression towards females.
2006 Sep
[Incomplete androgen insensitivity].
2006 Sep 17
Pharmacokinetics of boldenone and stanozolol and the results of quantification of anabolic and androgenic steroids in race horses and nonrace horses.
2007 Apr
Atrial fibrillation and anabolic steroid abuse.
2007 Apr 25
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
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
Factors influencing aggression toward females by male rats exposed to anabolic androgenic steroids during puberty.
2007 Jan
[Gas chromatography/tandem mass-spectrometry assay for trace amounts of 3'-hydroxystanozolol].
2007 Jan-Feb
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
Differential growth of the freshwater mussel, Lamellidens marginalis in relation to certain drugs.
2008 Jun
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
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
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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
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
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