CAS 53-39-4|Oxandrin|oxandrolone|(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|Anavar|Oxandrolone|17β-Hydroxy-17-methyl-2-oxa-5α-...

General Information

Structure

Molecular Formula

C₁₉H₃₀O₃

Molecular Mass

306.4397

Exact Mass

306.21949482

Charge

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

Canonic 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

Isomeric 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

Calculated Properties

JChem

LogD (pH = 7.4)

2.95

LogD (pH = 5.5)

2.95

Log P

2.95

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

-0.53

Polar Surface Area

46.53

Polarizability

35.27

Molar Refractivity

84.75

LOG S

-3.33

Data Source

Names and Identifiers

Synonyms

OxandrinAnavarOxandroloneSC 11585OxandrenProvitarProtivar17β-Hydroxy-17-methyl-2-oxa-5α-androstan-3-oneVasoromeLonavar17-Methyl-2-oxa-5α-androstan-17β-ol-3-one(5α,17β)-17-Hydroxy-17-methyl-2-oxaandrostan-3-oneNSC 67068Oxandrolonum [INN-Latin]Ossandrolone [DCIT]Oxandrolona [INN-Spanish]oxandroloneoxandroloneOxandrolone

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 (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 (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

Brand Name

OxandrinVasoromeLonavarProvitarAnavarProtivar

International Nonproprietary Name (INN)

oxandrolonaoxandrolonumoxandrolone

Names and Identifiers

Registration numbers

PubChem CID

5878

CAS Number

53-39-4

PubChem SID

1609639664650902756352998

Wikipedia Title

KEGG ID

Chemspider ID

CHEMBL

Medline Plus

Unique Ingredient Identifier

ATC CODE

DrugBank ID

CHEBI ID

Patent number

US2007196453US2007254029EP1862167EP1990049US2007189977US2007196452US2007196323

SureChEMBL Database

SCHEMBL148881

MetaboLights Database

MTBLS3038MTBLS1693MTBLS2871

KEGG DRUG Database

D00462

Beilstein Number

5480667

Drug Central Database

2,011

ACToR Database

53-39-4

CompTox Database

DTXSID8023399

Registration numbers

Properties

Physical Property

Hydrophobicity(logP)

4.2

Melting Point

214-217°C

Apperance

White Solid

Solubility

Chloroform

Safety Information

Storage Condition

-20°C

Controlled Substance, -20°C Freezer

MSDS Link

Download link

Product Information

Salt Data

Free Base

Certificate of Analysis

Download link

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule 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

Wikipedia

Oxandrolone

TRC

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.

Molecule Details

References

PubChem Literature

From Data Sources

• 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

• Amundson, E., et al.: J. Clin. Endocrinol. Metabol., 95, 1355 (2010)

• Fourches, D., et al.: Chem. Res. Toxicol., 23, 171 (2010)

• Cadwallader, A., et al.: Mol. Pharm., 7, 689 (2010)

• Bovee, T., et al.: J. Steroid Biochem. Mol. Biol., 118, 85 (2010)

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Synonyms

IUPAC name

IUPAC Traditional name

oxandrolone (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

Brand Name

OxandrinVasoromeLonavarProvitarAnavarProtivar

International Nonproprietary Name (INN)

oxandrolonaoxandrolonumoxandrolone

Registration numbers

PubChem CID

5878

CAS Number

53-39-4

PubChem SID

1609639664650902756352998

Wikipedia Title

KEGG ID

Chemspider ID

CHEMBL

Medline Plus

Unique Ingredient Identifier

ATC CODE

DrugBank ID

CHEBI ID

Patent number

US2007196453US2007254029EP1862167EP1990049US2007189977US2007196452US2007196323

SureChEMBL Database

SCHEMBL148881

MetaboLights Database

MTBLS3038MTBLS1693MTBLS2871

KEGG DRUG Database

D00462

Beilstein Number

5480667

Drug Central Database

ACToR Database

CompTox Database

Molecule Details

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

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

Wikipedia

Oxandrolone

TRC

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

PubChem Literature

From Data Sources

• 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

• Amundson, E., et al.: J. Clin. Endocrinol. Metabol., 95, 1355 (2010)

• Fourches, D., et al.: Chem. Res. Toxicol., 23, 171 (2010)

• Cadwallader, A., et al.: Mol. Pharm., 7, 689 (2010)

• Bovee, T., et al.: J. Steroid Biochem. Mol. Biol., 118, 85 (2010)

Bioactivity

PubChem BioAssay

Properties

Physical Property

Hydrophobicity(logP)

4.2

Melting Point

214-217°C

Apperance

White Solid

Solubility

Chloroform

Safety Information

Storage Condition

-20°C

Controlled Substance, -20°C Freezer

MSDS Link

Download link

Product Information

Salt Data

Free Base

Certificate of Analysis

Download link

Molecule

ID:503