tegaserod   

GtoPdb Ligand ID: 226

Synonyms: HTF 919 | SDZ HTF 919 | Zelnorm®
tegaserod is an approved drug (FDA (2002))
Compound class: Synthetic organic
Comment: There is some ambiguity as to the exact structure of tegaserod. The structure shown here is PubChem match using the CAS number submitted to the WHO for the INN. Alternative structure renderings for tegaserod are numerous: PubChem CID 5362436 has the highest submitter consensus in PubChem but may not match renderings in references for the biological activity; CID 5487301, and CHEMBL76370 are further alternatives.
Marketed formulations include tegaserod maleate (PubChem CID 6918369)- again with the caveat of alternative representations.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 5
Hydrogen bond donors 3
Rotatable bonds 8
Topological polar surface area 84.03
Molecular weight 301.19
XLogP 3.33
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES CCCCCN=C(NNC=C1C=Nc2c1cc(OC)cc2)N
Isomeric SMILES CCCCCN=C(NN/C=C/1\C=Nc2c1cc(OC)cc2)N
InChI InChI=1S/C16H23N5O/c1-3-4-5-8-18-16(17)21-20-11-12-10-19-15-7-6-13(22-2)9-14(12)15/h6-7,9-11,20H,3-5,8H2,1-2H3,(H3,17,18,21)/b12-11+
InChI Key JWXDRFUZDKKGDV-VAWYXSNFSA-N
Classification
Compound class Synthetic organic
Approved drug? Yes (FDA (2002))
IUPAC Name
1-[[(Z)-(5-methoxyindol-3-ylidene)methyl]amino]-2-pentylguanidine
International Nonproprietary Names
INN number INN
7606 tegaserod
Synonyms
HTF 919 | SDZ HTF 919 | Zelnorm®
Database Links
CAS Registry No. 145158-71-0 (source: Scifinder)
GtoPdb PubChem SID 135651238
PubChem CID 135409453
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Search UniChem for chemical match using the InChIKey JWXDRFUZDKKGDV-VAWYXSNFSA-N
Search UniChem for chemicals with the same backbone JWXDRFUZDKKGDV
Wikipedia Tegaserod