Identification

Name
Oxandrolone
Accession Number
DB00621  (APRD01151)
Type
Small Molecule
Groups
Approved, Investigational
Description

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

Structure
Thumb
Synonyms
  • Ossandrolone
  • Oxandrolon
  • Oxandrolona
  • Oxandrolone
  • Oxandrolonum
  • Protivar
External IDs
CB 8075 / NSC-67068 / SC 11585 / SC-11585
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
OxandrinTablet10 mg/1OralPhysicians Total Care, Inc.2005-09-132011-06-30Us
OxandrinTablet2.5 mg/1OralSavient Pharmaceuticals2007-04-09Not applicableUs
OxandrinTablet2.5 mg/1OralPhysicians Total Care, Inc.2005-09-132011-06-30Us
OxandrinTablet10 mg/1OralSavient Pharmaceuticals2007-04-09Not applicableUs
OxandroloneTablet10 mg/1OralActavis Pharma Company2007-01-012014-04-30Us
OxandroloneTablet2.5 mg/1OralActavis Pharma Company2007-01-012015-04-30Us00591 3544 01 nlmimage10 a71b53da
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
OxandroloneTablet2.5 mg/1OralUpsher-Smith Laboratories, LLC2006-12-01Not applicableUs00245 0271 11 nlmimage10 283c9444
OxandroloneTablet10 mg/1OralA S Medication Solutions2007-08-20Not applicableUs
OxandroloneTablet2.5 mg/1OralAmerican Health Packaging2012-11-14Not applicableUs
OxandroloneTablet2.5 mg/1Oralbryant ranch prepack2007-08-20Not applicableUs
OxandroloneTablet10 mg/1OralEon Labs, Inc.2006-12-012013-01-11Us
OxandroloneTablet10 mg/1OralPar Pharmaceutical, Inc.2007-08-20Not applicableUs
OxandroloneTablet10 mg/1OralUpsher-Smith Laboratories, LLC2007-03-22Not applicableUs
OxandroloneTablet2.5 mg/1OralEon Labs, Inc.2006-12-012013-01-11Us
OxandroloneTablet10 mg/1OralAmerican Health Packaging2015-12-09Not applicableUs
OxandroloneTablet2.5 mg/1OralPar Pharmaceutical, Inc.2007-08-20Not applicableUs
International/Other Brands
Anavar (Pfizer Inc.) / Oxandrin (Savient Pharmaceuticals) / Xtendrol (Atlantis)
Categories
UNII
7H6TM3CT4L
CAS number
53-39-4
Weight
Average: 306.4397
Monoisotopic: 306.219494826
Chemical Formula
C19H30O3
InChI Key
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

Pharmacology

Indication

Use to promote weight gain after weight loss following extensive surgery.

Associated Conditions
Associated Therapies
Pharmacodynamics

Oxandrolone 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 action

Oxandrolones interact with androgen receptors in target tissues.

TargetActionsOrganism
AAndrogen receptor
agonist
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism

Renal

Route of elimination
Not Available
Half life

0.55 hours (1st phage), 9 hours (2nd phase)

Clearance
Not Available
Toxicity

The oral LD50 of oxandrolone in mice and dogs is greater than 5,000 mg/kg.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinOxandrolone may increase the anticoagulant activities of (R)-warfarin.
(S)-WarfarinOxandrolone may increase the anticoagulant activities of (S)-Warfarin.
2,4-thiazolidinedioneOxandrolone may increase the hypoglycemic activities of 2,4-thiazolidinedione.
4-hydroxycoumarinOxandrolone may increase the anticoagulant activities of 4-hydroxycoumarin.
AcarboseOxandrolone may increase the hypoglycemic activities of Acarbose.
AcenocoumarolOxandrolone may increase the anticoagulant activities of Acenocoumarol.
AcetohexamideOxandrolone may increase the hypoglycemic activities of Acetohexamide.
AICA ribonucleotideOxandrolone may increase the hypoglycemic activities of AICA ribonucleotide.
AlbiglutideOxandrolone may increase the hypoglycemic activities of Albiglutide.
AldosteroneThe risk or severity of fluid retention can be increased when Aldosterone is combined with Oxandrolone.
Food Interactions
Not 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
Human Metabolome Database
HMDB0014759
KEGG Drug
D00462
KEGG Compound
C07346
PubChem Compound
5878
PubChem Substance
46509027
ChemSpider
5667
ChEBI
7820
ChEMBL
CHEMBL1200436
Therapeutic Targets Database
DAP000905
PharmGKB
PA164749395
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Oxandrolone
ATC Codes
A14AA08 — Oxandrolone
FDA label
Download (40.6 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1Active Not RecruitingTreatmentMalnutrition1
1CompletedNot AvailableTo Determine the Bioequivalence Under Fasting Conditions1
1CompletedTreatmentBioavailability1
1CompletedTreatmentCongenital Hypoplastic Anemia1
2CompletedTreatmentAnemias / Functional Iron Deficiency / Traumas1
2CompletedTreatmentDwarfism / Turner's Syndrome1
2CompletedTreatmentTurner's Syndrome1
2, 3CompletedTreatmentMinor burns1
2, 3RecruitingTreatmentMinor burns1
3CompletedSupportive CareUnspecified Adult Solid Tumor, Protocol Specific / Weight Changes1
3TerminatedTreatmentPressure Ulcers1
4CompletedTreatmentHIV Wasting Syndrome1
Not AvailableCompletedTreatmentMuscular Dystrophy1
Not AvailableCompletedTreatmentSpinal Cord Injuries (SCI)1

Pharmacoeconomics

Manufacturers
  • Savient pharmaceuticals inc
  • Par pharmaceutical inc
  • Roxane laboratories inc
  • Sandoz inc
  • Upsher smith laboratories inc
Packagers
  • A-S Medication Solutions LLC
  • BTG Pharmaceuticals Corp.
  • DSM Corp.
  • Eon Labs
  • Letco Medical Inc.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Par Pharmaceuticals
  • Pharmaceutics International Inc.
  • Physicians Total Care Inc.
  • Resource Optimization and Innovation LLC
  • Sandoz
  • Savient Pharmaceuticals
  • Upsher Smith Laboratories
  • Watson Pharmaceuticals
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)
US6670351No1992-10-202012-10-20Us
US5872147No1997-12-052017-12-05Us
US6090799No1997-07-182017-07-18Us
US6576659No1997-12-052017-12-05Us
US6828313No1997-12-052017-12-05Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)236.5 °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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This 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.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Steroid lactones
Direct Parent
Steroid lactones
Alternative Parents
17-hydroxysteroids / 3-oxo-5-alpha-steroids / Oxasteroids and derivatives / Naphthopyrans / Naphthalenes / Delta valerolactones / Pyrans / Oxanes / Tertiary alcohols / Cyclic alcohols and derivatives
show 6 more
Substituents
Steroid lactone / 3-oxosteroid / Hydroxysteroid / 3-oxo-5-alpha-steroid / 17-hydroxysteroid / Oxosteroid / 2-oxasteroid / Naphthopyran / Naphthalene / Delta valerolactone
show 18 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
3-oxo steroid, 17beta-hydroxy steroid, anabolic androgenic steroid, oxa-steroid (CHEBI:7820) / Androstane and derivatives (C07346)

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 ...
Gene Name
AR
Uniprot ID
P10275
Uniprot Name
Androgen receptor
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]

Drug created on June 13, 2005 07:24 / Updated on October 01, 2018 12:51