Vazegepant

Synopsis, Chemistry

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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

Vazegepant

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 Formula	C₃₆H₄₆N₈O₃
Molecular Weight	638.8 g/mol
XLogP3	3.1
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	6
Exact Mass	638.36928736 g/mol
Monoisotopic Mass	638.36928736 g/mol
Topological Polar Surface Area	117 Å²
Heavy Atom Count	47
Formal Charge	0
Complexity	1160
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1