U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
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

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1045.53 ng/mL
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
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
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:
unhealthy, 18-75 years
Health Status: unhealthy
Age Group: 18-75 years
Sex: M+F
Sources:
Other AEs: Nausea, Hypersensitivity...
Other AEs:
Nausea (2%)
Hypersensitivity (<1%)
Dyspnea (<1%)
Rash (grade 3, <1%)
Sources:
2250 mg single, oral
Overdose
Dose: 2250 mg
Route: oral
Route: single
Dose: 2250 mg
Sources:
healthy, adults
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:
unhealthy, adults
Health Status: unhealthy
Age Group: adults
Sex: M+F
Sources:
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:
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:
unhealthy, adults
Health Status: unhealthy
Age Group: adults
Sex: M+F
Sources:
Other AEs: Nausea, Urinary tract infection...
Other AEs:
Nausea (2%)
Urinary tract infection (1%)
Dizziness (1%)
Sources:
600 mg single, oral
Highest studied dose
Dose: 600 mg
Route: oral
Route: single
Dose: 600 mg
Sources:
unhealthy
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:
unhealthy, 18-75 years
Health Status: unhealthy
Age Group: 18-75 years
Sex: M+F
Sources:
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:
unhealthy, 18-75 years
Health Status: unhealthy
Age Group: 18-75 years
Sex: M+F
Sources:
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:
unhealthy, 18-75 years
Health Status: unhealthy
Age Group: 18-75 years
Sex: M+F
Sources:
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:
unhealthy, 18-75 years
Health Status: unhealthy
Age Group: 18-75 years
Sex: M+F
Sources:
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:
unhealthy, adults
Health Status: unhealthy
Age Group: adults
Sex: M+F
Sources:
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:
unhealthy, adults
Health Status: unhealthy
Age Group: adults
Sex: M+F
Sources:
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:
unhealthy, adults
Health Status: unhealthy
Age Group: adults
Sex: M+F
Sources:
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:
unhealthy, adults
Health Status: unhealthy
Age Group: adults
Sex: M+F
Sources:
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:
unhealthy, adults
Health Status: unhealthy
Age Group: adults
Sex: M+F
Sources:
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:
unhealthy, adults
Health Status: unhealthy
Age Group: adults
Sex: M+F
Sources:
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:
unhealthy, adults
Health Status: unhealthy
Age Group: adults
Sex: M+F
Sources:
OverviewDrug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no [IC50 6.04 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >100 uM]
no [IC50 >40 uM]
no [IC50 >40 uM]
no [IC50 >40 uM]
no [IC50 >40 uM]
no [IC50 >40 uM]
no [IC50 >50 uM]
no [Inhibition 5 uM]
no [Inhibition 5 uM]
no
no
no
no
weak
yes [IC50 1.08 uM]
yes [IC50 1.18 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
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
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
no
no
yes
yes
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

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

Sample Use Guides

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
TARGET -> INHIBITOR
Ki
METABOLIC ENZYME -> SUBSTRATE
MAJOR
TRANSPORTER -> SUBSTRATE
BINDER->LIGAND
BINDING
EXCRETED UNCHANGED
AMOUNT EXCRETED
FECAL
METABOLIC ENZYME -> INHIBITOR
WEAK
TIME-DEPENDENT INHIBITION
METABOLIC ENZYME -> SUBSTRATE
EXCRETED UNCHANGED
AMOUNT EXCRETED
URINE
TRANSPORTER -> SUBSTRATE
Related Record Type Details
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