U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of OXANDROLONE

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

HIDE SMILES / InChI

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

Description
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
62.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
OXANDRIN

Approved Use

Oxandrolone 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 Use

Oxandrolone 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

Cmax

ValueDoseCo-administeredAnalytePopulation
417 ng/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
3380 ng × h/mL
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

T1/2

ValueDoseCo-administeredAnalytePopulation
9.4 h
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

Doses

DosePopulationAdverse 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)
ALT increased (grade 3-4)
Other AEs:
Aspartate aminotransferase increased (grade 3-4, 14.8%)
ALT increased (grade 3-4, 14.8%)
Sources: Page: p.308
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
Liver failure
Hepatocellular carcinoma
High density lipoprotein decreased
Low density lipoprotein increased
Atherosclerosis
Coronary artery disease
Sources: Page: p.1
AEs

AEs

AESignificanceDosePopulation
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
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
Drug as perpetrator​

Drug as perpetrator​

PubMed

PubMed

TitleDatePubMed
Clinical significance of weight loss in cancer patients: rationale for the use of anabolic agents in the treatment of cancer-related cachexia.
2001 Jan
Management of puberty in constitutional delay of growth and puberty.
2001 Jul
Nutrition and its role in wound healing.
2001 Sep
Reversal of COPD-associated weight loss using the anabolic agent oxandrolone.
2002 Aug
Orexigenic and anabolic agents.
2002 Nov
Anabolic steroids, testosterone-precursors and virilizing androgens induce distinct activation profiles of androgen responsive promoter constructs.
2002 Nov
Androgen therapy in constitutional delay of growth.
2003
Nutritional and pharmacological support of the metabolic response to injury.
2003 Apr
Oxandrolone induced lean mass gain during recovery from severe burns is maintained after discontinuation of the anabolic steroid.
2003 Dec
Protein-energy malnutrition and involuntary weight loss: nutritional and pharmacological strategies to enhance wound healing.
2003 Jul
Relationship between body composition and cytokines in cachectic patients with chronic obstructive pulmonary disease.
2003 Jun
Drug increases lean tissue mass in patients with cancer.
2003 Mar
Combination megestrol acetate, oxandrolone, and dietary advice restores weight in human immunodeficiency virus.
2004 Aug
Management of Turner's syndrome.
2004 Feb
The long-term effect of oxandrolone on hepatic acute phase proteins in severely burned children.
2004 Jan
The right mix: using nutritional interventions and an anabolic agent to manage a stage IV ulcer.
2004 Jan-Feb
Hypovitaminosis D in acutely injured pediatric burn patients.
2004 Jun
Vitamin A and iron supplementation is as efficient as hormonal therapy in constitutionally delayed children.
2004 Jun
Comparing megestrol acetate therapy with oxandrolone therapy for HIV-related weight loss: similar results in 2 months.
2004 Mar 15
Oxandrolone does not improve outcome of ventilator dependent surgical patients.
2004 Sep
[Carbohydrate metabolism in patients with Turner syndrome. The effect of therapy with growth hormone, oxandrolone and a combination of both].
2005
Longitudinal monitoring of bone measured by quantitative multisite ultrasound in patients with Crohn's disease.
2005 Feb
Altering metabolism.
2005 May-Jun
Discussion of "Comparison of clinical and cost-effectiveness of 3 intervention strategies for HIV wasting".
2005 Oct 1
Corticosteroid-induced myopathy in spinal cord injury patients: a role for anticatabolic agents?
2006 Apr
Effects of oxandrolone, an anabolic steroid, on hemostasis.
2006 Feb
Oxandrolone in the treatment of HIV-associated weight loss in men: a randomized, double-blind, placebo-controlled study.
2006 Mar
Oxandrolone enhances skeletal muscle myosin synthesis and alters global gene expression profile in Duchenne muscular dystrophy.
2006 Mar
Oxandrolone.
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
Dimerization and DNA binding of the AR fragments were observed at 0.5–1 uM oxandrolone.
Substance Class Chemical
Created
by admin
on Wed Jul 05 22:39:24 UTC 2023
Edited
by admin
on Wed Jul 05 22:39:24 UTC 2023
Record UNII
7H6TM3CT4L
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
OXANDROLONE
HSDB   INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP   VANDF   WHO-DD  
USAN   INN  
Official Name English
2-OXAANDROSTAN-3-ONE, 17-HYDROXY-17-METHYL-, (5.ALPHA.,17.BETA.)-
Common Name English
OXANDROLONE [USAN]
Common Name English
OXANDROLONE [HSDB]
Common Name English
VASOROME
Brand Name English
17β-Hydroxy-17-methyl-2-oxa-5α-androstan-3-one
Common Name English
Oxandrolone [WHO-DD]
Common Name English
ANAVAR
Brand Name English
OXANDROLONE [MART.]
Common Name English
PROVITAR
Brand Name English
NSC-67068
Code English
SC 11585
Code English
OXANDROLONE [JAN]
Common Name English
OXANDROLONE CIII
USP-RS  
Common Name English
OXANDROLONE CIII [USP-RS]
Common Name English
OXANDROLONE [USP MONOGRAPH]
Common Name English
SC-11585
Code English
OXANDRIN
Brand Name English
LONAVAR
Brand Name English
oxandrolone [INN]
Common Name English
OXANDROLONE [ORANGE BOOK]
Common Name English
OXANDROLONE [MI]
Common Name English
OXANDROLONE [VANDF]
Common Name English
Classification Tree Code System Code
WHO-VATC QA14AA08
Created by admin on Wed Jul 05 22:39:24 UTC 2023 , Edited by admin on Wed Jul 05 22:39:24 UTC 2023
WIKIPEDIA Designer-drugs-Oxandrolone
Created by admin on Wed Jul 05 22:39:24 UTC 2023 , Edited by admin on Wed Jul 05 22:39:24 UTC 2023
FDA ORPHAN DRUG 45790
Created by admin on Wed Jul 05 22:39:24 UTC 2023 , Edited by admin on Wed Jul 05 22:39:24 UTC 2023
FDA ORPHAN DRUG 103797
Created by admin on Wed Jul 05 22:39:24 UTC 2023 , Edited by admin on Wed Jul 05 22:39:24 UTC 2023
NCI_THESAURUS C243
Created by admin on Wed Jul 05 22:39:24 UTC 2023 , Edited by admin on Wed Jul 05 22:39:24 UTC 2023
FDA ORPHAN DRUG 59091
Created by admin on Wed Jul 05 22:39:24 UTC 2023 , Edited by admin on Wed Jul 05 22:39:24 UTC 2023
DEA NO. 4000
Created by admin on Wed Jul 05 22:39:24 UTC 2023 , Edited by admin on Wed Jul 05 22:39:24 UTC 2023
NCI_THESAURUS C2360
Created by admin on Wed Jul 05 22:39:24 UTC 2023 , Edited by admin on Wed Jul 05 22:39:24 UTC 2023
LIVERTOX 719
Created by admin on Wed Jul 05 22:39:24 UTC 2023 , Edited by admin on Wed Jul 05 22:39:24 UTC 2023
FDA ORPHAN DRUG 45590
Created by admin on Wed Jul 05 22:39:24 UTC 2023 , Edited by admin on Wed Jul 05 22:39:24 UTC 2023
WHO-ATC A14AA08
Created by admin on Wed Jul 05 22:39:24 UTC 2023 , Edited by admin on Wed Jul 05 22:39:24 UTC 2023
FDA ORPHAN DRUG 75793
Created by admin on Wed Jul 05 22:39:24 UTC 2023 , Edited by admin on Wed Jul 05 22:39:24 UTC 2023
Code System Code Type Description
CAS
53-39-4
Created by admin on Wed Jul 05 22:39:24 UTC 2023 , Edited by admin on Wed Jul 05 22:39:24 UTC 2023
PRIMARY
PUBCHEM
5878
Created by admin on Wed Jul 05 22:39:24 UTC 2023 , Edited by admin on Wed Jul 05 22:39:24 UTC 2023
PRIMARY
DAILYMED
7H6TM3CT4L
Created by admin on Wed Jul 05 22:39:24 UTC 2023 , Edited by admin on Wed Jul 05 22:39:24 UTC 2023
PRIMARY
NSC
67068
Created by admin on Wed Jul 05 22:39:24 UTC 2023 , Edited by admin on Wed Jul 05 22:39:24 UTC 2023
PRIMARY
ECHA (EC/EINECS)
200-172-9
Created by admin on Wed Jul 05 22:39:24 UTC 2023 , Edited by admin on Wed Jul 05 22:39:24 UTC 2023
PRIMARY
IUPHAR
7092
Created by admin on Wed Jul 05 22:39:24 UTC 2023 , Edited by admin on Wed Jul 05 22:39:24 UTC 2023
PRIMARY
RS_ITEM_NUM
1482003
Created by admin on Wed Jul 05 22:39:24 UTC 2023 , Edited by admin on Wed Jul 05 22:39:24 UTC 2023
PRIMARY
CHEBI
7820
Created by admin on Wed Jul 05 22:39:24 UTC 2023 , Edited by admin on Wed Jul 05 22:39:24 UTC 2023
PRIMARY
DRUG BANK
DB00621
Created by admin on Wed Jul 05 22:39:24 UTC 2023 , Edited by admin on Wed Jul 05 22:39:24 UTC 2023
PRIMARY
HSDB
3373
Created by admin on Wed Jul 05 22:39:24 UTC 2023 , Edited by admin on Wed Jul 05 22:39:24 UTC 2023
PRIMARY
EPA CompTox
DTXSID8023399
Created by admin on Wed Jul 05 22:39:24 UTC 2023 , Edited by admin on Wed Jul 05 22:39:24 UTC 2023
PRIMARY
RXCUI
7779
Created by admin on Wed Jul 05 22:39:24 UTC 2023 , Edited by admin on Wed Jul 05 22:39:24 UTC 2023
PRIMARY RxNorm
SMS_ID
100000083029
Created by admin on Wed Jul 05 22:39:24 UTC 2023 , Edited by admin on Wed Jul 05 22:39:24 UTC 2023
PRIMARY
WIKIPEDIA
OXANDROLONE
Created by admin on Wed Jul 05 22:39:24 UTC 2023 , Edited by admin on Wed Jul 05 22:39:24 UTC 2023
PRIMARY
NCI_THESAURUS
C29306
Created by admin on Wed Jul 05 22:39:24 UTC 2023 , Edited by admin on Wed Jul 05 22:39:24 UTC 2023
PRIMARY
FDA UNII
7H6TM3CT4L
Created by admin on Wed Jul 05 22:39:24 UTC 2023 , Edited by admin on Wed Jul 05 22:39:24 UTC 2023
PRIMARY
ChEMBL
CHEMBL1200436
Created by admin on Wed Jul 05 22:39:24 UTC 2023 , Edited by admin on Wed Jul 05 22:39:24 UTC 2023
PRIMARY
EVMPD
SUB09496MIG
Created by admin on Wed Jul 05 22:39:24 UTC 2023 , Edited by admin on Wed Jul 05 22:39:24 UTC 2023
PRIMARY
INN
1325
Created by admin on Wed Jul 05 22:39:24 UTC 2023 , Edited by admin on Wed Jul 05 22:39:24 UTC 2023
PRIMARY
MESH
D010074
Created by admin on Wed Jul 05 22:39:24 UTC 2023 , Edited by admin on Wed Jul 05 22:39:24 UTC 2023
PRIMARY
DRUG CENTRAL
2011
Created by admin on Wed Jul 05 22:39:24 UTC 2023 , Edited by admin on Wed Jul 05 22:39:24 UTC 2023
PRIMARY
MERCK INDEX
M8290
Created by admin on Wed Jul 05 22:39:24 UTC 2023 , Edited by admin on Wed Jul 05 22:39:24 UTC 2023
PRIMARY Merck Index
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