Alosetron (CED0008076)

Record Information
Version1.0
Creation Date2016-05-25 18:24:00 UTC
Update Date2026-08-19 20:01:40 UTC
Accession NumberCHEM022211
Identification
Common NameAlosetron
ClassSmall Molecule
Description
Alosetron is an organic compound with the chemical formula C17H18N4O and an average molecular weight of 294.35 g/mol. Alosetron belongs to the n-alkylindoles, a subclass of indoles and derivatives within the organic compounds. It is further classified as an organoheterocyclic compound. The compound is utilized as a drug for functional gastrointestinal disorders. Its pharmacological activity is characterized by its role as an antagonist of two protein targets: 5-hydroxytryptamine receptor 3A (HTR3A) and 5-hydroxytryptamine receptor 3B (HTR3B). The recorded exposure route for this substance is oral. Alosetron is found in or released from seven recorded sources. These include healthcare, pharmaceuticals, and veterinary products, specifically drugs for functional gastrointestinal disorders. It is also associated with household cleaning and consumer products, including cigar cigarettes, tobacco smoke filters, and other smoking requisites. Additionally, it is linked to electrical and electronic equipment, specifically electrodes, electrically stimulated smoking devices, and conductors or conductive bodies characterized by the conductive materials.
Contaminant TypeNot Available
Chemical Structure
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
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-054p-9640000000-36ec950b2b5a4de0d766Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0390000000-3b813a9458d2bce7516fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-3390000000-9994f53a2714bf016b00Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-5090000000-aa22d1e533a9ade9a631Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-9470000000-de378c4e797603ddebd5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udj-9000000000-4320dc79a39aa798ebedNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0090000000-61b91fd4d7827b2dee3cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-1690000000-1c0db2dce26ffd0716f7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-4900000000-bac7a8e86a49765da618Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-0090000000-0a33faab2e775c338d55Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-0090000000-6aa9a0fa5a9c1aeeb778Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-9320000000-27c420ad3c1a98b56addNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0090000000-abdd2e02132168abe3faNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0190000000-c8bf656d3129fa7c6a2cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0290000000-dacd12d29c5302eb8887Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
622.0Log mg/kg[350:1100]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
243Drugs for functional gastrointestinal disordersHealthcare, pharmaceuticals & veterinary productsNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
632ApparelTextiles, leather & furnishingsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
Pathways
2 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
5-hydroxytryptamine receptor 5A structureClick to view 3D structure5-hydroxytryptamine receptor 5AP47898HumansPredicted (SEA)101.515
D(2) dopamine receptor structureClick to view 3D structureD(2) dopamine receptorP14416HumansPredicted (SEA)693.559
Click to view 3D structurecGMP-dependent protein kinase 1P00516Bos taurusPredicted (SEA)4.5931
5-hydroxytryptamine receptor 1A structureClick to view 3D structure5-hydroxytryptamine receptor 1AP08908HumansPredicted (SEA)823.723
5-hydroxytryptamine receptor 2A structureClick to view 3D structure5-hydroxytryptamine receptor 2AP28223HumansPredicted (SEA)1005.89
Click to view 3D structureMuscarinic acetylcholine receptor M3P08483Rattus norvegicusPredicted (SEA)29.8941
Click to view 3D structureMyosin light chain kinase, smooth muscleP11799Gallus gallusPredicted (SEA)85.5563
Click to view 3D structureD(2) dopamine receptorP61169RatPredicted (SEA)722.83
Click to view 3D structureAlpha-2A adrenergic receptorP22909Rattus norvegicusPredicted (SEA)93.8862
5-hydroxytryptamine receptor 3A structureClick to view 3D structure5-hydroxytryptamine receptor 3AP46098HumansPredicted (SEA)6.38364
Voltage-gated inwardly rectifying potassium channel KCNH2 structureClick to view 3D structureVoltage-gated inwardly rectifying potassium channel KCNH2Q12809HumansPredicted (SEA)111.402
5-hydroxytryptamine receptor 2B structureClick to view 3D structure5-hydroxytryptamine receptor 2BP41595HumansPredicted (SEA)48.2665
Cytochrome P450 1A2 structureClick to view 3D structureCytochrome P450 1A2P05177HumansPredicted (SEA)83.7658
Cytochrome P450 2D6 structureClick to view 3D structureCytochrome P450 2D6P10635HumansPredicted (SEA)124.247
Cytochrome P450 2C9 structureClick to view 3D structureCytochrome P450 2C9P11712HumansPredicted (SEA)161.148
Cytochrome P450 2C19 structureClick to view 3D structureCytochrome P450 2C19P33261HumansPredicted (SEA)80.2626
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansPredicted (SEA)206.145
Cytochrome P450 2B6 structureClick to view 3D structureCytochrome P450 2B6P20813HumansPredicted (SEA)6.53933
High affinity choline transporter 1 structureClick to view 3D structureHigh affinity choline transporter 1Q9GZV3HumansPredicted (SEA)17.2047
Sentrin-specific protease 8 structureClick to view 3D structureSentrin-specific protease 8Q96LD8HumansPredicted (SEA)2.56902
5-hydroxytryptamine receptor 2C structureClick to view 3D structure5-hydroxytryptamine receptor 2CP08909RatPredicted (SEA)104.707
Click to view 3D structureInterleukin-6 receptor subunit alphaP22273Rattus norvegicusPredicted (SEA)0.311397
Click to view 3D structureLeukotriene B4 receptor 1Q9R0Q2Rattus norvegicusPredicted (SEA)0.311397
Click to view 3D structure5-hydroxytryptamine receptor 2AP14842Rattus norvegicusPredicted (SEA)224.595
Click to view 3D structure5-hydroxytryptamine receptor 5AP30966Mus musculusPredicted (SEA)4.67095
Concentrations
Not Available
External Links
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.