Methyltestosterone (CHEM003705)

Record Information
Version1.0
Creation Date2014-09-11 05:14:39 UTC
Update Date2026-05-14 18:23:04 UTC
Accession NumberCHEM003705
Identification
Common NameMethyltestosterone
ClassSmall 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
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
17(alpha)-Methyl-Delta(4)-androsten-17(beta)-ol-3-oneChEBI
17-beta-Hydroxy-17-methylandrost-4-en-3-oneChEBI
17-MethyltestosteroneChEBI
17alpha-Methyl-3-oxo-4-androsten-17beta-olChEBI
17alpha-Methyl-Delta(4)-androsten-17beta-ol-3-oneChEBI
17alpha-MethyltestosteroneChEBI
17beta-Hydroxy-17-methylandrost-4-en-3-oneChEBI
4-Androstene-17alpha-methyl-17beta-ol-3-oneChEBI
AndroidChEBI
MethyltestosteronumChEBI
MetiltestosteronaChEBI
NSC-9701ChEBI
TestredChEBI
VirilonChEBI
17(a)-Methyl-delta(4)-androsten-17(b)-ol-3-oneGenerator
17(Α)-methyl-δ(4)-androsten-17(β)-ol-3-oneGenerator
17-b-Hydroxy-17-methylandrost-4-en-3-oneGenerator
17-Β-hydroxy-17-methylandrost-4-en-3-oneGenerator
17a-Methyl-3-oxo-4-androsten-17b-olGenerator
17Α-methyl-3-oxo-4-androsten-17β-olGenerator
17a-Methyl-delta(4)-androsten-17b-ol-3-oneGenerator
17Α-methyl-δ(4)-androsten-17β-ol-3-oneGenerator
17a-MethyltestosteroneGenerator
17Α-methyltestosteroneGenerator
17b-Hydroxy-17-methylandrost-4-en-3-oneGenerator
17Β-hydroxy-17-methylandrost-4-en-3-oneGenerator
4-Androstene-17a-methyl-17b-ol-3-oneGenerator
4-Androstene-17α-methyl-17β-ol-3-oneGenerator
17(a)-Methyl-δ(4)-androsten-17(b)-ol-3-oneHMDB
17a-Methyl-δ(4)-androsten-17b-ol-3-oneHMDB
17alpha-Methyl-delta-androsten-17beta-ol-3-oneHMDB
17 EpimethyltestosteroneHMDB
17 beta MethyltestosteroneHMDB
17alpha MethyltestosteroneHMDB
MesteronHMDB
17 beta-MethyltestosteroneHMDB
17-EpimethyltestosteroneHMDB
17beta Hydroxy 17 methyl 4 androsten 3 oneHMDB
17beta MethyltestosteroneHMDB
17beta-Hydroxy-17-methyl-4-androsten-3-oneHMDB
Android-25HMDB
Global pharmaceutical brand OF methyltestosteroneHMDB
ICN brand 1 OF methyltestosteroneHMDB
ICN brand 2 OF methyltestosteroneHMDB
17 alpha MethyltestosteroneHMDB
17-alpha-MethyltestosteroneHMDB
17alpha-Methyl-testosteroneHMDB
Android 25HMDB
Android 5HMDB
Android-5HMDB
MetandrenHMDB
Star brand OF methyltestosteroneHMDB
17 beta Hydroxy 17 methyl 4 androsten 3 oneHMDB
17 beta-Hydroxy-17-methyl-4-androsten-3-oneHMDB
17alpha Methyl testosteroneHMDB
17beta-MethyltestosteroneHMDB
Android 10HMDB
Android-10HMDB
MesteroneHMDB
MethitestHMDB
OretonHMDB
Schering brand OF methyltestosteroneHMDB
TestovironHMDB
MethyltestosteroneMeSH
Android (methyltestoterone)MeSH
Chemical FormulaC20H30O2
Average Molecular Mass302.451 g/mol
Monoisotopic Mass302.225 g/mol
CAS Registry Number58-18-4
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 IdentifierInChI=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 KeyGCKMFJBGXUYNAG-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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassAndrostane steroids
Direct ParentAndrogens 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 FrameworkAliphatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point163°C
Boiling PointNot Available
Solubility33.9 mg/L (at 25°C)
Predicted Properties
PropertyValueSource
Water Solubility0.014 g/LALOGPS
logP3.61ALOGPS
logP3.65ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)19.09ChemAxon
pKa (Strongest Basic)-0.53ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity89.07 m³·mol⁻¹ChemAxon
Polarizability35.85 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureThe methyl group aids to increase oral bioavailability.
Mechanism of ToxicityThe 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.
MetabolismHepatic. 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 ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesMethyltestosterone 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 LevelNot Available
Health EffectsNot Available
SymptomsSide effects include amnesia, anxiety, discolored hair, dizziness, dry skin, hirsutism, hostility, impaired urination, paresthesia, penis disorder, peripheral edema, sweating, and vasodilation.
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDDB06710
HMDB IDHMDB0015655
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkMethyltestosterone
Chemspider ID5788
ChEBI ID27436
PubChem Compound ID6010
Kegg Compound IDC07198
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=19199316
2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
3. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
4. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
5. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
6. The lipid handbook with CD-ROM