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
Anabolic agents and wound healing.	2001 May-Jun	11905983
9 clinical cases of nonhealing pressure ulcers in patients with spinal cord injury treated with an anabolic agent: a therapeutic trial.	2001 May-Jun	11905979
A pilot randomized trial of oxandrolone in inclusion body myositis.	2002 Apr 9	11940697
Favorable final height outcome in girls with Ullrich-Turner syndrome treated with low-dose growth hormone together with oxandrolone despite starting treatment after 10 years of age.	2002 Feb	11874177
Orexigenic and anabolic agents.	2002 Nov	12608509
Anabolic steroids, testosterone-precursors and virilizing androgens induce distinct activation profiles of androgen responsive promoter constructs.	2002 Nov	12589933
Anabolic treatment with GH, IGF-I, or anabolic steroids in patients with HIV-associated wasting.	2002 Sep	12163220
Pelvic ultrasound evaluation in patients with Turner syndrome during treatment with growth hormone.	2003 Aug	12905513
Improvement in steroid screening for doping control with special emphasis on stanozolol.	2003 Jan 24	12580506
Protein-energy malnutrition and involuntary weight loss: nutritional and pharmacological strategies to enhance wound healing.	2003 Jul	12831338
Androgen therapy improves muscle mass and strength but not muscle quality: results from two studies.	2003 Jul	12637255
[Optimizing estrogen treatment in Turner syndrome].	2003 Mar 23	12723527
Reversible azoospermia: anabolic steroids may profoundly affect human immunodeficiency virus-seropositive men undergoing assisted reproduction.	2003 May	12738106
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
Nutrition intervention is beneficial in oncology outpatients receiving radiotherapy to the gastrointestinal or head and neck area.	2004 Aug 2	15226773
Treatment outcome in Turner syndrome.	2004 Jan	15055914
Treatment guidelines for HIV-associated wasting.	2004 Jan-Feb	15002087
Hypovitaminosis D in acutely injured pediatric burn patients.	2004 Jun	15175591
Vitamin A and iron supplementation is as efficient as hormonal therapy in constitutionally delayed children.	2004 Jun	15163330
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
The pharmacologic modulation of the hypermetabolic response to burns.	2005	16250555
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
Use of oxandrolone in ventilator dependent surgical patients.	2005 Jun	15912055
Involuntary weight loss: interview with Lisa Capaldini, M.D.	2005 Mar 25	15906451
[Study of bone mass in Turner syndrome].	2005 May	15871826
Altering metabolism.	2005 May-Jun	15879740
Final height in girls with central idiopathic precocious puberty treated with gonadotropin-releasing hormone analog and oxandrolone.	2006 Apr	16449342
Effects of oxandrolone, an anabolic steroid, on hemostasis.	2006 Feb	16432848
The current status of treatment for inclusion-body myositis.	2006 Jan 24	16432142

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