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

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

Molecular Formula	C28H28F2N6O3
Molecular Weight	534.5571
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

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

Targets

Primary Target	Pharmacology	Condition	Potency
Calcitonin gene-related peptide type 1 receptor 7	Antagonist 2,778

Conditions

Condition	Modality	Targets	Highest Phase	Product
Acute migraine 7	Primary		Phase II 1,132	Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
1045.53 ng/mL	75 mg single, oral		RIMEGEPANT plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
4718.71 ng × h/mL	75 mg single, oral		RIMEGEPANT plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
10.398 h	75 mg single, oral		RIMEGEPANT plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
75 mg 1 times / day single, oral Recommended	unhealthy, 18-75 years	Other AEs: Nausea, Hypersensitivity...
2250 mg single, oral Overdose	healthy, adults
75 mg 1 times / day single, oral Recommended	unhealthy, adults	Other AEs: Nausea, Urinary tract infection...
75 mg 1 times / day single, oral Recommended	unhealthy, adults	Other AEs: Nausea, Urinary tract infection...
600 mg single, oral Highest studied dose	unhealthy

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AEs

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AE	Significance	Dose	Population
Nausea	2%	75 mg 1 times / day single, oral Recommended	unhealthy, 18-75 years
Dyspnea	<1%	75 mg 1 times / day single, oral Recommended	unhealthy, 18-75 years
Hypersensitivity	<1%	75 mg 1 times / day single, oral Recommended	unhealthy, 18-75 years
Rash	grade 3, <1%	75 mg 1 times / day single, oral Recommended	unhealthy, 18-75 years
Back pain	0.2%	75 mg 1 times / day single, oral Recommended	unhealthy, adults

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1,737 inhibitor 1,587 inducer 781	substrate 1,037 inhibitor 1,767	inhibitor 1,852	inhibitor 1,612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1,524 CYP2B6 810 CYP2C19 1,478 UGT1A1 204 P-gp 1,461 BCRP 699 OATP1B1 788 OATP1B3 706 OAT1 599 OAT3 642 MATE2 263 MATE1 306 OCT2 647 L-type Ca channels 9	P-gp 1,537 BCRP 561 OATP1B1 406 OATP1B3 350	CYP1A2 701 CYP2B6 547

Drug as perpetrator

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Target	Modality	Activity
OATP1B3 715	inhibitor 3,277	no [IC50 6.04 uM]
BCRP 773	inhibitor 3,277	no [IC50 >10 uM]
MATE2 263	inhibitor 3,277	no [IC50 >10 uM]
OAT1 603	inhibitor 3,277	no [IC50 >10 uM]
P-gp 1,650	inhibitor 3,277	no [IC50 >100 uM]

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Drug as victim

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Target	Modality	Activity	Clinical evidence
CYP3A4 1,737	substrate 3,367	major	yes (co-administration study)
CYP2C9 1,037	substrate 3,367	minor	no (co-administration study)
OATP1B1 406	substrate 3,367	no
OATP1B3 350	substrate 3,367	no
BCRP 561	substrate 3,367	yes

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Tox targets

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Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1,647	inhibitor 1,626

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
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

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PubMed

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Title	Date	PubMed
Asymmetric Synthesis of Heterocyclic Analogues of a CGRP Receptor Antagonist for Treating Migraine.	2015 Dec 18	26650258

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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

Substance Class	Chemical
Record UNII	997WVV895X
Record Status	`Validated (UNII)`
Record Version

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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

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Classification Tree

Code System

Code

Agent Affecting Nervous System

NCI_THESAURUS

C241

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Code System

Code

Type

Description

DRUG CENTRAL

5381

PRIMARY

PUBCHEM

51049968

PRIMARY

ChEMBL

CHEMBL2178422

PRIMARY

SMS_ID

300000023332

PRIMARY

WIKIPEDIA

Rimegepant

PRIMARY

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Related Record

Type

Details


					939Y0OZR1Y

CALCITONIN GENE-RELATED PEPTIDE TYPE 1 RECEPTOR

TARGET -> INHIBITOR

Qualification:

Ki

Amount:

0.027 NANOMOLAR (average)


					PUO0521HZV

CYTOCHROME P450 3A4

METABOLIC ENZYME -> SUBSTRATE

Interaction Type:

MAJOR


					76UB6O122H

ATP-BINDING CASSETTE SUB-FAMILY G MEMBER 2

TRANSPORTER -> SUBSTRATE


					6D53G0FD0Z

PLASMA PROTEIN FRACTION (HUMAN)

BINDER->LIGAND

Interaction Type:

BINDING

Amount:

96 % (average)


					997WVV895X

RIMEGEPANT

EXCRETED UNCHANGED

Interaction Type:

AMOUNT EXCRETED

Qualification:

FECAL

Amount:

MOLE PERCENT OF AMOUNT EXCRETED 42 % (average)

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Related Record

Type

Details


					RSF73ZBU2E

BMS-973013

METABOLITE -> PARENT


					RTN356FC1D

BMS-922755

METABOLITE -> PARENT

Amount:


					5P1OIT0UI6

BMS-946030

METABOLITE -> PARENT


					4H0LT3EI31

((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


					PE7B0Q417N

(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

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Related Record

Type

Details


					997WVV895X

RIMEGEPANT

ACTIVE MOIETY

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Name	Property Type	Amount	Parameters
Tmax	PHARMACOKINETIC	1.5 hours (average)	ORAL ADMINISTRATION

ORAL BIOAVAILABILITY	PHARMACOKINETIC	64 % (average)

Volume of Distribution	PHARMACOKINETIC	120 LITERS (average)	AT STEADY-STATE

Tmax	PHARMACOKINETIC	2.5 hours (average)	HIGH-FAT MEAL FED CONDITION ORAL ADMINISTRATION

Biological Half-life	PHARMACOKINETIC	11 hours (average)	IN HEALTHY SUBJECTS

SMILES

InChI

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Tox targets

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

Drug as perpetrator