Tegaserod maleateProduct ingredient for Tegaserod

Name
Tegaserod maleate
Drug Entry
Tegaserod

Novartis' brand name Zelnorm (tegaserod) had originally received approval from the US FDA in 2002 for the treatment of irritable bowel syndrome with constipation (IBS-C).5,8 It was, however, voluntarily withdrawn from widespread use in the US market in 2007 after concerns arose over the possibility that tegaserod could potentially cause dangerous cardiovascular events in patients.5,8 Since then, closer evaluations of the original data suggesting such cardiovascular risk have resulted in the limited reintroduction or 're-approval' of tegaserod for treatment of IBS-C specifically in female patients less than 65 years of age and whom are considered to be at a lower risk of a cardiovascular event than the broader population.5,8 Zelnorm (tegaserod) by Sloan Pharma subsequently gained re-approval in April of 2019.5 Nevertheless, tegaserod remains un-approved in certain regions.7

Despite the relative complications involved in its history of regulatory approval, ever since its first introduction in 2002 tegaserod remains the only therapy for IBS-C that possesses the unique mechanism of action of acting on serotonin-4 (5-HT(4)) receptors in smooth muscle cells and in the gastrointestinal wall to facilitate actions like esophageal relaxation, peristaltic gut movement, and natural secretions in the gut, among others.5,1,3,8,6

Accession Number
DBSALT001797
Structure
Synonyms
3-(5-Methoxy-1H-indol-3-ylmethylene)-N-pentylcarbazimidamide hydrogen maleate / Tegaserod maleate
UNII
E5XNT3RF5A
CAS Number
189188-57-6
Weight
Average: 417.466
Monoisotopic: 417.201218989
Chemical Formula
C20H27N5O5
InChI Key
CPDDZSSEAVLMRY-FEQFWAPWSA-N
InChI
InChI=1S/C16H23N5O.C4H4O4/c1-3-4-5-8-18-16(17)21-20-11-12-10-19-15-7-6-13(22-2)9-14(12)15;5-3(6)1-2-4(7)8/h6-7,9-11,19H,3-5,8H2,1-2H3,(H3,17,18,21);1-2H,(H,5,6)(H,7,8)/b20-11+;2-1-
IUPAC Name
(2Z)-but-2-enedioic acid; N'-[(E)-[(5-methoxy-1H-indol-3-yl)methylidene]amino]-N-pentylguanidine
SMILES
OC(=O)\C=C/C(O)=O.CCCCCNC(=N)N\N=C\C1=CNC2=C1C=C(OC)C=C2
KEGG Drug
D02730
ChemSpider
10482083
ChEBI
51044
ChEMBL
CHEMBL1516474
Wikipedia
Tegaserod
Predicted Properties
PropertyValueSource
Water Solubility0.0288 mg/mLALOGPS
logP2.76ALOGPS
logP2.95Chemaxon
logS-4ALOGPS
pKa (Strongest Acidic)15.24Chemaxon
pKa (Strongest Basic)8.5Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area85.29 Å2Chemaxon
Rotatable Bond Count9Chemaxon
Refractivity110.25 m3·mol-1Chemaxon
Polarizability34.96 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon