Basic Information
ID DDInter1896
Drug Type small molecule
Molecular Formula C29H26F3N5O3
Molecular Weight 549.554
CAS Number 1374248-77-7
Description Ubrogepant is indicated for the acute treatment of migraine headaches with or without aura in adults.[L10926] It was approved by the FDA on December 23, 2019, and is the first oral calcitonin gene-related peptide (CGRP) receptor antagonist approved for the acute treatment of migraine.[L10959] Several oral small molecule CGRP receptor antagonists, belonging to a class of medications referred to as "gepants", have been investigated for migraines, but only ubrogepant and [rimegepant] remain in clinical development.[A189207,A189213] Previous agents within this class were efficacious but limited by liver toxicity - this led to the development of ubrogepant, which was designed to be a hepatoxicity-free alternative to its predecessors.[A189195] Several parenteral monoclonal antibodies acting against the CGRP pathway (e.g. [erenumab], [fremanezumab], [galcanezumab]) have also been approved in recent years.[A189207] Ubrogepant was approved by Health Canada on November 10, 2022.[L43987] Compared to the current standard of therapy for migraine treatment, namely triptans such as [sumatriptan] and [almotriptan], CGRP antagonists present several advantages.[A189195] They appear to be better tolerated, do not contribute to medication overuse headaches, and carry no apparent cardiovascular risk, making them suitable for use in patients with cardiovascular disease.[A189195] The development of oral gepants, including ubrogepant, may therefore constitute a significant advance in migraine headache treatment and may become the new standard of therapy in the treatment of this debilitating condition.
ATC Classification N02CD04
IUPAC Name (6S)-N-[(3S,5S,6R)-6-methyl-2-oxo-5-phenyl-1-(2,2,2-trifluoroethyl)piperidin-3-yl]-2'-oxo-1',2',5,7-tetrahydrospiro[cyclopenta[b]pyridine-6,3'-pyrrolo[2,3-b]pyridine]-3-carboxamide
InChI DDOOFTLHJSMHLN-ZQHRPCGSSA-N
Canonical SMILES C[C@@H]1[C@@H](C[C@H](NC(=O)C2=CN=C3C[C@]4(CC3=C2)C(=O)NC2=NC=CC=C42)C(=O)N1CC(F)(F)F)C1=CC=CC=C1
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