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

Details

Stereochemistry ABSOLUTE
Molecular Formula C28H28F2N6O3
Molecular Weight 534.5582
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RIMEGEPANT

SMILES

c1cc([C@]2([H])CC[C@]([H])(c3c(cccn3)[C@@]2([H])N)OC(=O)N4CCC(CC4)n5c6cccnc6nc5O)c(c(c1)F)F

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 534.5582
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
n = 682
Health Status: unhealthy
Condition: migraine
Age Group: 18-75 years
Sex: M+F
Population Size: 682
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
n = 1
Health Status: healthy
Age Group: adults
Population Size: 1
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
n = 543
Health Status: unhealthy
Condition: migraine
Age Group: adults
Sex: M+F
Population Size: 543
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
n = 682
Health Status: unhealthy
Condition: migraine
Age Group: adults
Sex: M+F
Population Size: 682
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
n = 84
Health Status: unhealthy
Condition: migraine
Population Size: 84
Sources:
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
n = 682
Health Status: unhealthy
Condition: migraine
Age Group: 18-75 years
Sex: M+F
Population Size: 682
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
n = 682
Health Status: unhealthy
Condition: migraine
Age Group: 18-75 years
Sex: M+F
Population Size: 682
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
n = 682
Health Status: unhealthy
Condition: migraine
Age Group: 18-75 years
Sex: M+F
Population Size: 682
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
n = 682
Health Status: unhealthy
Condition: migraine
Age Group: 18-75 years
Sex: M+F
Population Size: 682
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
n = 543
Health Status: unhealthy
Condition: migraine
Age Group: adults
Sex: M+F
Population Size: 543
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
n = 543
Health Status: unhealthy
Condition: migraine
Age Group: adults
Sex: M+F
Population Size: 543
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
n = 543
Health Status: unhealthy
Condition: migraine
Age Group: adults
Sex: M+F
Population Size: 543
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
n = 543
Health Status: unhealthy
Condition: migraine
Age Group: adults
Sex: M+F
Population Size: 543
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
n = 682
Health Status: unhealthy
Condition: migraine
Age Group: adults
Sex: M+F
Population Size: 682
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
n = 682
Health Status: unhealthy
Condition: migraine
Age Group: adults
Sex: M+F
Population Size: 682
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
n = 682
Health Status: unhealthy
Condition: migraine
Age Group: adults
Sex: M+F
Population Size: 682
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 Sat Jun 26 09:25:56 UTC 2021
Edited
by admin
on Sat Jun 26 09:25:56 UTC 2021
Record UNII
997WVV895X
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
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
BMS-927711
Code 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 [WHO-DD]
Common Name English
RIMEGEPANT [USAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C241
Created by admin on Sat Jun 26 09:25:57 UTC 2021 , Edited by admin on Sat Jun 26 09:25:57 UTC 2021
Code System Code Type Description
DRUG CENTRAL
5381
Created by admin on Sat Jun 26 09:25:57 UTC 2021 , Edited by admin on Sat Jun 26 09:25:57 UTC 2021
PRIMARY
PUBCHEM
51049968
Created by admin on Sat Jun 26 09:25:57 UTC 2021 , Edited by admin on Sat Jun 26 09:25:57 UTC 2021
PRIMARY
ChEMBL
CHEMBL2178422
Created by admin on Sat Jun 26 09:25:57 UTC 2021 , Edited by admin on Sat Jun 26 09:25:57 UTC 2021
PRIMARY
WIKIPEDIA
Rimegepant
Created by admin on Sat Jun 26 09:25:57 UTC 2021 , Edited by admin on Sat Jun 26 09:25:57 UTC 2021
PRIMARY
INN
9751
Created by admin on Sat Jun 26 09:25:57 UTC 2021 , Edited by admin on Sat Jun 26 09:25:57 UTC 2021
PRIMARY
LACTMED
Rimegepant
Created by admin on Sat Jun 26 09:25:57 UTC 2021 , Edited by admin on Sat Jun 26 09:25:57 UTC 2021
PRIMARY
DRUG BANK
DB12457
Created by admin on Sat Jun 26 09:25:57 UTC 2021 , Edited by admin on Sat Jun 26 09:25:57 UTC 2021
PRIMARY
FDA UNII
997WVV895X
Created by admin on Sat Jun 26 09:25:57 UTC 2021 , Edited by admin on Sat Jun 26 09:25:57 UTC 2021
PRIMARY
CAS
1289023-67-1
Created by admin on Sat Jun 26 09:25:57 UTC 2021 , Edited by admin on Sat Jun 26 09:25:57 UTC 2021
PRIMARY
EPA CompTox
1289023-67-1
Created by admin on Sat Jun 26 09:25:57 UTC 2021 , Edited by admin on Sat Jun 26 09:25:57 UTC 2021
PRIMARY
NCI_THESAURUS
C152220
Created by admin on Sat Jun 26 09:25:57 UTC 2021 , Edited by admin on Sat Jun 26 09:25:57 UTC 2021
PRIMARY
RXCUI
2282307
Created by admin on Sat Jun 26 09:25:57 UTC 2021 , Edited by admin on Sat Jun 26 09:25:57 UTC 2021
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