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
Selectivity at GPCRs
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
CGRP receptor Hs Antagonist Antagonist 10.8 pKB - 5
pKB 10.8 [5]