Identification
- Generic Name
- Zavegepant
- DrugBank Accession Number
- DB15688
- Background
Zavegepant is an antagonist of the calcitonin gene-related peptide (CGRP) receptor currently in phase 3 trials in an intranasal formulation for the treatment of migraine. If FDA approved, it will join other previously-approved "-gepant" drugs rimegepant and ubrogepant as an additional treatment alternative for patients with migraine, particularly those for whom traditional triptan therapy has proven ineffective.
On April 15th, 2020, a phase 2 clinical trial (NCT04346615: Safety and Efficacy Trial of Vazegepant Intranasal for Hospitalized Patients With COVID-19 Requiring Supplemental Oxygen)1 began to investigate the use of intranasally administered zavegepant to combat the acute respiratory distress syndrome (ARDS) sometimes seen in patients with COVID-19. Acute lung injury activates the release of CGRP, which plays a role in the development of ARDS - CGRP antagonists, then, may help to blunt the significant inflammation associated with COVID-19.2 The clinical trial is expected to complete in September 2020.1
- Type
- Small Molecule
- Groups
- Investigational
- Structure
- Weight
- Average: 638.817
Monoisotopic: 638.369287373 - Chemical Formula
- C36H46N8O3
- Synonyms
- 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)-
- Vazegepant
- Zavegepant
- External IDs
- BHV-3500
- BMS-742413
Pharmacology
- Indication
Not Available
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
- Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.
- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism ACalcitonin gene-related peptide type 1 receptor antagonistHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Classification
- Not classified
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- ODU3ZAZ94J
- CAS number
- 1337918-83-8
- InChI Key
- JJVAPHYEOZSKJZ-JGCGQSQUSA-N
- 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
- 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
- SMILES
- 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
References
- General References
- External Links
- ChemSpider
- 30814207
- ChEMBL
- CHEMBL2397415
- ZINC
- ZINC000096271995
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 3 Completed Treatment Migraine 1 2, 3 Completed Treatment Acute Migraine 1 2, 3 Completed Treatment Migraine 1 2, 3 Recruiting Prevention Migraine 1 2, 3 Recruiting Treatment Coronavirus Disease 2019 (COVID‑19) / Covid 19 Infection 1 1 Recruiting Treatment Asthma 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Not Available
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.0696 mg/mL ALOGPS logP 2.85 ALOGPS logP 2.14 ChemAxon logS -4 ALOGPS pKa (Strongest Acidic) 12.38 ChemAxon pKa (Strongest Basic) 8.81 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 71.32 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 - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Not Available
Targets

- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Receptor for calcitonin-gene-related peptide (CGRP) together with RAMP1 and receptor for adrenomedullin together with RAMP3 (By similarity). Receptor for adrenomedullin together with RAMP2. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase.
- Specific Function
- Adrenomedullin receptor activity
- Gene Name
- CALCRL
- Uniprot ID
- Q16602
- Uniprot Name
- Calcitonin gene-related peptide type 1 receptor
- Molecular Weight
- 52928.98 Da
References
- Mercer SE, Chaturvedula PV, Conway CM, Cook DA, Davis CD, Pin SS, Macci R, Schartman R, Signor LJ, Widmann KA, Whiterock VJ, Chen P, Xu C, Herbst JJ, Kostich WA, Thalody G, Macor JE, Dubowchik GM: Azepino-indazoles as calcitonin gene-related peptide (CGRP) receptor antagonists. Bioorg Med Chem Lett. 2021 Jan 1;31:127624. doi: 10.1016/j.bmcl.2020.127624. Epub 2020 Oct 21. [Article]
- Practical Neurology: Vazegepant, Investigational Drug Being Studied for Migraine, to Enter Phase 2 Trial for COVID-19 Treatment [Link]
Drug created at May 21, 2020 14:18 / Updated at May 06, 2022 10:06