Telcagepant

Telcagepant (INN) (code name MK-0974) is a calcitonin gene-related peptide receptor antagonist which was an investigational drug for the acute treatment and prevention of migraine, developed by Merck & Co.[1]

Telcagepant
Clinical data
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
  • Development terminated
Pharmacokinetic data
Elimination half-life5–8 hours
Identifiers
IUPAC name
  • N-[(3R,6S)-6-(2,3-Difluorophenyl)hexahydro-2-oxo-1-(2,2,2-trifluoroethyl)-1H-azepin-3-yl]-4-(2,3-dihydro-2-oxo-1H-imidazo[4,5-b]pyridin-1-yl)-1-piperidinecarboxamide
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC26H27F5N6O3
Molar mass566.533 g·mol−1
3D model (JSmol)
SMILES
  • C1C[C@H](C(=O)N(C[C@@H]1C2=C(C(=CC=C2)F)F)CC(F)(F)F)NC(=O)N3CCC(CC3)N4C5=C(NC4=O)N=CC=C5
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 Y
  • Key:CGDZXLJGHVKVIE-DNVCBOLYSA-N Y
 NY (what is this?)  (verify)

In the acute treatment of migraine, it was found to have equal potency to rizatriptan[2] and zolmitriptan.[3]

A Phase IIa clinical trial studying telcagepant for the prophylaxis of episodic migraine was stopped on March 26, 2009, after the "identification of two patients with significant elevations in serum transaminases".[4] A memo to study locations stated that telcagepant had preliminarily been reported to increase the hepatic liver enzyme alanine transaminase (ALT) levels in "11 out of 660 randomized (double-blinded) study participants." All study participants were told to stop taking the medication.[5]

In July 2011, Merck announced that it had discontinued development of telcagepant.[6]

See also

References
  1. Molecule of the Month February 2009
  2. Ho TW, Mannix LK, Fan X, Assaid C, Furtek C, Jones CJ, et al. (April 2008). "Randomized controlled trial of an oral CGRP receptor antagonist, MK-0974, in acute treatment of migraine". Neurology. 70 (16): 1304–12. doi:10.1212/01.WNL.0000286940.29755.61. PMID 17914062. S2CID 11612471.
  3. Ho TW, Ferrari MD, Dodick DW, Galet V, Kost J, Fan X, et al. (December 2008). "Efficacy and tolerability of MK-0974 (telcagepant), a new oral antagonist of calcitonin gene-related peptide receptor, compared with zolmitriptan for acute migraine: a randomised, placebo-controlled, parallel-treatment trial". Lancet. 372 (9656): 2115–23. doi:10.1016/S0140-6736(08)61626-8. PMID 19036425. S2CID 43069027.
  4. Clinical trial number NCT00797667 for "MK0974 for Migraine Prophylaxis in Patients With Episodic Migraine" at ClinicalTrials.gov
  5. Merck & Co.: Memo to all US study locations involved in protocol MK0974-049
  6. "Press release: Merck Announces Second Quarter 2011 Financial Results". Merck. July 29, 2011. Archived from the original on April 12, 2013.
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