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Identification
NameOxandrolone
Accession NumberDB00621  (APRD01151)
TypeSmall Molecule
GroupsApproved, Investigational
DescriptionA synthetic hormone with anabolic and androgenic properties. [PubChem]
Structure
Thumb
Synonyms
Ossandrolone
Oxandrolon
Oxandrolona
Oxandrolone
Oxandrolonum
Protivar
External Identifiers
  • CB 8075
  • SC 11585
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
OxandroloneTablet2.5 mg/1OralWatson Laboratories, Inc.2007-01-012016-03-01Us
OxandroloneTablet10 mg/1OralWatson Laboratories, Inc.2007-01-012016-03-01Us
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
OxandroloneTablet2.5 mg/1OralUpsher Smith Laboratories, Inc.2006-12-01Not applicableUs
OxandroloneTablet10 mg/1OralAmerican Health Packaging2015-03-30Not applicableUs
OxandroloneTablet10 mg/1OralUpsher Smith Laboratories, Inc.2007-03-22Not applicableUs
OxandroloneTablet2.5 mg/1OralPar Pharmaceutical, Inc.2007-08-20Not applicableUs
OxandroloneTablet10 mg/1OralA S Medication Solutions Llc2007-08-20Not applicableUs
OxandroloneTablet10 mg/1OralPar Pharmaceutical, Inc.2007-08-20Not applicableUs
OxandroloneTablet2.5 mg/1OralAmerican Health Packaging2015-03-30Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
AnavarPfizer Inc.
OxandrinSavient Pharmaceuticals
XtendrolAtlantis
Brand mixturesNot Available
SaltsNot Available
Categories
UNII7H6TM3CT4L
CAS number53-39-4
WeightAverage: 306.4397
Monoisotopic: 306.219494826
Chemical FormulaC19H30O3
InChI KeyQSLJIVKCVHQPLV-PEMPUTJUSA-N
InChI
InChI=1S/C19H30O3/c1-17-11-22-16(20)10-12(17)4-5-13-14(17)6-8-18(2)15(13)7-9-19(18,3)21/h12-15,21H,4-11H2,1-3H3/t12-,13+,14-,15-,17-,18-,19-/m0/s1
IUPAC Name
(1S,2S,7S,10R,11S,14S,15S)-14-hydroxy-2,14,15-trimethyl-4-oxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-one
SMILES
[H][C@@]12CC[C@](C)(O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])CC(=O)OC[C@]12C
Pharmacology
IndicationUse to promote weight gain after weight loss following extensive surgery.
Structured Indications
PharmacodynamicsOxandrolone is an anabolic steroids indicated as adjunctive therapy to promote weight gain after weight loss following extensive surgery, chronic infections, or severe trauma, and in some patients who without definite pathophysiologic reasons fail to gain or to maintain normal weight, to offset the protein catabolism associated with prolonged administration of corticosteroids, and for the relief of the bone pain frequently accompanying osteoporosis. Anabolic steroids are synthetic derivatives of testosterone.
Mechanism of actionOxandrolones interact with androgen receptors in target tissues.
TargetKindPharmacological actionActionsOrganismUniProt ID
Androgen receptorProteinyes
agonist
HumanP10275 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Renal

Route of eliminationNot Available
Half life0.55 hours (1st phage), 9 hours (2nd phase)
ClearanceNot Available
ToxicityThe oral LD50 of oxandrolone in mice and dogs is greater than 5,000 mg/kg.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
16-Bromoepiandrosterone16-Bromoepiandrosterone may increase the fluid retaining activities of Oxandrolone.Investigational
19-norandrostenedione19-norandrostenedione may increase the fluid retaining activities of Oxandrolone.Experimental, Illicit
4-Androstenedione4-Androstenedione may increase the fluid retaining activities of Oxandrolone.Experimental, Illicit
5-androstenedione5-androstenedione may increase the fluid retaining activities of Oxandrolone.Experimental, Illicit
AcarboseOxandrolone may increase the hypoglycemic activities of Acarbose.Approved, Investigational
AcenocoumarolOxandrolone may increase the anticoagulant activities of Acenocoumarol.Approved
AlbiglutideOxandrolone may increase the hypoglycemic activities of Albiglutide.Approved
AlclometasoneAlclometasone may increase the fluid retaining activities of Oxandrolone.Approved
AldosteroneAldosterone may increase the fluid retaining activities of Oxandrolone.Experimental
AlogliptinOxandrolone may increase the hypoglycemic activities of Alogliptin.Approved
AmcinonideAmcinonide may increase the fluid retaining activities of Oxandrolone.Approved
AnecortaveAnecortave may increase the fluid retaining activities of Oxandrolone.Investigational
BeclomethasoneBeclomethasone may increase the fluid retaining activities of Oxandrolone.Investigational
Beclomethasone dipropionateBeclomethasone dipropionate may increase the fluid retaining activities of Oxandrolone.Approved, Investigational
BetamethasoneBetamethasone may increase the fluid retaining activities of Oxandrolone.Approved, Vet Approved
BromocriptineOxandrolone may increase the hypoglycemic activities of Bromocriptine.Approved, Investigational
BudesonideBudesonide may increase the fluid retaining activities of Oxandrolone.Approved
C1 Esterase Inhibitor (Human)Oxandrolone may increase the thrombogenic activities of C1 Esterase Inhibitor (Human).Approved
C1 Esterase Inhibitor (Recombinant)Oxandrolone may increase the thrombogenic activities of C1 Esterase Inhibitor (Recombinant).Approved
CanagliflozinOxandrolone may increase the hypoglycemic activities of Canagliflozin.Approved
ChlorpropamideOxandrolone may increase the hypoglycemic activities of Chlorpropamide.Approved
CiclesonideCiclesonide may increase the fluid retaining activities of Oxandrolone.Approved, Investigational
ClobetasolClobetasol may increase the fluid retaining activities of Oxandrolone.Investigational
Clobetasol propionateClobetasol propionate may increase the fluid retaining activities of Oxandrolone.Approved
ClocortoloneClocortolone may increase the fluid retaining activities of Oxandrolone.Approved
Cortisone acetateCortisone acetate may increase the fluid retaining activities of Oxandrolone.Approved
CyclosporineOxandrolone may increase the hepatotoxic activities of Cyclosporine.Approved, Investigational, Vet Approved
DapagliflozinOxandrolone may increase the hypoglycemic activities of Dapagliflozin.Approved
dehydroepiandrosterone sulfatedehydroepiandrosterone sulfate may increase the fluid retaining activities of Oxandrolone.Investigational
DesoximetasoneDesoximetasone may increase the fluid retaining activities of Oxandrolone.Approved
Desoxycorticosterone acetateDesoxycorticosterone acetate may increase the fluid retaining activities of Oxandrolone.Approved
Desoxycorticosterone PivalateDesoxycorticosterone Pivalate may increase the fluid retaining activities of Oxandrolone.Experimental, Vet Approved
DexamethasoneDexamethasone may increase the fluid retaining activities of Oxandrolone.Approved, Investigational, Vet Approved
Dexamethasone isonicotinateDexamethasone isonicotinate may increase the fluid retaining activities of Oxandrolone.Vet Approved
DicoumarolOxandrolone may increase the anticoagulant activities of Dicoumarol.Approved
DiflorasoneDiflorasone may increase the fluid retaining activities of Oxandrolone.Approved
DifluocortoloneDifluocortolone may increase the fluid retaining activities of Oxandrolone.Approved
DifluprednateDifluprednate may increase the fluid retaining activities of Oxandrolone.Approved
DisopyramideOxandrolone may increase the hypoglycemic activities of Disopyramide.Approved
DulaglutideOxandrolone may increase the hypoglycemic activities of Dulaglutide.Approved
EmpagliflozinOxandrolone may increase the hypoglycemic activities of Empagliflozin.Approved
EquileninEquilenin may increase the fluid retaining activities of Oxandrolone.Experimental
EquilinEquilin may increase the fluid retaining activities of Oxandrolone.Approved
EstroneEstrone may increase the fluid retaining activities of Oxandrolone.Approved
Estrone sulfateEstrone sulfate may increase the fluid retaining activities of Oxandrolone.Approved
Ethyl biscoumacetateOxandrolone may increase the anticoagulant activities of Ethyl biscoumacetate.Withdrawn
ExenatideOxandrolone may increase the hypoglycemic activities of Exenatide.Approved, Investigational
fluasteronefluasterone may increase the fluid retaining activities of Oxandrolone.Investigational
FludrocortisoneFludrocortisone may increase the fluid retaining activities of Oxandrolone.Approved
FluindioneOxandrolone may increase the anticoagulant activities of Fluindione.Investigational
FlumethasoneFlumethasone may increase the fluid retaining activities of Oxandrolone.Approved, Vet Approved
FlunisolideFlunisolide may increase the fluid retaining activities of Oxandrolone.Approved, Investigational
Fluocinolone AcetonideFluocinolone Acetonide may increase the fluid retaining activities of Oxandrolone.Approved, Investigational, Vet Approved
FluocinonideFluocinonide may increase the fluid retaining activities of Oxandrolone.Approved, Investigational
FluocortoloneFluocortolone may increase the fluid retaining activities of Oxandrolone.Approved, Withdrawn
FluorometholoneFluorometholone may increase the fluid retaining activities of Oxandrolone.Approved
FluprednideneFluprednidene may increase the fluid retaining activities of Oxandrolone.Approved, Withdrawn
FluprednisoloneFluprednisolone may increase the fluid retaining activities of Oxandrolone.Approved
FlurandrenolideFlurandrenolide may increase the fluid retaining activities of Oxandrolone.Approved
Fluticasone furoateFluticasone furoate may increase the fluid retaining activities of Oxandrolone.Approved
Fluticasone PropionateFluticasone Propionate may increase the fluid retaining activities of Oxandrolone.Approved
FormestaneFormestane may increase the fluid retaining activities of Oxandrolone.Approved, Investigational, Withdrawn
GliclazideOxandrolone may increase the hypoglycemic activities of Gliclazide.Approved
GlimepirideOxandrolone may increase the hypoglycemic activities of Glimepiride.Approved
GlipizideOxandrolone may increase the hypoglycemic activities of Glipizide.Approved
GlyburideOxandrolone may increase the hypoglycemic activities of Glyburide.Approved
HE3286HE3286 may increase the fluid retaining activities of Oxandrolone.Investigational
HydrocortisoneHydrocortisone may increase the fluid retaining activities of Oxandrolone.Approved, Vet Approved
Insulin AspartOxandrolone may increase the hypoglycemic activities of Insulin Aspart.Approved
Insulin DetemirOxandrolone may increase the hypoglycemic activities of Insulin Detemir.Approved
Insulin GlargineOxandrolone may increase the hypoglycemic activities of Insulin Glargine.Approved
Insulin GlulisineOxandrolone may increase the hypoglycemic activities of Insulin Glulisine.Approved
Insulin HumanOxandrolone may increase the hypoglycemic activities of Insulin Human.Approved, Investigational
Insulin LisproOxandrolone may increase the hypoglycemic activities of Insulin Lispro.Approved
IstaroximeIstaroxime may increase the fluid retaining activities of Oxandrolone.Investigational
LanreotideOxandrolone may increase the hypoglycemic activities of Lanreotide.Approved
LiraglutideOxandrolone may increase the hypoglycemic activities of Liraglutide.Approved
ME-609ME-609 may increase the fluid retaining activities of Oxandrolone.Investigational
MecaserminOxandrolone may increase the hypoglycemic activities of Mecasermin.Approved, Investigational
MedrysoneMedrysone may increase the fluid retaining activities of Oxandrolone.Approved
MelengestrolMelengestrol may increase the fluid retaining activities of Oxandrolone.Vet Approved
MetforminOxandrolone may increase the hypoglycemic activities of Metformin.Approved
MethylprednisoloneMethylprednisolone may increase the fluid retaining activities of Oxandrolone.Approved, Vet Approved
MifepristoneOxandrolone may increase the hypoglycemic activities of Mifepristone.Approved, Investigational
MiglitolOxandrolone may increase the hypoglycemic activities of Miglitol.Approved
MometasoneMometasone may increase the fluid retaining activities of Oxandrolone.Approved, Vet Approved
NateglinideOxandrolone may increase the hypoglycemic activities of Nateglinide.Approved, Investigational
NCX 1022NCX 1022 may increase the fluid retaining activities of Oxandrolone.Investigational
OctreotideOxandrolone may increase the hypoglycemic activities of Octreotide.Approved, Investigational
Oleoyl estroneOleoyl estrone may increase the fluid retaining activities of Oxandrolone.Investigational
ParamethasoneParamethasone may increase the fluid retaining activities of Oxandrolone.Approved
PasireotideOxandrolone may increase the hypoglycemic activities of Pasireotide.Approved
PentamidineOxandrolone may increase the hypoglycemic activities of Pentamidine.Approved
PhenindioneOxandrolone may increase the anticoagulant activities of Phenindione.Approved
PhenprocoumonOxandrolone may increase the anticoagulant activities of Phenprocoumon.Approved
PioglitazoneOxandrolone may increase the hypoglycemic activities of Pioglitazone.Approved, Investigational
PramlintideOxandrolone may increase the hypoglycemic activities of Pramlintide.Approved, Investigational
PrasteronePrasterone may increase the fluid retaining activities of Oxandrolone.Approved, Nutraceutical
PrednicarbatePrednicarbate may increase the fluid retaining activities of Oxandrolone.Approved
PrednisolonePrednisolone may increase the fluid retaining activities of Oxandrolone.Approved, Vet Approved
PrednisonePrednisone may increase the fluid retaining activities of Oxandrolone.Approved, Vet Approved
PregnenolonePregnenolone may increase the fluid retaining activities of Oxandrolone.Experimental
QuinineOxandrolone may increase the hypoglycemic activities of Quinine.Approved
RepaglinideOxandrolone may increase the hypoglycemic activities of Repaglinide.Approved, Investigational
RimexoloneRimexolone may increase the fluid retaining activities of Oxandrolone.Approved
RosiglitazoneOxandrolone may increase the hypoglycemic activities of Rosiglitazone.Approved, Investigational
SaxagliptinOxandrolone may increase the hypoglycemic activities of Saxagliptin.Approved
SitagliptinOxandrolone may increase the hypoglycemic activities of Sitagliptin.Approved, Investigational
SulfadiazineOxandrolone may increase the hypoglycemic activities of Sulfadiazine.Approved, Vet Approved
SulfamethoxazoleOxandrolone may increase the hypoglycemic activities of Sulfamethoxazole.Approved
SulfisoxazoleOxandrolone may increase the hypoglycemic activities of Sulfisoxazole.Approved, Vet Approved
SunitinibOxandrolone may increase the hypoglycemic activities of Sunitinib.Approved, Investigational
TixocortolTixocortol may increase the fluid retaining activities of Oxandrolone.Approved
TolazamideOxandrolone may increase the hypoglycemic activities of Tolazamide.Approved
TolbutamideOxandrolone may increase the hypoglycemic activities of Tolbutamide.Approved
TriamcinoloneTriamcinolone may increase the fluid retaining activities of Oxandrolone.Approved, Vet Approved
WarfarinOxandrolone may increase the anticoagulant activities of Warfarin.Approved
Food InteractionsNot Available
References
Synthesis Reference

John Cabaj, “Process for the synthesis of oxandrolone.” U.S. Patent US20030032817, issued February 13, 2003.

US20030032817
General References
  1. Demling RH, DeSanti L: Oxandrolone induced lean mass gain during recovery from severe burns is maintained after discontinuation of the anabolic steroid. Burns. 2003 Dec;29(8):793-7. [PubMed:14636753 ]
External Links
ATC CodesA14AA08
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelDownload (40.6 KB)
MSDSNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9908
Blood Brain Barrier+0.9537
Caco-2 permeable+0.6616
P-glycoprotein substrateSubstrate0.6489
P-glycoprotein inhibitor INon-inhibitor0.5085
P-glycoprotein inhibitor IINon-inhibitor0.7936
Renal organic cation transporterNon-inhibitor0.7934
CYP450 2C9 substrateNon-substrate0.7807
CYP450 2D6 substrateNon-substrate0.8763
CYP450 3A4 substrateSubstrate0.7065
CYP450 1A2 substrateNon-inhibitor0.832
CYP450 2C9 inhibitorNon-inhibitor0.7894
CYP450 2D6 inhibitorNon-inhibitor0.966
CYP450 2C19 inhibitorNon-inhibitor0.8868
CYP450 3A4 inhibitorNon-inhibitor0.8455
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9822
Ames testNon AMES toxic0.9499
CarcinogenicityNon-carcinogens0.9501
BiodegradationNot ready biodegradable0.9469
Rat acute toxicity1.5177 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9712
hERG inhibition (predictor II)Non-inhibitor0.7133
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Savient pharmaceuticals inc
  • Par pharmaceutical inc
  • Roxane laboratories inc
  • Sandoz inc
  • Upsher smith laboratories inc
Packagers
Dosage forms
FormRouteStrength
TabletOral10 mg/1
TabletOral2.5 mg/1
Prices
Unit descriptionCostUnit
Oxandrin 10 mg tablet27.02USD tablet
Oxandrolone 10 mg tablet18.31USD tablet
Oxandrolone 100% powder9.54USD g
Oxandrin 2.5 mg tablet8.08USD tablet
Oxandrolone 2.5 mg tablet5.53USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5872147 No1997-12-052017-12-05Us
US6090799 No1997-07-182017-07-18Us
US6576659 No1997-12-052017-12-05Us
US6670351 No1992-10-202012-10-20Us
US6828313 No1997-12-052017-12-05Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point236.5 °CPhysProp
logP4.2Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.014 mg/mLALOGPS
logP3.36ALOGPS
logP2.95ChemAxon
logS-4.3ALOGPS
pKa (Strongest Basic)-0.53ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity84.75 m3·mol-1ChemAxon
Polarizability35.29 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as steroid lactones. These are sterol lipids containing a lactone moiety linked to the steroid skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroid lactones
Direct ParentSteroid lactones
Alternative Parents
Substituents
  • Steroid lactone
  • 3-oxo-5-alpha-steroid
  • 17-hydroxysteroid
  • Oxosteroid
  • Hydroxysteroid
  • 3-oxosteroid
  • 2-oxasteroid
  • Naphthopyran
  • Naphthalene
  • Delta_valerolactone
  • Delta valerolactone
  • Pyran
  • Oxane
  • Tertiary alcohol
  • Cyclic alcohol
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Zinc ion binding
Specific Function:
Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription factor activity is modulated by bound coactivator and corepressor proteins. Transcription activation is down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3 and ZIPK/DAPK3.
Gene Name:
AR
Uniprot ID:
P10275
Molecular Weight:
98987.9 Da
References
  1. Juul A: The effects of oestrogens on linear bone growth. Hum Reprod Update. 2001 May-Jun;7(3):303-13. [PubMed:11392377 ]
  2. Zhao J, Bauman WA, Huang R, Caplan AJ, Cardozo C: Oxandrolone blocks glucocorticoid signaling in an androgen receptor-dependent manner. Steroids. 2004 May;69(5):357-66. [PubMed:15219414 ]
  3. Bi LX, Wiren KM, Zhang XW, Oliveira GV, Klein GL, Mainous EG, Herndon DN: The effect of oxandrolone treatment on human osteoblastic cells. J Burns Wounds. 2007 Mar 7;6:e4. [PubMed:17364004 ]
  4. Cadwallader AB, Rollins DE, Lim CS: Effect of anabolic-androgenic steroids and glucocorticoids on the kinetics of hAR and hGR nucleocytoplasmic translocation. Mol Pharm. 2010 Jun 7;7(3):689-98. doi: 10.1021/mp900259w. [PubMed:20230007 ]
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on December 07, 2016 02:37