Pergolide methanesulfonate (CHEM017553)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 04:27:38 UTC
Update Date2016-11-09 01:15:37 UTC
Accession NumberCHEM017553
Identification
Common NamePergolide methanesulfonate
ClassSmall Molecule
DescriptionA methanesulfonate salt obtained from pergolide by mixing eqimolar amount of pergolide and methanesulfonic acid. A dopamine D2 receptor agonist which also has D1 and D2 agonist properties, it is used in the management of Parkinson's disease, although it was withdrawn from the U.S. and Canadian markets in 2007 due to an increased risk of cardiac valve dysfunction.
Contaminant Sources
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(8beta)-8-[(Methylsulfanyl)methyl]-6-propylergolin-6-ium methanesulfonateChEBI
Pergolide mesilateChEBI
Pergolide methanesulfonateChEBI
Pergolide monomesylateChEBI
Pergolide monomethanesulfonateChEBI
PermaxChEBI
(8b)-8-[(Methylsulfanyl)methyl]-6-propylergolin-6-ium methanesulfonateGenerator
(8b)-8-[(Methylsulfanyl)methyl]-6-propylergolin-6-ium methanesulfonic acidGenerator
(8b)-8-[(Methylsulphanyl)methyl]-6-propylergolin-6-ium methanesulphonateGenerator
(8b)-8-[(Methylsulphanyl)methyl]-6-propylergolin-6-ium methanesulphonic acidGenerator
(8beta)-8-[(Methylsulfanyl)methyl]-6-propylergolin-6-ium methanesulfonic acidGenerator
(8beta)-8-[(Methylsulphanyl)methyl]-6-propylergolin-6-ium methanesulphonateGenerator
(8beta)-8-[(Methylsulphanyl)methyl]-6-propylergolin-6-ium methanesulphonic acidGenerator
(8Β)-8-[(methylsulfanyl)methyl]-6-propylergolin-6-ium methanesulfonateGenerator
(8Β)-8-[(methylsulfanyl)methyl]-6-propylergolin-6-ium methanesulfonic acidGenerator
(8Β)-8-[(methylsulphanyl)methyl]-6-propylergolin-6-ium methanesulphonateGenerator
(8Β)-8-[(methylsulphanyl)methyl]-6-propylergolin-6-ium methanesulphonic acidGenerator
Pergolide mesilic acidGenerator
Pergolide methanesulfonic acidGenerator
Pergolide methanesulphonateGenerator
Pergolide methanesulphonic acidGenerator
Pergolide monomesylic acidGenerator
Pergolide monomethanesulfonic acidGenerator
Pergolide monomethanesulphonateGenerator
Pergolide monomethanesulphonic acidGenerator
Pergolide mesylic acidGenerator
Draxis brand OF pergolide mesylateMeSH
elanco Brand OF pergolide mesylateMeSH
Lilly brand OF pergolide mesylateMeSH
Mesylate, pergolideMeSH
CelanceMeSH
ParkotilMeSH
Athena brand OF pergolide mesylateMeSH
PharkenMeSH
Lilly brand OF pergolideMeSH
PergolideMeSH
Chemical FormulaC20H30N2O3S2
Average Molecular Mass410.590 g/mol
Monoisotopic Mass410.170 g/mol
CAS Registry Number66104-23-2
IUPAC Name(2R,4R,7R)-4-[(methylsulfanyl)methyl]-6-propyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),9,12,14-tetraene; methanesulfonic acid
Traditional Namemethanesulfonic acid; pergolide
SMILESCS(O)(=O)=O.[H][C@]1(CSC)CN(CCC)[C@]2([H])CC3=CNC4=CC=CC(=C34)[C@@]2([H])C1
InChI IdentifierInChI=1S/C19H26N2S.CH4O3S/c1-3-7-21-11-13(12-22-2)8-16-15-5-4-6-17-19(15)14(10-20-17)9-18(16)21;1-5(2,3)4/h4-6,10,13,16,18,20H,3,7-9,11-12H2,1-2H3;1H3,(H,2,3,4)/t13-,16-,18-;/m1./s1
InChI KeyUWCVGPLTGZWHGS-ZORIOUSZSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as indoloquinolines. These are polycyclic aromatic compounds containing an indole fused to a quinoline.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassIndoloquinolines
Direct ParentIndoloquinolines
Alternative Parents
Substituents
  • Ergoline skeleton
  • Indoloquinoline
  • Benzoquinoline
  • Pyrroloquinoline
  • 3-alkylindole
  • Indole
  • Indole or derivatives
  • Alkaloid or derivatives
  • Isoindole or derivatives
  • Aralkylamine
  • Benzenoid
  • Piperidine
  • Heteroaromatic compound
  • Pyrrole
  • Tertiary aliphatic amine
  • Tertiary amine
  • Sulfenyl compound
  • Dialkylthioether
  • Azacycle
  • Thioether
  • Amine
  • Organosulfur compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkNot Available
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 Solubility0.00058 g/LALOGPS
logP4.17ALOGPS
logP4.23ChemAxon
logS-5.7ALOGPS
pKa (Strongest Acidic)17.35ChemAxon
pKa (Strongest Basic)9.49ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area19.03 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity97.02 m³·mol⁻¹ChemAxon
Polarizability38.41 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-066u-2921000000-cbf8af93caff98e067a4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000900000-37c0db4b1612257e354cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000900000-37c0db4b1612257e354cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-0000900000-37c0db4b1612257e354cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000900000-3098984ce709b6184fc9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0000900000-3098984ce709b6184fc9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-0000900000-3098984ce709b6184fc9Spectrum
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 IDDBSALT002445
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkPergolide
Chemspider IDNot Available
ChEBI ID8021
PubChem Compound ID47812
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=6889702
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=8748627