Alosetron hydrochlorideProduct ingredient for Alosetron

Name
Alosetron hydrochloride
Drug Entry
Alosetron

Alosetron 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 Alosetron was voluntarily withdrawn from the US market in November 2000 by the manufacturer due to numerous reports of severe adverse effects including ischemic colitis, severely obstructed or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.

Accession Number
DBSALT000247
Structure
Synonyms
Alosetron HCl
UNII
2F5R1A46YW
CAS Number
122852-69-1
Weight
Average: 330.812
Monoisotopic: 330.124738957
Chemical Formula
C17H19ClN4O
InChI Key
FNYQZOVOVDSGJH-UHFFFAOYSA-N
InChI
InChI=1S/C17H18N4O.ClH/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);1H
IUPAC Name
5-methyl-2-[(4-methyl-1H-imidazol-5-yl)methyl]-1H,2H,3H,4H,5H-pyrido[4,3-b]indol-1-one hydrochloride
SMILES
Cl.CN1C2=C(C3=CC=CC=C13)C(=O)N(CC1=C(C)N=CN1)CC2
PubChem Compound
60758
ChemSpider
54758
ChEBI
53783
ChEMBL
CHEMBL1200885
Wikipedia
Alosetron
Predicted Properties
PropertyValueSource
Water Solubility0.439 mg/mLALOGPS
logP1.78ALOGPS
logP0.98Chemaxon
logS-2.8ALOGPS
pKa (Strongest Acidic)14.04Chemaxon
pKa (Strongest Basic)6.48Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area53.92 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity86.25 m3·mol-1Chemaxon
Polarizability32.4 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon