zavegepant   Click here for help

GtoPdb Ligand ID: 11513

Synonyms: BHV-3500 | BMS-742413 | BMS742413 | Zavzpret®
Approved drug
zavegepant is an approved drug (FDA (2023))
Compound class: Synthetic organic
Comment: Zavegepant is a CGRP receptor antagonist [1,3], that was developed as a drug to treat and/or prevent migraine. It was designed for intranasal administration.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 8
Hydrogen bond donors 3
Rotatable bonds 9
Topological polar surface area 120.67
Molecular weight 638.37
XLogP 3.56
No. Lipinski's rules broken 0
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Canonical SMILES CN1CCC(CC1)N1CCN(CC1)C(=O)[C@H](NC(=O)N1CCC(CC1)c1cc2ccccc2[nH]c1=O)Cc1cc(C)c2c(c1)cn[nH]2
Isomeric SMILES CN1CCC(CC1)N1CCN(CC1)C(=O)[C@H](NC(=O)N1CCC(CC1)c1cc2ccccc2[nH]c1=O)Cc1cc(C)c2c(c1)cn[nH]2
InChI InChI=1S/C36H46N8O3/c1-24-19-25(20-28-23-37-40-33(24)28)21-32(35(46)43-17-15-42(16-18-43)29-9-11-41(2)12-10-29)39-36(47)44-13-7-26(8-14-44)30-22-27-5-3-4-6-31(27)38-34(30)45/h3-6,19-20,22-23,26,29,32H,7-18,21H2,1-2H3,(H,37,40)(H,38,45)(H,39,47)/t32-/m1/s1
1. Chaturvedula PV, Mercer SE, Pin SS, Thalody G, Xu C, Conway CM, Keavy D, Signor L, Cantor GH, Mathias N et al.. (2013)
Discovery of (R)-N-(3-(7-methyl-1H-indazol-5-yl)-1-(4-(1-methylpiperidin-4-yl)-1-oxopropan-2-yl)-4-(2-oxo-1,2-dihydroquinolin-3-yl)piperidine-1-carboxamide (BMS-742413): a potent human CGRP antagonist with superior safety profile for the treatment of migraine through intranasal delivery.
Bioorg Med Chem Lett, 23 (11): 3157-61. [PMID:23632269]
2. Dhillon S. (2023)
Zavegepant: First Approval.
Drugs, 83 (9): 825-831. [PMID:37227596]
3. Mercer SE, Chaturvedula PV, Conway CM, Cook DA, Davis CD, Pin SS, Macci R, Schartman R, Signor LJ, Widmann KA et al.. (2021)
Azepino-indazoles as calcitonin gene-related peptide (CGRP) receptor antagonists.
Bioorg Med Chem Lett, 31: 127624. [PMID:33096162]