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2D Structure
Also known as: Vazegepant, Bms-742413, Bhv-3500, Zavegepant [usan], Odu3zaz94j, Bms-742413-01
Molecular Formula
C36H46N8O3
Molecular Weight
638.8  g/mol
InChI Key
JJVAPHYEOZSKJZ-JGCGQSQUSA-N
FDA UNII
ODU3ZAZ94J

Zavegepant is a highly soluble small molecule calcitonin gene related peptide (CGRP) receptor antagonist, with potential analgesic and immunomodulating activities. Upon administration, zavegepant targets, binds to and inhibits the activity of CGRP receptors located on mast cells in the brain. This may inhibit neurogenic inflammation caused by trigeminal nerve release of CGRP. In addition, by blocking the CGRP receptors located in smooth muscle cells within vessel walls, zavegepant inhibits the pathologic dilation of intracranial arteries. Zavegepant, by blocking the CGRP receptors, also suppresses the transmission of pain by inhibiting the central relay of pain signals from the trigeminal nerve to the caudal trigeminal nucleus. Altogether, this may relieve migraine. As CGRP receptors induce the release of pro-inflammatory mediators, such as interleukin-6 (IL-6), from inflammatory cells, zavegepant may prevent an IL-6-mediated inflammatory response. Zavegepant may also inhibit the CGRP-mediated induction of eosinophil migration and the stimulation of beta-integrin-mediated T cell adhesion to fibronectin at the site of inflammation, and may abrogate the CGRP-mediated polarization of the T cell response towards the pro-inflammatory state characterized by Th17 and IL-17. This may improve lung inflammation and oxygenation, prevent edema, and further lung injury. CGRP, a 37 amino-acid peptide expressed in and released from a subset of polymodal primary sensory neurons of the trigeminal ganglion and nerve fibers projecting to the airways and by pulmonary neuroendocrine cells, plays an important role in pain transmission, inflammation, and neurogenic vasodilatation. It is released upon acute lung injury and upregulation of transient receptor potential (TRP) channels.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
N-[(2R)-3-(7-methyl-1H-indazol-5-yl)-1-[4-(1-methylpiperidin-4-yl)piperazin-1-yl]-1-oxopropan-2-yl]-4-(2-oxo-1H-quinolin-3-yl)piperidine-1-carboxamide
2.1.2 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
2.1.3 InChI Key
JJVAPHYEOZSKJZ-JGCGQSQUSA-N
2.1.4 Canonical SMILES
CC1=CC(=CC2=C1NN=C2)CC(C(=O)N3CCN(CC3)C4CCN(CC4)C)NC(=O)N5CCC(CC5)C6=CC7=CC=CC=C7NC6=O
2.1.5 Isomeric SMILES
CC1=CC(=CC2=C1NN=C2)C[C@H](C(=O)N3CCN(CC3)C4CCN(CC4)C)NC(=O)N5CCC(CC5)C6=CC7=CC=CC=C7NC6=O
2.2 Other Identifiers
2.2.1 UNII
ODU3ZAZ94J
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Bms 742413

2. Bms-742413

3. 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

2.3.2 Depositor-Supplied Synonyms

1. Vazegepant

2. Bms-742413

3. Bhv-3500

4. Zavegepant [usan]

5. Odu3zaz94j

6. Bms-742413-01

7. 1337918-83-8

8. Chembl2397415

9. N-[(2r)-3-(7-methyl-1h-indazol-5-yl)-1-[4-(1-methylpiperidin-4-yl)piperazin-1-yl]-1-oxopropan-2-yl]-4-(2-oxo-1h-quinolin-3-yl)piperidine-1-carboxamide

10. 1-piperidinecarboxamide, 4-(1,2-dihydro-2-oxo-3-quinolinyl)-n-((1r)-1-((7-methyl-1h-indazol-5-yl)methyl)-2-(4-(1-methyl-4-piperidinyl)-1-piperazinyl)-2-oxoethyl)-

11. 4-(1,2-dihydro-2-oxo-3-quinolinyl)-n-((1r)-1-((7-methyl-1h-indazol-5-yl)methyl)-2-(4-(1-methyl-4-piperidinyl)-1-piperazinyl)-2-oxoethyl)-1-piperidinecarboxamide

12. Zavegepant [inn]

13. Unii-odu3zaz94j

14. Vazegepant [who-dd]

15. Schembl107428

16. Gtpl11513

17. Ex-a6698

18. Bdbm50436107

19. Bms742413

20. Who 11512

21. Hy-134992

22. Cs-0168642

2.4 Create Date
2011-11-07
3 Chemical and Physical Properties
Molecular Weight 638.8 g/mol
Molecular Formula C36H46N8O3
XLogP33.1
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count6
Rotatable Bond Count6
Exact Mass638.36928736 g/mol
Monoisotopic Mass638.36928736 g/mol
Topological Polar Surface Area117 Ų
Heavy Atom Count47
Formal Charge0
Complexity1160
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1