Vazegepant
Identification
- Name
- Vazegepant
- Accession Number
- DB15688
- Description
Vazegepant 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 vazegepant 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
Structure for Vazegepant (DB15688)
- 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)-
- External IDs
- BHV-3500
- BMS-742413
Pharmacology
- Indication
- Not Available
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- 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
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
- Not Available
- Affected organisms
- 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
Products
Categories
- Drug Categories
- Classification
- Not classified
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)[[email protected]@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 Not Yet Recruiting Treatment Migraine 1 2, 3 Completed Treatment Migraine 1 2, 3 Recruiting Treatment Acute Migraine 1 2, 3 Recruiting Treatment Covid-19 Infection / Novel Coronavirus Infectious Disease (COVID-19) 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
- Practical Neurology: Vazegepant, Investigational Drug Being Studied for Migraine, to Enter Phase 2 Trial for COVID-19 Treatment [Link]
Drug created on May 21, 2020 08:18 / Updated on June 12, 2020 10:53
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