STANOZOLOL

US Previously Marketed

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 Search

SMILES

C[C@]1(O)CC[C@H]2[C@@H]3CC[C@H]4CC5=C(C[C@]4(C)[C@H]3CC[C@]12C)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
Sources: https://www.drugs.com/mtm/stanozolol.html
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

Approval Year

Targets

Primary Target	Pharmacology	Potency
Low-affinity glucocorticoid-binding protein 1 Target ID: Low-affinity glucocorticoid-binding protein Sources: https://www.ncbi.nlm.nih.gov/pubmed/14698206	Binding Agent 1076	30.0 nM [Ki]
Stanosolol binding protein 1 Target ID: Stanosolol binding protein Sources: https://www.ncbi.nlm.nih.gov/pubmed/10965910	Binding Agent 1076	30.0 nM [Kd]
Androgen Receptor 169 Target ID: CHEMBL1871 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6539197 \| http://www.genome.jp/dbget-bin/www_bget?D00444	Agonist 2752	4.5 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Angioedema 20 Sources: https://www.drugs.com/mtm/stanozolol.html https://www.ncbi.nlm.nih.gov/pubmed/17765757	Preventing		Approved 8583	WINSTROL Approved Use WINSTROL (anabolic steroids) is indicated prophylactically to decrease the frequency and severity of attacks of angioedema. Launch Date 1962

T_1/2

Value	Dose	Co-administered	Analyte	Population
9 h REVIEW https://books.google.com/books?id=w4ZUJAdleTsC&pg=PA358#v=onepage&q&f=false#page=358	single, oral		STANOZOLOL plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:9249	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:9249
ChemicalBook	CB0247357	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB0247357
eMolecules	31228973	https://www.emolecules.com/cgi-bin/more?vid=31228973
eMolecules	594442	https://www.emolecules.com/cgi-bin/more?vid=594442
MolPort	MolPort-003-959-588	https://www.molport.com/shop/molecule-link/MolPort-003-959-588
ZINC	ZINC000004097376	http://zinc15.docking.org/substances/ZINC000004097376

PubMed

Title	Date	PubMed
Masseteric hypertrophy associated with administration of anabolic steroids and unilateral mastication: a case report.	2001 Nov	11709687
Effects of withdrawal from anabolic androgenic steroids on aggression in adult male rats.	2002 Apr 1	12062318
Hair analysis of seven bodybuilders for anabolic steroids, ephedrine, and clenbuterol.	2002 Jan	12064656
Sources of variability in genetic association studies: insights from the analysis of hepatic lipase (LIPC).	2002 May	11968086
Hepatatis in growth promoter treated cows.	2002 Nov	12489869
Sports medicine update.	2002 Oct	12383079
Chronic administration of anabolic steroids disrupts pubertal onset and estrous cyclicity in rats.	2003 Feb	12533409
Improvement in steroid screening for doping control with special emphasis on stanozolol.	2003 Jan 24	12580506
Androgens in childhood acquired aplastic anaemia in Chandigarh, India.	2004 Jul	15267042
Applicability of the SHBG androgen sensitivity test in the differential diagnosis of 46,XY gonadal dysgenesis, true hermaphroditism, and androgen insensitivity syndrome.	2004 May	15146368
Nonhealing ulcer secondary to factor V Leiden mutation and cryofibrinogenemia.	2004 Nov	15577768
Detection of stanozolol and its metabolites in equine urine by liquid chromatography-electrospray ionization ion trap mass spectrometry.	2004 Nov 5	15458725
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	16259046
[Management of male sterility in patients taking anabolic steroids].	2005 Apr	15906618
[Influence of Shenmai injection on blood serum tumor necrosis factor and bone marrow CD34+ cell's apoptosis of chronic aplastic anemia patient].	2005 Aug	16245914
Analysis of anabolic steroids in the horse: development of a generic ELISA for the screening of 17alpha-alkyl anabolic steroid metabolites.	2005 Aug	16040239
Detection, quantification and confirmation of anabolic steroids in equine plasma by liquid chromatography and tandem mass spectrometry.	2005 Dec 27	16289956
First synthesis of a pentadeuterated 3'-hydroxystanozolol--an internal standard in doping analysis.	2005 Feb	15631866
Effects of chronic anabolic steroid treatment on tonic and reflex cardiovascular control in male rats.	2005 Jan	15748831
Intracerebroventricular self-administration of commonly abused anabolic-androgenic steroids in male hamsters (Mesocricetus auratus): nandrolone, drostanolone, oxymetholone, and stanozolol.	2005 Jun	15998196
Anabolic steroid-induced rhabdomyolysis.	2005 Jun	15974170
Mitochondrial function in diaphragm of emphysematous hamsters after treatment with nandrolone.	2006	18046906
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	17066372
Quantitative detection of doping substances by a localised surface plasmon sensor.	2006 Jan 15	15935632
Gas chromatography/mass spectrometry characterization of urinary metabolites of danazol after oral administration in human.	2006 Jan 2	16288903
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	16328719
Screening for anabolic steroids in doping analysis by liquid chromatography/electrospray ion trap mass spectrometry.	2006 May	16177960
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	17128560
[Incomplete androgen insensitivity].	2006 Sep 17	17131800
Angioedema: clinical and etiological aspects.	2007	18317527
Pharmacokinetics of boldenone and stanozolol and the results of quantification of anabolic and androgenic steroids in race horses and nonrace horses.	2007 Apr	17348894
Atrial fibrillation and anabolic steroid abuse.	2007 Apr 25	17337078
Nanomolar concentrations of anabolic-androgenic steroids amplify excitotoxic neuronal death in mixed mouse cortical cultures.	2007 Aug 24	17662261
Guidelines for evaluation and management of urticaria in adults and children.	2007 Dec	18021095
Effects of anabolic androgenic steroids on the development and expression of running wheel activity and circadian rhythms in male rats.	2007 Dec 5	17716697
[Prevalence of the use of anabolic agents among strength training apprentices in Porto Alegre, RS].	2007 Feb	17435863
High amounts of 17-methylated anabolic-androgenic steroids in effervescent tablets on the dietary supplement market.	2007 Feb	17146762
Lupus nephritis remission, albeit with positive anti-doping test.	2007 Jan	17254825
Factors influencing aggression toward females by male rats exposed to anabolic androgenic steroids during puberty.	2007 Jan	17049521
[Gas chromatography/tandem mass-spectrometry assay for trace amounts of 3'-hydroxystanozolol].	2007 Jan-Feb	17338339
Clinical study on effect of Astragalus Injection and its immuno-regulation action in treating chronic aplastic anemia.	2007 Jun	17609906
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	17386703
Current anti-doping policy: a critical appraisal.	2007 Mar 29	17394662
Determination of synthetic hormones in animal urine by high-performance liquid chromatography/mass spectrometry.	2007 Mar-Apr	17474533
[Clinical experiment of cytokines induced killer cells for treatment of benzene poisoning].	2007 Sep	17997890
Hereditary angioedema: Safety of long-term stanozolol therapy.	2007 Sep	17765757
Hereditary angioedema: a current state-of-the-art review, V: attenuated androgens for the treatment of hereditary angioedema.	2008 Jan	18220148
Natural selection and adaptive evolution of leptin in the ochotona family driven by the cold environmental stress.	2008 Jan 23	18213380
Differential growth of the freshwater mussel, Lamellidens marginalis in relation to certain drugs.	2008 Jun	18214892
Simultaneous immunochemical detection of stanozolol and the main human metabolite, 3'-hydroxy-stanozolol, in urine and serum samples.	2008 May 15	18339300

Patents

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 `Mon Mar 31 18:28:19 GMT 2025` Edited by `admin` on `Mon Mar 31 18:28:19 GMT 2025`
Record UNII	4R1VB9P8V3
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

STANOZOLOL

Official Name

English

STANOZOLOL CIII

Preferred 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 [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C243