Identification

Name
Stanozolol
Accession Number
DB06718
Type
Small Molecule
Groups
Approved, Vet approved
Description

Stanozolol is a synthetic anabolic steroid with therapeutic uses in treating hereditary angioedema. Stanozolol is derived from testosterone, and has been abused by several high profile professional athletes.

Structure
Thumb
Synonyms
  • androstanazol
  • androstanazole
External IDs
NSC-43193 / WIN 14833
International/Other Brands
Stromba / Winstrol / Winstrol Depot
Categories
UNII
4R1VB9P8V3
CAS number
10418-03-8
Weight
Average: 328.4916
Monoisotopic: 328.251463656
Chemical Formula
C21H32N2O
InChI Key
LKAJKIOFIWVMDJ-IYRCEVNGSA-N
InChI
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
IUPAC Name
(1S,2S,10S,13R,14S,17S,18S)-2,17,18-trimethyl-6,7-diazapentacyclo[11.7.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁸]icosa-4,7-dien-17-ol
SMILES
[H][C@@]12CC[C@](C)(O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])CC3=NNC=C3C[C@]12C

Pharmacology

Indication

Stanozolol is a synthetic anabolic steroid with therapeutic uses in treating C1-inhibitor deficient hereditary angioedema. C1-inhibitor is a protease that inhibits the complement system (part of the innate immune system), a biochemical chain of reactions which assists the body in removing pathogens from the body. Stanozolol may help control attacks of hereditary angioedema. Stanozolol can be administered orally or intramuscularly.

Pharmacodynamics

Stanozolol is a synthetic anabolic-androgenic steroid (AAS), which promotes cell growth (anabolism) and development/maintenance of masculine characteristics (androgenism).

Mechanism of action

Stanozolol binds to androgen receptors, such as membrane bound receptor proteins LAGS and stanozolol-binding protein (STBP).

TargetActionsOrganism
U Stanozolol Binding Protein (STBP)
other
Human
ULow-affinity glucocorticoid-binding protein (LAGS)
negative modulator
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life

24 hours

Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
16-Bromoepiandrosterone16-Bromoepiandrosterone may increase the fluid retaining activities of Stanozolol.Investigational
19-norandrostenedione19-norandrostenedione may increase the fluid retaining activities of Stanozolol.Experimental, Illicit
5-androstenedione5-androstenedione may increase the fluid retaining activities of Stanozolol.Experimental, Illicit
AcarboseStanozolol may increase the hypoglycemic activities of Acarbose.Approved, Investigational
AcenocoumarolStanozolol may increase the anticoagulant activities of Acenocoumarol.Approved, Investigational
AlbiglutideStanozolol may increase the hypoglycemic activities of Albiglutide.Approved
AlclometasoneAlclometasone may increase the fluid retaining activities of Stanozolol.Approved
AldosteroneAldosterone may increase the fluid retaining activities of Stanozolol.Experimental, Investigational
AlogliptinStanozolol may increase the hypoglycemic activities of Alogliptin.Approved
AmcinonideAmcinonide may increase the fluid retaining activities of Stanozolol.Approved
AndrostenedioneAndrostenedione may increase the fluid retaining activities of Stanozolol.Experimental, Illicit
AnecortaveAnecortave may increase the fluid retaining activities of Stanozolol.Investigational
anecortave acetateanecortave acetate may increase the fluid retaining activities of Stanozolol.Investigational
AtamestaneAtamestane may increase the fluid retaining activities of Stanozolol.Investigational
Beclomethasone dipropionateThe risk or severity of fluid retention can be increased when Beclomethasone dipropionate is combined with Stanozolol.Approved, Investigational
BetamethasoneBetamethasone may increase the fluid retaining activities of Stanozolol.Approved, Vet Approved
BromocriptineStanozolol may increase the hypoglycemic activities of Bromocriptine.Approved, Investigational
BudesonideThe risk or severity of fluid retention can be increased when Budesonide is combined with Stanozolol.Approved
CanagliflozinStanozolol may increase the hypoglycemic activities of Canagliflozin.Approved
ChlorpropamideStanozolol may increase the hypoglycemic activities of Chlorpropamide.Approved, Investigational
CiclesonideCiclesonide may increase the fluid retaining activities of Stanozolol.Approved, Investigational
ClobetasolClobetasol may increase the fluid retaining activities of Stanozolol.Approved, Investigational
Clobetasol propionateClobetasol propionate may increase the fluid retaining activities of Stanozolol.Approved
ClobetasoneClobetasone may increase the fluid retaining activities of Stanozolol.Approved
ClocortoloneClocortolone may increase the fluid retaining activities of Stanozolol.Approved
ClorindioneStanozolol may increase the anticoagulant activities of Clorindione.Experimental
Conestat alfaStanozolol may increase the thrombogenic activities of Conestat alfa.Approved, Investigational
Cortexolone 17α-propionateCortexolone 17α-propionate may increase the fluid retaining activities of Stanozolol.Investigational
CorticosteroneCorticosterone may increase the fluid retaining activities of Stanozolol.Experimental
Cortisone acetateCortisone acetate may increase the fluid retaining activities of Stanozolol.Approved, Investigational
CyclosporineStanozolol may increase the hepatotoxic activities of Cyclosporine.Approved, Investigational, Vet Approved
DapagliflozinStanozolol may increase the hypoglycemic activities of Dapagliflozin.Approved
DeflazacortDeflazacort may increase the fluid retaining activities of Stanozolol.Approved, Investigational
DesonideDesonide may increase the fluid retaining activities of Stanozolol.Approved, Investigational
DesoximetasoneDesoximetasone may increase the fluid retaining activities of Stanozolol.Approved
Desoxycorticosterone acetateDesoxycorticosterone acetate may increase the fluid retaining activities of Stanozolol.Approved
Desoxycorticosterone PivalateDesoxycorticosterone Pivalate may increase the fluid retaining activities of Stanozolol.Experimental, Vet Approved
DexamethasoneThe risk or severity of fluid retention can be increased when Dexamethasone is combined with Stanozolol.Approved, Investigational, Vet Approved
Dexamethasone isonicotinateDexamethasone isonicotinate may increase the fluid retaining activities of Stanozolol.Vet Approved
DicoumarolStanozolol may increase the anticoagulant activities of Dicoumarol.Approved
DiflorasoneDiflorasone may increase the fluid retaining activities of Stanozolol.Approved
DifluocortoloneDifluocortolone may increase the fluid retaining activities of Stanozolol.Approved, Investigational, Withdrawn
DifluprednateDifluprednate may increase the fluid retaining activities of Stanozolol.Approved
DiphenadioneStanozolol may increase the anticoagulant activities of Diphenadione.Experimental
DisopyramideStanozolol may increase the hypoglycemic activities of Disopyramide.Approved
DulaglutideStanozolol may increase the hypoglycemic activities of Dulaglutide.Approved, Investigational
EmpagliflozinStanozolol may increase the hypoglycemic activities of Empagliflozin.Approved
EquileninEquilenin may increase the fluid retaining activities of Stanozolol.Experimental
EquilinEquilin may increase the fluid retaining activities of Stanozolol.Approved
EstroneEstrone may increase the fluid retaining activities of Stanozolol.Approved
Estrone sulfateEstrone sulfate may increase the fluid retaining activities of Stanozolol.Approved
Ethyl biscoumacetateStanozolol may increase the anticoagulant activities of Ethyl biscoumacetate.Withdrawn
ExenatideStanozolol may increase the hypoglycemic activities of Exenatide.Approved, Investigational
FluasteroneFluasterone may increase the fluid retaining activities of Stanozolol.Investigational
FludrocortisoneFludrocortisone may increase the fluid retaining activities of Stanozolol.Approved, Investigational
FluindioneStanozolol may increase the anticoagulant activities of Fluindione.Approved, Investigational
FlumethasoneFlumethasone may increase the fluid retaining activities of Stanozolol.Approved, Vet Approved
FlunisolideFlunisolide may increase the fluid retaining activities of Stanozolol.Approved, Investigational
Fluocinolone AcetonideFluocinolone Acetonide may increase the fluid retaining activities of Stanozolol.Approved, Investigational, Vet Approved
FluocinonideFluocinonide may increase the fluid retaining activities of Stanozolol.Approved, Investigational
FluocortoloneFluocortolone may increase the fluid retaining activities of Stanozolol.Approved, Withdrawn
FluorometholoneFluorometholone may increase the fluid retaining activities of Stanozolol.Approved, Investigational
FluprednideneFluprednidene may increase the fluid retaining activities of Stanozolol.Approved, Withdrawn
FluprednisoloneFluprednisolone may increase the fluid retaining activities of Stanozolol.Approved
FlurandrenolideFlurandrenolide may increase the fluid retaining activities of Stanozolol.Approved
FluticasoneFluticasone may increase the fluid retaining activities of Stanozolol.Approved, Experimental, Investigational
Fluticasone furoateFluticasone furoate may increase the fluid retaining activities of Stanozolol.Approved
Fluticasone propionateThe risk or severity of fluid retention can be increased when Fluticasone propionate is combined with Stanozolol.Approved
FormestaneFormestane may increase the fluid retaining activities of Stanozolol.Approved, Investigational, Withdrawn
GabexateStanozolol may increase the thrombogenic activities of Gabexate.Investigational
GliclazideStanozolol may increase the hypoglycemic activities of Gliclazide.Approved
GlimepirideStanozolol may increase the hypoglycemic activities of Glimepiride.Approved
GlipizideStanozolol may increase the hypoglycemic activities of Glipizide.Approved, Investigational
GlyburideStanozolol may increase the hypoglycemic activities of Glyburide.Approved
HalcinonideHalcinonide may increase the fluid retaining activities of Stanozolol.Approved, Investigational, Withdrawn
HE3286HE3286 may increase the fluid retaining activities of Stanozolol.Investigational
Human C1-esterase inhibitorStanozolol may increase the thrombogenic activities of Human C1-esterase inhibitor.Approved
HydrocortisoneThe risk or severity of fluid retention can be increased when Hydrocortisone is combined with Stanozolol.Approved, Vet Approved
Hydrocortisone acetateThe risk or severity of fluid retention can be increased when Hydrocortisone acetate is combined with Stanozolol.Approved, Vet Approved
Hydrocortisone butyrateThe risk or severity of fluid retention can be increased when Hydrocortisone butyrate is combined with Stanozolol.Approved, Vet Approved
Insulin AspartStanozolol may increase the hypoglycemic activities of Insulin Aspart.Approved
Insulin DetemirStanozolol may increase the hypoglycemic activities of Insulin Detemir.Approved
Insulin GlargineStanozolol may increase the hypoglycemic activities of Insulin Glargine.Approved
Insulin GlulisineStanozolol may increase the hypoglycemic activities of Insulin Glulisine.Approved
Insulin HumanStanozolol may increase the hypoglycemic activities of Insulin Human.Approved, Investigational
Insulin LisproStanozolol may increase the hypoglycemic activities of Insulin Lispro.Approved
IstaroximeIstaroxime may increase the fluid retaining activities of Stanozolol.Investigational
LiraglutideStanozolol may increase the hypoglycemic activities of Liraglutide.Approved
LoteprednolLoteprednol may increase the fluid retaining activities of Stanozolol.Approved
ME-609ME-609 may increase the fluid retaining activities of Stanozolol.Investigational
MecaserminStanozolol may increase the hypoglycemic activities of Mecasermin.Approved, Investigational
MedrysoneMedrysone may increase the fluid retaining activities of Stanozolol.Approved
MelengestrolMelengestrol may increase the fluid retaining activities of Stanozolol.Vet Approved
MetforminStanozolol may increase the hypoglycemic activities of Metformin.Approved
MethylprednisoloneThe risk or severity of fluid retention can be increased when Methylprednisolone is combined with Stanozolol.Approved, Vet Approved
MifepristoneStanozolol may increase the hypoglycemic activities of Mifepristone.Approved, Investigational
MiglitolStanozolol may increase the hypoglycemic activities of Miglitol.Approved
MometasoneMometasone may increase the fluid retaining activities of Stanozolol.Approved, Vet Approved
NateglinideStanozolol may increase the hypoglycemic activities of Nateglinide.Approved, Investigational
NCX 1022NCX 1022 may increase the fluid retaining activities of Stanozolol.Investigational
Oleoyl-estroneOleoyl-estrone may increase the fluid retaining activities of Stanozolol.Investigational
ParamethasoneParamethasone may increase the fluid retaining activities of Stanozolol.Approved
PentamidineStanozolol may increase the hypoglycemic activities of Pentamidine.Approved, Investigational
PhenindioneStanozolol may increase the anticoagulant activities of Phenindione.Approved, Investigational
PhenprocoumonStanozolol may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational
PioglitazoneStanozolol may increase the hypoglycemic activities of Pioglitazone.Approved, Investigational
PramlintideStanozolol may increase the hypoglycemic activities of Pramlintide.Approved, Investigational
PrasteronePrasterone may increase the fluid retaining activities of Stanozolol.Approved, Investigational, Nutraceutical
Prasterone sulfatePrasterone sulfate may increase the fluid retaining activities of Stanozolol.Investigational
PrednicarbatePrednicarbate may increase the fluid retaining activities of Stanozolol.Approved, Investigational
PrednisoloneThe risk or severity of fluid retention can be increased when Prednisolone is combined with Stanozolol.Approved, Vet Approved
PrednisonePrednisone may increase the fluid retaining activities of Stanozolol.Approved, Vet Approved
PregnenolonePregnenolone may increase the fluid retaining activities of Stanozolol.Approved, Experimental, Investigational
QuinineStanozolol may increase the hypoglycemic activities of Quinine.Approved
RepaglinideStanozolol may increase the hypoglycemic activities of Repaglinide.Approved, Investigational
RimexoloneRimexolone may increase the fluid retaining activities of Stanozolol.Approved
RosiglitazoneStanozolol may increase the hypoglycemic activities of Rosiglitazone.Approved, Investigational
SaxagliptinStanozolol may increase the hypoglycemic activities of Saxagliptin.Approved
SitagliptinStanozolol may increase the hypoglycemic activities of Sitagliptin.Approved, Investigational
SulfadiazineStanozolol may increase the hypoglycemic activities of Sulfadiazine.Approved, Investigational, Vet Approved
SulfamethoxazoleStanozolol may increase the hypoglycemic activities of Sulfamethoxazole.Approved
SulfisoxazoleStanozolol may increase the hypoglycemic activities of Sulfisoxazole.Approved, Vet Approved
SunitinibStanozolol may increase the hypoglycemic activities of Sunitinib.Approved, Investigational
TioclomarolStanozolol may increase the anticoagulant activities of Tioclomarol.Experimental
TixocortolTixocortol may increase the fluid retaining activities of Stanozolol.Approved, Withdrawn
TolazamideStanozolol may increase the hypoglycemic activities of Tolazamide.Approved, Investigational
TolbutamideStanozolol may increase the hypoglycemic activities of Tolbutamide.Approved, Investigational
TriamcinoloneTriamcinolone may increase the fluid retaining activities of Stanozolol.Approved, Vet Approved
UlobetasolUlobetasol may increase the fluid retaining activities of Stanozolol.Approved
WarfarinStanozolol may increase the anticoagulant activities of Warfarin.Approved
Food Interactions
Not Available

References

General References
  1. Guilarte M, Luengo O, Nogueiras C, Labrador-Horrillo M, Munoz E, Lopez A, Cardona V: Acquired angioedema associated with hereditary angioedema due to C1 inhibitor deficiency. J Investig Allergol Clin Immunol. 2008;18(2):126-30. [PubMed:18447143]
  2. Thevis M, Schanzer W: Synthetic anabolic agents: steroids and nonsteroidal selective androgen receptor modulators. Handb Exp Pharmacol. 2010;(195):99-126. doi: 10.1007/978-3-540-79088-4_5. [PubMed:20020362]
  3. Sloane DE, Lee CW, Sheffer AL: Hereditary angioedema: Safety of long-term stanozolol therapy. J Allergy Clin Immunol. 2007 Sep;120(3):654-8. [PubMed:17765757]
External Links
Human Metabolome Database
HMDB0003116
KEGG Drug
D00444
KEGG Compound
C07311
PubChem Compound
25249
PubChem Substance
99443270
ChemSpider
23582
ChEBI
9249
ChEMBL
CHEMBL2079587
PharmGKB
PA165958391
Wikipedia
Stanozolol
ATC Codes
A14AA02 — Stanozolol

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00173 mg/mLALOGPS
logP4.33ALOGPS
logP3.81ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)16.23ChemAxon
pKa (Strongest Basic)2.86ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area48.91 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity96.8 m3·mol-1ChemAxon
Polarizability39.22 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9745
Caco-2 permeable+0.5
P-glycoprotein substrateSubstrate0.6928
P-glycoprotein inhibitor INon-inhibitor0.7667
P-glycoprotein inhibitor IINon-inhibitor0.8443
Renal organic cation transporterNon-inhibitor0.7071
CYP450 2C9 substrateNon-substrate0.792
CYP450 2D6 substrateNon-substrate0.7667
CYP450 3A4 substrateSubstrate0.6765
CYP450 1A2 substrateInhibitor0.5646
CYP450 2C9 inhibitorNon-inhibitor0.5135
CYP450 2D6 inhibitorNon-inhibitor0.8852
CYP450 2C19 inhibitorInhibitor0.6303
CYP450 3A4 inhibitorInhibitor0.6272
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5576
Ames testNon AMES toxic0.6989
CarcinogenicityNon-carcinogens0.8476
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.5131 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9218
hERG inhibition (predictor II)Non-inhibitor0.6182
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as estrane steroids. These are steroids with a structure based on the estrane skeleton.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Estrane steroids
Direct Parent
Estrane steroids
Alternative Parents
17-hydroxysteroids / Tertiary alcohols / Pyrazoles / Heteroaromatic compounds / Cyclic alcohols and derivatives / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Hydrocarbon derivatives
Substituents
Estrane-skeleton / Hydroxysteroid / 17-hydroxysteroid / Azole / Cyclic alcohol / Pyrazole / Tertiary alcohol / Heteroaromatic compound / Organoheterocyclic compound / Azacycle
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
tertiary alcohol, organic heteropentacyclic compound, 17beta-hydroxy steroid, anabolic androgenic steroid (CHEBI:9249) / Androstane and derivatives (C07311)

Targets

1. Stanozolol Binding Protein (STBP)
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Other
References
  1. Luzardo OP, Machin RP, Diaz-Chico BN, Fernandez L: Photoaffinity labeling identification of a specific binding protein for the anabolic steroids stanozolol and danazol: an oligomeric protein regulated by age, pituitary hormones, and ethinyl estradiol. Endocrinology. 2000 Sep;141(9):3377-87. [PubMed:10965910]
  2. Betancor-Hernandez E, Perez-Machin R, Henriquez-Hernandez L, Mateos-Diaz C, Novoa-Mogollon J, Fernandez-Perez L: 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. J Steroid Biochem Mol Biol. 2003 Dec;87(4-5):253-64. [PubMed:14698206]
2. Low-affinity glucocorticoid-binding protein (LAGS)
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Negative modulator
References
  1. Betancor-Hernandez E, Perez-Machin R, Henriquez-Hernandez L, Mateos-Diaz C, Novoa-Mogollon J, Fernandez-Perez L: 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. J Steroid Biochem Mol Biol. 2003 Dec;87(4-5):253-64. [PubMed:14698206]

Drug created on May 17, 2010 12:57 / Updated on August 02, 2018 05:38