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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
SaltsNot Available
Brand names
NameCompany
AnavarPfizer Inc.
OxandrinSavient Pharmaceuticals
OxandroloneSandoz
XtendrolAtlantis
Brand mixturesNot 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[8.7.0.0^{2,7}.0^{11,15}]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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassLipids
ClassSteroids and Steroid Derivatives
SubclassKetosteroids
Direct parentKetosteroids
Alternative parentsHydroxysteroids; Other Steroids and Derivatives; Oxasteroids and Derivatives; Naphthopyrans; Naphthalenes; Sesquiterpenes; Delta Valerolactones; Pyrans; Oxanes; Tertiary Alcohols; Carboxylic Acid Esters; Cyclic Alcohols and Derivatives; Polyamines
Substituentssesquiterpene backbone; naphthopyran; acene; naphthalene; delta valerolactone; oxane; pyran; cyclic alcohol; tertiary alcohol; lactone; carboxylic acid ester; polyamine; carboxylic acid derivative; alcohol
Classification descriptionThis compound belongs to the ketosteroids. These are steroid derivatives comprising a ketone group attached to steroid skeleton.
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
Property Value Probability
Human Intestinal Absorption + 0.9908
Blood Brain Barrier + 0.9537
Caco-2 permeable + 0.6616
P-glycoprotein substrate Substrate 0.6489
P-glycoprotein inhibitor I Non-inhibitor 0.5085
P-glycoprotein inhibitor II Non-inhibitor 0.7936
Renal organic cation transporter Non-inhibitor 0.7934
CYP450 2C9 substrate Non-substrate 0.7807
CYP450 2D6 substrate Non-substrate 0.8763
CYP450 3A4 substrate Substrate 0.7065
CYP450 1A2 substrate Non-inhibitor 0.832
CYP450 2C9 substrate Non-inhibitor 0.7894
CYP450 2D6 substrate Non-inhibitor 0.966
CYP450 2C19 substrate Non-inhibitor 0.8868
CYP450 3A4 substrate Non-inhibitor 0.8455
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9822
Ames test Non AMES toxic 0.9499
Carcinogenicity Non-carcinogens 0.9501
Biodegradation Not ready biodegradable 0.9469
Rat acute toxicity 1.5177 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9712
hERG inhibition (predictor II) Non-inhibitor 0.7133
Pharmacoeconomics
Manufacturers
  • Savient pharmaceuticals inc
  • Par pharmaceutical inc
  • Roxane laboratories inc
  • Sandoz inc
  • Upsher smith laboratories inc
Packagers
Dosage forms
FormRouteStrength
TabletOral
Prices
Unit descriptionCostUnit
Oxandrin 10 mg tablet27.02USDtablet
Oxandrolone 10 mg tablet18.31USDtablet
Oxandrolone 100% powder9.54USDg
Oxandrin 2.5 mg tablet8.08USDtablet
Oxandrolone 2.5 mg tablet5.53USDtablet
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 Solubility0.014ALOGPS
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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
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
ResourceLink
KEGG DrugD00462
KEGG CompoundC07346
PubChem Compound5878
PubChem Substance46509027
ChemSpider5667
ChEBI7820
ChEMBLCHEMBL1200436
Therapeutic Targets DatabaseDAP000905
PharmGKBPA164749395
RxListhttp://www.rxlist.com/cgi/generic2/oxandrolone.htm
Drugs.comhttp://www.drugs.com/cdi/oxandrolone.html
WikipediaOxandrolone
ATC CodesA14AA08
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelshow(40.6 KB)
MSDSNot Available
Interactions
Drug Interactions
Drug
WarfarinOxandrolone may increase the serum concentration and anticoagulant effect of warfarin. Monitor for changes in prothrombin time and therapeutic effects of warfarin if oxandrolone is initiated, discontinued or dose changed.
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