ubrogepant   Click here for help

GtoPdb Ligand ID: 10176

Synonyms: MK-1602 | MK1602 | Ubrelvy®
Approved drug
ubrogepant is an approved drug (FDA (2019))
Compound class: Synthetic organic
Comment: Ubrogepant (MK-1602) is an orally available calcitonin gene-related peptide receptor antagonist that was developed by Allergan for the acute treatment of migraine [1,3-4,6]. Notably it was the first oral CGRP receptor antagonist to be approved to treat migraines as they are occurring. Previously approved CGRP/CGRP receptor-targeting drugs (e.g. fremanezumab, galcanezumab and erenumab) have been indicated for migraine prevention.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 8
Hydrogen bond donors 2
Rotatable bonds 6
Topological polar surface area 104.29
Molecular weight 549.2
XLogP 3.91
No. Lipinski's rules broken 0
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Canonical SMILES O=C(c1cnc2c(c1)CC1(C2)C(=O)Nc2c1cccn2)NC1CC(c2ccccc2)C(N(C1=O)CC(F)(F)F)C
Isomeric SMILES O=C(c1cnc2c(c1)C[C@@]1(C2)C(=O)Nc2c1cccn2)N[C@H]1C[C@@H](c2ccccc2)[C@H](N(C1=O)CC(F)(F)F)C
InChI InChI=1S/C29H26F3N5O3/c1-16-20(17-6-3-2-4-7-17)11-22(26(39)37(16)15-29(30,31)32)35-25(38)19-10-18-12-28(13-23(18)34-14-19)21-8-5-9-33-24(21)36-27(28)40/h2-10,14,16,20,22H,11-13,15H2,1H3,(H,35,38)(H,33,36,40)/t16-,20-,22+,28+/m1/s1
1. Bell IM, Fraley ME, Gallicchio SN, Ginnetti A, Mitchell HJ, Paone DV, Staas DD, Stevenson HE, Wang C, Zartman CB. (2012)
Piperidinone carboxamide azaindane cgrp receptor antagonists.
Patent number: WO2012064910A1. Assignee: Merck Sharp & Dohme Corp.. Priority date: 12/11/2010. Publication date: 18/05/2012.
2. Dodick DW, Lipton RB, Ailani J, Lu K, Finnegan M, Trugman JM, Szegedi A. (2019)
Ubrogepant for the Treatment of Migraine.
N Engl J Med, 381 (23): 2230-2241. [PMID:31800988]
3. Edvinsson L, Haanes KA, Warfvinge K, Krause DN. (2018)
CGRP as the target of new migraine therapies - successful translation from bench to clinic.
Nat Rev Neurol, 14 (6): 338-350. [PMID:29691490]
4. Lambru G, Andreou AP, Guglielmetti M, Martelletti P. (2018)
Emerging drugs for migraine treatment: an update.
Expert Opin Emerg Drugs, 23 (4): 301-318. [PMID:30484333]
5. Moore E, Fraley ME, Bell IM, Burgey CS, White RB, Li CC, Regan CP, Danziger A, Stranieri Michener M, Hostetler E et al.. (2020)
Characterization of Ubrogepant: A Potent and Selective Antagonist of the Human Calcitonin Gene‒Related Peptide Receptor.
J Pharmacol Exp Ther, [Epub ahead of print]. [PMID:31992609]
6. Tfelt-Hansen P, Loder E. (2019)
The Emperor's New Gepants: Are the Effects of the New Oral CGRP Antagonists Clinically Meaningful?.
Headache, 59 (1): 113-117. [PMID:30451300]
7. Voss T, Lipton RB, Dodick DW, Dupre N, Ge JY, Bachman R, Assaid C, Aurora SK, Michelson D. (2016)
A phase IIb randomized, double-blind, placebo-controlled trial of ubrogepant for the acute treatment of migraine.
Cephalalgia, 36 (9): 887-98. [PMID:27269043]