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Substance Name: Oxymetholone [USAN:USP:INN:BAN:JAN]
RN: 434-07-1
UNII: L76T0ZCA8K
InChIKey: ICMWWNHDUZJFDW-DHODBPELSA-N

Note

  • A synthetic hormone with anabolic and androgenic properties. It is used mainly in the treatment of anemias. According to the Fourth Annual Report on Carcinogens (NTP 85-002), this compound may reasonably be anticipated to be a carcinogen. (From Merck Index, 11th ed)

Molecular Formula

  • C21-H32-O3

Molecular Weight

  • 332.4808
 

Classification Codes

Classification Codes

  • Anabolic Agents
  • Androgen
  • Androgens
  • Drug / Therapeutic Agent
  • Hormone
  • Hormones
  • Hormones, Hormone Substitutes, and Hormone Antagonists
  • Human Data
  • Mutation Data
  • Reproductive Effect
  • Tumor Data

Superlist Classification Codes

  • DEA Schedule III
  • Reasonably Anticipated to be a Carcinogen

Names and Synonyms

Name of Substance

  • Oxymetholone
  • Oxymetholone [USAN:USP:INN:BAN:JAN]

MeSH Heading

  • Oxymetholone

Synonyms

  • 17-alpha-Methyl-2-hydroxymethylene-17-hydroxy-5-alpha-androstan-3-one
  • 17-beta-Hydroxy-2-(hydroxymethylene)-17-alpha-methyl-5-alpha-androstan-3-one
  • 17-beta-Hydroxy-2-hydroxymethylene-17-alpha-methyl-3-androstanone
  • 17-Hydroxy-2-(hydroxymethylene)-17-methyl-5-alpha-17-beta-androst-3-one
  • 17-Hydroxy-5-alpha-androstan-3-one
  • 17alpha-Methyl-2-hydroxymethylene-17-hydroxy-5alpha-androstan-3-one
  • 17beta-Hydroxy-2-(hydroxymethylene)-17-methyl-5alpha-androstan-3-one
  • 2-Hydroxymethylene-17-alpha-methyl-17-beta-hydroxy-3-androstanone
  • 2-Hydroxymethylene-17-alpha-methyl-5-alpha-androstan-17-beta-ol-3-one
  • 2-Hydroxymethylene-17-alpha-methyl-dihydrotestosterone
  • 2-Hydroxymethylene-17alpha-methyl-17beta-hydroxy-3-adrostanone
  • 2-Hydroxymethylene-17alpha-methyl-17beta-hydroxy-5alpha-androstan-3-one
  • 2-Hydroxymethylene-17alpha-methyl-5alpha-androstan-17beta-ol-3-one
  • 2-Hydroxymethylene-17alpha-methylandrostan-17beta-ol-3-one
  • 2-Hydroxymethylene-17alpha-methyldihydrotestosterone
  • 4,5-Dihydro-2-hydroxymethylene-17-alpha-methyltestosterone
  • 4,5alpha-Dihydro-2-hydroxymethylene-17alpha-methyltestosterone
  • 5alpha-Androstan-3-one, 17beta-hydroxy-2-(hydroxymethylene)-17-methyl-
  • Adroidin
  • Adroyd
  • Anadrol
  • Anadrol-50
  • Anadroyd
  • Anapolon
  • Anasteron
  • Anasterone
  • Androstan-3-one, 17-hydroxy-2-(hydroxymethylene)-17-methyl-, (alpha,17beta)-
  • Becorel
  • CCRIS 492
  • CI 406
  • CI-406
  • Dynasten
  • EINECS 207-098-6
  • HMD
  • HSDB 3374
  • Methabol
  • Nastenon
  • NSC 26198
  • NSC-26,198
  • Ossimetolone
  • Ossimetolone [DCIT]
  • Oximetalonu
  • Oximetholonum
  • Oximetolona
  • Oximetolona [INN-Spanish]
  • Oxitosona-50
  • Oxymethalone
  • Oxymethenolone
  • Oxymetholone
  • Oxymetholonum
  • Oxymetholonum [INN-Latin]
  • Pavisoid
  • Plenastril
  • Protanabol
  • Roboral
  • Synasteron
  • UNII-L76T0ZCA8K
  • Zenalosyn

Systematic Names

  • 5-alpha,17-beta-Androstan-3-one, 17-hydroxy-2-(hydroxymethylene)-17-methyl-
  • 5-alpha-Androstan-3-one, 17-beta-hydroxy-2-(hydroxymethylene)-17-methyl- (8CI)
  • Androstan-3-one, 17-hydroxy-2-(hydroxymethylene)-17-methyl-, (5-alpha,17-beta)- (9CI)
  • Androstan-3-one, 17-hydroxy-2-(hydroxymethylene)-17-methyl-, (5alpha,17beta)-
  • Androstano(2,3-c)(1,2,5)oxadiazol-17-ol, 17-methyl-, (5-alpha,17-beta)- (9CI)
  • Oxymetholone

Superlist Names

  • 17alpha-Methyl-2-hydroxymethylene-17beta-hydroxy-5alpha-androstan-3-one
  • Androstan-3-one, 17-hydroxy-2-(hydroxymethylene)-17-methyl-, (5alpha,17beta)-
  • DEA No. 4000
  • Oxymetholone
  • Oxymetholone [Androgenic steroids, anabolic]

Registry Numbers

CAS Registry Number

  • 434-07-1

FDA UNII

  • L76T0ZCA8K

System Generated Number

  • 0000434071

Structure Descriptors

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

InChIKey

ICMWWNHDUZJFDW-DHODBPELSA-N

Smiles

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

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
human TDLo oral 46mg/kg/14W-I (46mg/kg) LIVER: LIVER FUNCTION TESTS IMPAIRED JAMA, Journal of the American Medical Association. Vol. 240, Pg. 243, 1978.
rat LD50 intraperitoneal > 1gm/kg (1000mg/kg)   Drugs in Japan Vol. 6, Pg. 156, 1982.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 179 deg C   EXP
log P (octanol-water) 3.610 (none)   EST
Atmospheric OH Rate Constant 1.12E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.