Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C19H30O3 |
Molecular Weight | 306.4397 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 7 / 7 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12CC[C@](C)(O)[C@@]1(C)CC[C@@]3([H])[C@@]2([H])CC[C@@]4([H])CC(=O)OC[C@]34C
InChI
InChIKey=QSLJIVKCVHQPLV-PEMPUTJUSA-N
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
Molecular Formula | C19H30O3 |
Molecular Weight | 306.4397 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 7 / 7 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: description was created based on several sources, including:
https://www.drugs.com/pro/oxandrolone.html Mosby, M.H. (2015) "Mosby's Drug Reference for Health Professions", p.1205 Retrieved from https://books.google.ru/books?id=IuF1BwAAQBAJ
Curator's Comment: description was created based on several sources, including:
https://www.drugs.com/pro/oxandrolone.html Mosby, M.H. (2015) "Mosby's Drug Reference for Health Professions", p.1205 Retrieved from https://books.google.ru/books?id=IuF1BwAAQBAJ
Oxandrolone is a synthetic, orally active anabolic-androgenic steroid. Oxandrolones interact with androgen receptors in target tissues. Oxandrin is 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. Side effects include: elevated aminotransferases (ALT, AST), lipid abnormalities (e.g., decreased HDL cholesterol concentrations). Cardiovascular side effects have included edema, with and without congestive heart failure. Oxandrolone may inhibit the metabolism of oral hypoglycemic agents. In patients with edema, concomitant administration with adrenal cortical steroids or ACTH may increase the edema.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1871 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15219414 |
62.0 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Palliative | OXANDRIN Approved UseOxandrolone is 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 (See DOSAGE AND ADMINISTRATION). Launch Date-1.71936006E11 |
|||
Secondary | OXANDRIN Approved UseOxandrolone is 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 (See DOSAGE AND ADMINISTRATION). Launch Date-1.71936006E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
417 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4729902 |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
OXANDROLONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3380 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4729902 |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
OXANDROLONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
9.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4729902 |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
OXANDROLONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Doses
Dose | Population | Adverse events |
---|---|---|
80 mg 1 times / day multiple, oral Highest studied dose Dose: 80 mg, 1 times / day Route: oral Route: multiple Dose: 80 mg, 1 times / day Sources: Page: p.308 |
unhealthy, 39.5+/-7.5 n = 68 Health Status: unhealthy Condition: Weight loss Age Group: 39.5+/-7.5 Sex: M+F Population Size: 68 Sources: Page: p.308 |
Disc. AE: Aspartate aminotransferase increased, ALT increased... Other AEs: Aspartate aminotransferase increased, ALT increased... AEs leading to discontinuation/dose reduction: Aspartate aminotransferase increased (grade 3-4) Other AEs:ALT increased (grade 3-4) Aspartate aminotransferase increased (grade 3-4, 14.8%) Sources: Page: p.308ALT increased (grade 3-4, 14.8%) |
5 mg 4 times / day multiple, oral Recommended Dose: 5 mg, 4 times / day Route: oral Route: multiple Dose: 5 mg, 4 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Weight loss Sources: Page: p.1 |
Disc. AE: Peliosis hepatis, Liver failure... AEs leading to discontinuation/dose reduction: Peliosis hepatis Sources: Page: p.1Liver failure Hepatocellular carcinoma High density lipoprotein decreased Low density lipoprotein increased Atherosclerosis Coronary artery disease |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
ALT increased | grade 3-4, 14.8% | 80 mg 1 times / day multiple, oral Highest studied dose Dose: 80 mg, 1 times / day Route: oral Route: multiple Dose: 80 mg, 1 times / day Sources: Page: p.308 |
unhealthy, 39.5+/-7.5 n = 68 Health Status: unhealthy Condition: Weight loss Age Group: 39.5+/-7.5 Sex: M+F Population Size: 68 Sources: Page: p.308 |
Aspartate aminotransferase increased | grade 3-4, 14.8% | 80 mg 1 times / day multiple, oral Highest studied dose Dose: 80 mg, 1 times / day Route: oral Route: multiple Dose: 80 mg, 1 times / day Sources: Page: p.308 |
unhealthy, 39.5+/-7.5 n = 68 Health Status: unhealthy Condition: Weight loss Age Group: 39.5+/-7.5 Sex: M+F Population Size: 68 Sources: Page: p.308 |
ALT increased | grade 3-4 Disc. AE |
80 mg 1 times / day multiple, oral Highest studied dose Dose: 80 mg, 1 times / day Route: oral Route: multiple Dose: 80 mg, 1 times / day Sources: Page: p.308 |
unhealthy, 39.5+/-7.5 n = 68 Health Status: unhealthy Condition: Weight loss Age Group: 39.5+/-7.5 Sex: M+F Population Size: 68 Sources: Page: p.308 |
Aspartate aminotransferase increased | grade 3-4 Disc. AE |
80 mg 1 times / day multiple, oral Highest studied dose Dose: 80 mg, 1 times / day Route: oral Route: multiple Dose: 80 mg, 1 times / day Sources: Page: p.308 |
unhealthy, 39.5+/-7.5 n = 68 Health Status: unhealthy Condition: Weight loss Age Group: 39.5+/-7.5 Sex: M+F Population Size: 68 Sources: Page: p.308 |
Atherosclerosis | Disc. AE | 5 mg 4 times / day multiple, oral Recommended Dose: 5 mg, 4 times / day Route: oral Route: multiple Dose: 5 mg, 4 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Weight loss Sources: Page: p.1 |
Coronary artery disease | Disc. AE | 5 mg 4 times / day multiple, oral Recommended Dose: 5 mg, 4 times / day Route: oral Route: multiple Dose: 5 mg, 4 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Weight loss Sources: Page: p.1 |
Hepatocellular carcinoma | Disc. AE | 5 mg 4 times / day multiple, oral Recommended Dose: 5 mg, 4 times / day Route: oral Route: multiple Dose: 5 mg, 4 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Weight loss Sources: Page: p.1 |
High density lipoprotein decreased | Disc. AE | 5 mg 4 times / day multiple, oral Recommended Dose: 5 mg, 4 times / day Route: oral Route: multiple Dose: 5 mg, 4 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Weight loss Sources: Page: p.1 |
Liver failure | Disc. AE | 5 mg 4 times / day multiple, oral Recommended Dose: 5 mg, 4 times / day Route: oral Route: multiple Dose: 5 mg, 4 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Weight loss Sources: Page: p.1 |
Low density lipoprotein increased | Disc. AE | 5 mg 4 times / day multiple, oral Recommended Dose: 5 mg, 4 times / day Route: oral Route: multiple Dose: 5 mg, 4 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Weight loss Sources: Page: p.1 |
Peliosis hepatis | Disc. AE | 5 mg 4 times / day multiple, oral Recommended Dose: 5 mg, 4 times / day Route: oral Route: multiple Dose: 5 mg, 4 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Weight loss Sources: Page: p.1 |
PubMed
Title | Date | PubMed |
---|---|---|
The anabolic steroid oxandrolone increases muscle mass in prepubertal boys with constitutional delay of growth. | 2001 Jun |
|
The effects of oestrogens on linear bone growth. | 2001 May-Jun |
|
Exercise treatment for HIV-associated metabolic and anthropomorphic complications. | 2001 Oct |
|
Nutrition and its role in wound healing. | 2001 Sep |
|
Remission of clinical signs in early duchenne muscular dystrophy on intermittent low-dosage prednisolone therapy. | 2002 |
|
Orexigenic and anabolic agents. | 2002 Nov |
|
The patient.com, 1 year later. | 2002 Nov-Dec |
|
Body cell mass repletion and improved quality of life in HIV-infected individuals receiving oxandrolone. | 2002 Nov-Dec |
|
Pelvic ultrasound evaluation in patients with Turner syndrome during treatment with growth hormone. | 2003 Aug |
|
Protein-energy malnutrition and involuntary weight loss: nutritional and pharmacological strategies to enhance wound healing. | 2003 Jul |
|
Current pharmacotherapy for the treatment of severe burns. | 2003 Mar |
|
[Optimizing estrogen treatment in Turner syndrome]. | 2003 Mar 23 |
|
Combination megestrol acetate, oxandrolone, and dietary advice restores weight in human immunodeficiency virus. | 2004 Aug |
|
Screening of free 17-alkyl-substituted anabolic steroids in human urine by liquid chromatography-electrospray ionization tandem mass spectrometry. | 2004 Feb |
|
Optimization of treatment in Turner's syndrome. | 2004 Mar |
|
Oxandrolone does not improve outcome of ventilator dependent surgical patients. | 2004 Sep |
|
Longitudinal monitoring of bone measured by quantitative multisite ultrasound in patients with Crohn's disease. | 2005 Feb |
|
The role of anabolic hormones for wound healing in catabolic states. | 2005 Jan 17 |
|
Metacarpophalangeal pattern profile analysis as a tool for early diagnosis of Turner syndrome. | 2005 Jul |
|
[Study of bone mass in Turner syndrome]. | 2005 May |
|
Oxandrolone enhances skeletal muscle myosin synthesis and alters global gene expression profile in Duchenne muscular dystrophy. | 2006 Mar |
|
Oxandrolone. | 2006 Sep |
|
Advances in burn critical care. | 2006 Sep |
Patents
Sample Use Guides
The daily adult dosage is 2.5 mg to 20 mg given in 2 to 4 divided doses. The desired response may be achieved with as little as 2.5 mg or as much as 20 mg daily. A course
of therapy of 2 to 4 weeks is usually adequate.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10077001
Dimerization and DNA binding of the AR fragments were observed at 0.5–1 uM
oxandrolone.
Substance Class |
Chemical
Created
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admin
on
Edited
Fri Dec 16 16:15:21 UTC 2022
by
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on
Fri Dec 16 16:15:21 UTC 2022
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Record UNII |
7H6TM3CT4L
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Record Status |
Validated (UNII)
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Record Version |
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WHO-VATC |
QA14AA08
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WIKIPEDIA |
Designer-drugs-Oxandrolone
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FDA ORPHAN DRUG |
45790
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FDA ORPHAN DRUG |
103797
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NCI_THESAURUS |
C243
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FDA ORPHAN DRUG |
59091
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DEA NO. |
4000
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NCI_THESAURUS |
C2360
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LIVERTOX |
719
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FDA ORPHAN DRUG |
45590
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WHO-ATC |
A14AA08
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FDA ORPHAN DRUG |
75793
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53-39-4
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5878
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7H6TM3CT4L
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67068
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200-172-9
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7092
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1482003
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7820
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DB00621
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3373
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DTXSID8023399
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7779
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PRIMARY | RxNorm | ||
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OXANDROLONE
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PRIMARY | |||
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C29306
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7H6TM3CT4L
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CHEMBL1200436
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SUB09496MIG
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1325
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D010074
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2011
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M8290
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PRIMARY | Merck Index |
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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ACTIVE MOIETY |