OXANDROLONE

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 2637		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 8307	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
Protein catabolism 1 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2006/076761lbl.pdf	Secondary		Approved 8307	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

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 1695

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2C9 1747	inhibitor 3185 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
The anabolic steroid oxandrolone increases muscle mass in prepubertal boys with constitutional delay of growth.	2001 Jun	11453521
The effects of oestrogens on linear bone growth.	2001 May-Jun	11392377
Exercise treatment for HIV-associated metabolic and anthropomorphic complications.	2001 Oct	11688790
Nutrition and its role in wound healing.	2001 Sep	11889741
Remission of clinical signs in early duchenne muscular dystrophy on intermittent low-dosage prednisolone therapy.	2002	12363102
Orexigenic and anabolic agents.	2002 Nov	12608509
The patient.com, 1 year later.	2002 Nov-Dec	12477977
Body cell mass repletion and improved quality of life in HIV-infected individuals receiving oxandrolone.	2002 Nov-Dec	12405647
Pelvic ultrasound evaluation in patients with Turner syndrome during treatment with growth hormone.	2003 Aug	12905513
Protein-energy malnutrition and involuntary weight loss: nutritional and pharmacological strategies to enhance wound healing.	2003 Jul	12831338
Current pharmacotherapy for the treatment of severe burns.	2003 Mar	12614189
[Optimizing estrogen treatment in Turner syndrome].	2003 Mar 23	12723527
Combination megestrol acetate, oxandrolone, and dietary advice restores weight in human immunodeficiency virus.	2004 Aug	16215131
Screening of free 17-alkyl-substituted anabolic steroids in human urine by liquid chromatography-electrospray ionization tandem mass spectrometry.	2004 Feb	15013688
Optimization of treatment in Turner's syndrome.	2004 Mar	15134303
Oxandrolone does not improve outcome of ventilator dependent surgical patients.	2004 Sep	15319718
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
[Study of bone mass in Turner syndrome].	2005 May	15871826
Oxandrolone enhances skeletal muscle myosin synthesis and alters global gene expression profile in Duchenne muscular dystrophy.	2006 Mar	16263771
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 16 16:15:21 UTC 2022` Edited by `admin` on `Fri Dec 16 16:15:21 UTC 2022`
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

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

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