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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H32O3
Molecular Weight 332.4778
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of OXYMETHOLONE

SMILES

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

Description
Curator's Comment:: 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

CNS Active
3656
Curator's Comment:: Known to be CNS active in rats. Human data not available.

Originator

Syntex
45
Curator's Comment:: Ringold et al, 1959 (Syntex SA)

Approval Year

1960
89
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2456
Anemia
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Androgen Receptor
Approved
7997
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

64540800000
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
inhibitor
1318
inhibitor
1421

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP3A
175

CYP2C19
1215
CYP450
58
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP2C19
1277
 unlikely [IC50 206 uM]
CYP3A
244
 unlikely [IC50 300 uM]
CYP2D6
1455
 unlikely [IC50 383 uM]
CYP2C9
1362
 unlikely [IC50 67.5 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP450
58
 no
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:7864
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:7864
PubMed

PubMed

TitleDatePubMed
Association of androgenic-anabolic steroid therapy with development of hepatocellular carcinoma.
1972 Dec 16
Aplastic anaemia, oxymetholone and acute myeloid leukaemia.
1972 Oct 28
Androgen-induced hepatoma.
1975 Feb 22
Polycythaemia in androgen-dependent aplastic anaemia.
1976 Jan 24
Carcinoma of the breast. Occurence after treatment with melphalan for multiple myeloma.
1976 Oct 4
Nonfatal methazolamide-induced aplastic anemia.
1978 Jul
Pure red blood cell aplasia complicating chronic lymphatic leukemia.
1983 Sep-Oct
Poststeroid balance disorder--a case report in a body builder.
1999 Aug
Review of oxymetholone: a 17alpha-alkylated anabolic-androgenic steroid.
2001 Jun
Androgens and liver tumors: Fanconi's anemia and non-Fanconi's conditions.
2004 Nov
Characterization of spontaneous and chemically induced cardiac lesions in rodent model systems: the national toxicology program experience.
2005
Direct and indirect effects of androgens on survival of hematopoietic progenitor cells in vitro.
2005 Jun
Hepatocellular adenomas associated with anabolic androgenic steroid abuse in bodybuilders: a report of two cases and a review of the literature.
2005 May
Oxymetholone ameliorates insulin sensitivity in maintenance hemodialysis patients: a randomized controlled trial.
2009 Apr
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.
2011 Jul 14
The anabolic androgenic steroid fluoxymesterone inhibits 11β-hydroxysteroid dehydrogenase 2-dependent glucocorticoid inactivation.
2012 Apr
Genomic models of short-term exposure accurately predict long-term chemical carcinogenicity and identify putative mechanisms of action.
2014
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 Jun
Patents

Patents

JP2005500299A
34
JPH01216940A
8

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.
Route of Administration: Oral
In Vitro Use Guide
0.1 to 10 uM oxymetholone tested on normal CD34+ cells
Name Type Language
OXYMETHOLONE
HSDB   INN   MART.   MI   ORANGE BOOK   USAN   USP   VANDF   WHO-DD  
USAN   INN  
Official Name English
OXYMETHOLONE CIII
USP-RS  
Common Name English
CI-406
Code English
ANADROL-50
Brand Name English
OXYMETHOLONE [USP]
Common Name English
17.BETA.-HYDROXY-2-(HYDROXYMETHYLENE)-17-METHYL-5.ALPHA.-ANDROSTAN-3-ONE
Systematic Name English
ADROYD
Brand Name English
ANDROSTAN-3-ONE, 17-HYDROXY-2-(HYDROXYMETHYLENE)-17-METHYL-, (2Z,5.ALPHA.,17.BETA.)-
Systematic Name English
NSC-26198
Code English
OXYMETHOLONE [INN]
Common Name English
OXYMETHOLONE [ORANGE BOOK]
Common Name English
HMD
Code English
OXYMETHOLONE [WHO-DD]
Common Name English
OXYMETHOLONE [HSDB]
Common Name English
OXYMETHOLONE CIII [USP-RS]
Common Name English
ANAPOLON
Brand Name English
OXYMETHOLONE [USAN]
Common Name English
ANDROSTAN-3-ONE, 17-HYDROXY-2-(HYDROXYMETHYLENE)-17-METHYL-, (5.ALPHA.,17.BETA.)-
Common Name English
STANOZOLOL IMPURITY B [EP]
Common Name English
OXYMETHOLONE [JAN]
Common Name English
OXYMETHOLONE [MI]
Common Name English
PARDROYD
Brand Name English
OXYMETHOLONE [MART.]
Common Name English
OXYMETHOLONE [VANDF]
Common Name English
NSC-26,198
Code English
ANASTERON
Brand Name English
Classification Tree Code System Code
NCI_THESAURUS C243
Created by admin on Sat Jun 26 11:20:30 UTC 2021 , Edited by admin on Sat Jun 26 11:20:30 UTC 2021
DEA NO. 4000
Created by admin on Sat Jun 26 11:20:30 UTC 2021 , Edited by admin on Sat Jun 26 11:20:30 UTC 2021
WHO-VATC QA14AA05
Created by admin on Sat Jun 26 11:20:30 UTC 2021 , Edited by admin on Sat Jun 26 11:20:30 UTC 2021
LIVERTOX 727
Created by admin on Sat Jun 26 11:20:30 UTC 2021 , Edited by admin on Sat Jun 26 11:20:30 UTC 2021
WHO-ATC A14AA05
Created by admin on Sat Jun 26 11:20:30 UTC 2021 , Edited by admin on Sat Jun 26 11:20:30 UTC 2021
NCI_THESAURUS C2360
Created by admin on Sat Jun 26 11:20:30 UTC 2021 , Edited by admin on Sat Jun 26 11:20:30 UTC 2021
Code System Code Type Description
ChEMBL
CHEMBL1200585
Created by admin on Sat Jun 26 11:20:30 UTC 2021 , Edited by admin on Sat Jun 26 11:20:30 UTC 2021
PRIMARY
MESH
D010110
Created by admin on Sat Jun 26 11:20:30 UTC 2021 , Edited by admin on Sat Jun 26 11:20:30 UTC 2021
PRIMARY
FDA UNII
L76T0ZCA8K
Created by admin on Sat Jun 26 11:20:30 UTC 2021 , Edited by admin on Sat Jun 26 11:20:30 UTC 2021
PRIMARY
HSDB
3374
Created by admin on Sat Jun 26 11:20:30 UTC 2021 , Edited by admin on Sat Jun 26 11:20:30 UTC 2021
PRIMARY
CAS
78964-17-7
Created by admin on Sat Jun 26 11:20:30 UTC 2021 , Edited by admin on Sat Jun 26 11:20:30 UTC 2021
ALTERNATIVE
WIKIPEDIA
OXYMETHOLONE
Created by admin on Sat Jun 26 11:20:30 UTC 2021 , Edited by admin on Sat Jun 26 11:20:30 UTC 2021
PRIMARY
NCI_THESAURUS
C723
Created by admin on Sat Jun 26 11:20:30 UTC 2021 , Edited by admin on Sat Jun 26 11:20:30 UTC 2021
PRIMARY
RXCUI
7813
Created by admin on Sat Jun 26 11:20:30 UTC 2021 , Edited by admin on Sat Jun 26 11:20:30 UTC 2021
PRIMARY RxNorm
USP_CATALOG
1487007
Created by admin on Sat Jun 26 11:20:30 UTC 2021 , Edited by admin on Sat Jun 26 11:20:30 UTC 2021
PRIMARY USP-RS
DRUG CENTRAL
2033
Created by admin on Sat Jun 26 11:20:30 UTC 2021 , Edited by admin on Sat Jun 26 11:20:30 UTC 2021
PRIMARY
EVMPD
SUB09568MIG
Created by admin on Sat Jun 26 11:20:30 UTC 2021 , Edited by admin on Sat Jun 26 11:20:30 UTC 2021
PRIMARY
PUBCHEM
5281034
Created by admin on Sat Jun 26 11:20:30 UTC 2021 , Edited by admin on Sat Jun 26 11:20:30 UTC 2021
PRIMARY
INN
1022
Created by admin on Sat Jun 26 11:20:30 UTC 2021 , Edited by admin on Sat Jun 26 11:20:30 UTC 2021
PRIMARY
MERCK INDEX
M8336
Created by admin on Sat Jun 26 11:20:30 UTC 2021 , Edited by admin on Sat Jun 26 11:20:30 UTC 2021
PRIMARY Merck Index
DRUG BANK
DB06412
Created by admin on Sat Jun 26 11:20:30 UTC 2021 , Edited by admin on Sat Jun 26 11:20:30 UTC 2021
PRIMARY
CAS
434-07-1
Created by admin on Sat Jun 26 11:20:30 UTC 2021 , Edited by admin on Sat Jun 26 11:20:30 UTC 2021
PRIMARY
EPA CompTox
434-07-1
Created by admin on Sat Jun 26 11:20:30 UTC 2021 , Edited by admin on Sat Jun 26 11:20:30 UTC 2021
PRIMARY
ECHA (EC/EINECS)
207-098-6
Created by admin on Sat Jun 26 11:20:30 UTC 2021 , Edited by admin on Sat Jun 26 11:20:30 UTC 2021
PRIMARY
ACTIVE MOIETY
Structure of OXYMETHOLONE
METABOLITE (PARENT)
Structure of BA-2664
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
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