Zavegepant hydrochlorideProduct ingredient for Zavegepant
- Name
- Zavegepant hydrochloride
- Drug Entry
- Zavegepant
Zavegepant (BHV-3500) is a calcitonin gene-related peptide (CGRP) receptor antagonist.5 CGRP is released from sensory nerves and acts as a strong vasodilator, and thanks to these properties, it is involved in pain pathways. CGRP receptors are expressed in the central and peripheral nervous system; however, CGRP does not cross the blood-brain barrier, suggesting that it acts on peripheral nerves. In migraine, CGRP innervates pain-producing meningeal blood vessels and is released by trigeminal nerve stimulation. Since they inhibit these mechanisms and desensitize neuronal circuits, the use of CGRP receptor antagonists is beneficial in the treatment of migraine.2
Small molecule CGRP antagonists are also known as "gepants", and this category includes other drugs such as rimegepant and ubrogepant. Zavegepant is a third-generation CGRP receptor antagonist that is small in size and highly soluble. Due to its pharmacological properties, it can be administered intranasally.1,2 In March 2023, the FDA approved the use of zavegepant nasal spray for the acute treatment of migraine with or without aura in adults.5,6 A clinical trial (NCT04804033) is currently investigating the efficacy and safety of oral zavegepant in migraine prevention, and another one (NCT04987944) is evaluating the safety and efficacy of oral zavegepant (150 mg bid) in subjects with mild allergic asthma.3
- Accession Number
- DBSALT003479
- Structure
Structure for Zavegepant hydrochloride (DBSALT003479)
- Synonyms
- 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 HYDROCHLORIDE / BHV-3500 HYDROCHLORIDE
- External IDs
- BMS-742413-03
- UNII
- 000QCM6HAL
- CAS Number
- 1414976-20-7
- Weight
- Average: 675.28
Monoisotopic: 674.3459651 - Chemical Formula
- C36H47ClN8O3
- InChI Key
- VQDUWCSSPSOSNA-RYWNGCACSA-N
- InChI
- InChI=1S/C36H46N8O3.ClH/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);1H/t32-;/m1./s1
- 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-1,2-dihydroquinolin-3-yl)piperidine-1-carboxamide hydrochloride
- SMILES
- Cl.CN1CCC(CC1)N1CCN(CC1)C(=O)[C@@H](CC1=CC2=C(NN=C2)C(C)=C1)NC(=O)N1CCC(CC1)C1=CC2=C(NC1=O)C=CC=C2
- External Links
- ChemSpider
- 81367517
- ChEMBL
- CHEMBL4650220
- Wikipedia
- Zavegepant
- Predicted Properties
Property Value Source logP 2.14 Chemaxon pKa (Strongest Acidic) 11.33 Chemaxon pKa (Strongest Basic) 8.79 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 116.91 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 186.53 m3·mol-1 Chemaxon Polarizability 71.37 Å3 Chemaxon Number of Rings 7 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon