17-HYDROXY-2-(HYDROXYMETHYLENE)-17-METHYLANDROSTAN-3-ONE, (2E,5.ALPHA.,17.BETA.)-

First approved in 1960

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

Structure of 17-HYDROXY-2-(HYDROXYMETHYLENE)-17-METHYLANDROSTAN-3-ONE, (2E,5.ALPHA.,17.BETA.)-

Structure Search

SMILES

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

InChI

InChIKey=ICMWWNHDUZJFDW-CCTJMHFWSA-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

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11440282
Curator's Comment: Description was created based on several sources, includinghttp://medapharma.us/products/pi/Anadrol-50_PI.pdf https://www.ncbi.nlm.nih.gov/pubmed/11365560

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 169 Target ID: CHEMBL1871 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6539197	Agonist 2752

Conditions

Condition	Modality	Targets	Highest Phase	Product
Anemia 70 Sources: http://medapharma.us/products/pi/Anadrol-50_PI.pdf	Primary		Approved 8583	ANADROL-50 Approved Use Anadrol®-50 Tablets is indicated in 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. Anadrol®-50 Tablets should not replace other supportive measures such as transfusion, correction of iron, folic acid, vitamin B12 or pyridoxine deficiency, antibacterial therapy and the appropriate use of corticosteroids. Launch Date 1972

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
	inhibitor 2438	inhibitor 2507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP3A 227 CYP2C19 2057	CYP450 59

Drug as perpetrator

Target	Modality	Activity
CYP2C19 2141	inhibitor 4027 Sources: https://ascpt.onlinelibrary.wiley.com/doi/abs/10.1016/S0009-9236(99)80075-7	unlikely [IC50 206 uM]
CYP3A 317	inhibitor 4027 Sources: https://ascpt.onlinelibrary.wiley.com/doi/abs/10.1016/S0009-9236(99)80075-7	unlikely [IC50 300 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://ascpt.onlinelibrary.wiley.com/doi/abs/10.1016/S0009-9236(99)80075-7 Page: 4.0	unlikely [IC50 383 uM]
CYP2C9 2497	inhibitor 4027 Sources: https://ascpt.onlinelibrary.wiley.com/doi/abs/10.1016/S0009-9236(99)80075-7	unlikely [IC50 67.5 uM]

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP450 59	substrate 4014 Sources: https://ascpt.onlinelibrary.wiley.com/doi/abs/10.1016/S0009-9236(99)80075-7 Page: 4.0	no

Sourcing

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

PubMed

Title	Date	PubMed
Utilization of human nuclear receptors as an early counter screen for off-target activity: a case study with a compendium of 615 known drugs.	2015-06	25752796
Genomic models of short-term exposure accurately predict long-term chemical carcinogenicity and identify putative mechanisms of action.	2014	25058030
The anabolic androgenic steroid fluoxymesterone inhibits 11β-hydroxysteroid dehydrogenase 2-dependent glucocorticoid inactivation.	2012-04	22273746
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.	2011-07-14	21599003
Oxymetholone ameliorates insulin sensitivity in maintenance hemodialysis patients: a randomized controlled trial.	2009-04	19356374
Direct and indirect effects of androgens on survival of hematopoietic progenitor cells in vitro.	2005-06	15953861
Hepatocellular adenomas associated with anabolic androgenic steroid abuse in bodybuilders: a report of two cases and a review of the literature.	2005-05	15849280
Characterization of spontaneous and chemically induced cardiac lesions in rodent model systems: the national toxicology program experience.	2005	16046796
Androgens and liver tumors: Fanconi's anemia and non-Fanconi's conditions.	2004-11	15495253
Review of oxymetholone: a 17alpha-alkylated anabolic-androgenic steroid.	2001-06	11440282
Poststeroid balance disorder--a case report in a body builder.	1999-08	10496122
Pure red blood cell aplasia complicating chronic lymphatic leukemia.	1983-09-01	6614043
Nonfatal methazolamide-induced aplastic anemia.	1978-07	677225
Carcinoma of the breast. Occurence after treatment with melphalan for multiple myeloma.	1976-10-04	183029
Polycythaemia in androgen-dependent aplastic anaemia.	1976-01-24	1247773
Androgen-induced hepatoma.	1975-02-22	48615
Association of androgenic-anabolic steroid therapy with development of hepatocellular carcinoma.	1972-12-16	4117807
Aplastic anaemia, oxymetholone and acute myeloid leukaemia.	1972-10-28	4509114

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

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:04:26 GMT 2025` Edited by `admin` on `Mon Mar 31 18:04:26 GMT 2025`
Record UNII	77LW93C64T
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

17-HYDROXY-2-(HYDROXYMETHYLENE)-17-METHYLANDROSTAN-3-ONE, (2E,5.ALPHA.,17.BETA.)-

Systematic Name

English

ANDROSTAN-3-ONE, 17-HYDROXY-2-(HYDROXYMETHYLENE)-17-METHYL-, (2E,5.ALPHA.,17.BETA.)-

Preferred Name

English

Code System Code Type Description

FDA UNII

77LW93C64T

Created by admin on Mon Mar 31 18:04:26 GMT 2025 , Edited by admin on Mon Mar 31 18:04:26 GMT 2025

PRIMARY

PUBCHEM

3032303

Created by admin on Mon Mar 31 18:04:26 GMT 2025 , Edited by admin on Mon Mar 31 18:04:26 GMT 2025

PRIMARY

CAS

156197-08-9

Created by admin on Mon Mar 31 18:04:26 GMT 2025 , Edited by admin on Mon Mar 31 18:04:26 GMT 2025

PRIMARY

Details

SMILES

InChI

DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/11440282Curator's Comment: Description was created based on several sources, includinghttp://medapharma.us/products/pi/Anadrol-50_PI.pdf https://www.ncbi.nlm.nih.gov/pubmed/11365560

CNS Activity

Originator

Approval Year

Targets

Conditions

Approved Use

Launch Date

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Sourcing

PubMed

Patents

Sample Use Guides

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11440282
Curator's Comment: Description was created based on several sources, includinghttp://medapharma.us/products/pi/Anadrol-50_PI.pdf https://www.ncbi.nlm.nih.gov/pubmed/11365560

Drug as perpetrator