Oxymetholone (CED0009610)

Record Information

Version

1.0

Creation Date

2016-05-22 03:48:20 UTC

Update Date

2026-05-14 18:20:09 UTC

Accession Number

CHEM016944

Identification

Common Name

Oxymetholone

Class

Small Molecule

Description

Oxymetholone is an organic compound with the formula C21H32O3 and an average molecular weight of 332.48 g/mol. Oxymetholone belongs to the androstane steroids, a subclass of steroids and steroid derivatives within the organic compounds. It is classified under the superclass of lipids and lipid-like molecules. The compound is found in or released from three recorded sources: anabolic steroids within healthcare, pharmaceuticals, and veterinary products; video games within electrical and electronic equipment; and non-electric simulated smoking devices within household cleaning and consumer products. The recorded route of exposure for this substance is oral. In terms of protein targets, oxymetholone acts as an agonist and activator of the androgen receptor (AR).

Contaminant Type

Human Neurotoxin

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Anadrol-50	Kegg
Oxymetholone, (17 beta)-isomer	MeSH
Anapolon 50	MeSH
Oxymetholone, (5 alpha,17 alpha)-isomer	MeSH
Oxymethalone	MeSH
Anadrol	MeSH
Hydroxymetholone	MeSH

Chemical Formula

C₂₁H₃₂O₃

Average Molecular Mass

332.484 g/mol

Monoisotopic Mass

332.235 g/mol

CAS Registry Number

434-07-1

IUPAC Name

(1S,2S,4Z,7S,10R,11S,14S,15S)-14-hydroxy-4-(hydroxymethylidene)-2,14,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-one

Traditional Name

anadrol

SMILES

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

InChI Identifier

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

InChI Key

ICMWWNHDUZJFDW-DHODBPELSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Androstane steroids

Direct Parent

Androgens and derivatives

Alternative Parents

Substituents

Androgen-skeleton
3-oxosteroid
3-oxo-5-alpha-steroid
17-hydroxysteroid
Oxosteroid
Hydroxysteroid
Cyclic alcohol
Vinylogous acid
Tertiary alcohol
Cyclic ketone
Ketone
Enol
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Androstane and derivatives (C07393 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.035 g/L	ALOGPS
logP	3.17	ALOGPS
logP	3.55	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	8.87	ChemAxon
pKa (Strongest Basic)	-0.53	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	94.6 m³·mol⁻¹	ChemAxon
Polarizability	38.84 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0159-0029000000-837a16f06ea4e19d3724	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-015a-0197000000-562f73fad2f0aa99ef2a	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0002-2491000000-55be86482ae4c9508381	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-0009000000-0171ca7dbd60b149046e	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-01q9-0029000000-e16d2f7d47cfe4be1991	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0pvv-3093000000-916b2711de9ff518122b	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
2497.0	Log mg/kg	[1400:4400]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
270	Anabolic steroids	Healthcare, pharmaceuticals & veterinary products	Not Available
539	Video Games	Electrical & Electronic Equipment	Not Available
559	Non Electric Simulated Smoking Devices	Household cleaning & consumer products	Not Available
624	Merry Go Rounds	Recreation & sports surfaces	Not Available

Pathways

1 pathway

Oxymetholone Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Androgen receptor	P15207	Rattus norvegicus	Predicted (SEA)	10.9767
Click to view 3D structure	Progesterone receptor	Q690N0	Bos taurus	Predicted (SEA)	6.61718
Click to view 3D structure	G-protein coupled bile acid receptor 1	Q8TDU6	Humans	Predicted (SEA)	26.313
Click to view 3D structure	Sex hormone-binding globulin	P04278	Humans	Predicted (SEA)	12.3002
Click to view 3D structure	Glucocorticoid receptor	P04150	Humans	Predicted (SEA)	36.4334
Click to view 3D structure	Corticosteroid-binding globulin	P08185	Humans	Predicted (SEA)	14.7135
Click to view 3D structure	Aldo-keto reductase family 1 member B10	O60218	Humans	Predicted (SEA)	24.7561
Click to view 3D structure	Cytochrome P450 7B1	O75881	Humans	Predicted (SEA)	0.622794
Click to view 3D structure	Sex hormone-binding globulin	P08689	Rattus norvegicus	Predicted (SEA)	1.16774
Click to view 3D structure	Estrogen receptor	P03372	Humans	Predicted (SEA)	85.6341
Click to view 3D structure	Cytochrome P450 2C9	P11712	Humans	Predicted (SEA)	1149.21
Click to view 3D structure	Cytochrome P450 2C19	P33261	Humans	Predicted (SEA)	663.742
Click to view 3D structure	Aromatase	P11511	Humans	Predicted (SEA)	77.46
Click to view 3D structure	Androgen receptor	P10275	Humans	Predicted (SEA)	84.155
Click to view 3D structure	Progesterone receptor	P06401	Humans	Predicted (SEA)	60.8002
Click to view 3D structure	Glucose-6-phosphate 1-dehydrogenase	Q9GRG7	Trypanosoma brucei	Predicted (SEA)	9.03051
Click to view 3D structure	Mineralocorticoid receptor	P08235	Humans	Predicted (SEA)	41.805
Click to view 3D structure	Androgen receptor	P19091	Mus musculus	Predicted (SEA)	15.3363
Click to view 3D structure	Adenosine receptor A3	P0DMS8	Humans	Predicted (SEA)	482.665
Click to view 3D structure	Gamma-aminobutyric acid type B receptor subunit 1	Q9Z0U4	Rattus norvegicus	Predicted (SEA)	6.38364
Click to view 3D structure	3-oxo-5-alpha-steroid 4-dehydrogenase 2	P31213	Humans	Predicted (SEA)	13.8572
Click to view 3D structure	E3 ubiquitin-protein ligase ZFP91	Q96JP5	Humans	Predicted (SEA)	3.50322
Click to view 3D structure	3-oxo-5-alpha-steroid 4-dehydrogenase 1	P18405	Humans	Predicted (SEA)	13.3122
Click to view 3D structure	Potassium-transporting ATPase alpha chain 2	P54707	Humans	Predicted (SEA)	3.81461
Click to view 3D structure	Cytochrome P450 2D6	P10635	Humans	Predicted (SEA)	3820.76