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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

Molecular Formula C21H32O3
Molecular Weight 332.4778
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

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

Originator

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

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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

6.4540799E10
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as perpetrator​Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
no
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
Nonfatal methazolamide-induced aplastic anemia.
1978 Jul
Review of oxymetholone: a 17alpha-alkylated anabolic-androgenic steroid.
2001 Jun
Characterization of spontaneous and chemically induced cardiac lesions in rodent model systems: the national toxicology program experience.
2005
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.
2011 Jul 14
Patents

Sample Use Guides

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
0.1 to 10 uM oxymetholone tested on normal CD34+ cells
Substance Class Chemical
Created
by admin
on Sat Jun 26 11:20:29 UTC 2021
Edited
by admin
on Sat Jun 26 11:20:29 UTC 2021
Record UNII
L76T0ZCA8K
Record Status Validated (UNII)
Record Version
  • Download
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
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TARGET -> AGONIST
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