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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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Click here for structure editor
Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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. 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]