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Identification
NameOxandrolone
Accession NumberDB00621  (APRD01151)
TypeSmall Molecule
GroupsApproved, Investigational
Description

A synthetic hormone with anabolic and androgenic properties. [PubChem]

Structure
Thumb
Synonyms
SynonymLanguageCode
OssandroloneNot AvailableDCIT
OxandrolonGermanINN
OxandrolonaSpanishINN
OxandroloneFrenchINN
OxandrolonumLatinINN
ProtivarNot AvailableIS
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Oxandrolonetablet2.5 mgoralWatson Laboratories, Inc.2007-01-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Oxandrolonetablet10 mgoralWatson Laboratories, Inc.2007-01-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Oxandrolonetablet2.5 mgoralUpsher Smith Laboratories, Inc.2006-12-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Oxandrolonetablet10 mgoralUpsher Smith Laboratories, Inc.2007-03-22Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Oxandrolonetablet2.5 mgoralPar Pharmaceutical Inc.2007-08-20Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Oxandrolonetablet10 mgoralPar Pharmaceutical Inc.2007-08-20Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Oxandrolonetablet10 mgoralA S Medication Solutions Llc2007-08-20Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Oxandrolonetablet2.5 mgoralAmerican Health Packaging2013-06-24Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Over the Counter ProductsNot Available
International Brands
NameCompany
AnavarPfizer Inc.
OxandrinSavient Pharmaceuticals
XtendrolAtlantis
Brand mixturesNot Available
SaltsNot Available
Categories
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
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.
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 substrateNon-inhibitor0.7894
CYP450 2D6 substrateNon-inhibitor0.966
CYP450 2C19 substrateNon-inhibitor0.8868
CYP450 3A4 substrateNon-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
Pharmacoeconomics
Manufacturers
  • Savient pharmaceuticals inc
  • Par pharmaceutical inc
  • Roxane laboratories inc
  • Sandoz inc
  • Upsher smith laboratories inc
Packagers
Dosage forms
FormRouteStrength
Tabletoral10 mg
Tabletoral2.5 mg
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
CountryPatent NumberApprovedExpires (estimated)
United States58721471997-12-052017-12-05
United States66703511992-10-202012-10-20
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
SpectraNot Available
References
Synthesis Reference

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

US20030032817
General Reference
  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
External Links
ATC CodesA14AA08
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelDownload (40.6 KB)
MSDSNot Available
Interactions
Drug Interactions
Drug
AcarboseMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
AcenocoumarolMay enhance the anticoagulant effect of Vitamin K Antagonists.
AlbiglutideMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
AlogliptinMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
BromocriptineMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
C1 esterase inhibitorMay enhance the thrombogenic effect of C1 inhibitors.
CanagliflozinMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
ChlorpropamideMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
CorticotropinCorticosteroids (Systemic) may enhance the fluid-retaining effect of Androgens.
Cortisone acetateCorticosteroids (Systemic) may enhance the fluid-retaining effect of Androgens.
DapagliflozinMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
DisopyramideMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
DulaglutideMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
EmpagliflozinMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
ExenatideMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
FludrocortisoneCorticosteroids (Systemic) may enhance the fluid-retaining effect of Androgens.
GliclazideMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
GlimepirideMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
GlipizideMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
GlyburideMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
inhaled insulinMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
Insulin AspartMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
Insulin DetemirMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
Insulin GlargineMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
Insulin GlulisineMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
Insulin LisproMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
Insulin RegularMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
LanreotideMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
LinagliptinMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
LiraglutideMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
MecaserminMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
MetforminMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
MethylprednisoloneCorticosteroids (Systemic) may enhance the fluid-retaining effect of Androgens.
MifepristoneMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
MiglitolMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
NateglinideMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
OctreotideMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
PasireotideMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
PentamidineMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
PioglitazoneMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
PramlintideMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
PrednisoneCorticosteroids (Systemic) may enhance the fluid-retaining effect of Androgens.
QuinineMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
RepaglinideMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
RosiglitazoneMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
SaxagliptinMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
SitagliptinMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
SulfadiazineMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
SulfamethoxazoleMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
SulfisoxazoleMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
SunitinibMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
TolazamideMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
TolbutamideMay enhance the hypoglycemic effect of Blood Glucose Lowering Agents. Exceptions: Danazol.
Food InteractionsNot Available

Targets

1. Androgen receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Androgen receptor P10275 Details

References:

  1. Juul A: The effects of oestrogens on linear bone growth. Hum Reprod Update. 2001 May-Jun;7(3):303-13. Pubmed
  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
  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
  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. Pubmed
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on January 20, 2014 10:13