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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/1oralA S Medication Solutions Llc2007-08-20Not applicableUs
Oxandrolonetablet10 mg/1oralUpsher Smith Laboratories, Inc.2007-03-22Not applicableUs
Oxandrolonetablet2.5 mg/1oralAmerican Health Packaging2015-03-30Not applicableUs
Oxandrolonetablet2.5 mg/1oralPar Pharmaceutical Inc.2007-08-20Not applicableUs
Oxandrolonetablet10 mg/1oralAmerican Health Packaging2015-03-30Not applicableUs
Oxandrolonetablet10 mg/1oralPar Pharmaceutical Inc.2007-08-20Not 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 KeyInChIKey=QSLJIVKCVHQPLV-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
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
Pharmacology
IndicationUse to promote weight gain after weight loss following extensive surgery.
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.
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
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
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
Interactions
Drug Interactions
Drug
4-Androstenedione4-Androstenedione may increase the fluid retaining activities of Oxandrolone.
AcarboseOxandrolone may increase the hypoglycemic activities of Acarbose.
AcenocoumarolOxandrolone may increase the anticoagulant activities of Acenocoumarol.
AlbiglutideOxandrolone may increase the hypoglycemic activities of Albiglutide.
AlclometasoneAlclometasone may increase the fluid retaining activities of Oxandrolone.
AldosteroneAldosterone may increase the fluid retaining activities of Oxandrolone.
AlogliptinOxandrolone may increase the hypoglycemic activities of Alogliptin.
AmcinonideAmcinonide may increase the fluid retaining activities of Oxandrolone.
Beclomethasone dipropionateBeclomethasone dipropionate may increase the fluid retaining activities of Oxandrolone.
BetamethasoneBetamethasone may increase the fluid retaining activities of Oxandrolone.
BromocriptineOxandrolone may increase the hypoglycemic activities of Bromocriptine.
BudesonideBudesonide may increase the fluid retaining activities of Oxandrolone.
C1 Esterase Inhibitor (Human)Oxandrolone may increase the thrombogenic activities of C1 Esterase Inhibitor (Human).
C1 Esterase Inhibitor (Recombinant)Oxandrolone may increase the thrombogenic activities of C1 Esterase Inhibitor (Recombinant).
CanagliflozinOxandrolone may increase the hypoglycemic activities of Canagliflozin.
ChlorpropamideOxandrolone may increase the hypoglycemic activities of Chlorpropamide.
CiclesonideCiclesonide may increase the fluid retaining activities of Oxandrolone.
Clobetasol propionateClobetasol propionate may increase the fluid retaining activities of Oxandrolone.
ClocortoloneClocortolone may increase the fluid retaining activities of Oxandrolone.
Cortisone acetateCortisone acetate may increase the fluid retaining activities of Oxandrolone.
CyclosporineOxandrolone may increase the hepatotoxic activities of Cyclosporine.
DapagliflozinOxandrolone may increase the hypoglycemic activities of Dapagliflozin.
DehydroepiandrosteroneDehydroepiandrosterone may increase the fluid retaining activities of Oxandrolone.
dehydroepiandrosterone sulfatedehydroepiandrosterone sulfate may increase the fluid retaining activities of Oxandrolone.
DesoximetasoneDesoximetasone may increase the fluid retaining activities of Oxandrolone.
Desoxycorticosterone acetateDesoxycorticosterone acetate may increase the fluid retaining activities of Oxandrolone.
DexamethasoneDexamethasone may increase the fluid retaining activities of Oxandrolone.
Dexamethasone isonicotinateDexamethasone isonicotinate may increase the fluid retaining activities of Oxandrolone.
DicoumarolOxandrolone may increase the anticoagulant activities of Dicoumarol.
DiflorasoneDiflorasone may increase the fluid retaining activities of Oxandrolone.
DifluocortoloneDifluocortolone may increase the fluid retaining activities of Oxandrolone.
DifluprednateDifluprednate may increase the fluid retaining activities of Oxandrolone.
DisopyramideOxandrolone may increase the hypoglycemic activities of Disopyramide.
DulaglutideOxandrolone may increase the hypoglycemic activities of Dulaglutide.
EmpagliflozinOxandrolone may increase the hypoglycemic activities of Empagliflozin.
EquileninEquilenin may increase the fluid retaining activities of Oxandrolone.
EquilinEquilin may increase the fluid retaining activities of Oxandrolone.
EstroneEstrone may increase the fluid retaining activities of Oxandrolone.
Ethyl biscoumacetateOxandrolone may increase the anticoagulant activities of Ethyl biscoumacetate.
ExenatideOxandrolone may increase the hypoglycemic activities of Exenatide.
FludrocortisoneFludrocortisone may increase the fluid retaining activities of Oxandrolone.
FlumethasoneFlumethasone may increase the fluid retaining activities of Oxandrolone.
FlunisolideFlunisolide may increase the fluid retaining activities of Oxandrolone.
Fluocinolone AcetonideFluocinolone Acetonide may increase the fluid retaining activities of Oxandrolone.
FluocinonideFluocinonide may increase the fluid retaining activities of Oxandrolone.
FluocortoloneFluocortolone may increase the fluid retaining activities of Oxandrolone.
FluorometholoneFluorometholone may increase the fluid retaining activities of Oxandrolone.
FluprednideneFluprednidene may increase the fluid retaining activities of Oxandrolone.
FluprednisoloneFluprednisolone may increase the fluid retaining activities of Oxandrolone.
FlurandrenolideFlurandrenolide may increase the fluid retaining activities of Oxandrolone.
Fluticasone furoateFluticasone furoate may increase the fluid retaining activities of Oxandrolone.
Fluticasone PropionateFluticasone Propionate may increase the fluid retaining activities of Oxandrolone.
GliclazideOxandrolone may increase the hypoglycemic activities of Gliclazide.
GlimepirideOxandrolone may increase the hypoglycemic activities of Glimepiride.
GlipizideOxandrolone may increase the hypoglycemic activities of Glipizide.
GlyburideOxandrolone may increase the hypoglycemic activities of Glyburide.
HydrocortisoneHydrocortisone may increase the fluid retaining activities of Oxandrolone.
Insulin AspartOxandrolone may increase the hypoglycemic activities of Insulin Aspart.
Insulin DetemirOxandrolone may increase the hypoglycemic activities of Insulin Detemir.
Insulin GlargineOxandrolone may increase the hypoglycemic activities of Insulin Glargine.
Insulin GlulisineOxandrolone may increase the hypoglycemic activities of Insulin Glulisine.
Insulin HumanOxandrolone may increase the hypoglycemic activities of Insulin Human.
Insulin LisproOxandrolone may increase the hypoglycemic activities of Insulin Lispro.
LanreotideOxandrolone may increase the hypoglycemic activities of Lanreotide.
LiraglutideOxandrolone may increase the hypoglycemic activities of Liraglutide.
MecaserminOxandrolone may increase the hypoglycemic activities of Mecasermin.
MedrysoneMedrysone may increase the fluid retaining activities of Oxandrolone.
MelengestrolMelengestrol may increase the fluid retaining activities of Oxandrolone.
MetforminOxandrolone may increase the hypoglycemic activities of Metformin.
MethylprednisoloneMethylprednisolone may increase the fluid retaining activities of Oxandrolone.
MifepristoneOxandrolone may increase the hypoglycemic activities of Mifepristone.
MiglitolOxandrolone may increase the hypoglycemic activities of Miglitol.
MometasoneMometasone may increase the fluid retaining activities of Oxandrolone.
NateglinideOxandrolone may increase the hypoglycemic activities of Nateglinide.
OctreotideOxandrolone may increase the hypoglycemic activities of Octreotide.
ParamethasoneParamethasone may increase the fluid retaining activities of Oxandrolone.
PasireotideOxandrolone may increase the hypoglycemic activities of Pasireotide.
PentamidineOxandrolone may increase the hypoglycemic activities of Pentamidine.
PhenindioneOxandrolone may increase the anticoagulant activities of Phenindione.
PhenprocoumonOxandrolone may increase the anticoagulant activities of Phenprocoumon.
PioglitazoneOxandrolone may increase the hypoglycemic activities of Pioglitazone.
PramlintideOxandrolone may increase the hypoglycemic activities of Pramlintide.
PrednicarbatePrednicarbate may increase the fluid retaining activities of Oxandrolone.
PrednisolonePrednisolone may increase the fluid retaining activities of Oxandrolone.
PrednisonePrednisone may increase the fluid retaining activities of Oxandrolone.
PregnenolonePregnenolone may increase the fluid retaining activities of Oxandrolone.
QuinineOxandrolone may increase the hypoglycemic activities of Quinine.
RepaglinideOxandrolone may increase the hypoglycemic activities of Repaglinide.
RimexoloneRimexolone may increase the fluid retaining activities of Oxandrolone.
RosiglitazoneOxandrolone may increase the hypoglycemic activities of Rosiglitazone.
SaxagliptinOxandrolone may increase the hypoglycemic activities of Saxagliptin.
SitagliptinOxandrolone may increase the hypoglycemic activities of Sitagliptin.
SulfadiazineOxandrolone may increase the hypoglycemic activities of Sulfadiazine.
SulfamethoxazoleOxandrolone may increase the hypoglycemic activities of Sulfamethoxazole.
SulfisoxazoleOxandrolone may increase the hypoglycemic activities of Sulfisoxazole.
SunitinibOxandrolone may increase the hypoglycemic activities of Sunitinib.
TixocortolTixocortol may increase the fluid retaining activities of Oxandrolone.
TolazamideOxandrolone may increase the hypoglycemic activities of Tolazamide.
TolbutamideOxandrolone may increase the hypoglycemic activities of Tolbutamide.
TriamcinoloneTriamcinolone may increase the fluid retaining activities of Oxandrolone.
WarfarinOxandrolone may increase the anticoagulant activities of Warfarin.
Food InteractionsNot Available

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 September 30, 2016 02:25