RIMEGEPANT SULFATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	2C28H28F2N6O3.3H2O.H2O4S
Molecular Weight	1221.239
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

O.O.O.OS(O)(=O)=O.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.N[C@H]7[C@@H](CC[C@@H](OC(=O)N8CCC(CC8)N9C(=O)NC%10=C9C=CC=N%10)C%11=C7C=CC=N%11)C%12=CC=CC(F)=C%12F

InChI

InChIKey=SOGUOEZRYKUOHR-CQZKMDJHSA-N

InChI=1S/2C28H28F2N6O3.H2O4S.3H2O/c2*29-20-6-1-4-17(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;1-5(2,3)4;;;/h2*1-7,12-13,16,18,22,24H,8-11,14-15,31H2,(H,33,34,37);(H2,1,2,3,4);3*1H2/t2*18-,22+,24-;;;;/m00..../s1

HIDE SMILES / InChI

Molecular Formula	C28H28F2N6O3
Molecular Weight	534.5571
Charge	0
Count	MOL RATIO 2 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	H2O4S
Molecular Weight	98.078
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	H2O
Molecular Weight	18.0153
Charge	0
Count	MOL RATIO 3 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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	1383NM3Q0H
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

RIMEGEPANT SULFATE

Official Name

English

RIMEGEPANT SULFATE [USAN]

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, SULFATE, HYDRATE (2:1:3)

Systematic Name

English

NURTEC ODT

Brand Name

English

Di{(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}, monosulfate, trihydrate

Systematic Name

English

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