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 [1,3-5]. 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
SMILES / InChI / InChIKey
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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
InChI Key DDOOFTLHJSMHLN-ZQHRPCGSSA-N
References
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. 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]
6. 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]