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This repository is under review for potential modification in compliance with Administration directives.

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 of RIMEGEPANT

SMILES

N[C@H]1[C@@H](CC[C@@H](OC(=O)N2CCC(CC2)N3C(=O)NC4=C3C=CC=N4)C5=NC=CC=C15)C6=C(F)C(F)=CC=C6

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
Molecular Formula C28H28F2N6O3
Molecular Weight 534.5571
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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

2020
691
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2849
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase II
1147
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
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

Doses

DosePopulationAdverse 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
Health Status: unhealthy
Age Group: 18-75 years
Sex: M+F
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
Health Status: healthy
Age Group: adults
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
Health Status: unhealthy
Age Group: adults
Sex: M+F
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
Health Status: unhealthy
Age Group: adults
Sex: M+F
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
Health Status: unhealthy
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

AEs

AESignificanceDosePopulation
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
Health Status: unhealthy
Age Group: 18-75 years
Sex: M+F
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
Health Status: unhealthy
Age Group: 18-75 years
Sex: M+F
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
Health Status: unhealthy
Age Group: 18-75 years
Sex: M+F
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
Health Status: unhealthy
Age Group: 18-75 years
Sex: M+F
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
Health Status: unhealthy
Age Group: adults
Sex: M+F
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
Health Status: unhealthy
Age Group: adults
Sex: M+F
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
Health Status: unhealthy
Age Group: adults
Sex: M+F
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
Health Status: unhealthy
Age Group: adults
Sex: M+F
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
Health Status: unhealthy
Age Group: adults
Sex: M+F
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
Health Status: unhealthy
Age Group: adults
Sex: M+F
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
Health Status: unhealthy
Age Group: adults
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/31311674/
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
substrate
1946

inhibitor
2252

inducer
1087
substrate
1193

inhibitor
2438
inhibitor
2507
inhibitor
2217

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP1A2
2153

CYP2B6
926

CYP2C19
2057

UGT1A1
246

P-gp
1741

BCRP
910

OATP1B1
1079

OATP1B3
961

OAT1
725

OAT3
747

MATE2
267

MATE1
415

OCT2
779

L-type Ca channels
9
P-gp
2052

BCRP
697

OATP1B1
503

OATP1B3
435
CYP1A2
832

CYP2B6
669
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
OATP1B3
970
 no [IC50 6.04 uM]
BCRP
985
 no [IC50 >10 uM]
MATE2
267
 no [IC50 >10 uM]
OAT1
730
 no [IC50 >10 uM]
P-gp
1932
 no [IC50 >100 uM]
CYP1A2
2333
 no [IC50 >40 uM]
CYP2B6
1160
 no [IC50 >40 uM]
CYP2C19
2141
 no [IC50 >40 uM]
CYP2C9
2497
 no [IC50 >40 uM]
CYP2D6
2546
 no [IC50 >40 uM]
UGT1A1
303
 no [IC50 >50 uM]
OAT3
749
 no [Inhibition 5 uM]
OATP1B1
1095
 no [Inhibition 5 uM]
CYP1A2
2333
 no
CYP2B6
1160
 no
CYP3A4
2633
 no
L-type Ca channels
9
 no
CYP3A4
2633
 weak
OCT2
782
 yes [IC50 1.08 uM]
MATE1
416
 yes [IC50 1.18 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP3A4
1946
 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
Page: 8.0
CYP2C9
1193
 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.
Page: 8.0
OATP1B1
503
 no
OATP1B3
435
 no
BCRP
697
 yes
P-gp
2052
 yes
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
2263
Sourcing

Sourcing

Vendor/AggregatorIDURL
AA Blocks
AA009C73
https://www.aablocks.com/goods/Goods/detail?id=AA009C73
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
AK Scientific, Inc. (AKSCI)
3504AH
http://www.aksci.com/item_detail.php?cat=3504AH
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
eNovation Chemicals
D663125
https://www.enovationchem.com/ProductDetails.asp?ProductID=D663125
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
PubMed

PubMed

TitleDatePubMed
Asymmetric Synthesis of Heterocyclic Analogues of a CGRP Receptor Antagonist for Treating Migraine.
2015 Dec 18
Patents

Patents

20110251223
3
20120245356
3

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
Substance Class Chemical
Created
by admin
on Wed Apr 02 09:16:55 GMT 2025
Edited
by admin
on Wed Apr 02 09:16:55 GMT 2025
Record UNII
997WVV895X
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
rimegepant [INN]
Preferred Name English
RIMEGEPANT
INN   USAN   WHO-DD  
USAN   INN  
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 [USAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C241
Created by admin on Wed Apr 02 09:16:55 GMT 2025 , Edited by admin on Wed Apr 02 09:16:55 GMT 2025
Code System Code Type Description
DRUG CENTRAL
5381
Created by admin on Wed Apr 02 09:16:55 GMT 2025 , Edited by admin on Wed Apr 02 09:16:55 GMT 2025
PRIMARY
PUBCHEM
51049968
Created by admin on Wed Apr 02 09:16:55 GMT 2025 , Edited by admin on Wed Apr 02 09:16:55 GMT 2025
PRIMARY
ChEMBL
CHEMBL2178422
Created by admin on Wed Apr 02 09:16:55 GMT 2025 , Edited by admin on Wed Apr 02 09:16:55 GMT 2025
PRIMARY
SMS_ID
300000023332
Created by admin on Wed Apr 02 09:16:55 GMT 2025 , Edited by admin on Wed Apr 02 09:16:55 GMT 2025
PRIMARY
WIKIPEDIA
Rimegepant
Created by admin on Wed Apr 02 09:16:55 GMT 2025 , Edited by admin on Wed Apr 02 09:16:55 GMT 2025
PRIMARY
INN
9751
Created by admin on Wed Apr 02 09:16:55 GMT 2025 , Edited by admin on Wed Apr 02 09:16:55 GMT 2025
PRIMARY
LACTMED
Rimegepant
Created by admin on Wed Apr 02 09:16:55 GMT 2025 , Edited by admin on Wed Apr 02 09:16:55 GMT 2025
PRIMARY
DRUG BANK
DB12457
Created by admin on Wed Apr 02 09:16:55 GMT 2025 , Edited by admin on Wed Apr 02 09:16:55 GMT 2025
PRIMARY
EPA CompTox
DTXSID70156003
Created by admin on Wed Apr 02 09:16:55 GMT 2025 , Edited by admin on Wed Apr 02 09:16:55 GMT 2025
PRIMARY
FDA UNII
997WVV895X
Created by admin on Wed Apr 02 09:16:55 GMT 2025 , Edited by admin on Wed Apr 02 09:16:55 GMT 2025
PRIMARY
CAS
1289023-67-1
Created by admin on Wed Apr 02 09:16:55 GMT 2025 , Edited by admin on Wed Apr 02 09:16:55 GMT 2025
PRIMARY
DAILYMED
997WVV895X
Created by admin on Wed Apr 02 09:16:55 GMT 2025 , Edited by admin on Wed Apr 02 09:16:55 GMT 2025
PRIMARY
MERCK INDEX
m12192
Created by admin on Wed Apr 02 09:16:55 GMT 2025 , Edited by admin on Wed Apr 02 09:16:55 GMT 2025
PRIMARY
NCI_THESAURUS
C152220
Created by admin on Wed Apr 02 09:16:55 GMT 2025 , Edited by admin on Wed Apr 02 09:16:55 GMT 2025
PRIMARY
RXCUI
2282307
Created by admin on Wed Apr 02 09:16:55 GMT 2025 , Edited by admin on Wed Apr 02 09:16:55 GMT 2025
PRIMARY
USAN
ZZ-71
Created by admin on Wed Apr 02 09:16:55 GMT 2025 , Edited by admin on Wed Apr 02 09:16:55 GMT 2025
PRIMARY
Related Record Type Details
CALCITONIN GENE-RELATED PEPTIDE TYPE 1 RECEPTOR
TARGET -> INHIBITOR
Ki
CYTOCHROME P450 3A4
METABOLIC ENZYME -> SUBSTRATE
MAJOR
ATP-BINDING CASSETTE SUB-FAMILY G MEMBER 2
TRANSPORTER -> SUBSTRATE
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
BINDING
Structure of RIMEGEPANT
EXCRETED UNCHANGED
AMOUNT EXCRETED
FECAL
CYTOCHROME P450 3A4
METABOLIC ENZYME -> INHIBITOR
WEAK
TIME-DEPENDENT INHIBITION
CYTOCHROME P450 2C9
METABOLIC ENZYME -> SUBSTRATE
Structure of RIMEGEPANT
EXCRETED UNCHANGED
AMOUNT EXCRETED
URINE
MULTIDRUG RESISTANCE PROTEIN 1
TRANSPORTER -> SUBSTRATE
Related Record Type Details
Structure of BMS-973013
METABOLITE -> PARENT
Structure of BMS-922755
METABOLITE -> PARENT
Structure of BMS-946030
METABOLITE -> PARENT
Structure of ((5S,6S,9R)-5-AMINO-6-(2,3-DIFLUOROPHENYL)-6,7,8,9-TETRAHYDRO-5H-CYCLOHEPTA(B)PYRIDIN-9-YL) 4-HYDROXYPIPERIDINE-1-CARBOXYLATE
METABOLITE -> PARENT
Structure of (2S,3S,4S,5R,6S)-6-(((5S,6S,9R)-6-(2,3-DIFLUOROPHENYL)-9-HYDROXY-6,7,8,9-TETRAHYDRO-5H-CYCLOHEPTA(B)PYRIDIN-5-YL)CARBAMOYLOXY)-3,4,5-TRIHYDROXY-TETRAHYDROPYRAN-2-CARBOXYLIC ACID
METABOLITE -> PARENT
Related Record Type Details
Structure of RIMEGEPANT
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Tmax PHARMACOKINETIC ORAL ADMINISTRATION

ORAL BIOAVAILABILITY PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC AT STEADY-STATE

Tmax PHARMACOKINETIC HIGH-FAT MEAL

FED CONDITION

ORAL ADMINISTRATION

Biological Half-life PHARMACOKINETIC IN HEALTHY SUBJECTS

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