DrugBank: Oxandrolone (DB00621)

targets (1)

Identification

Name

Oxandrolone

Accession Number

DB00621 (APRD01151)

Type

small molecule

Groups

approved

Description

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

Structure

Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure

Synonyms

Ossandrolone [DCIT]
Oxandrolona [INN-Spanish]
oxandrolone
Oxandrolonum [INN-Latin]

Brand names

Anavar
Lonavar
Oxandrin
Protivar
Provitar
Vasorome

Brand name mixtures

Not Available

Categories

Anabolic Agents
Androgens

CAS number

53-39-4

Weight

Average: 306.4397
Monoisotopic: 306.219494826

Chemical Formula

C₁₉H₃₀O₃

InChI Key

InChIKey=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

Plain Text

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

Plain Text

Mass Spec

Not Available

Taxonomy

Kingdom

Organic

Classes

Steroids and Steroid Derivatives

Substructures

Steroids and Steroid Derivatives
Carboxylic Acids and Derivatives
Hydroxy Compounds
Pyrans
Acetates
Lactones
Ethers
Alcohols and Polyols
Heterocyclic compounds

Pharmacology

Indication

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

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.

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

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

Form	Route	Strength
Tablet	Oral

Prices

Unit description	Cost	Unit
Oxandrin 10 mg tablet	27.02 USD	tablet
Oxandrolone 10 mg tablet	18.31 USD	tablet
Oxandrolone 100% powder	9.54 USD	g
Oxandrin 2.5 mg tablet	8.08 USD	tablet
Oxandrolone 2.5 mg tablet	5.53 USD	tablet

Patents

Country	Patent Number	Approved	Expires
United States	5872147	1997-12-05	2017-12-05
United States	6670351	1992-10-20	2012-10-20

Properties

State

solid

Melting point

236.5 oC

Experimental Properties

Property	Value	Source
logP	4.2	PhysProp

Predicted Properties

Property	Value	Source
water solubility	1.40e-02 g/l	ALOGPS
logP	3.36	ALOGPS
logP	2.95	ChemAxon Molconvert
logS	-4.34	ALOGPS
pKa		ChemAxon Molconvert
hydrogen acceptor count	2	ChemAxon Molconvert
hydrogen donor count	1	ChemAxon Molconvert
polar surface area	46.53	ChemAxon Molconvert
rotatable bond count	0	ChemAxon Molconvert
refractivity	84.75	ChemAxon Molconvert
polarizability	35.29	ChemAxon Molconvert

References

Synthesis Reference

Not Available

General Reference

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

Resource	Link
KEGG Drug	D00462
KEGG Compound	C07346
PubChem Compound	5878
PubChem Substance	46509027
ChemSpider	5667
ChEBI	7820
ChEMBL	7820
Therapeutic Targets Database	DAP000905
PharmGKB	PA450729
Drug Product Database	0
RxList	http://www.rxlist.com/cgi/generic2/oxandrolone.htm
Drugs.com	http://www.drugs.com/cdi/oxandrolone.html
Wikipedia	http://en.wikipedia.org/wiki/Oxandrolone

ATC Codes

A14AA08

AHFS Codes

Not Available

PDB Entries

Not Available

FDA label

show (40.6 KB)

MSDS

Not Available

Interactions

Drug Interactions

Not Available

Food Interactions

Not Available

Targets
1. Androgen receptor Pharmacological action: yes Actions: agonist The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Activated, but not phosphorylated, by HIPK3 Organism class: human UniProt ID: P10275 Gene: AR Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Juul A: The effects of oestrogens on linear bone growth. Hum Reprod Update. 2001 May-Jun;7(3):303-13. Pubmed 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 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 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 Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

Targets

1. Androgen receptor

Pharmacological action: yes
Actions: agonist

The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Activated, but not phosphorylated, by HIPK3

Organism class: human
UniProt ID: P10275 Link_out

Gene: AR

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

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

Comments

Drug created on June 13, 2005 07:24 / Updated on April 19, 2011 15:05

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.