This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.
Identification
- Generic Name
- Telcagepant
- DrugBank Accession Number
- DB12228
- Background
Telcagepant has been investigated for the treatment of Migraine. It is an antagonist of the receptor for calcitonin gene-related peptide (CGRP), a primary neuropeptide involved in the pathophysiology of migraine. CGRP and its receptors are found in areas of the central and peripheral nervous system that are important for the transmission of migraine pain. During migraine attacks, CGRP activates these receptors and facilitates the transmission of pain impulses.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for Telcagepant (DB12228)
- Weight
- Average: 566.523
Monoisotopic: 566.206479785 - Chemical Formula
- C26H27F5N6O3
- Synonyms
- Telcagepant
- External IDs
- MK-0974
- MK0974
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
Telcagepant blocks the binding of CGRP to receptors within the areas of the central and peripheral nervous system that are important for the transmission of migraine pain and thereby is believed to inhibit the transmission of pain signals that lead to migraine headaches.
Target Actions Organism UCalcitonin gene-related peptide type 1 receptor Not Available Humans UCalcitonin gene-related peptide 1 Not Available Humans UCalcitonin gene-related peptide 2 Not Available Humans - 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
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Telcagepant potassium L303VER2NG 953077-35-5 VESUVMGLUABQCA-LEVQAPRMSA-M
Categories
- Drug Categories
- Not Available
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Carboxylic acids and derivatives
- Sub Class
- Amino acids, peptides, and analogues
- Direct Parent
- Alpha amino acids and derivatives
- Alternative Parents
- Imidazopyridines / Piperidinecarboxamides / Caprolactams / Fluorobenzenes / Azepanes / N-substituted imidazoles / Aryl fluorides / Pyridines and derivatives / Tertiary carboxylic acid amides / Heteroaromatic compounds show 8 more
- Substituents
- 1-piperidinecarboxamide / Alkyl fluoride / Alkyl halide / Alpha-amino acid or derivatives / Aromatic heteropolycyclic compound / Aryl fluoride / Aryl halide / Azacycle / Azepane / Azole show 26 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- D42O649ALL
- CAS number
- 781649-09-0
- InChI Key
- CGDZXLJGHVKVIE-DNVCBOLYSA-N
- InChI
- InChI=1S/C26H27F5N6O3/c27-18-4-1-3-17(21(18)28)15-6-7-19(23(38)36(13-15)14-26(29,30)31)33-24(39)35-11-8-16(9-12-35)37-20-5-2-10-32-22(20)34-25(37)40/h1-5,10,15-16,19H,6-9,11-14H2,(H,33,39)(H,32,34,40)/t15-,19-/m1/s1
- IUPAC Name
- N-[(3R,6S)-6-(2,3-difluorophenyl)-2-oxo-1-(2,2,2-trifluoroethyl)azepan-3-yl]-4-{2-oxo-1H,2H,3H-imidazo[4,5-b]pyridin-1-yl}piperidine-1-carboxamide
- SMILES
- FC1=C(F)C(=CC=C1)[C@@H]1CC[C@@H](NC(=O)N2CCC(CC2)N2C(=O)NC3=C2C=CC=N3)C(=O)N(CC(F)(F)F)C1
References
- General References
- Salvatore CA, Hershey JC, Corcoran HA, Fay JF, Johnston VK, Moore EL, Mosser SD, Burgey CS, Paone DV, Shaw AW, Graham SL, Vacca JP, Williams TM, Koblan KS, Kane SA: Pharmacological characterization of MK-0974 [N-[(3R,6S)-6-(2,3-difluorophenyl)-2-oxo-1-(2,2,2-trifluoroethyl)azepan-3-yl]-4-( 2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxamide], a potent and orally active calcitonin gene-related peptide receptor antagonist for the treatment of migraine. J Pharmacol Exp Ther. 2008 Feb;324(2):416-21. Epub 2007 Nov 26. [Article]
- Paone DV, Shaw AW, Nguyen DN, Burgey CS, Deng JZ, Kane SA, Koblan KS, Salvatore CA, Mosser SD, Johnston VK, Wong BK, Miller-Stein CM, Hershey JC, Graham SL, Vacca JP, Williams TM: Potent, orally bioavailable calcitonin gene-related peptide receptor antagonists for the treatment of migraine: discovery of N-[(3R,6S)-6-(2,3-difluorophenyl)-2-oxo-1- (2,2,2-trifluoroethyl)azepan-3-yl]-4- (2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin- 1-yl)piperidine-1-carboxamide (MK-0974). J Med Chem. 2007 Nov 15;50(23):5564-7. Epub 2007 Oct 11. [Article]
- Ho TW, Mannix LK, Fan X, Assaid C, Furtek C, Jones CJ, Lines CR, Rapoport AM: Randomized controlled trial of an oral CGRP receptor antagonist, MK-0974, in acute treatment of migraine. Neurology. 2008 Apr 15;70(16):1304-12. Epub 2007 Oct 3. [Article]
- Link AS, Kuris A, Edvinsson L: Treatment of migraine attacks based on the interaction with the trigemino-cerebrovascular system. J Headache Pain. 2008 Feb;9(1):5-12. doi: 10.1007/s10194-008-0011-4. Epub 2008 Jan 23. [Article]
- External Links
- PubChem Compound
- 11319053
- PubChem Substance
- 347828507
- ChemSpider
- 9494017
- BindingDB
- 50224431
- ChEMBL
- CHEMBL236593
- ZINC
- ZINC000028827350
- PDBe Ligand
- N7R
- Wikipedia
- Telcagepant
- PDB Entries
- 3n7r
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 3 Completed Treatment Cardiovascular Disease (CVD) / Migraine / Peripheral Vascular Disease Patient / Stroke / Transient Ischemic Attack / Vascular Diseases 1 3 Completed Treatment Migraine 4 2 Completed Treatment Migraine 2 2 Terminated Treatment Migraine 1 2, 3 Completed Treatment Migraine 1 1 Completed Treatment Angina Pectoris / Calcitonin Gene-related Peptide Receptor / Coronary Heart Disease (CHD) 1 1 Completed Treatment Migraine 5
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 0.0936 mg/mL ALOGPS logP 2.44 ALOGPS logP 2.63 Chemaxon logS -3.8 ALOGPS pKa (Strongest Acidic) 10.69 Chemaxon pKa (Strongest Basic) 3.16 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 97.88 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 134.6 m3·mol-1 Chemaxon Polarizability 52.43 Å3 Chemaxon Number of Rings 5 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- 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
- Chan KY, Edvinsson L, Eftekhari S, Kimblad PO, Kane SA, Lynch J, Hargreaves RJ, de Vries R, Garrelds IM, van den Bogaerdt AJ, Danser AH, Maassenvandenbrink A: Characterization of the calcitonin gene-related peptide receptor antagonist telcagepant (MK-0974) in human isolated coronary arteries. J Pharmacol Exp Ther. 2010 Sep 1;334(3):746-52. doi: 10.1124/jpet.110.165993. Epub 2010 Jun 23. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Receptor binding
- Specific Function
- CGRP induces vasodilation. It dilates a variety of vessels including the coronary, cerebral and systemic vasculature. Its abundance in the CNS also points toward a neurotransmitter or neuromodulato...
- Gene Name
- CALCA
- Uniprot ID
- P06881
- Uniprot Name
- Calcitonin gene-related peptide 1
- Molecular Weight
- 13897.755 Da
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Neuropeptide hormone activity
- Specific Function
- CGRP induces vasodilation. It dilates a variety of vessels including the coronary, cerebral and systemic vasculature. Its abundance in the CNS also points toward a neurotransmitter or neuromodulato...
- Gene Name
- CALCB
- Uniprot ID
- P10092
- Uniprot Name
- Calcitonin gene-related peptide 2
- Molecular Weight
- 13705.56 Da
Drug created at October 20, 2016 21:40 / Updated at February 21, 2021 18:53