Oxandrolone (CED0007111)

Record Information
Version1.0
Creation Date2016-05-25 18:21:40 UTC
Update Date2026-05-14 16:44:19 UTC
Accession NumberCHEM022148
Identification
Common NameOxandrolone
ClassSmall Molecule
Description
Oxandrolone is an organic compound with the formula C19H30O3 and an average molecular weight of 306.44 g/mol. Oxandrolone belongs to the steroid lactones, a subclass of steroids and steroid derivatives within the organic compounds. It is found in healthcare, pharmaceuticals, and veterinary products as an anabolic steroid and is administered via the oral exposure route. In terms of its biological activity, it acts as an agonist of the Androgen receptor (AR).
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
OxandrolonaChEBI
OxandrolonumChEBI
OxandrinKegg
OssandroloneHMDB
AnavarHMDB
Chemical FormulaC19H30O3
Average Molecular Mass306.440 g/mol
Monoisotopic Mass306.219 g/mol
CAS Registry Number53-39-4
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
Traditional Nameoxandrolone
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
InChI IdentifierInChI=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
InChI KeyQSLJIVKCVHQPLV-PEMPUTJUSA-N
Chemical Taxonomy
Description 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-oxosteroid
  • Hydroxysteroid
  • 3-oxo-5-alpha-steroid
  • 17-hydroxysteroid
  • Oxosteroid
  • 2-oxasteroid
  • Naphthopyran
  • Naphthalene
  • Delta valerolactone
  • Delta_valerolactone
  • Oxane
  • Pyran
  • Tertiary alcohol
  • Cyclic alcohol
  • Lactone
  • Carboxylic acid ester
  • Organoheterocyclic compound
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organooxygen compound
  • Organic oxygen compound
  • Organic oxide
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.014 g/LALOGPS
logP3.36ALOGPS
logP2.95ChemAxon
logS-4.3ALOGPS
pKa (Strongest Basic)-0.53ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity84.75 m³·mol⁻¹ChemAxon
Polarizability35.29 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-002f-0390000000-881235f7ef2bc770fa8bNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0jbl-2159000000-7b4f8fa117bf83f48aa4Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-052r-0093000000-ff28afe3ea6df5ec0584Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-054t-0291000000-adf27119d3b4725b18e1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0ukd-6970000000-1edee804a2bf0d5c829dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0049000000-7f9b88506345bf035691Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4r-0096000000-dad47b16a1db69463c49Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-052f-3090000000-503154ac4d18300bfe1eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-052r-0094000000-7513b9a9e1ce7a869a43Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-052o-3921000000-6631cde6a07b4265f680Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-2910000000-219252917ee3c72fbb77Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0009000000-a47a32e502bdb7f0b448Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0009000000-d08fe2354b6f2c905ec2Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0abi-0095000000-dc0690497cd4a795781fNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
2506.0Log mg/kg[1400:4500]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
270Anabolic steroidsHealthcare, pharmaceuticals & veterinary productsNot Available
Pathways
2 pathways
Oxandrolone Drug Metabolism
Oxandrolone Drug Metabolism
Oxandrolone Drug Metabolism Action Pathway
Oxandrolone Drug Metabolism Action Pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Androgen receptor structureClick to view 3D structureAndrogen receptorP15207Rattus norvegicusPredicted (SEA)9.49761
Click to view 3D structureProgesterone receptorQ690N0Bos taurusPredicted (SEA)4.82665
G-protein coupled bile acid receptor 1 structureClick to view 3D structureG-protein coupled bile acid receptor 1Q8TDU6HumansPredicted (SEA)21.3307
Sex hormone-binding globulin structureClick to view 3D structureSex hormone-binding globulinP04278HumansPredicted (SEA)10.2761
Glucocorticoid receptor structureClick to view 3D structureGlucocorticoid receptorP04150HumansPredicted (SEA)28.2593
Corticosteroid-binding globulin structureClick to view 3D structureCorticosteroid-binding globulinP08185HumansPredicted (SEA)11.9109
Aldo-keto reductase family 1 member B10 structureClick to view 3D structureAldo-keto reductase family 1 member B10O60218HumansPredicted (SEA)18.7617
Click to view 3D structureSex hormone-binding globulinP08689Rattus norvegicusPredicted (SEA)0.544945
Estrogen receptor structureClick to view 3D structureEstrogen receptorP03372HumansPredicted (SEA)70.1422
Cytochrome P450 2C19 structureClick to view 3D structureCytochrome P450 2C19P33261HumansPredicted (SEA)412.601
Click to view 3D structureCytochrome P450 7B1O75881HumansPredicted (SEA)0.778492
Aromatase structureClick to view 3D structureAromataseP11511HumansPredicted (SEA)58.3869
Cytochrome P450 2C9 structureClick to view 3D structureCytochrome P450 2C9P11712HumansPredicted (SEA)882.654
Click to view 3D structureGlucose-6-phosphate 1-dehydrogenaseQ9GRG7Trypanosoma bruceiPredicted (SEA)7.78492
Androgen receptor structureClick to view 3D structureAndrogen receptorP10275HumansPredicted (SEA)68.5852
Progesterone receptor structureClick to view 3D structureProgesterone receptorP06401HumansPredicted (SEA)53.4046
Androgen receptor structureClick to view 3D structureAndrogen receptorP19091Mus musculusPredicted (SEA)12.5337
E3 ubiquitin-protein ligase ZFP91 structureClick to view 3D structureE3 ubiquitin-protein ligase ZFP91Q96JP5HumansPredicted (SEA)1.16774
Mineralocorticoid receptor structureClick to view 3D structureMineralocorticoid receptorP08235HumansPredicted (SEA)42.2721
Gamma-aminobutyric acid type B receptor subunit 1 structureClick to view 3D structureGamma-aminobutyric acid type B receptor subunit 1Q9Z0U4Rattus norvegicusPredicted (SEA)5.83869
3-oxo-5-alpha-steroid 4-dehydrogenase 2 structureClick to view 3D structure3-oxo-5-alpha-steroid 4-dehydrogenase 2P31213HumansPredicted (SEA)11.6774
Adenosine receptor A3 structureClick to view 3D structureAdenosine receptor A3P0DMS8HumansPredicted (SEA)408.708
Sodium-dependent serotonin transporter structureClick to view 3D structureSodium-dependent serotonin transporterP31645HumansPredicted (SEA)875.804
Click to view 3D structure3-oxo-5-alpha-steroid 4-dehydrogenase 1P18405HumansPredicted (SEA)11.366
Click to view 3D structure3-keto-steroid reductase/17-beta-hydroxysteroid dehydrogenase 7P56937HumansPredicted (SEA)3.89246
Concentrations
Not Available
External Links
DrugBank IDDB00621
HMDB IDHMDB0014759
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkOxandrolone
Chemspider ID5667
ChEBI ID7820
PubChem Compound ID5878
Kegg Compound IDC07346
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
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.
2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
3. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
4. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
5. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
6. The lipid handbook with CD-ROM