RIMEGEPANT

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C28H28F2N6O3
Molecular Weight	534.5571
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

N[C@H]1[C@@H](CC[C@@H](OC(=O)N2CCC(CC2)N3C(=O)NC4=C3C=CC=N4)C5=C1C=CC=N5)C6=CC=CC(F)=C6F

InChI

InChIKey=KRNAOFGYEFKHPB-ANJVHQHFSA-N

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

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/?term=23965396

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Calcitonin gene-related peptide type 1 receptor 7 Target ID: CHEMBL3798 Sources: https://www.ncbi.nlm.nih.gov/pubmed/?term=23153230	Antagonist 2778

Conditions

Condition	Modality	Targets	Highest Phase	Product
Acute migraine 7 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23965396	Primary		Phase II 1132	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
1045.53 ng/mL OTHER https://www.biohavenpharma.com/sites/default/files/documents/rimegepant-ph1-elderly-pk-2019-ahs.pdf	75 mg single, oral dose: 75 mg route of administration: Oral experiment type: SINGLE co-administered:		RIMEGEPANT plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
4718.71 ng × h/mL OTHER https://www.biohavenpharma.com/sites/default/files/documents/rimegepant-ph1-elderly-pk-2019-ahs.pdf	75 mg single, oral dose: 75 mg route of administration: Oral experiment type: SINGLE co-administered:		RIMEGEPANT plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
10.398 h OTHER https://www.biohavenpharma.com/sites/default/files/documents/rimegepant-ph1-elderly-pk-2019-ahs.pdf	75 mg single, oral dose: 75 mg route of administration: Oral experiment type: SINGLE co-administered:		RIMEGEPANT plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
75 mg 1 times / day single, oral Recommended Dose: 75 mg, 1 times / day Route: oral Route: single Dose: 75 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/212728s000lbl.pdf	unhealthy, 18-75 years n = 682 Health Status: unhealthy Condition: migraine Age Group: 18-75 years Sex: M+F Population Size: 682 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/212728s000lbl.pdf	Other AEs: Nausea, Hypersensitivity... Other AEs: Nausea (2%) Hypersensitivity (<1%) Dyspnea (<1%) Rash (grade 3, <1%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/212728s000lbl.pdf
2250 mg single, oral Overdose Dose: 2250 mg Route: oral Route: single Dose: 2250 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000MedR.pdf	healthy, adults n = 1 Health Status: healthy Age Group: adults Population Size: 1 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000MedR.pdf	Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000MedR.pdf
75 mg 1 times / day single, oral Recommended Dose: 75 mg, 1 times / day Route: oral Route: single Dose: 75 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/31291516/	unhealthy, adults n = 543 Health Status: unhealthy Condition: migraine Age Group: adults Sex: M+F Population Size: 543 Sources: https://pubmed.ncbi.nlm.nih.gov/31291516/	Other AEs: Nausea, Urinary tract infection... Other AEs: Nausea (1.8%) Urinary tract infection (1.5%) Transaminases increased (2.3%) Back pain (0.2%) Sources: https://pubmed.ncbi.nlm.nih.gov/31291516/
75 mg 1 times / day single, oral Recommended Dose: 75 mg, 1 times / day Route: oral Route: single Dose: 75 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/31311674/	unhealthy, adults n = 682 Health Status: unhealthy Condition: migraine Age Group: adults Sex: M+F Population Size: 682 Sources: https://pubmed.ncbi.nlm.nih.gov/31311674/	Other AEs: Nausea, Urinary tract infection... Other AEs: Nausea (2%) Urinary tract infection (1%) Dizziness (1%) Sources: https://pubmed.ncbi.nlm.nih.gov/31311674/
600 mg single, oral Highest studied dose Dose: 600 mg Route: oral Route: single Dose: 600 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000MedR.pdf	unhealthy n = 84 Health Status: unhealthy Condition: migraine Population Size: 84 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000MedR.pdf	Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000MedR.pdf

AEs

AE	Significance	Dose	Population
Nausea	2%	75 mg 1 times / day single, oral Recommended Dose: 75 mg, 1 times / day Route: oral Route: single Dose: 75 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/212728s000lbl.pdf	unhealthy, 18-75 years n = 682 Health Status: unhealthy Condition: migraine Age Group: 18-75 years Sex: M+F Population Size: 682 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/212728s000lbl.pdf
Dyspnea	<1%	75 mg 1 times / day single, oral Recommended Dose: 75 mg, 1 times / day Route: oral Route: single Dose: 75 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/212728s000lbl.pdf	unhealthy, 18-75 years n = 682 Health Status: unhealthy Condition: migraine Age Group: 18-75 years Sex: M+F Population Size: 682 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/212728s000lbl.pdf
Hypersensitivity	<1%	75 mg 1 times / day single, oral Recommended Dose: 75 mg, 1 times / day Route: oral Route: single Dose: 75 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/212728s000lbl.pdf	unhealthy, 18-75 years n = 682 Health Status: unhealthy Condition: migraine Age Group: 18-75 years Sex: M+F Population Size: 682 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/212728s000lbl.pdf
Rash	grade 3, <1%	75 mg 1 times / day single, oral Recommended Dose: 75 mg, 1 times / day Route: oral Route: single Dose: 75 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/212728s000lbl.pdf	unhealthy, 18-75 years n = 682 Health Status: unhealthy Condition: migraine Age Group: 18-75 years Sex: M+F Population Size: 682 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/212728s000lbl.pdf
Back pain	0.2%	75 mg 1 times / day single, oral Recommended Dose: 75 mg, 1 times / day Route: oral Route: single Dose: 75 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/31291516/	unhealthy, adults n = 543 Health Status: unhealthy Condition: migraine Age Group: adults Sex: M+F Population Size: 543 Sources: https://pubmed.ncbi.nlm.nih.gov/31291516/
Urinary tract infection	1.5%	75 mg 1 times / day single, oral Recommended Dose: 75 mg, 1 times / day Route: oral Route: single Dose: 75 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/31291516/	unhealthy, adults n = 543 Health Status: unhealthy Condition: migraine Age Group: adults Sex: M+F Population Size: 543 Sources: https://pubmed.ncbi.nlm.nih.gov/31291516/
Nausea	1.8%	75 mg 1 times / day single, oral Recommended Dose: 75 mg, 1 times / day Route: oral Route: single Dose: 75 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/31291516/	unhealthy, adults n = 543 Health Status: unhealthy Condition: migraine Age Group: adults Sex: M+F Population Size: 543 Sources: https://pubmed.ncbi.nlm.nih.gov/31291516/
Transaminases increased	2.3%	75 mg 1 times / day single, oral Recommended Dose: 75 mg, 1 times / day Route: oral Route: single Dose: 75 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/31291516/	unhealthy, adults n = 543 Health Status: unhealthy Condition: migraine Age Group: adults Sex: M+F Population Size: 543 Sources: https://pubmed.ncbi.nlm.nih.gov/31291516/
Dizziness	1%	75 mg 1 times / day single, oral Recommended Dose: 75 mg, 1 times / day Route: oral Route: single Dose: 75 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/31311674/	unhealthy, adults n = 682 Health Status: unhealthy Condition: migraine Age Group: adults Sex: M+F Population Size: 682 Sources: https://pubmed.ncbi.nlm.nih.gov/31311674/
Urinary tract infection	1%	75 mg 1 times / day single, oral Recommended Dose: 75 mg, 1 times / day Route: oral Route: single Dose: 75 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/31311674/	unhealthy, adults n = 682 Health Status: unhealthy Condition: migraine Age Group: adults Sex: M+F Population Size: 682 Sources: https://pubmed.ncbi.nlm.nih.gov/31311674/
Nausea	2%	75 mg 1 times / day single, oral Recommended Dose: 75 mg, 1 times / day Route: oral Route: single Dose: 75 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/31311674/	unhealthy, adults n = 682 Health Status: unhealthy Condition: migraine Age Group: adults Sex: M+F Population Size: 682 Sources: https://pubmed.ncbi.nlm.nih.gov/31311674/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1737 inhibitor 1587 inducer 781	substrate 1037 inhibitor 1767	inhibitor 1852	inhibitor 1612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1524 CYP2B6 810 CYP2C19 1478 UGT1A1 204 P-gp 1461 BCRP 699 OATP1B1 788 OATP1B3 706 OAT1 599 OAT3 642 MATE2 263 MATE1 306 OCT2 647 L-type Ca channels 9	P-gp 1537 BCRP 561 OATP1B1 406 OATP1B3 350	CYP1A2 701 CYP2B6 547

Drug as perpetrator

Target	Modality	Activity
OATP1B3 715	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000ClinPharmR.pdf#page=37 Page: 37.0	no [IC50 6.04 uM]
BCRP 773	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000ClinPharmR.pdf#page=37 Page: 37.0	no [IC50 >10 uM]
MATE2 263	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000ClinPharmR.pdf#page=37 Page: 37.0	no [IC50 >10 uM]
OAT1 603	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000ClinPharmR.pdf#page=37 Page: 37.0	no [IC50 >10 uM]
P-gp 1650	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000ClinPharmR.pdf#page=37 Page: 37.0	no [IC50 >100 uM]
CYP1A2 1692	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000ClinPharmR.pdf#page=16 Page: 16.0	no [IC50 >40 uM]
CYP2B6 1001	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000ClinPharmR.pdf#page=16 Page: 16.0	no [IC50 >40 uM]
CYP2C19 1553	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000ClinPharmR.pdf#page=16 Page: 16.0	no [IC50 >40 uM]
CYP2C9 1819	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000ClinPharmR.pdf#page=16 Page: 16.0	no [IC50 >40 uM]
CYP2D6 1891	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000ClinPharmR.pdf#page=16 Page: 16.0	no [IC50 >40 uM]
UGT1A1 254	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000ClinPharmR.pdf#page=16 Page: 16.0	no [IC50 >50 uM]
OAT3 644	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000ClinPharmR.pdf#page=37 Page: 37.0	no [Inhibition 5 uM]
OATP1B1 803	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000ClinPharmR.pdf#page=37 Page: 37.0	no [Inhibition 5 uM]
CYP1A2 1692	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000ClinPharmR.pdf#page=16 Page: 16.0	no
CYP2B6 1001	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000ClinPharmR.pdf#page=16 Page: 16.0	no
CYP3A4 1925	inducer 1573 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000ClinPharmR.pdf#page=16 Page: 16.0	no
L-type Ca channels 9	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000PharmR.pdf#page=16 Page: 16.0	no
CYP3A4 1925	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000ClinPharmR.pdf#page=16 Page: 16.0	weak
OCT2 648	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000ClinPharmR.pdf#page=37 Page: 37.0	yes [IC50 1.08 uM]
MATE1 308	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000ClinPharmR.pdf#page=37 Page: 37.0	yes [IC50 1.18 uM]

Drug as victim

Target	Modality	Activity	Clinical evidence
CYP3A4 1737	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000ClinPharmR.pdf#page=8 Page: 8.0	major	yes (co-administration study) Comment: In a dedicated drug interaction study, concomitant administration of 75 mg rimegepant (single dose) with itraconazole (200 mg once daily; at steady state) resulted in increased exposures of rimegepant (AUC by 4-fold & Cmax by ~1.5-fold). It is recommended to avoid concomitant administration of rimegepant with a strong inhibitor of CYP3A4 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000ClinPharmR.pdf#page=8 Page: 8.0
CYP2C9 1037	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000ClinPharmR.pdf#page=8 Page: 8.0	minor	no (co-administration study) Comment: In a dedicated drug interaction study, concomitant administration of 75 mg rimegepant (single dose) with fluconazole (400 mg once daily; at steady state) resulted in increased exposures of rimegepant (AUC by 1.8-fold) with no relevant effect on Cmax. Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000ClinPharmR.pdf#page=8 Page: 8.0
OATP1B1 406	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000ClinPharmR.pdf#page=36 Page: 36.0	no
OATP1B3 350	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000ClinPharmR.pdf#page=36 Page: 36.0	no
BCRP 561	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000ClinPharmR.pdf#page=7 Page: 7.0	yes
P-gp 1537	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000ClinPharmR.pdf#page=7 Page: 7.0	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1647	inhibitor 1626 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000PharmR.pdf#page=16 Page: 16.0

Sourcing

Vendor/Aggregator	ID	URL
AA Blocks	AA009C73	https://www.aablocks.com/goods/Goods/detail?id=AA009C73
AK Scientific, Inc. (AKSCI)	3504AH	http://www.aksci.com/item_detail.php?cat=3504AH
AbMole Bioscience	M9165	http://www.abmole.com/products/rimegepant.html
Achemtek	0102-014007	http://www.achemtek.com/1289023-67-1
Adooq BioScience	A13102	https://www.adooq.com/bms-927711.html
Ambinter	Amb24059710	http://www.ambinter.com/reference/24059710
Aurum Pharmatech LLC	W-5991	http://www.Aurumpharmatech.com/Product/ProductDetails/W_5991
BioCrick	BCC1433	http://www.biocrick.com/BMS-927711-BCC1433.html
Chem Scene	CS-1027	http://www.chemscene.com/1289023-67-1.html
Chemspace	CSSB00102527123	https://chem-space.com/CSSB00102527123
DC Chemicals	DC12800	http://www.dcchemicals.com/product_show-Rimegepant.html
Excenen	EX-A1922	https://www.excenen.com/searchresultlist.php?id=1289023-67-1
Lab Network	LN01301576	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01301576
MedChem Express	HY-15498	https://www.medchemexpress.com/BMS-927711.html
MuseChem	I001123	https://www.musechem.com/product/I001123.html
Selleck Chemicals	S6659	http://www.selleckchem.com/products/bms-927711.html
Smolecule	S541433	http://www.smolecule.com/products/s541433
THE BioTek	bt-280698	https://www.thebiotek.com/product/inhibitors/bt-280698
eNovation Chemicals	D663125	https://www.enovationchem.com/ProductDetails.asp?ProductID=D663125

PubMed

Title	Date	PubMed

Patents

Sample Use Guides

In Vivo Use Guide

10 mg, 25 mg, 75 mg, 150 mg, 300 mg, 600 mg one per day

Route of Administration: Oral

In Vitro Use Guide

Unknown

Name

Type

Language

RIMEGEPANT

Official Name

English

(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

Systematic Name

English

Rimegepant [WHO-DD]

Common Name

English

BMS-927711

Code

English

RIMEGEPANT [MI]

Common Name

English

1-PIPERIDINECARBOXYLIC ACID, 4-(2,3-DIHYDRO-2-OXO-1H-IMIDAZO(4,5-B)PYRIDIN-1-YL)-, (5S,6S,9R)-5-AMINO-6-(2,3-DIFLUOROPHENYL)-6,7,8,9-TETRAHYDRO-5H-CYCLOHEPTA(B)PYRIDIN-9-YL ESTER

Systematic Name

English

BHV-3000

Common Name

English

rimegepant [INN]

Common Name

English

RIMEGEPANT [USAN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C241