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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2007-04-12 20:54:27 UTC
Update Date2021-09-14 15:40:23 UTC
HMDB IDHMDB0006036
Secondary Accession Numbers
  • HMDB06036
Metabolite Identification
Common NameMesterolone
DescriptionMesterolone is a synthetic anabolic androgenic steroid (AAS) with reported abuses in human sports. As for other AAS, mesterolone is also a potential doping agent in equine sports. In humans, mesterolone exhibits no inhibitory effects on hypophysial gonadotropin secretion or on spermatogenesis, unlike most androgens. Mesterolone has been used in the treatment of primary nocturnal enuresis in boys six to ten years of age. Mesterolone probably modulates the autonomic innervation of the vesical musculature with correction of the defective neural mechanism which is believed to be implicated in the pathogenesis of nocturnal enuresis. Mesterolone has been utilized in hypogonadism patients to increase total ejaculation volume and the concentration of fructose in the spermatic plasma to normal levels. Mesterolone treatment decreases cholesterol, beta-lipoproteins, fatty acid esters, free fatty acids, triglycerides and glycerol in human serum. (PMID: 4880965 , 17616252 , 10796496 , 17636603 , 2087834 , 6111418 , 6142498 , 6386424 , 7558381 , 792898 ).
Structure
Data?1582752372
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 Weight304.4669
Monoisotopic Molecular Weight304.240230268
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
CAS Registry Number1424-00-6
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 Identifier
InChI=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
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point204 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0064 g/LALOGPS
logP10(3.75) g/LALOGPS
logP10(3.7) g/LChemAxon
logS10(-4.7) g/LALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+173.41431661259
DarkChem[M-H]-171.84631661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Mesterolone,1TMS,#1C[C@H]1CC(=O)C[C@@H]2CC[C@H]3[C@@H]4CC[C@H](O[Si](C)(C)C)[C@@]4(C)CC[C@@H]3[C@@]12C2678.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
Mesterolone,1TMS,#2C[C@H]1C=C(O[Si](C)(C)C)C[C@@H]2CC[C@H]3[C@@H]4CC[C@H](O)[C@@]4(C)CC[C@@H]3[C@@]12C2610.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
Mesterolone,1TMS,#3C[C@H]1CC(O[Si](C)(C)C)=C[C@@H]2CC[C@H]3[C@@H]4CC[C@H](O)[C@@]4(C)CC[C@@H]3[C@@]12C2627.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
Mesterolone,1TBDMS,#1C[C@H]1CC(=O)C[C@@H]2CC[C@H]3[C@@H]4CC[C@H](O[Si](C)(C)C(C)(C)C)[C@@]4(C)CC[C@@H]3[C@@]12C2925.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
Mesterolone,1TBDMS,#2C[C@H]1C=C(O[Si](C)(C)C(C)(C)C)C[C@@H]2CC[C@H]3[C@@H]4CC[C@H](O)[C@@]4(C)CC[C@@H]3[C@@]12C2846.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
Mesterolone,1TBDMS,#3C[C@H]1CC(O[Si](C)(C)C(C)(C)C)=C[C@@H]2CC[C@H]3[C@@H]4CC[C@H](O)[C@@]4(C)CC[C@@H]3[C@@]12C2862.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Mesterolone GC-MS (Non-derivatized) - 70eV, Positivesplash10-03g1-0290000000-6711f2fd4cedd8b8ebe92017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Mesterolone GC-MS (1 TMS) - 70eV, Positivesplash10-03dj-2029000000-d49394c5377c1d8824802017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Mesterolone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mesterolone 10V, Positive-QTOFsplash10-052r-0195000000-44dcd42d89336ba3b7502017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mesterolone 20V, Positive-QTOFsplash10-052r-0291000000-412b4cbbe59f184a654f2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mesterolone 40V, Positive-QTOFsplash10-052o-1790000000-09c00b6e9a55d7df23002017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mesterolone 10V, Negative-QTOFsplash10-0udi-0029000000-e48e22f298cdef5479312017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mesterolone 20V, Negative-QTOFsplash10-0udi-0059000000-231f9da9a32e84b9b6042017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mesterolone 40V, Negative-QTOFsplash10-007c-3090000000-69a7d162e0bb3918d70b2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mesterolone 10V, Negative-QTOFsplash10-0udi-0009000000-f9d10b76ade80bd401ad2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mesterolone 20V, Negative-QTOFsplash10-0udi-0009000000-f9d10b76ade80bd401ad2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mesterolone 40V, Negative-QTOFsplash10-0udj-0094000000-7cb92f7f18ba376864182021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mesterolone 10V, Positive-QTOFsplash10-0a4i-0079000000-2860312a6cf9370e19572021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mesterolone 20V, Positive-QTOFsplash10-0a4r-0960000000-9c3e64e51c3a7c290a002021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mesterolone 40V, Positive-QTOFsplash10-0a4i-3910000000-a9991caf02a89a9820902021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB13587
Phenol Explorer Compound IDNot Available
FooDB IDFDB023812
KNApSAcK IDNot Available
Chemspider ID14296
KEGG Compound IDD04947
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMesterolone
METLIN IDNot Available
PubChem Compound15020
PDB IDNot Available
ChEBI ID529213
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
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. [PubMed:4880965 ]
  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. [PubMed:17616252 ]
  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. [PubMed:10796496 ]
  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. [PubMed:17636603 ]
  5. Schell H: [Objective assessment of therapeutic hair growth--methods, possibilities and problems]. Z Hautkr. 1990 Dec;65(12):1080-4. [PubMed:2087834 ]
  6. Cooper AJ: Short-term treatment in sexual dysfunction: a review. Compr Psychiatry. 1981 Mar-Apr;22(2):206-17. [PubMed:6111418 ]
  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. [PubMed:6142498 ]
  8. Schill WB, Michalopoulos M: Treatment of male fertility disturbances. Current concepts. Drugs. 1984 Sep;28(3):263-80. [PubMed:6386424 ]
  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. [PubMed:7558381 ]
  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. [PubMed:792898 ]