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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

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
833
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2575
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase II
1101
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
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

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
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

Overview

CYP3A4CYP2C9CYP2D6hERG
substrate
1601

inhibitor
1467

inducer
707
substrate
936

inhibitor
1604
inhibitor
1702
inhibitor
1475

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP1A2
1383

CYP2B6
717

CYP2C19
1325

UGT1A1
192

P-gp
1330

BCRP
643

OATP1B1
733

OATP1B3
657

OAT1
554

OAT3
588

MATE2
251

MATE1
290

OCT2
594

L-type Ca channels
8
P-gp
1400

BCRP
515

OATP1B1
370

OATP1B3
319
CYP1A2
637

CYP2B6
501
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
OATP1B3
666
 no [IC50 6.04 uM]
BCRP
713
 no [IC50 >10 uM]
MATE2
251
 no [IC50 >10 uM]
OAT1
558
 no [IC50 >10 uM]
P-gp
1514
 no [IC50 >100 uM]
CYP1A2
1532
 no [IC50 >40 uM]
CYP2B6
884
 no [IC50 >40 uM]
CYP2C19
1392
 no [IC50 >40 uM]
CYP2C9
1648
 no [IC50 >40 uM]
CYP2D6
1738
 no [IC50 >40 uM]
UGT1A1
240
 no [IC50 >50 uM]
OAT3
590
 no [Inhibition 5 uM]
OATP1B1
748
 no [Inhibition 5 uM]
CYP1A2
1532
 no
CYP2B6
884
 no
CYP3A4
1772
 no
L-type Ca channels
8
 no
CYP3A4
1772
 weak
OCT2
595
 yes [IC50 1.08 uM]
MATE1
292
 yes [IC50 1.18 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP3A4
1601
 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
936
 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
370
 no
OATP1B3
319
 no
BCRP
515
 yes
P-gp
1400
 yes
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
1507
Sourcing

Sourcing

Vendor/AggregatorIDURL
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

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 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
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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