ContaminantDB: Methyltestosterone

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (4)XML

Record Information

Version

1.0

Creation Date

2014-09-11 05:14:39 UTC

Update Date

2026-03-31 18:51:36 UTC

Accession Number

CHEM003705

Identification

Common Name

Methyltestosterone

Class

Small Molecule

Description

A synthetic anabolic steroid used for treating men with testosterone deficiency or similar androgen replacement therapies. Also, has antineoplastic properties and so has been used secondarily in women with advanced breast cancer. Methyltestosterone is a schedule III drug in the US.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Anabolic Agent
Antineoplastic Agent, Hormonal
Drug
Ester
Hormone Replacement Agent
Metabolite
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
17(alpha)-Methyl-Delta(4)-androsten-17(beta)-ol-3-one	ChEBI
17-beta-Hydroxy-17-methylandrost-4-en-3-one	ChEBI
17-Methyltestosterone	ChEBI
17alpha-Methyl-3-oxo-4-androsten-17beta-ol	ChEBI
17alpha-Methyl-Delta(4)-androsten-17beta-ol-3-one	ChEBI
17alpha-Methyltestosterone	ChEBI
17beta-Hydroxy-17-methylandrost-4-en-3-one	ChEBI
4-Androstene-17alpha-methyl-17beta-ol-3-one	ChEBI
Android	ChEBI
Methyltestosteronum	ChEBI
Metiltestosterona	ChEBI
NSC-9701	ChEBI
Testred	ChEBI
Virilon	ChEBI
17(a)-Methyl-delta(4)-androsten-17(b)-ol-3-one	Generator
17(Α)-methyl-δ(4)-androsten-17(β)-ol-3-one	Generator
17-b-Hydroxy-17-methylandrost-4-en-3-one	Generator
17-Β-hydroxy-17-methylandrost-4-en-3-one	Generator
17a-Methyl-3-oxo-4-androsten-17b-ol	Generator
17Α-methyl-3-oxo-4-androsten-17β-ol	Generator
17a-Methyl-delta(4)-androsten-17b-ol-3-one	Generator
17Α-methyl-δ(4)-androsten-17β-ol-3-one	Generator
17a-Methyltestosterone	Generator
17Α-methyltestosterone	Generator
17b-Hydroxy-17-methylandrost-4-en-3-one	Generator
17Β-hydroxy-17-methylandrost-4-en-3-one	Generator
4-Androstene-17a-methyl-17b-ol-3-one	Generator
4-Androstene-17α-methyl-17β-ol-3-one	Generator
17(a)-Methyl-δ(4)-androsten-17(b)-ol-3-one	HMDB
17a-Methyl-δ(4)-androsten-17b-ol-3-one	HMDB
17alpha-Methyl-delta-androsten-17beta-ol-3-one	HMDB
17 Epimethyltestosterone	HMDB
17 beta Methyltestosterone	HMDB
17alpha Methyltestosterone	HMDB
Mesteron	HMDB
17 beta-Methyltestosterone	HMDB
17-Epimethyltestosterone	HMDB
17beta Hydroxy 17 methyl 4 androsten 3 one	HMDB
17beta Methyltestosterone	HMDB
17beta-Hydroxy-17-methyl-4-androsten-3-one	HMDB
Android-25	HMDB
Global pharmaceutical brand OF methyltestosterone	HMDB
ICN brand 1 OF methyltestosterone	HMDB
ICN brand 2 OF methyltestosterone	HMDB
17 alpha Methyltestosterone	HMDB
17-alpha-Methyltestosterone	HMDB
17alpha-Methyl-testosterone	HMDB
Android 25	HMDB
Android 5	HMDB
Android-5	HMDB
Metandren	HMDB
Star brand OF methyltestosterone	HMDB
17 beta Hydroxy 17 methyl 4 androsten 3 one	HMDB
17 beta-Hydroxy-17-methyl-4-androsten-3-one	HMDB
17alpha Methyl testosterone	HMDB
17beta-Methyltestosterone	HMDB
Android 10	HMDB
Android-10	HMDB
Mesterone	HMDB
Methitest	HMDB
Oreton	HMDB
Schering brand OF methyltestosterone	HMDB
Testoviron	HMDB
Methyltestosterone	MeSH
Android (methyltestoterone)	MeSH

Chemical Formula

C₂₀H₃₀O₂

Average Molecular Mass

302.451 g/mol

Monoisotopic Mass

302.225 g/mol

CAS Registry Number

58-18-4

IUPAC Name

(1S,2R,10R,11S,14S,15S)-14-hydroxy-2,14,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

Traditional Name

(1S,2R,10R,11S,14S,15S)-14-hydroxy-2,14,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

SMILES

[H][C@@]12CC[C@](C)(O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C

InChI Identifier

InChI=1S/C20H30O2/c1-18-9-6-14(21)12-13(18)4-5-15-16(18)7-10-19(2)17(15)8-11-20(19,3)22/h12,15-17,22H,4-11H2,1-3H3/t15-,16+,17+,18+,19+,20+/m1/s1

InChI Key

GCKMFJBGXUYNAG-HLXURNFRSA-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-oxo-delta-4-steroid
3-oxosteroid
Hydroxysteroid
Oxosteroid
17-hydroxysteroid
Delta-4-steroid
Cyclohexenone
Tertiary alcohol
Cyclic alcohol
Ketone
Cyclic ketone
Organooxygen compound
Alcohol
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

enone (CHEBI:27436 )
3-oxo Delta(4)-steroid (CHEBI:27436 )
17beta-hydroxy steroid (CHEBI:27436 )
C19 steroids (androgens) and derivatives (C07198 )
C19 steroids (androgens) and derivatives (LMST02020029 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	163°C
Boiling Point	Not Available
Solubility	33.9 mg/L (at 25°C)

Predicted Properties

Property	Value	Source
Water Solubility	0.014 g/L	ALOGPS
logP	3.61	ALOGPS
logP	3.65	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	19.09	ChemAxon
pKa (Strongest Basic)	-0.53	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	89.07 m³·mol⁻¹	ChemAxon
Polarizability	35.85 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dr-0290000000-371930adb441ed456954	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0aba-1219000000-f0c8c14754130edea3b1	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0udi-1329000000-c8db8c2a5d8403c476e1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-052b-6910000000-9318ec38a89b29c5640a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0udj-5869000000-d793d0f4b0e7a48b07f6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0f9i-0951000000-9748785b49ecb149e24a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0139000000-8aa4cb730b0ff1f71ea4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0k92-4933000000-7acf74ca59be288f2614	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0009000000-ae79c4e9732d83ed38d9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-05gi-0900000000-d1cbdda02301f6a94288	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-00ea-0910000000-3f3f55e272ef7299acdf	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-054k-9400000000-bf00a69bc23c369a2331	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-0udi-0009000000-d366eb35472b9a72d3ba	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-052b-9600000000-ff447f9aa855eb5ec701	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-052b-8900000000-f4aa99526d10876e16d4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-05gi-0900000000-988e08204d56c840af72	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-00ea-0910000000-4231a8d617491b200562	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0f9i-0951000000-ef720a8b9da17a0ec5a3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0f79-0195000000-6ddd9c839c0b3b88c691	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0f79-0391000000-2fe2bafacddeeeb1f5f5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gbc-3890000000-9798d48acbfa04cc8bf0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0029000000-5462129b9677fa78ae8a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0059000000-989aea076743d8116d13	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052u-0190000000-c80d428af7a5f339800c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udr-0169000000-ad3e6ae0c33f0dc6369e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000j-0941000000-ec696476679a2f83bba5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01tl-2910000000-96766b244c1b4bb1e6a8	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-006x-7921000000-0e8f2747a2f3c8166048	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

The methyl group aids to increase oral bioavailability.

Mechanism of Toxicity

The effects of testosterone in humans and other vertebrates occur by way of two main mechanisms: by activation of the androgen receptor (directly or as DHT), and by conversion to estradiol and activation of certain estrogen receptors. Free testosterone (T) is transported into the cytoplasm of target tissue cells, where it can bind to the androgen receptor, or can be reduced to 5α-dihydrotestosterone (DHT) by the cytoplasmic enzyme 5α-reductase. DHT binds to the same androgen receptor even more strongly than T, so that its androgenic potency is about 2.5 times that of T. The T-receptor or DHT-receptor complex undergoes a structural change that allows it to move into the cell nucleus and bind directly to specific nucleotide sequences of the chromosomal DNA. The areas of binding are called hormone response elements (HREs), and influence transcriptional activity of certain genes, producing the androgen effects.

Metabolism

Hepatic. Testosterone is metabolized to 17-keto steroids through two different pathways. The major active metabolites are estradiol and dihydrotestosterone (DHT). Route of Elimination: 90% urine / 10% feces Half Life: 6-8 hours

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Methyltestosterone is an anabolic steroid hormone used to treat men with a testosterone deficiency. It is also used in women to treat breast cancer, breast pain, swelling due to pregnancy, and with the addition of estrogen it can treat symptoms of menopause.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Side effects include amnesia, anxiety, discolored hair, dizziness, dry skin, hirsutism, hostility, impaired urination, paresthesia, penis disorder, peripheral edema, sweating, and vasodilation.

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB06710

HMDB ID

HMDB0015655

FooDB ID

Not Available

Phenol Explorer ID