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53-39-4 molecular structure
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(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 and InChIs

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

Cite this record

CBID:503 http://www.chembase.cn/molecule-503.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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[8.7.0.02,7.011,15]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
CAS Number
53-39-4
PubChem SID
160963966
46509027
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

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources

CALCULATED PROPERTIES

CALCULATED PROPERTIES

ALOGPS 2.1 JChem
Log P 3.36  LOG S -4.34 
Solubility (Water) 1.40e-02 g/l 
Log P 2.9536674  Molar Refractivity 84.749 cm3
Polarizability 34.19302 Å3 Polar Surface Area 46.53 Å2
Rotatable Bonds Lipinski's Rule of Five true 
H Acceptors H Donor
LogD (pH = 5.5) 2.9536672  LogD (pH = 7.4) 2.9536674 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
Chloroform expand Show data source
Apperance
White Solid expand Show data source
Melting Point
214-217°C expand Show data source
Hydrophobicity(logP)
4.2 expand Show data source
Storage Condition
-20°C expand Show data source
Controlled Substance, -20°C Freezer expand Show data source
MSDS Link
Download expand Show data source
Admin Routes
Oral expand Show data source
Bioavailability
97% expand Show data source
Excretion
Urinary:90%; Fecal:7% expand Show data source
Half Life
9 hours expand Show data source
Metabolism
Hepatic expand Show data source
Legal Status
Schedule III (US) expand Show data source
Pregnancy Category
X expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Selleck Chemicals Selleck Chemicals Wikipedia Wikipedia TRC TRC
DrugBank - DB00621 external link
Item Information
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 external link
Related research area: Endocrinology
Toronto Research Chemicals - O845050 external link
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

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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)
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PATENTS

PATENTS

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INTERNET

INTERNET

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