OXANDROLONE

US Previously Marketed

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

[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
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 167 Target ID: CHEMBL1871 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15219414	Agonist 2678		62.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Osteoporosis 97 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2006/076761lbl.pdf	Palliative		Approved 8429	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 8429	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	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

T_1/2

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: https://pubmed.ncbi.nlm.nih.gov/16540931 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: https://pubmed.ncbi.nlm.nih.gov/16540931 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: https://pubmed.ncbi.nlm.nih.gov/16540931 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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/13718s20s21lbl.pdf Page: p.1	unhealthy Health Status: unhealthy Condition: Weight loss Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/13718s20s21lbl.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/13718s20s21lbl.pdf Page: p.1

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 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: https://pubmed.ncbi.nlm.nih.gov/16540931 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: https://pubmed.ncbi.nlm.nih.gov/16540931 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: https://pubmed.ncbi.nlm.nih.gov/16540931 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: https://pubmed.ncbi.nlm.nih.gov/16540931 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: https://pubmed.ncbi.nlm.nih.gov/16540931 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: https://pubmed.ncbi.nlm.nih.gov/16540931 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: https://pubmed.ncbi.nlm.nih.gov/16540931 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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/13718s20s21lbl.pdf Page: p.1	unhealthy Health Status: unhealthy Condition: Weight loss Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/13718s20s21lbl.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/13718s20s21lbl.pdf Page: p.1	unhealthy Health Status: unhealthy Condition: Weight loss Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/13718s20s21lbl.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/13718s20s21lbl.pdf Page: p.1	unhealthy Health Status: unhealthy Condition: Weight loss Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/13718s20s21lbl.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/13718s20s21lbl.pdf Page: p.1	unhealthy Health Status: unhealthy Condition: Weight loss Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/13718s20s21lbl.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/13718s20s21lbl.pdf Page: p.1	unhealthy Health Status: unhealthy Condition: Weight loss Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/13718s20s21lbl.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/13718s20s21lbl.pdf Page: p.1	unhealthy Health Status: unhealthy Condition: Weight loss Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/13718s20s21lbl.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/13718s20s21lbl.pdf Page: p.1	unhealthy Health Status: unhealthy Condition: Weight loss Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/13718s20s21lbl.pdf Page: p.1

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
	inhibitor 1767

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2C9 1819	inhibitor 3277 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
ZINC	ZINC000003813047	http://zinc15.docking.org/substances/ZINC000003813047
eMolecules	2728084	https://www.emolecules.com/cgi-bin/more?vid=2728084
eMolecules	32278134	https://www.emolecules.com/cgi-bin/more?vid=32278134

PubMed

Title	Date	PubMed
Oxandrolone induced lean mass gain during recovery from severe burns is maintained after discontinuation of the anabolic steroid.	2003 Dec	14636753
Successful treatment of anabolic steroid-induced azoospermia with human chorionic gonadotropin and human menopausal gonadotropin.	2003 Jun	12801577
AIDS wasting syndrome: trends, influence on opportunistic infections, and survival.	2003 Jun 1	12794565
The steroid-responsive hiccup reflex arc: competitive binding to the corticosteroid-receptor?	2003 Jun-Aug	14523351
The anabolic androgenic steroid oxandrolone in the treatment of wasting and catabolic disorders: review of efficacy and safety.	2004	15025546
Combination megestrol acetate, oxandrolone, and dietary advice restores weight in human immunodeficiency virus.	2004 Aug	16215131
Efficient oxidizing methods for the synthesis of oxandrolone intermediates.	2004 Aug	15304998
Effects of long-term oxandrolone administration in severely burned children.	2004 Aug	15300183
Nutrition intervention is beneficial in oncology outpatients receiving radiotherapy to the gastrointestinal or head and neck area.	2004 Aug 2	15226773
Management of Turner's syndrome.	2004 Feb	15116948
Screening of free 17-alkyl-substituted anabolic steroids in human urine by liquid chromatography-electrospray ionization tandem mass spectrometry.	2004 Feb	15013688
Treatment outcome in Turner syndrome.	2004 Jan	15055914
The long-term effect of oxandrolone on hepatic acute phase proteins in severely burned children.	2004 Jan	14749563
[Therapeutic approach of hereditary angioedema].	2004 Jul-Sep	15499486
Support of the metabolic response to burn injury.	2004 Jun 5	15183630
Oxandrolone treatment of childhood hereditary angioedema.	2004 Mar	15049404
Oxandrolone blocks glucocorticoid signaling in an androgen receptor-dependent manner.	2004 May	15219414
Effects of androgen therapy on adipose tissue and metabolism in older men.	2004 Oct	15472177
Exercise and oxandrolone studied.	2004 Sep	15630778
Oxandrolone does not improve outcome of ventilator dependent surgical patients.	2004 Sep	15319718
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
A comparison of the clinical and cost-effectiveness of 3 intervention strategies for AIDS wasting.	2005 Apr 1	15764956
Screening of anabolic steroids in horse urine by liquid chromatography-tandem mass spectrometry.	2005 Apr 29	15862683
Six-week improvements in muscle mass and strength during androgen therapy in older men.	2005 Dec	16424293
Longitudinal monitoring of bone measured by quantitative multisite ultrasound in patients with Crohn's disease.	2005 Feb	15681906
The role of anabolic hormones for wound healing in catabolic states.	2005 Jan 17	16921407
Metacarpophalangeal pattern profile analysis as a tool for early diagnosis of Turner syndrome.	2005 Jul	16134322
Use of oxandrolone in ventilator dependent surgical patients.	2005 Jun	15912055
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 Mar	15952414
Involuntary weight loss: interview with Lisa Capaldini, M.D.	2005 Mar 25	15906451
Influence of hormonal therapy on growth rate and bone age progression in patients with Turner syndrome.	2005 Mar-Apr	16335681
[Study of bone mass in Turner syndrome].	2005 May	15871826
Altering metabolism.	2005 May-Jun	15879740
Post burn muscle wasting and the effects of treatments.	2005 Oct	16109499
Discussion of "Comparison of clinical and cost-effectiveness of 3 intervention strategies for HIV wasting".	2005 Oct 1	16186743
Metabolic and hormonal changes of severely burned children receiving long-term oxandrolone treatment.	2005 Sep	16135924
Longitudinal monitoring of bone accretion measured by quantitative multi-site ultrasound (QUS) of bones in patients with delayed puberty (a pilot study).	2005 Sep	15616757
Final height in girls with central idiopathic precocious puberty treated with gonadotropin-releasing hormone analog and oxandrolone.	2006 Apr	16449342
Corticosteroid-induced myopathy in spinal cord injury patients: a role for anticatabolic agents?	2006 Apr	16172629
Effects of oxandrolone, an anabolic steroid, on hemostasis.	2006 Feb	16432848
Influence of X chromosome and hormones on human brain development: a magnetic resonance imaging and proton magnetic resonance spectroscopy study of Turner syndrome.	2006 Feb 1	16139817
The current status of treatment for inclusion-body myositis.	2006 Jan 24	16432142
Oxandrolone steroid use and impaired coagulation.	2006 Jan 9	16401821
Oxandrolone in the treatment of HIV-associated weight loss in men: a randomized, double-blind, placebo-controlled study.	2006 Mar	16540931
Oxandrolone enhances skeletal muscle myosin synthesis and alters global gene expression profile in Duchenne muscular dystrophy.	2006 Mar	16263771
Effects of oxandrolone on outcome measures in the severely burned: a multicenter prospective randomized double-blind trial.	2006 Mar-Apr	16566555
Androgen therapy induces muscle protein anabolism in older women.	2006 Oct	16895962
Oxandrolone.	2006 Sep	16932191
Advances in burn critical care.	2006 Sep	16917429

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 `Fri Dec 15 15:07:29 GMT 2023` Edited by `admin` on `Fri Dec 15 15:07:29 GMT 2023`
Record UNII	7H6TM3CT4L
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

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

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

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