(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

• ChemBase ID: 503
• Molecular Formular: C19H30O3
• Molecular Mass: 306.4397
• Monoisotopic Mass: 306.21949482
• SMILES: O[C@@]1([C@@]2([C@H]([C@H]3[C@@H]([C@@]4([C@@H](CC3)CC(=O)OC4)C)CC2)CC1)C)C
• Canonical SMILES: O=C1OC[C@]2([C@H](C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@]2(C)O)C)C
• 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
• InChIKey: QSLJIVKCVHQPLV-PEMPUTJUSA-N

NAMES AND DATABASE IDS

Names

• 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; (1S,2S,7S,10R,11S,14S,15S)-14-hydroxy-2,14,15-trimethyl-4-oxatetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-5-one
• IUPAC Traditional name: oxandrolone
• Brand Name: Anavar; Lonavar; Oxandrin; Protivar; Provitar; Vasorome
• Synonyms: Ossandrolone [DCIT]; Oxandrolona [INN-Spanish]; Oxandrolonum [INN-Latin]; oxandrolone; Oxandrolone; 17β-Hydroxy-17-methyl-2-oxa-5α-androstan-3-one; (5α,17β)-17-Hydroxy-17-methyl-2-oxaandrostan-3-one; 17-Methyl-2-oxa-5α-androstan-17β-ol-3-one; Lonavar; NSC 67068; Oxandren; Protivar; Provitar; SC 11585; Vasorome; Oxandrin; Anavar

Database IDs

• CAS Number: 53-39-4
• PubChem SID: 46509027; 160963966
• PubChem CID: 5878
• CHEBI ID: 7820
• ATC CODE: A14AA08
• CHEMBL: 1200436
• Chemspider ID: 5667
• DrugBank ID: DB00621
• KEGG ID: D00462
• Unique Ingredient Identifier: 7H6TM3CT4L
• Wikipedia Title: Oxandrolone
• Medline Plus: a604024

CALCULATED PROPERTIES

ALOGPS 2.1

• Log P: 3.36
• LOG S: -4.34
• Solubility (Water): 1.40e-02 g/l

JChem

• Log P: 2.9536674
• Molar Refractivity: 84.749 cm^3
• Polarizability: 34.19302 Å^3
• Polar Surface Area: 46.53 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 2.9536672
• LogD (pH = 7.4): 2.9536674

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: White Solid
• Melting Point: 214-217°C
• Hydrophobicity(logP): 4.2

Safety Information

• Storage Condition: -20°C; Controlled Substance, -20°C Freezer

Pharmacology Properties

• Admin Routes: Oral
• Bioavailability: 97%
• Excretion: Urinary:90%; Fecal:7%
• Half Life: 9 hours
• Metabolism: Hepatic
• Legal Status: Schedule III (US)
• Pregnancy Category: X

Product Information

• Salt Data: Free Base

DETAILS

DrugBank - DB00621

• Drug Groups: approved; investigational
• Description: A synthetic hormone with anabolic and androgenic properties. [PubChem]
• Indication: Use to promote weight gain after weight loss following extensive surgery.
• Pharmacology: 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.
• Toxicity: The oral LD50 of oxandrolone in mice and dogs is greater than 5,000 mg/kg.
• Affected Organisms: Humans and other mammals
• Biotransformation: Renal
• Half Life: 0.55 hours (1st phage), 9 hours (2nd phase)
• 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. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

Selleck Chemicals - S1753

Related research area: Endocrinology

Toronto Research Chemicals - O845050

A synthetic, anabolic steroid. Used to promote muscle growth and combat involuntary weight loss. It has also been used to treat cases of osteoporosis.

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. Pubmed
• http://en.wikipedia.org/wiki/Oxandrolone
• Cadwallader, A., et al.: Mol. Pharm., 7, 689 (2010)
• Amundson, E., et al.: J. Clin. Endocrinol. Metabol., 95, 1355 (2010)
• Bovee, T., et al.: J. Steroid Biochem. Mol. Biol., 118, 85 (2010)
• Fourches, D., et al.: Chem. Res. Toxicol., 23, 171 (2010)