Identification
- Summary
Oxandrolone is an androgenic hormone used to treat muscle loss from prolonged corticosteroid treatment and to treat bone pain associated with osteoporosis.
- Brand Names
- Oxandrin
- Generic Name
- Oxandrolone
- DrugBank Accession Number
- DB00621
- Background
A synthetic hormone with anabolic and androgenic properties.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Oxandrolone (DB00621)
- Weight
- Average: 306.4397
Monoisotopic: 306.219494826 - Chemical Formula
- C19H30O3
- Synonyms
- Ossandrolone
- Oxandrolon
- Oxandrolona
- Oxandrolone
- Oxandrolonum
- External IDs
- CB 8075
- NSC-67068
- SC 11585
- SC-11585
Pharmacology
- Indication
Use to promote weight gain after weight loss following extensive surgery.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Management of Pain •••••••••••• Management of Protein catabolism •••••••••••• - Associated Therapies
- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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.
Target Actions Organism AAndrogen receptor agonistHumans - 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
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
The oral LD50 of oxandrolone in mice and dogs is greater than 5,000 mg/kg.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbrocitinib The metabolism of Abrocitinib can be decreased when combined with Oxandrolone. Acarbose Oxandrolone may increase the hypoglycemic activities of Acarbose. Acenocoumarol The metabolism of Acenocoumarol can be decreased when combined with Oxandrolone. Acetohexamide The metabolism of Acetohexamide can be decreased when combined with Oxandrolone. Acetylsalicylic acid The metabolism of Acetylsalicylic acid can be decreased when combined with Oxandrolone. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Images
- International/Other Brands
- Anavar (Pfizer Inc.) / Xtendrol (Atlantis)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Oxandrin Tablet 2.5 mg/1 Oral Physicians Total Care, Inc. 2005-09-13 2011-06-30 US 
Oxandrin Tablet 10 mg/1 Oral Physicians Total Care, Inc. 2005-09-13 2011-06-30 US Oxandrin Tablet 10 mg/1 Oral Savient Pharmaceuticals 2007-04-09 Not applicable US Oxandrin Tablet 2.5 mg/1 Oral Savient Pharmaceuticals 2007-04-09 Not applicable US Oxandrolone Tablet 10 mg/1 Oral Actavis Pharma Company 2007-01-01 2014-04-30 US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Oxandrolone Tablet 10 mg/1 Oral Eon Labs, Inc. 2006-12-01 2013-01-11 US Oxandrolone Tablet 10 mg/1 Oral American Health Packaging 2015-12-09 2020-03-31 US Oxandrolone Tablet 2.5 mg/1 Oral Upsher-Smith Laboratories, LLC 2006-12-01 Not applicable US 
Oxandrolone Tablet 2.5 mg/1 Oral Eon Labs, Inc. 2006-12-01 2013-01-11 US Oxandrolone Tablet 2.5 mg/1 Oral bryant ranch prepack 2007-08-20 Not applicable US
Categories
- ATC Codes
- A14AA08 — Oxandrolone
- Drug Categories
- Alimentary Tract and Metabolism
- Anabolic Agents
- Anabolic Agents for Systemic Use
- Anabolic Steroids
- Androgens
- Androstan Derivatives
- Androstanes
- Androstanols
- Cytochrome P-450 CYP2C9 Inhibitors
- Cytochrome P-450 CYP2C9 Inhibitors (strength unknown)
- Cytochrome P-450 Enzyme Inhibitors
- Fused-Ring Compounds
- Hormones
- Hormones, Hormone Substitutes, and Hormone Antagonists
- Steroids
- Thyroxine-binding globulin inhibitors
- Chemical TaxonomyProvided by Classyfire
- 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
- 17-hydroxysteroid / 2-oxasteroid / 3-oxo-5-alpha-steroid / 3-oxosteroid / Alcohol / Aliphatic heteropolycyclic compound / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Cyclic alcohol 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)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 7H6TM3CT4L
- CAS number
- 53-39-4
- 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[8.7.0.0^{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
References
- Synthesis Reference
John Cabaj, "Process for the synthesis of oxandrolone." U.S. Patent US20030032817, issued February 13, 2003.
US20030032817- General References
- 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. [Article]
- External Links
- Human Metabolome Database
- HMDB0014759
- KEGG Drug
- D00462
- KEGG Compound
- C07346
- PubChem Compound
- 5878
- PubChem Substance
- 46509027
- ChemSpider
- 5667
- 7779
- ChEBI
- 7820
- ChEMBL
- CHEMBL1200436
- ZINC
- ZINC000003813047
- Therapeutic Targets Database
- DAP000905
- PharmGKB
- PA164749395
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Oxandrolone
- FDA label
- Download (40.6 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Treatment HIV Wasting Syndrome 1 4 Recruiting Supportive Care Ligament Tear Knee 1 3 Completed Supportive Care Unspecified Adult Solid Tumor, Protocol Specific / Weight Changes 1 3 Terminated Treatment Pressure Ulcers 1 3 Withdrawn Treatment Trauma Injury 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
Form Route Strength Tablet Oral 10 mg/1 Tablet Oral 2.5 mg/1 Tablet Oral - Prices
Unit description Cost Unit Oxandrin 10 mg tablet 27.02USD tablet Oxandrolone 10 mg tablet 18.31USD tablet Oxandrolone 100% powder 9.54USD g Oxandrin 2.5 mg tablet 8.08USD tablet Oxandrolone 2.5 mg tablet 5.53USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US6670351 No 2003-12-30 2012-10-20 US US5872147 No 1999-02-16 2017-12-05 US US6090799 No 2000-07-18 2017-07-18 US US6576659 No 2003-06-10 2017-12-05 US US6828313 No 2004-12-07 2017-12-05 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 236.5 °C PhysProp logP 4.2 Not Available - Predicted Properties
Property Value Source Water Solubility 0.014 mg/mL ALOGPS logP 3.36 ALOGPS logP 2.95 Chemaxon logS -4.3 ALOGPS pKa (Strongest Basic) -0.53 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 46.53 Å2 Chemaxon Rotatable Bond Count 0 Chemaxon Refractivity 84.75 m3·mol-1 Chemaxon Polarizability 35.4 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - 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 inhibitor Non-inhibitor 0.7894 CYP450 2D6 inhibitor Non-inhibitor 0.966 CYP450 2C19 inhibitor Non-inhibitor 0.8868 CYP450 3A4 inhibitor 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
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-002f-0390000000-881235f7ef2bc770fa8b Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-000i-0292000000-dcc564e82bd87106ca8e Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0a4i-0009000000-bee758ff7663da83888f Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0a4i-0029000000-32cd1a27291be39697e9 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-06s2-2972000000-b9ec057b244feb3e3440 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0a4i-1393000000-c0034a7f76be84e2f75c Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0006-2910000000-ea60659aa99b2749a41b Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 181.0304255 predictedDarkChem Lite v0.1.0 [M-H]- 181.0553255 predictedDarkChem Lite v0.1.0 [M-H]- 171.64246 predictedDeepCCS 1.0 (2019) [M+H]+ 181.1360255 predictedDarkChem Lite v0.1.0 [M+H]+ 181.4066255 predictedDarkChem Lite v0.1.0 [M+H]+ 173.53787 predictedDeepCCS 1.0 (2019) [M+Na]+ 180.9939255 predictedDarkChem Lite v0.1.0 [M+Na]+ 179.33519 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- 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
- Juul A: The effects of oestrogens on linear bone growth. Hum Reprod Update. 2001 May-Jun;7(3):303-13. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP2C9
- Uniprot ID
- P11712
- Uniprot Name
- Cytochrome P450 2C9
- Molecular Weight
- 55627.365 Da
References
- Wiggins BS, Saseen JJ, Page RL 2nd, Reed BN, Sneed K, Kostis JB, Lanfear D, Virani S, Morris PB: Recommendations for Management of Clinically Significant Drug-Drug Interactions With Statins and Select Agents Used in Patients With Cardiovascular Disease: A Scientific Statement From the American Heart Association. Circulation. 2016 Nov 22;134(21):e468-e495. doi: 10.1161/CIR.0000000000000456. Epub 2016 Oct 17. [Article]
Drug created at June 13, 2005 13:24 / Updated at December 02, 2023 06:53