Mesterolone (CHEM036024)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 07:09:46 UTC
Update Date2016-11-09 01:21:25 UTC
Accession NumberCHEM036024
Identification
Common NameMesterolone
ClassSmall Molecule
DescriptionMesterolone is a synthetic anabolic-androgenic steroid (AAS) and derivative of dihydrotestosterone (DHT). It is inactivated by 3α-hydroxysteroid dehydrogenase in skeleta muscules so it is considered a weak androgen. It is not a substrate for aromatase so it is not converted into estrogen. Mesterolone demonstrated to have minimal effect on sperm counts and levels of FSH or LH [A27177, A27178]. Experiments of mesterolone serving as a potential treatment of depression are still undergoing.
Contaminant Sources
  • FooDB Chemicals
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
ProvironMeSH
VistimonMeSH
SH-723MesteroloneChEMBL, HMDB
(1a,5a,17b)-17-Hydroxy-1-methyl-androstan-3-oneHMDB
17b-Hydroxy-1a-methyl-5a-androstan-3-oneHMDB
1a-Methyl-17b-hydroxy-5a-androstan-3-oneHMDB
1a-Methyl-5a-androstan-17b-ol-3-oneHMDB
1a-Methyl-5a-dihydrotestosteroneHMDB
AndrovironHMDB
MesteranumHMDB
MestoranumHMDB
Provirone 25HMDB
SH 723HMDB
TestiwopHMDB
Jenapharm brand OF mesteroloneMeSH, HMDB
Schering brand OF mesteroloneMeSH, HMDB
Mesterolone jenapharm brandMeSH, HMDB
Mesterolone schering brandMeSH, HMDB
Chemical FormulaC20H32O2
Average Molecular Mass304.467 g/mol
Monoisotopic Mass304.240 g/mol
CAS Registry Number1424-00-6
IUPAC Name(1S,2S,3S,7S,10R,11S,14S,15S)-14-hydroxy-2,3,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-one
Traditional Nameproviron
SMILES[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])CC(=O)C[C@H](C)[C@]12C
InChI IdentifierInChI=1S/C20H32O2/c1-12-10-14(21)11-13-4-5-15-16-6-7-18(22)19(16,2)9-8-17(15)20(12,13)3/h12-13,15-18,22H,4-11H2,1-3H3/t12-,13-,15-,16-,17-,18-,19-,20-/m0/s1
InChI KeyUXYRZJKIQKRJCF-TZPFWLJSSA-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-oxosteroid
  • 3-oxo-5-alpha-steroid
  • 17-hydroxysteroid
  • Oxosteroid
  • Hydroxysteroid
  • Cyclic alcohol
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0064 g/LALOGPS
logP3.75ALOGPS
logP3.7ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)19.38ChemAxon
pKa (Strongest Basic)-0.88ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity88.15 m³·mol⁻¹ChemAxon
Polarizability36.46 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03g1-0290000000-6711f2fd4cedd8b8ebe9Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-03dj-2029000000-d49394c5377c1d882480Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0195000000-44dcd42d89336ba3b750Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-0291000000-412b4cbbe59f184a654fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052o-1790000000-09c00b6e9a55d7df2300Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0029000000-e48e22f298cdef547931Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0059000000-231f9da9a32e84b9b604Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-007c-3090000000-69a7d162e0bb3918d70bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-f9d10b76ade80bd401adSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0009000000-f9d10b76ade80bd401adSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udj-0094000000-7cb92f7f18ba37686418Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0079000000-2860312a6cf9370e1957Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-0960000000-9c3e64e51c3a7c290a00Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-3910000000-a9991caf02a89a982090Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB13587
HMDB IDHMDB0006036
FooDB IDFDB023812
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkMesterolone
Chemspider ID14296
ChEBI ID529213
PubChem Compound ID15020
Kegg Compound IDD04947
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Petry R, Rausch-Stroomann JG, Hienz HA, Senge T, Mauss J: Androgen treatment without inhibiting effect on hypophysis and male gonads. Biochemical and morphological studies after treatment with Mesterolone. Acta Endocrinol (Copenh). 1968 Nov;59(3):497-507.
2. Ho EN, Leung DK, Leung GN, Wan TS, Wong HN, Xu X, Yeung JH: Metabolic studies of mesterolone in horses. Anal Chim Acta. 2007 Jul 16;596(1):149-55. Epub 2007 Jun 3.
3. Vandekerckhove P, Lilford R, Vail A, Hughes E: Androgens versus placebo or no treatment for idiopathic oligo/asthenospermia. Cochrane Database Syst Rev. 2000;(2):CD000150.
4. Vandekerckhove P, Lilford R, Vail A, Hughes E: WITHDRAWN: Androgens versus placebo or no treatment for idiopathic oligo/asthenospermia. Cochrane Database Syst Rev. 2007 Jul 18;(4):CD000150.
5. Schell H: [Objective assessment of therapeutic hair growth--methods, possibilities and problems]. Z Hautkr. 1990 Dec;65(12):1080-4.
6. Cooper AJ: Short-term treatment in sexual dysfunction: a review. Compr Psychiatry. 1981 Mar-Apr;22(2):206-17.
7. Itil TM: The discovery of antidepressant drugs by computer-analyzed human cerebral bio-electrical potentials (CEEG). Prog Neurobiol. 1983;20(3-4):185-249.
8. Schill WB, Michalopoulos M: Treatment of male fertility disturbances. Current concepts. Drugs. 1984 Sep;28(3):263-80.
9. Mbizvo MT: Functional motion changes during sperm transit to the site of fertilization and in-vitro applications: a review. Int J Androl. 1995 Jun;18 Suppl 1:1-6.
10. Herrmann WM, Beach RC: Psychotropic effects of androgens: a review of clinical observations and new human experimental findings. Pharmakopsychiatr Neuropsychopharmakol. 1976 Sep;9(5):205-19.