ubrogepant

Ubrogepant, sold under the brand name Ubrelvy, is a medication used for the acute (immediate) treatment of migraine with or without aura (a sensory phenomenon or visual disturbance) in adults. It is not indicated for the preventive treatment of migraine. Ubrogepant is a small-molecule calcitonin gene-related peptide receptor antagonist. It is the first drug in this class approved for the acute treatment of migraine.

Chemical data

Formula: C29H26F3N5O3
Molecular weight: 549.5 g/mol
IUPAC name: (3S)-N-[(3S,5S,6R)-6-methyl-2-oxo-5-phenyl-1-(2,2,2-trifluoroethyl)piperidin-3-yl]-2-oxospiro[1H-pyrrolo[2,3-b]pyridine-3,6'-5,7-dihydrocyclopenta[b]pyridine]-3'-carboxamide
SMILES: C[C@@H]1[C@@H](C[C@@H](C(=O)N1CC(F)(F)F)NC(=O)C2=CC3=C(C[C@@]4(C3)C5=C(NC4=O)N=CC=C5)N=C2)C6=CC=CC=C6
InChIKey: DDOOFTLHJSMHLN-ZQHRPCGSSA-N
XLogP: 3.1
Polar surface area: 104 Å²
H-bond donors: 2
H-bond acceptors: 8
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Small molecule
First approval: 2019
Admin. routes: oral
Indications: migraine disorder

via ChEMBL · EBI

Wikidata facts

Subclass of: chemical compound
Mass: 549.199

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subject has role: calcitonin gene-related peptide receptor antagonist
canonical SMILES: CC1C(CC(C(=O)N1CC(F)(F)F)NC(=O)C2=CC3=C(CC4(C3)C5=C(NC4=O)N=CC=C5)N=C2)C6=CC=CC=C6
chemical formula: C₂₉H₂₆F₃N₅O₃
isomeric SMILES: C[C@@H]1[C@@H](C[C@@H](C(=O)N1CC(F)(F)F)NC(=O)C2=CC3=C(C[C@@]4(C3)C5=C(NC4=O)N=CC=C5)N=C2)C6=CC=CC=C6

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Encyclopedic overview

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The most common side effects are nausea, tiredness and dry mouth. Ubrogepant is contraindicated for co-administration with strong CYP3A4 inhibitors.

Excerpted from Wikipedia’s “ubrogepant” article, available under the CC BY-SA 4.0 licence.

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