OXANDROLONE

First approved in 1964

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 Search

SMILES

C[C@]1(O)CC[C@H]2[C@@H]3CC[C@H]4CC(=O)OC[C@]4(C)[C@H]3CC[C@]12C

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
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2006/076761lbl.pdf
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Androgen Receptor 169 Target ID: CHEMBL1871 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15219414	Agonist 2752		62.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Osteoporosis 101 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2006/076761lbl.pdf	Palliative		Approved 8583	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 1964
Protein catabolism 1 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2006/076761lbl.pdf	Secondary		Approved 8583	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 1964

C_max

Value	Dose	Analyte	Population
23 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32265605/	0.2 mg/kg single, buccal dose: 0.2 mg/kg route of administration: Buccal experiment type: SINGLE co-administered:	OXANDROLONE plasma	Homo sapiens population: UNHEALTHY age: NEWBORN sex: FEMALE / MALE food status: UNKNOWN
44.6 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32265605/	10 mg single, buccal dose: 10 mg route of administration: Buccal experiment type: SINGLE co-administered:	OXANDROLONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
15.1 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32265605/	0.1 mg/kg 2 times / day multiple, buccal dose: 0.1 mg/kg route of administration: Buccal experiment type: MULTIPLE co-administered:	OXANDROLONE plasma	Homo sapiens population: UNHEALTHY age: NEWBORN sex: FEMALE / MALE food status: UNKNOWN
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	Analyte	Population
58.6 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32265605/	0.2 mg/kg single, buccal dose: 0.2 mg/kg route of administration: Buccal experiment type: SINGLE co-administered:	OXANDROLONE plasma	Homo sapiens population: UNHEALTHY age: NEWBORN sex: FEMALE / MALE food status: UNKNOWN
249 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32265605/	10 mg single, buccal dose: 10 mg route of administration: Buccal experiment type: SINGLE co-administered:	OXANDROLONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
36.9 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32265605/	0.1 mg/kg 2 times / day multiple, buccal dose: 0.1 mg/kg route of administration: Buccal experiment type: MULTIPLE co-administered:	OXANDROLONE plasma	Homo sapiens population: UNHEALTHY age: NEWBORN sex: FEMALE / MALE food status: UNKNOWN
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

T_1/2

Value	Dose	Analyte	Population
2.87 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32265605/	0.2 mg/kg single, buccal dose: 0.2 mg/kg route of administration: Buccal experiment type: SINGLE co-administered:	OXANDROLONE plasma	Homo sapiens population: UNHEALTHY age: NEWBORN sex: FEMALE / MALE food status: UNKNOWN
2.19 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32265605/	0.1 mg/kg 2 times / day multiple, buccal dose: 0.1 mg/kg route of administration: Buccal experiment type: MULTIPLE co-administered:	OXANDROLONE plasma	Homo sapiens population: UNHEALTHY age: NEWBORN sex: FEMALE / MALE food status: UNKNOWN
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: https://pubmed.ncbi.nlm.nih.gov/16540931	unhealthy, 39.5+/-7.5 Health Status: unhealthy Age Group: 39.5+/-7.5 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/16540931	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: https://pubmed.ncbi.nlm.nih.gov/16540931
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/13718s20s21lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/13718s20s21lbl.pdf	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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/13718s20s21lbl.pdf

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: https://pubmed.ncbi.nlm.nih.gov/16540931	unhealthy, 39.5+/-7.5 Health Status: unhealthy Age Group: 39.5+/-7.5 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/16540931
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: https://pubmed.ncbi.nlm.nih.gov/16540931	unhealthy, 39.5+/-7.5 Health Status: unhealthy Age Group: 39.5+/-7.5 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/16540931
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: https://pubmed.ncbi.nlm.nih.gov/16540931	unhealthy, 39.5+/-7.5 Health Status: unhealthy Age Group: 39.5+/-7.5 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/16540931
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: https://pubmed.ncbi.nlm.nih.gov/16540931	unhealthy, 39.5+/-7.5 Health Status: unhealthy Age Group: 39.5+/-7.5 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/16540931
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/13718s20s21lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/13718s20s21lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/13718s20s21lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/13718s20s21lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/13718s20s21lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/13718s20s21lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/13718s20s21lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/13718s20s21lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/13718s20s21lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/13718s20s21lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/13718s20s21lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/13718s20s21lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/13718s20s21lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/13718s20s21lbl.pdf

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
	inhibitor 2438

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2C9 2497	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/27754879/; https://link.springer.com/article/10.1186/s12902-018-0315-6	likely

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:7820	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:7820
ChemicalBook	CB6112482	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB6112482
eMolecules	2728084	https://www.emolecules.com/cgi-bin/more?vid=2728084
eMolecules	32278134	https://www.emolecules.com/cgi-bin/more?vid=32278134
ZINC	ZINC000003813047	http://zinc15.docking.org/substances/ZINC000003813047

PubMed

Title	Date	PubMed
Androgen therapy induces muscle protein anabolism in older women.	2006-10	16895962
Oxandrolone.	2006-09	16932191
Advances in burn critical care.	2006-09	16917429
Final height in girls with central idiopathic precocious puberty treated with gonadotropin-releasing hormone analog and oxandrolone.	2006-04	16449342
Corticosteroid-induced myopathy in spinal cord injury patients: a role for anticatabolic agents?	2006-04	16172629
Effects of oxandrolone on outcome measures in the severely burned: a multicenter prospective randomized double-blind trial.	2006-03-29	16566555
Oxandrolone in the treatment of HIV-associated weight loss in men: a randomized, double-blind, placebo-controlled study.	2006-03	16540931
Oxandrolone enhances skeletal muscle myosin synthesis and alters global gene expression profile in Duchenne muscular dystrophy.	2006-03	16263771
Influence of X chromosome and hormones on human brain development: a magnetic resonance imaging and proton magnetic resonance spectroscopy study of Turner syndrome.	2006-02-01	16139817
Effects of oxandrolone, an anabolic steroid, on hemostasis.	2006-02	16432848
The current status of treatment for inclusion-body myositis.	2006-01-24	16432142
Oxandrolone steroid use and impaired coagulation.	2006-01-09	16401821
Influence of hormonal therapy on growth rate and bone age progression in patients with Turner syndrome.	2005-12-13	16335681
Six-week improvements in muscle mass and strength during androgen therapy in older men.	2005-12	16424293
Discussion of "Comparison of clinical and cost-effectiveness of 3 intervention strategies for HIV wasting".	2005-10-01	16186743
Post burn muscle wasting and the effects of treatments.	2005-10	16109499
Metabolic and hormonal changes of severely burned children receiving long-term oxandrolone treatment.	2005-09	16135924
Longitudinal monitoring of bone accretion measured by quantitative multi-site ultrasound (QUS) of bones in patients with delayed puberty (a pilot study).	2005-09	15616757
Metacarpophalangeal pattern profile analysis as a tool for early diagnosis of Turner syndrome.	2005-07	16134322
Use of oxandrolone in ventilator dependent surgical patients.	2005-06	15912055
Altering metabolism.	2005-05-10	15879740
[Study of bone mass in Turner syndrome].	2005-05	15871826
Screening of anabolic steroids in horse urine by liquid chromatography-tandem mass spectrometry.	2005-04-29	15862683
A comparison of the clinical and cost-effectiveness of 3 intervention strategies for AIDS wasting.	2005-04-01	15764956
Involuntary weight loss: interview with Lisa Capaldini, M.D.	2005-03-25	15906451
Final height in a patient with Laron syndrome after long-term therapy with rhlGF-I and short-term therapy with LHRH-analogue and oxandrolone during puberty.	2005-03	15952414
Longitudinal monitoring of bone measured by quantitative multisite ultrasound in patients with Crohn's disease.	2005-02	15681906
The role of anabolic hormones for wound healing in catabolic states.	2005-01-17	16921407
The pharmacologic modulation of the hypermetabolic response to burns.	2005	16250555
[Carbohydrate metabolism in patients with Turner syndrome. The effect of therapy with growth hormone, oxandrolone and a combination of both].	2005	15996336
[Therapeutic approach of hereditary angioedema].	2004-10-23	15499486
Effects of androgen therapy on adipose tissue and metabolism in older men.	2004-10	15472177
Exercise and oxandrolone studied.	2004-09	15630778
Oxandrolone does not improve outcome of ventilator dependent surgical patients.	2004-09	15319718
Nutrition intervention is beneficial in oncology outpatients receiving radiotherapy to the gastrointestinal or head and neck area.	2004-08-02	15226773
Combination megestrol acetate, oxandrolone, and dietary advice restores weight in human immunodeficiency virus.	2004-08	16215131
Efficient oxidizing methods for the synthesis of oxandrolone intermediates.	2004-08	15304998
Effects of long-term oxandrolone administration in severely burned children.	2004-08	15300183
Support of the metabolic response to burn injury.	2004-06-05	15183630
Hypovitaminosis D in acutely injured pediatric burn patients.	2004-06	15175591
Vitamin A and iron supplementation is as efficient as hormonal therapy in constitutionally delayed children.	2004-06	15163330
Oxandrolone blocks glucocorticoid signaling in an androgen receptor-dependent manner.	2004-05	15219414
Comparing megestrol acetate therapy with oxandrolone therapy for HIV-related weight loss: similar results in 2 months.	2004-03-15	14999637
Treatment guidelines for HIV-associated wasting.	2004-03-06	15002087
Optimization of treatment in Turner's syndrome.	2004-03	15134303
Oxandrolone treatment of childhood hereditary angioedema.	2004-03	15049404
Management of Turner's syndrome.	2004-02	15116948
Screening of free 17-alkyl-substituted anabolic steroids in human urine by liquid chromatography-electrospray ionization tandem mass spectrometry.	2004-02	15013688
Treatment outcome in Turner syndrome.	2004-01	15055914
The anabolic androgenic steroid oxandrolone in the treatment of wasting and catabolic disorders: review of efficacy and safety.	2004	15025546

Patents

Sample Use Guides

In Vivo Use Guide

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

Dimerization and DNA binding of the AR fragments were observed at 0.5–1 uM oxandrolone.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:47:18 GMT 2025` Edited by `admin` on `Mon Mar 31 17:47:18 GMT 2025`
Record UNII	7H6TM3CT4L
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

OXANDROLONE CIII

Preferred Name

English

OXANDROLONE

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

17?-Hydroxy-17-methyl-2-oxa-5?-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 [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