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MedKoo Cat#: 319680 | Name: Rimegepant
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Rimegepant, also known as BMS-927711 and BHV-3000, is a potent, selective, competitive, and orally active calcitonin gene-related peptide (CGRP) antagonist in clinical trials for treating migraines. Rimegepant has shown in vivo efficacy without vasoconstriction effect. BMS-927711 is superior to placebo at several different doses (75 mg, 150 mg, and 300 mg) and has an excellent tolerability profile.

Chemical Structure

Rimegepant
Rimegepant
CAS#1289023-67-1 (free base)

Theoretical Analysis

MedKoo Cat#: 319680

Name: Rimegepant

CAS#: 1289023-67-1 (free base)

Chemical Formula: C28H28F2N6O3

Exact Mass: 534.2191

Molecular Weight: 534.57

Elemental Analysis: C, 62.91; H, 5.28; F, 7.11; N, 15.72; O, 8.98

Price and Availability

Size Price Availability Quantity
5mg USD 150.00 Ready to ship
10mg USD 250.00 Ready to ship
25mg USD 450.00 Ready to ship
50mg USD 750.00 Ready to ship
100mg USD 1,250.00 Ready to ship
200mg USD 2,250.00 Ready to ship
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Related CAS #
1289023-67-1 (free base) 1374024-48-2 (0.5 sulfate 1.5 hydrate) 1642783-82-1 (0.5 sulfate) 2377164-85-5 (0.5 sulfate 3 hydrate)
Synonym
BHV-3000; BHV 3000; BHV3000; BMS-927711; BMS 927711; BMS927711; Rimegepant
IUPAC/Chemical Name
(5S,6S,9R)-5-amino-6-(2,3-difluorophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-9-yl 4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxylate
InChi Key
KRNAOFGYEFKHPB-ANJVHQHFSA-N
InChi Code
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
SMILES Code
FC1=CC=CC([C@H]2[C@H](N)C(C=CC=N3)=C3[C@H](OC(N4CCC(N5C6=C(N=CC=C6)NC5=O)CC4)=O)CC2)=C1F
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Biological target:
Rimegepant (BMS-927711) is a calcitonin gene-related peptide (CGRP) receptor antagonist with a Ki of 0.027 nM and an IC50 of 0.14 nM for hCGRP receptor.
In vitro activity:
Rimegepant antagonized signaling through both the CGRP and AMY1 receptors but was approximately 30-fold more effective at blocking the CGRP receptor (p < 0.05; unpaired t-test, t = 13.32, df = 6). Interestingly, at the AMY1 receptor, rimegepant was approximately fourfold less effective at antagonizing amylin signaling than αCGRP signaling, with mean pKB values ± s.e.m of 7.48 ± 0.19 (n = 5, amylin) and 8.07 ± 0.11 (n = 4, αCGRP), respectively (p < 0.05; unpaired t-test, t = 2.57, df = 7). The ability of rimegepant to block AM signaling at the human AM1 and AM2 receptors was determined. Rimegepant (10 µM) did not significantly antagonize AM signaling at either the AM1 or AM2 receptors (Table 1). Reference: Front Pharmacol. 2020; 11: 1240. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7468408/
In vivo activity:
First, rimegepant (100mg/kg) was tested in the 60-minute MCAO model but encountered 75% (6/8) mortality compared with none (0/8) in the vehicle group (p = 0.007, Fisher exact test; Fig 3). The only 2 surviving mice in the rimegepant group had infarct volumes of 85 and 109mm3 and neurological deficit scores of 13 and 16, compared with a median infarct volume of 62mm3 and neurological deficit score of 11 in the vehicle group. Once again, the residual collateral CBF in rimegepant-treated animals was lower than in the vehicle group (p = 0.014, 2-way ANOVA for repeated measures). Reference: Ann Neurol. 2020 Oct; 88(4): 771–784. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7540520/
Solvent mg/mL mM
Solubility
DMSO 43.3 81.06
DMSO:PBS (pH 7.2) (1:4) 0.2 0.37
DMF 5.0 9.35
Ethanol 3.7 6.83
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 534.57 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Pan KS, Siow A, Hay DL, Walker CS. Antagonism of CGRP Signaling by Rimegepant at Two Receptors. Front Pharmacol. 2020 Aug 20;11:1240. doi: 10.3389/fphar.2020.01240. PMID: 32973499; PMCID: PMC7468408. 2. Mulder IA, Li M, de Vries T, Qin T, Yanagisawa T, Sugimoto K, van den Bogaerdt A, Danser AHJ, Wermer MJH, van den Maagdenberg AMJM, MaassenVanDenBrink A, Ferrari MD, Ayata C. Anti-migraine Calcitonin Gene-Related Peptide Receptor Antagonists Worsen Cerebral Ischemic Outcome in Mice. Ann Neurol. 2020 Oct;88(4):771-784. doi: 10.1002/ana.25831. Epub 2020 Aug 7. PMID: 32583883; PMCID: PMC7540520. 3. Luo G, Chen L, Conway CM, Denton R, Keavy D, Signor L, Kostich W, Lentz KA, Santone KS, Schartman R, Browning M, Tong G, Houston JG, Dubowchik GM, Macor JE. Discovery of (5S,6S,9R)-5-amino-6-(2,3-difluorophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-9-yl 4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxylate (BMS-927711): an oral calcitonin gene-related peptide (CGRP) antagonist in clinical trials for treating migraine. J Med Chem. 2012 Dec 13;55(23):10644-51. doi: 10.1021/jm3013147. Epub 2012 Nov 15. PMID: 23153230.
In vitro protocol:
1. Pan KS, Siow A, Hay DL, Walker CS. Antagonism of CGRP Signaling by Rimegepant at Two Receptors. Front Pharmacol. 2020 Aug 20;11:1240. doi: 10.3389/fphar.2020.01240. PMID: 32973499; PMCID: PMC7468408.
In vivo protocol:
1. Mulder IA, Li M, de Vries T, Qin T, Yanagisawa T, Sugimoto K, van den Bogaerdt A, Danser AHJ, Wermer MJH, van den Maagdenberg AMJM, MaassenVanDenBrink A, Ferrari MD, Ayata C. Anti-migraine Calcitonin Gene-Related Peptide Receptor Antagonists Worsen Cerebral Ischemic Outcome in Mice. Ann Neurol. 2020 Oct;88(4):771-784. doi: 10.1002/ana.25831. Epub 2020 Aug 7. PMID: 32583883; PMCID: PMC7540520. 2. Luo G, Chen L, Conway CM, Denton R, Keavy D, Signor L, Kostich W, Lentz KA, Santone KS, Schartman R, Browning M, Tong G, Houston JG, Dubowchik GM, Macor JE. Discovery of (5S,6S,9R)-5-amino-6-(2,3-difluorophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-9-yl 4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxylate (BMS-927711): an oral calcitonin gene-related peptide (CGRP) antagonist in clinical trials for treating migraine. J Med Chem. 2012 Dec 13;55(23):10644-51. doi: 10.1021/jm3013147. Epub 2012 Nov 15. PMID: 23153230.
1: Wells-Gatnik WD, Pellesi L, Martelletti P. Rimegepant and atogepant: novel drugs providing innovative opportunities in the management of migraine. Expert Rev Neurother. 2024 Sep 12:1-11. doi: 10.1080/14737175.2024.2401558. Epub ahead of print. PMID: 39264231. 2: Ailani J, Gandhi P, Lalla A, Halker Singh R, McAllister P, Smith JH, Dabruzzo B, Chalermpalanupap N, Kelton K, Nahas SJ. Cost per treatment responder analysis of atogepant compared to rimegepant for the preventive treatment of episodic migraine. Headache. 2024 Sep 9. doi: 10.1111/head.14824. Epub ahead of print. PMID: 39248007. 3: Tian S, Yang Y, Tan S, Luo J, Yang C, Liu Q, Guo Y. Cost-effectiveness analysis of rimegepant for on-demand acute treatment of migraine in China. Front Neurol. 2024 Aug 23;15:1411576. doi: 10.3389/fneur.2024.1411576. PMID: 39246609; PMCID: PMC11377259. 4: Rimegepant for migraine. Aust Prescr. 2024 Aug;47(4):134-135. doi: 10.18773/austprescr.2024.029. PMID: 39228462; PMCID: PMC11368539. 5: Boucherie DM, Dammers R, Vincent A, Danser AHJ, MaassenVanDenBrink A. Comparison of gepant effects at therapeutic plasma concentrations: connecting pharmacodynamics and pharmacokinetics. J Headache Pain. 2024 Aug 28;25(1):141. doi: 10.1186/s10194-024-01846-8. PMID: 39198753; PMCID: PMC11351853. 6: Zhang Y, Li T, Zhao H, Xiao X, Hu X, Wang B, Huang Y, Yin Z, Zhong Y, Li Y, Li J. High-sensitive sensory neurons exacerbate rosacea-like dermatitis in mice by activating γδ T cells directly. Nat Commun. 2024 Aug 23;15(1):7265. doi: 10.1038/s41467-024-50970-1. PMID: 39179539; PMCID: PMC11344132. 7: Pellesi L, Martelletti P. Situational prevention in migraine: are we doing the right thing? J Headache Pain. 2024 Aug 22;25(1):137. doi: 10.1186/s10194-024-01841-z. PMID: 39174943; PMCID: PMC11340082. 8: Liang Q, Liao X, Wu H, Huang Y, Liang T, Li H. Real-world study of adverse events associated with gepant use in migraine treatment based on the VigiAccess and U.S. Food and Drug Administration's adverse event reporting system databases. Front Pharmacol. 2024 Jul 31;15:1431562. doi: 10.3389/fphar.2024.1431562. PMID: 39144633; PMCID: PMC11322337. 9: Lipton RB, Thiry A, Morris BA, Croop R. Efficacy and Safety of Rimegepant 75 mg Oral Tablet, a CGRP Receptor Antagonist, for the Acute Treatment of Migraine: A Randomized, Double-Blind, Placebo-Controlled Trial. J Pain Res. 2024 Jul 22;17:2431-2441. doi: 10.2147/JPR.S453806. PMID: 39070853; PMCID: PMC11277999. 10: Mehta P, Ngo D, Tinajero J. Concomitant use of calcitonin gene-related peptide (CGRP) antagonists with azole antifungals in patients with hematological malignancies. J Oncol Pharm Pract. 2024 Jul 25:10781552241265884. doi: 10.1177/10781552241265884. Epub ahead of print. PMID: 39052976. 11: Bishay AE, Fijany AJ, Holan C, Mubang RN, Montorfano L, Olsson SE, Troia T, Bakian A, Kassis SA, Tran BV. Analyzing Google Search Trends for Migraine Surgery and Nurtec in Response to Public Announcements. Plast Reconstr Surg Glob Open. 2024 Jul 18;12(7):e5996. doi: 10.1097/GOX.0000000000005996. PMID: 39027895; PMCID: PMC11257674. 12: True D, Mullin K, Croop R. Safety of Rimegepant in Adults with Migraine and Cardiovascular Risk Factors: Analysis of a Multicenter, Long-Term, Open-Label Study. Pain Ther. 2024 Oct;13(5):1203-1218. doi: 10.1007/s40122-024-00626-1. Epub 2024 Jul 10. PMID: 38985436; PMCID: PMC11393218. 13: Tükel EY, Ateş O, Kiraz Y. In Silico Drug Repurposing Against PSMB8 as a Potential Target for Acute Myeloid Leukemia Treatment. Mol Biotechnol. 2024 Jul 2. doi: 10.1007/s12033-024-01224-4. Epub ahead of print. PMID: 38954355. 14: Jiang L, Zhou Y, Tang S, Yang D, Zhang Y, Zhang J, Yang F, Zhou T, Xia X, Chen Q, Jiang L, Jiang Y, Feng X. Nociceptive adenosine A2A receptor on trigeminal nerves orchestrates CGRP release to regulate the progression of oral squamous cell carcinoma. Int J Oral Sci. 2024 Jun 18;16(1):46. doi: 10.1038/s41368-024-00308-w. PMID: 38886342; PMCID: PMC11183250. 15: Singh P, Ponnada RK, Sharma R, Sumadhura B, Kumar A, Datusalia AK. Safety and Efficacy of Calcitonin Gene-related Peptide Receptor Antagonists and Selective Serotonin Receptor Agonist in the Management of Migraine: A Systematic Review and Meta-analysis. CNS Neurol Disord Drug Targets. 2024 Jun 5. doi: 10.2174/0118715273304677240529062909. Epub ahead of print. PMID: 38847252. 16: Berman G, Thiry A, Croop R. Safety of Rimegepant in Patients Using Preventive Migraine Medications: A Subgroup Analysis of a Long-Term, Open-Label Study Conducted in the United States. J Pain Res. 2024 May 21;17:1805-1814. doi: 10.2147/JPR.S453937. PMID: 38799274; PMCID: PMC11127653. 17: Fullerton T, Pixton G. Long-Term Use of Rimegepant 75 mg for the Acute Treatment of Migraine is Associated with a Reduction in the Utilization of Select Analgesics and Antiemetics. J Pain Res. 2024 May 15;17:1751-1760. doi: 10.2147/JPR.S456006. PMID: 38764606; PMCID: PMC11102748. 18: Croop R, Berman G, Kudrow D, Mullin K, Thiry A, Lovegren M, L'Italien G, Lipton RB. A multicenter, open-label long-term safety study of rimegepant for the acute treatment of migraine. Cephalalgia. 2024 Apr;44(4):3331024241232944. doi: 10.1177/03331024241232944. PMID: 38659334. 19: Yu S, Guo A, Wang Z, Liu J, Tan G, Yang Q, Zhang M, Yibulaiyin H, Chen H, Zhang Y, Croop R, Sun Y, Liu Y, Zhao Q, Lu Z. Rimegepant orally disintegrating tablet 75 mg for acute treatment of migraine in adults from China: a subgroup analysis of a double-blind, randomized, placebo-controlled, phase 3 clinical trial. J Headache Pain. 2024 Apr 16;25(1):57. doi: 10.1186/s10194-024-01731-4. PMID: 38627638; PMCID: PMC11020209. 20: Johnston K, Powell LC, Popoff E, L'Italien GJ, Pawinski R, Ahern A, Large S, Tran T, Jenkins A. Cost-effectiveness of rimegepant oral lyophilisate compared to best supportive care for the acute treatment of migraine in the UK. J Med Econ. 2024 Jan-Dec;27(1):627-643. doi: 10.1080/13696998.2024.2340932. Epub 2024 Apr 27. PMID: 38590236. .