Telcagepant

Telcagepant
Clinical data
Routes of; administration	Oral
ATC code	none;
Legal status
Legal status	Development terminated;
Pharmacokinetic data
Elimination half-life	5–8 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	781649-09-0 ;
PubChem CID	11319053;
IUPHAR/BPS	703;
ChemSpider	9494017 ;
UNII	D42O649ALL;
KEGG	D09391 ;
ChEMBL	ChEMBL236593 ;
CompTox Dashboard (EPA)	DTXSID50999410 ;
Chemical and physical data
Formula	C26H27F5N6O3
Molar mass	566.533 g·mol−1
3D model (JSmol)	Interactive image;
	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 ; Key:CGDZXLJGHVKVIE-DNVCBOLYSA-N ;
	(what is this?) (verify)

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]

In the acute treatment of migraine, it was found to have equal efficacy 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]

References

^ Molecule of the Month February 2009
^ 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.
^ 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.
^ Clinical trial number NCT00797667 for "MK0974 for Migraine Prophylaxis in Patients With Episodic Migraine" at ClinicalTrials.gov
^ Merck & Co.: Memo to all US study locations involved in protocol MK0974-049
^ "Press release: Merck Announces Second Quarter 2011 Financial Results". Merck. July 29, 2011. Archived from the original on April 12, 2013.

[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.

[1]

[2]

[3]

[4]

[5]

[6]

Clinical data


Routes of administration	Oral
ATC code	none
Legal status
Legal status	Development terminated
Pharmacokinetic data
Elimination half-life	5–8 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	781649-09-0^N
PubChem CID	11319053
IUPHAR/BPS	703
ChemSpider	9494017^Y
UNII	D42O649ALL
KEGG	D09391^Y
ChEMBL	ChEMBL236593^Y
CompTox Dashboard (EPA)	DTXSID50999410
Chemical and physical data
Formula	C₂₆H₂₇F₅N₆O₃
Molar mass	566.533 g·mol⁻¹
3D model (JSmol)	Interactive image
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)

Telcagepant

See also

References