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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 OXYMETHOLONE

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

Description
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

CNS Active
4002
Curator's Comment: Known to be CNS active in rats. Human data not available.

Originator

Syntex
47
Curator's Comment: Ringold et al, 1959 (Syntex SA)

Approval Year

1960
105
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2752
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
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

Overview

CYP3A4CYP2C9CYP2D6hERG
inhibitor
2438
inhibitor
2507

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP3A
227

CYP2C19
2057
CYP450
59
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP2C19
2141
 unlikely [IC50 206 uM]
CYP3A
317
 unlikely [IC50 300 uM]
CYP2D6
2546
 unlikely [IC50 383 uM]
CYP2C9
2497
 unlikely [IC50 67.5 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP450
59
 no
Sourcing

Sourcing

Vendor/AggregatorIDURL
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

PubMed

TitleDatePubMed
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
Genomic models of short-term exposure accurately predict long-term chemical carcinogenicity and identify putative mechanisms of action.
2014
The anabolic androgenic steroid fluoxymesterone inhibits 11β-hydroxysteroid dehydrogenase 2-dependent glucocorticoid inactivation.
2012-04
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.
2011-07-14
Oxymetholone ameliorates insulin sensitivity in maintenance hemodialysis patients: a randomized controlled trial.
2009-04
Direct and indirect effects of androgens on survival of hematopoietic progenitor cells in vitro.
2005-06
Hepatocellular adenomas associated with anabolic androgenic steroid abuse in bodybuilders: a report of two cases and a review of the literature.
2005-05
Characterization of spontaneous and chemically induced cardiac lesions in rodent model systems: the national toxicology program experience.
2005
Androgens and liver tumors: Fanconi's anemia and non-Fanconi's conditions.
2004-11
Review of oxymetholone: a 17alpha-alkylated anabolic-androgenic steroid.
2001-06
Poststeroid balance disorder--a case report in a body builder.
1999-08
Pure red blood cell aplasia complicating chronic lymphatic leukemia.
1983-09-01
Nonfatal methazolamide-induced aplastic anemia.
1978-07
Carcinoma of the breast. Occurence after treatment with melphalan for multiple myeloma.
1976-10-04
Polycythaemia in androgen-dependent aplastic anaemia.
1976-01-24
Androgen-induced hepatoma.
1975-02-22
Association of androgenic-anabolic steroid therapy with development of hepatocellular carcinoma.
1972-12-16
Aplastic anaemia, oxymetholone and acute myeloid leukaemia.
1972-10-28
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. 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 18:21:03 GMT 2025
Edited
by admin
on Mon Mar 31 18:21:03 GMT 2025
Record UNII
L76T0ZCA8K
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
OXYMETHOLONE CIII
USP-RS  
Preferred Name English
OXYMETHOLONE
HSDB   INN   MART.   MI   ORANGE BOOK   USAN   USP   VANDF   WHO-DD  
USAN   INN  
Official Name English
CI-406
Code English
ANADROL-50
Brand Name English
17?-Hydroxy-2-(hydroxymethylene)-17-methyl-5?-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
OXYMETHOLONE [USP MONOGRAPH]
Common Name English
HMD
Code English
OXYMETHOLONE [HSDB]
Common Name English
STANOZOLOL IMPURITY B [EP IMPURITY]
Common Name English
OXYMETHOLONE CIII [USP-RS]
Common Name English
Oxymetholone [WHO-DD]
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
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 Mon Mar 31 18:21:03 GMT 2025 , Edited by admin on Mon Mar 31 18:21:03 GMT 2025
DEA NO. 4000
Created by admin on Mon Mar 31 18:21:03 GMT 2025 , Edited by admin on Mon Mar 31 18:21:03 GMT 2025
WIKIPEDIA Designer-drugs-Oxymetholone
Created by admin on Mon Mar 31 18:21:03 GMT 2025 , Edited by admin on Mon Mar 31 18:21:03 GMT 2025
WHO-VATC QA14AA05
Created by admin on Mon Mar 31 18:21:03 GMT 2025 , Edited by admin on Mon Mar 31 18:21:03 GMT 2025
LIVERTOX 727
Created by admin on Mon Mar 31 18:21:03 GMT 2025 , Edited by admin on Mon Mar 31 18:21:03 GMT 2025
WHO-ATC A14AA05
Created by admin on Mon Mar 31 18:21:03 GMT 2025 , Edited by admin on Mon Mar 31 18:21:03 GMT 2025
NCI_THESAURUS C2360
Created by admin on Mon Mar 31 18:21:03 GMT 2025 , Edited by admin on Mon Mar 31 18:21:03 GMT 2025
Code System Code Type Description
ChEMBL
CHEMBL1200585
Created by admin on Mon Mar 31 18:21:03 GMT 2025 , Edited by admin on Mon Mar 31 18:21:03 GMT 2025
PRIMARY
MESH
D010110
Created by admin on Mon Mar 31 18:21:03 GMT 2025 , Edited by admin on Mon Mar 31 18:21:03 GMT 2025
PRIMARY
FDA UNII
L76T0ZCA8K
Created by admin on Mon Mar 31 18:21:03 GMT 2025 , Edited by admin on Mon Mar 31 18:21:03 GMT 2025
PRIMARY
SMS_ID
100000083305
Created by admin on Mon Mar 31 18:21:03 GMT 2025 , Edited by admin on Mon Mar 31 18:21:03 GMT 2025
PRIMARY
HSDB
3374
Created by admin on Mon Mar 31 18:21:03 GMT 2025 , Edited by admin on Mon Mar 31 18:21:03 GMT 2025
PRIMARY
NSC
26198
Created by admin on Mon Mar 31 18:21:03 GMT 2025 , Edited by admin on Mon Mar 31 18:21:03 GMT 2025
PRIMARY
CAS
78964-17-7
Created by admin on Mon Mar 31 18:21:03 GMT 2025 , Edited by admin on Mon Mar 31 18:21:03 GMT 2025
ALTERNATIVE
CHEBI
7864
Created by admin on Mon Mar 31 18:21:03 GMT 2025 , Edited by admin on Mon Mar 31 18:21:03 GMT 2025
PRIMARY
RS_ITEM_NUM
1487007
Created by admin on Mon Mar 31 18:21:03 GMT 2025 , Edited by admin on Mon Mar 31 18:21:03 GMT 2025
PRIMARY
WIKIPEDIA
OXYMETHOLONE
Created by admin on Mon Mar 31 18:21:03 GMT 2025 , Edited by admin on Mon Mar 31 18:21:03 GMT 2025
PRIMARY
NCI_THESAURUS
C723
Created by admin on Mon Mar 31 18:21:03 GMT 2025 , Edited by admin on Mon Mar 31 18:21:03 GMT 2025
PRIMARY
RXCUI
7813
Created by admin on Mon Mar 31 18:21:03 GMT 2025 , Edited by admin on Mon Mar 31 18:21:03 GMT 2025
PRIMARY RxNorm
DRUG CENTRAL
2033
Created by admin on Mon Mar 31 18:21:03 GMT 2025 , Edited by admin on Mon Mar 31 18:21:03 GMT 2025
PRIMARY
EVMPD
SUB09568MIG
Created by admin on Mon Mar 31 18:21:03 GMT 2025 , Edited by admin on Mon Mar 31 18:21:03 GMT 2025
PRIMARY
PUBCHEM
5281034
Created by admin on Mon Mar 31 18:21:03 GMT 2025 , Edited by admin on Mon Mar 31 18:21:03 GMT 2025
PRIMARY
INN
1022
Created by admin on Mon Mar 31 18:21:03 GMT 2025 , Edited by admin on Mon Mar 31 18:21:03 GMT 2025
PRIMARY
MERCK INDEX
m8336
Created by admin on Mon Mar 31 18:21:03 GMT 2025 , Edited by admin on Mon Mar 31 18:21:03 GMT 2025
PRIMARY Merck Index
DRUG BANK
DB06412
Created by admin on Mon Mar 31 18:21:03 GMT 2025 , Edited by admin on Mon Mar 31 18:21:03 GMT 2025
PRIMARY
CAS
434-07-1
Created by admin on Mon Mar 31 18:21:03 GMT 2025 , Edited by admin on Mon Mar 31 18:21:03 GMT 2025
PRIMARY
EPA CompTox
DTXSID5023794
Created by admin on Mon Mar 31 18:21:03 GMT 2025 , Edited by admin on Mon Mar 31 18:21:03 GMT 2025
PRIMARY
ECHA (EC/EINECS)
207-098-6
Created by admin on Mon Mar 31 18:21:03 GMT 2025 , Edited by admin on Mon Mar 31 18:21:03 GMT 2025
PRIMARY
Related Record Type Details
ALPHA-1A ADRENERGIC RECEPTOR
TARGET -> AGONIST
ALPHA-2A ADRENERGIC RECEPTOR
TARGET -> AGONIST
Related Record Type Details
Structure of BA-2664
METABOLITE -> PARENT
Related Record Type Details
Structure of STANOZOLOL
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (TLC)
EP
Related Record Type Details
Structure of OXYMETHOLONE
ACTIVE MOIETY
NIH
NCATS
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