telcagepant   Click here for help

GtoPdb Ligand ID: 703

Synonyms: MK 0974  | MK-0974 | MK0974
PDB Ligand
Compound class: Synthetic organic
Comment: Telcagepant (MK-0974) is a calcitonin gene-related peptide receptor antagonist. It was developed by Merck for the acute treatment and prevention of migraine.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 7
Hydrogen bond donors 2
Rotatable bonds 7
Topological polar surface area 103.33
Molecular weight 566.21
XLogP 3.74
No. Lipinski's rules broken 0
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Canonical SMILES O=C(N1CCC(CC1)n1c(=O)[nH]c2c1cccn2)NC1CCC(CN(C1=O)CC(F)(F)F)c1cccc(c1F)F
Isomeric SMILES O=C(N1CCC(CC1)n1c(=O)[nH]c2c1cccn2)N[C@@H]1CC[C@H](CN(C1=O)CC(F)(F)F)c1cccc(c1F)F
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
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Summary of Clinical Use Click here for help
Telcagepant (MK-0974) progressed to Phase 3 clinical trial as a migraine treatment. Click here to link to's full list of telcagepant trials. Development of this agent has been discontinued. Results that show that daily dosing with telcagepant caused elevation of transaminase activity (i.e. acute hepatocellular toxicity) as an adverse event in two separate trials [2-3] are likely to have influenced the decision to terminate development of telcagepant as a migraine prevention drug [1]. The toxic effect was likely due to the compound's structure rather than any on-target effect.