Rimegepant

Rimegepant, sold under the brand name Nurtec ODT among others, is a medication used for the acute treatment of migraine with or without aura in adults and the prophylactic/ preventive treatment of episodic migraine in adults.^[8][10] It is taken by mouth to dissolve on or under the tongue.^[8] It works by blocking CGRP receptors.^[11]

Rimegepant

Clinical data
Trade names	Nurtec ODT, Vydura
Other names	BHV-3000, BMS-927711
AHFS/Drugs.com	Monograph
MedlinePlus	a620031
License data	US DailyMed: Rimegepant
Pregnancy category	AU: B1[1][2]
Routes of administration	By mouth
Drug class	Calcitonin gene-related peptide receptor antagonist
ATC code	N02CD06 (WHO)
Legal status
Legal status	AU: S4 (Prescription only)[3][1] CA: ℞-only[4][5][6][7] US: ℞-only[8] EU: Rx-only[9] In general: ℞ (Prescription only)
Identifiers
IUPAC name [(5S,6S,9R)-5-Amino-6-(2,3-difluorophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-9-yl] 4-(2-oxo-3H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxylate
CAS Number	1289023-67-1
PubChem CID	51049968
DrugBank	DB12457
ChemSpider	27289072
UNII	997WVV895X
KEGG	D10663 D10662
ChEMBL	ChEMBL2178422
CompTox Dashboard (EPA)	DTXSID70156003
Chemical and physical data
Formula	C28H28F2N6O3
Molar mass	534.568 g·mol−1
3D model (JSmol)	Interactive image
SMILES N[C@@H]1c2cccnc2[C@H](OC(=O)N2CCC(n3c(=O)[nH]c4ncccc43)CC2)CC[C@H]1c1cccc(F)c1F
InChI InChI=1S/C28H28F2N6O3/c29-20-6-1-4-17(23(20)30)18-8-9-22(25-19(24(18)31)5-2-12-32-25)39-28(38)35-14-10-16(11-15-35)36-21-7-3-13-33-26(21)34-27(36)37/h1-7,12-13,16,18,22,24H,8-11,14-15,31H2,(H,33,34,37)/t18-,22+,24-/m0/s1 Key:KRNAOFGYEFKHPB-ANJVHQHFSA-N

In the United States, rimegepant was approved for treating acute migraine in February 2020,^[12] and its approval was extended to preventing episodic migraine in June 2021.^[8] It is produced and marketed by Pfizer.^[13] In March 2021, rimegepant was approved for medical use in the United Arab Emirates and in Israel.^[14][15] It was approved for medical use in Canada in December 2023.^[4] In the United Kingdom, rimegepant is approved by NICE for the prophylaxis and treatment of acute migraine in adults.^[16]

Medical uses

Rimegepant is indicated for the treatment of acute migraine with or without aura in adults and for the preventative treatment of episodic migraine in adults.^[8][10][9]

Mechanism of action

Rimegepant is a small molecule calcitonin gene-related peptide (CGRP) receptor antagonist.^[11]

History

Rimegepant was developed by Biohaven Pharmaceuticals, which markets the drug in the United States after receiving FDA approval in February 2020.^[12][17] Approval was based on evidence from one clinical trial of 1,351 subjects with migraine headaches.^[10]

Society and culture

Legal status

In February 2022, the Committee for Medicinal Products for Human Use (CHMP) of the European Medicines Agency (EMA) adopted a positive opinion, recommending the granting of a marketing authorization for the medicinal product Vydura, intended for the prophylaxis and acute treatment of migraine.^[18] The applicant for this medicinal product is Biohaven Pharmaceutical Ireland DAC.^[18] Rimegepant was approved for medical use in the European Union in April 2022.^[9][19]

Economics

Pfizer reported revenue of US$928 million for Nurtec ODT/Vydura in 2023.^[20]

Marketing

American singer, songwriter and actress Lady Gaga is featured in advertisements for rimegepant, under the Nurtec ODT brand. Her involvement sparked criticism of the role of celebrities in pharmaceutical endorsements. ^[21]