OXYMETHOLONE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H32O3
Molecular Weight	332.477
Optical Activity	UNSPECIFIED
Defined Stereocenters	7 / 7
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

SMILES

[H][C@@]12CC[C@](C)(O)[C@@]1(C)CC[C@@]3([H])[C@@]2([H])CC[C@@]4([H])CC(=O)\C(C[C@]34C)=C/O

InChI

InChIKey=ICMWWNHDUZJFDW-DHODBPELSA-N

InChI=1S/C21H32O3/c1-19-11-13(12-22)18(23)10-14(19)4-5-15-16(19)6-8-20(2)17(15)7-9-21(20,3)24/h12,14-17,22,24H,4-11H2,1-3H3/b13-12-/t14-,15+,16-,17-,19-,20-,21-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C21H32O3
Molecular Weight	332.477
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	7 / 7
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description

Oxymetholone (17beta-hydroxy-2-[hydroxymethylene]-17-methyl-5alpha-androstan-3-one) is a 17alpha-alkylated anabolic-androgenic steroid and a synthetic derivative of testosterone. It has been approved by the US Food and Drug Administration for the treatment of anemias caused by deficient red cell production. Acquired aplastic anemia, congenital aplastic anemia, myelofibrosis and the hypoplastic anemias due to the administration of myelotoxic drugs often respond. Drug interactions exist with cimetidine, paroxetine, and haloperidol, but are not expected with indinavir, ritonavir, clarithromycin, or itraconazole.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Androgen Receptor 167	Agonist 2,678

Conditions

Condition	Modality	Targets	Highest Phase	Product
Anemia 68	Primary		Approved 8,429	ANADROL-50

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
	inhibitor 1,767	inhibitor 1,852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP3A 214 CYP2C19 1,478	CYP450 65

Drug as perpetrator

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Target	Modality	Activity
CYP2C19 1,553	inhibitor 3,277	unlikely [IC50 206 uM]
CYP3A 298	inhibitor 3,277	unlikely [IC50 300 uM]
CYP2D6 1,891	inhibitor 3,277	unlikely [IC50 383 uM]
CYP2C9 1,819	inhibitor 3,277	unlikely [IC50 67.5 uM]

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Drug as victim

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Target	Modality	Activity	Metabolite	Clinical evidence
CYP450 65	substrate 3,367	no

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
ChEBI	CHEBI:7864	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:7864
eMolecules	29780638	https://www.emolecules.com/cgi-bin/more?vid=29780638

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PubMed

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Title	Date	PubMed
Review of oxymetholone: a 17alpha-alkylated anabolic-androgenic steroid.	2001 Jun	11440282
Hepatocellular adenomas associated with anabolic androgenic steroid abuse in bodybuilders: a report of two cases and a review of the literature.	2005 May	15849280

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Patents

Sample Use Guides

In Vivo Use Guide

The recommended daily dose in children and adults is 1-5 mg/kg of body weight per day. The usual effective dose is 1-2 mg/kg/day but higher doses may be required, and the dose should be individualized. Response is not often immediate, and a minimum trial of three to six months should be given. Following remission, some patients may be maintained without the drug; others may be maintained on an established lower daily dosage. A continued maintenance dose is usually necessary in patients with congenital aplastic anemia.

Route of Administration: Oral

In Vitro Use Guide

0.1 to 10 uM oxymetholone tested on normal CD34+ cells