Ubrogepant Explained

Tradename:Ubrelvy
Dailymedid:Ubrogepant
Routes Of Administration:By mouth
Atc Prefix:N02
Atc Suffix:CD04
Legal Ca:Rx-only
Legal Ca Comment:[1] [2] [3]
Legal Us:Rx-only
Legal Us Comment:[4]
Protein Bound:87% (in vitro)
Elimination Half-Life:5-7 hrs
Excretion:fecal/biliary
Cas Number:1374248-77-7
Pubchem:68748835
Drugbank:DB15328
Chemspiderid:28536135
Unii:AD0O8X2QJR
Kegg:D10673
Chembl:2364638
Synonyms:MK-1602
Iupac Name:(6S)-N-[(3''S'',5''S'',6''R'')-6-Methyl-2-oxo-5-phenyl-1-(2,2,2-trifluoroethyl)-3-piperidinyl]-2'-oxo-1',2',5,7-tetrahydrospiro[cyclopenta[b]pyridine-6,3'-pyrrolo[2,3-b]pyridine]-3-carboxamide
C:29
H:26
F:3
N:5
O:3
Smiles:C[C@@H]1[C@H](c2ccccc2)C[C@H](NC(=O)c2cnc3c(c2)C[C@@]2(C3)C(=O)Nc3ncccc32)C(=O)N1CC(F)(F)F
Stdinchi: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
Stdinchikey:DDOOFTLHJSMHLN-ZQHRPCGSSA-N

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.[5] It is not indicated for the preventive treatment of migraine.[6] Ubrogepant is a small-molecule calcitonin gene-related peptide receptor antagonist.[7] [8] It is the first drug in this class approved for the acute treatment of migraine.

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

History

Ubrogepant, also known as MK-1602, was discovered by scientists at Merck.[9]

The effectiveness of ubrogepant for the acute treatment of migraine was demonstrated in two randomized, double-blind, placebo-controlled trials. In these studies, 1,439 adult patients with a history of migraine, with and without aura, received the approved doses of ubrogepant to treat an ongoing migraine.[10] In both studies, the percentages of patients achieving pain relief two hours after treatment (defined as a reduction in headache severity from moderate or severe pain to no pain) and whose most bothersome migraine symptom (nausea, light sensitivity or sound sensitivity) stopped two hours after treatment were significantly greater among patients receiving ubrogepant (19–21% depending on the dose) compared to those receiving placebo (12%).[11] Patients were allowed to take their usual acute treatment of migraine at least two hours after taking ubrogepant. 23% of patients were taking a preventive medication for migraine.

In December 2019, the US Food and Drug Administration approved Ubrelvy produced by Allergan USA, Inc. for treatment of migraine after onset.[12]

Notes and References

  1. Web site: Ubrelvy Product information . . 2 January 2023.
  2. Web site: Summary Basis of Decision - Ubrelvy . . 30 March 2023 . 24 April 2023.
  3. Web site: Details for: Ubrelvy . . 11 May 2023 . 3 March 2024.
  4. Web site: Ubrelvy- ubrogepant tablet . DailyMed . 4 June 2021.
  5. Web site: 2019. Ubrogepant Prescribing Information. FDA.gov. U.S. Food and Drug Administration.
  6. FDA approves new treatment for adults with migraine. U.S. Food and Drug Administration (FDA). 23 December 2019. https://web.archive.org/web/20191223222802/https://www.fda.gov/news-events/press-announcements/fda-approves-new-treatment-adults-migraine. 23 December 2019. live. 23 December 2019.
  7. Tfelt-Hansen P, Olesen J . Possible site of action of CGRP antagonists in migraine . Cephalalgia . 31 . 6 . 748–750 . April 2011 . 21383046 . 10.1177/0333102411398403 . 22049557 . free .
  8. Spreitzer H . Neue Wirkstoffe: Ubrogepant . Österreichische Apotheker-Zeitung . 22 May 2018 . 11/2018 . German.
  9. Moore E, Fraley ME, Bell IM, Burgey CS, White RB, Li CC, Regan CP, Danziger A, Stranieri Michener M, Hostetler E, Banerjee P, Salvatore C . 6 . Characterization of Ubrogepant: A Potent and Selective Antagonist of the Human Calcitonin Gene‒Related Peptide Receptor . The Journal of Pharmacology and Experimental Therapeutics . jpet.119.261065 . January 2020 . 31992609 . 10.1124/jpet.119.261065 . 210946813 . free .
  10. Web site: Drug Trials Snapshots: Ubrelvy . 13 January 2020 . U.S. Food and Drug Administration (FDA) .
  11. Dodick DW, Lipton RB, Ailani J, Lu K, Finnegan M, Trugman JM, Szegedi A . Ubrogepant for the Treatment of Migraine . The New England Journal of Medicine . 381 . 23 . 2230–2241 . December 2019 . 31800988 . 10.1056/NEJMoa1813049 . 208645302 . free .
  12. News: Allergan's acute migraine treatment wins U.S. FDA approval. Maddipatla M . 23 December 2019. 24 Dec 2019. Reuters.