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
Differential growth of the freshwater mussel, Lamellidens marginalis in relation to certain drugs.	2008-06	18214892
Simultaneous immunochemical detection of stanozolol and the main human metabolite, 3'-hydroxy-stanozolol, in urine and serum samples.	2008-05-15	18339300
Natural selection and adaptive evolution of leptin in the ochotona family driven by the cold environmental stress.	2008-01-23	18213380
Hereditary angioedema: a current state-of-the-art review, V: attenuated androgens for the treatment of hereditary angioedema.	2008-01	18220148
Effects of anabolic androgenic steroids on the development and expression of running wheel activity and circadian rhythms in male rats.	2007-12-05	17716697
Guidelines for evaluation and management of urticaria in adults and children.	2007-12	18021095
[Clinical experiment of cytokines induced killer cells for treatment of benzene poisoning].	2007-09	17997890
Hereditary angioedema: Safety of long-term stanozolol therapy.	2007-09	17765757
Nanomolar concentrations of anabolic-androgenic steroids amplify excitotoxic neuronal death in mixed mouse cortical cultures.	2007-08-24	17662261
Clinical study on effect of Astragalus Injection and its immuno-regulation action in treating chronic aplastic anemia.	2007-06	17609906
Determination of synthetic hormones in animal urine by high-performance liquid chromatography/mass spectrometry.	2007-05-04	17474533
Atrial fibrillation and anabolic steroid abuse.	2007-04-25	17337078
Pharmacokinetics of boldenone and stanozolol and the results of quantification of anabolic and androgenic steroids in race horses and nonrace horses.	2007-04	17348894
Current anti-doping policy: a critical appraisal.	2007-03-29	17394662
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.	2007-03-14	17386703
[Gas chromatography/tandem mass-spectrometry assay for trace amounts of 3'-hydroxystanozolol].	2007-03-07	17338339
[Prevalence of the use of anabolic agents among strength training apprentices in Porto Alegre, RS].	2007-02	17435863
High amounts of 17-methylated anabolic-androgenic steroids in effervescent tablets on the dietary supplement market.	2007-02	17146762
Lupus nephritis remission, albeit with positive anti-doping test.	2007-01	17254825
Factors influencing aggression toward females by male rats exposed to anabolic androgenic steroids during puberty.	2007-01	17049521
Angioedema: clinical and etiological aspects.	2007	18317527
[Incomplete androgen insensitivity].	2006-09-17	17131800
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.	2006-09	17128560
Androgen receptor gene mutations in androgen insensitivity syndrome cause distinct patterns of reduced activation of androgen-responsive promoter constructs.	2006-09	16930995
Physical provocation of pubertal anabolic androgenic steroid exposed male rats elicits aggression towards females.	2006-09	16870187
Successful treatment of primary refractory anemia with a combination regimen of all-trans retinoic acid, calcitriol, and androgen.	2006-08	16445979
Immunosuppressive therapy for acquired severe aplastic anemia (SAA): a prospective comparison of four different regimens.	2006-07	16797409
Impaired vasoreactivity in bodybuilders using androgenic anabolic steroids.	2006-07	16796605
[Turner syndrome].	2006-06-28	16817448
Clinical observation on treatment of chronic aplastic anemia by Shengxuening and cyclosporin A.	2006-06	16800995
Synchronous bilateral ductal carcinoma in situ of the male breast associated with gynecomastia in a 30-year-old patient following repeated injections of stanozolol.	2006-05	16328719
Screening for anabolic steroids in doping analysis by liquid chromatography/electrospray ion trap mass spectrometry.	2006-05	16177960
[Cholestatic injury by stanozolol intake].	2006-03	16737422
Stacking anabolic androgenic steroids (AAS) during puberty in rats: a neuroendocrine and behavioral assessment.	2006-03	16603236
[Plasmapheresis in the treatment of cholestasis-induced pruritus].	2006-02-20	16499841
Quantitative detection of doping substances by a localised surface plasmon sensor.	2006-01-15	15935632
Gas chromatography/mass spectrometry characterization of urinary metabolites of danazol after oral administration in human.	2006-01-02	16288903
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
Detection, quantification and confirmation of anabolic steroids in equine plasma by liquid chromatography and tandem mass spectrometry.	2005-12-27	16289956
Acquired angioedema secondary to hormone replacement therapy.	2005-10	16272680
[Influence of Shenmai injection on blood serum tumor necrosis factor and bone marrow CD34+ cell's apoptosis of chronic aplastic anemia patient].	2005-08	16245914
Analysis of anabolic steroids in the horse: development of a generic ELISA for the screening of 17alpha-alkyl anabolic steroid metabolites.	2005-08	16040239
Intracerebroventricular self-administration of commonly abused anabolic-androgenic steroids in male hamsters (Mesocricetus auratus): nandrolone, drostanolone, oxymetholone, and stanozolol.	2005-06	15998196
Anabolic steroid-induced rhabdomyolysis.	2005-06	15974170
Hepatocellular adenomas associated with anabolic androgenic steroid abuse in bodybuilders: a report of two cases and a review of the literature.	2005-05	15849280
[Management of male sterility in patients taking anabolic steroids].	2005-04	15906618
Anabolic-androgenic steroid interaction with rat androgen receptor in vivo and in vitro: a comparative study.	2005-04	15876413
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
The detection of danazol and its significance in doping analysis.	1992-01-01	1640693

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