Alosetron (CHEM022211)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:24:00 UTC
Update Date2016-11-09 01:17:27 UTC
Accession NumberCHEM022211
Identification
Common NameAlosetron
ClassSmall Molecule
DescriptionAlosetron is a 5-HT3 antagonist used only for the management of severe diarrhoea-predominant irritable bowel syndrome (IBS) in women. Alosetron has an antagonist action on the 5-HT3 receptors and thus may modulate serotonin-sensitive gastrointestinal (GI) processes. Alosetron was voluntarily withdrawn from the US market in November 2000 by the manufacturer due to numerous reports of severe adverse effects including ischemic colitis, severely obstructed or ruptured bowel, and death. In June 2002, the FDA approved a supplemental new drug application allowing the remarketing of the drug under restricted conditions of use.
Contaminant Sources
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2,3,4,5-Tetrahydro-5-methyl-2-((5-methyl-1H-imidazol-4-yl)methyl)-1H-pyrido(4,3-b)indol-1-oneChEBI
Alosetron HCLHMDB
Alosetron monohydrochlorideHMDB
LotronexHMDB
Alosetron hydrochlorideHMDB
2,3,4,5-Tetrahydro-5-methyl-2-((5-methylimidazol-4-yl)methyl)-1H-pyrido(4,3-b)indol-1-one monohydrochlorideHMDB
GlaxoSmithKline brand OF alosetron hydrochlorideHMDB
Chemical FormulaC17H18N4O
Average Molecular Mass294.351 g/mol
Monoisotopic Mass294.148 g/mol
CAS Registry Number122852-42-0
IUPAC Name5-methyl-2-[(5-methyl-1H-imidazol-4-yl)methyl]-1H,2H,3H,4H,5H-pyrido[4,3-b]indol-1-one
Traditional Namealosetron
SMILESCN1C2=C(C3=CC=CC=C13)C(=O)N(CC1=C(C)NC=N1)CC2
InChI IdentifierInChI=1S/C17H18N4O/c1-11-13(19-10-18-11)9-21-8-7-15-16(17(21)22)12-5-3-4-6-14(12)20(15)2/h3-6,10H,7-9H2,1-2H3,(H,18,19)
InChI KeyJSWZEAMFRNKZNL-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as n-alkylindoles. N-alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 1-position.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassN-alkylindoles
Direct ParentN-alkylindoles
Alternative Parents
Substituents
  • N-alkylindole
  • Indole
  • N-methylpyrrole
  • Substituted pyrrole
  • Benzenoid
  • Imidazole
  • Heteroaromatic compound
  • Pyrrole
  • Vinylogous amide
  • Azole
  • Tertiary carboxylic acid amide
  • Lactam
  • Carboxamide group
  • Carboxylic acid derivative
  • Azacycle
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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 Solubility0.44 g/LALOGPS
logP1.85ALOGPS
logP1.21ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)13.32ChemAxon
pKa (Strongest Basic)6.81ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area53.92 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity86.41 m³·mol⁻¹ChemAxon
Polarizability32.52 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-054p-9640000000-36ec950b2b5a4de0d766Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0udi-0390000000-3b813a9458d2bce7516fSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0udi-3390000000-9994f53a2714bf016b00Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-5090000000-aa22d1e533a9ade9a631Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9470000000-de378c4e797603ddebd5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udj-9000000000-4320dc79a39aa798ebedSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0090000000-61b91fd4d7827b2dee3cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-1690000000-1c0db2dce26ffd0716f7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-4900000000-bac7a8e86a49765da618Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0090000000-0a33faab2e775c338d55Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0090000000-6aa9a0fa5a9c1aeeb778Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-9320000000-27c420ad3c1a98b56addSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0090000000-abdd2e02132168abe3faSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0190000000-c8bf656d3129fa7c6a2cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-0290000000-dacd12d29c5302eb8887Spectrum
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 IDDB00969
HMDB IDHMDB0015104
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAlosetron
Chemspider ID2015
ChEBI ID253342
PubChem Compound ID2099
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Camilleri M: Pharmacology and clinical experience with alosetron. Expert Opin Investig Drugs. 2000 Jan;9(1):147-59.
2. Mayer EA, Bradesi S: Alosetron and irritable bowel syndrome. Expert Opin Pharmacother. 2003 Nov;4(11):2089-98.
3. Andresen V, Hollerbach S: Reassessing the benefits and risks of alosetron: what is its place in the treatment of irritable bowel syndrome? Drug Saf. 2004;27(5):283-92.
4. Rahimi R, Nikfar S, Abdollahi M: Efficacy and tolerability of alosetron for the treatment of irritable bowel syndrome in women and men: a meta-analysis of eight randomized, placebo-controlled, 12-week trials. Clin Ther. 2008 May;30(5):884-901. doi: 10.1016/j.clinthera.2008.05.002.
5. Lewis JH: Alosetron for severe diarrhea-predominant irritable bowel syndrome: safety and efficacy in perspective. Expert Rev Gastroenterol Hepatol. 2010 Feb;4(1):13-29. doi: 10.1586/egh.09.72.