Rimegepant sulfateProduct ingredient for Rimegepant
- Name
- Rimegepant sulfate
- Drug Entry
- Rimegepant
Rimegepant is an oral antagonist of the CGRP receptor developed by Biohaven Pharmaceuticals.5 It received FDA approval on February 27, 2020 for the acute treatment migraine headache,7 and was subsequently approved by the European Commission in April 2022 for both the treatment and prevention of migraines.10 While several parenteral antagonists of CGRP and its receptor have been approved for migraine therapy (e.g. erenumab, fremanezumab, galcanezumab), rimegepant and ubrogepant were the only CGRP antagonists that possessed oral bioavailability2 until the approval of atogepant in 2021.9
The current standard of migraine therapy involves abortive treatment with "triptans", such as sumatriptan, but these medications are contraindicated in patients with pre-existing cerebrovascular and cardiovascular disease due to their vasoconstrictive properties.2 Antagonism of the CGRP pathway has become an attractive target for migraine therapy as, unlike the triptans, oral CGRP antagonists have no observed vasoconstrictive properties and are therefore safer for use in patients with contraindications to standard therapy.1,2
- Accession Number
- DBSALT002938
- Structure
- Synonyms
- Rimegepant sulfate
- UNII
- 1383NM3Q0H
- CAS Number
- 1374024-48-2
- Weight
- Average: 1221.25
Monoisotopic: 1220.437263995 - Chemical Formula
- C56H64F4N12O13S
- InChI Key
- SOGUOEZRYKUOHR-CQZKMDJHSA-N
- InChI
- InChI=1S/2C28H28F2N6O3.H2O4S.3H2O/c2*29-20-6-1-4-17(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;1-5(2,3)4;;;/h2*1-7,12-13,16,18,22,24H,8-11,14-15,31H2,(H,33,34,37);(H2,1,2,3,4);3*1H2/t2*18-,22+,24-;;;;/m00..../s1
- IUPAC Name
- bis((5S,6S,9R)-5-amino-6-(2,3-difluorophenyl)-5H,6H,7H,8H,9H-cyclohepta[b]pyridin-9-yl 4-{2-oxo-1H,2H,3H-imidazo[4,5-b]pyridin-1-yl}piperidine-1-carboxylate) sulfuric acid trihydrate
- SMILES
- O.O.O.OS(O)(=O)=O.N[C@H]1[C@@H](CC[C@@H](OC(=O)N2CCC(CC2)N2C(=O)NC3=NC=CC=C23)C2=C1C=CC=N2)C1=C(F)C(F)=CC=C1.N[C@H]1[C@@H](CC[C@@H](OC(=O)N2CCC(CC2)N2C(=O)NC3=NC=CC=C23)C2=C1C=CC=N2)C1=C(F)C(F)=CC=C1
- External Links
- ChemSpider
- 29398960
- ChEMBL
- CHEMBL2364629
- Predicted Properties
Property Value Source Water Solubility 0.0755 mg/mL ALOGPS logP 2.68 ALOGPS logP 2.95 Chemaxon logS -3.8 ALOGPS pKa (Strongest Acidic) 10.7 Chemaxon pKa (Strongest Basic) 8.95 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 113.68 Å2 Chemaxon Rotatable Bond Count 8 Chemaxon Refractivity 139.58 m3·mol-1 Chemaxon Polarizability 54.23 Å3 Chemaxon Number of Rings 12 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon