Details of the Drug

General Information of Drug (ID: DMHOAUG)

Drug Name

Rimegepant

Synonyms

BMS-927711; 1289023-67-1; UNII-997WVV895X; BMS 927711; CHEMBL2178422; 997WVV895X; (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; Rimegepant [USAN:INN]; Rimegepant (USAN/INN); SCHEMBL1670580; DTXSID70156003; C28H28F2N6O3; EX-A1922; 3504AH; ZINC68267814; BDBM50400098; AKOS030526382; DB12457; CS-1027; NCGC00378677-01; HY-15498; KB-145921; W-5991

Indication

Disease Entry	ICD 11	Status	REF
Migraine	8A80	Approved	[1]

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 1

Molecular Weight (mw)

534.6

Topological Polar Surface Area (xlogp)

2.3

Rotatable Bond Count (rotbonds)

4

Hydrogen Bond Donor Count (hbonddonor)

2

Hydrogen Bond Acceptor Count (hbondacc)

8

ADMET Property

Absorption Tmax: The time to maximum plasma concentration (Tmax) is 11.7 h [2]
Bioavailability: The bioavailability of drug is 55% [2]
Elimination: Following oral administration of radiolabeled rimegepant in healthy subjects, 78% of the administered radioactivity was recovered in feces and 24% in urine [3]
Half-life: The concentration or amount of drug in body reduced by one-half in 11 hours [3]
Metabolism: The drug is metabolized via the CYP3A4 and CYP2C9 [3]
Vd: The volume of distribution (Vd) of drug is 120 L [3]

Chemical Identifiers

Formula: C28H28F2N6O3
IUPAC Name: [(5S,6S,9R)-5-amino-6-(2,3-difluorophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-9-yl] 4-(2-oxo-3H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxylate
Canonical SMILES: C1C[C@H](C2=C(C=CC=N2)[C@H]([C@@H]1C3=C(C(=CC=C3)F)F)N)OC(=O)N4CCC(CC4)N5C6=C(NC5=O)N=CC=C6
InChI: 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
InChIKey: KRNAOFGYEFKHPB-ANJVHQHFSA-N

Cross-matching ID

PubChem CID: 51049968
CAS Number: 1289023-67-1
DrugBank ID: DB12457
TTD ID: D0V9VG
VARIDT ID: DR00758
ACDINA ID: D01393

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Calcitonin gene-related peptide receptor (CGRPR)	TTY6O0Q	CALRL_HUMAN	Antagonist	[1]

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Molecular Interaction Atlas (MIA)

MIA Detail

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Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Rimegepant (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Ag-221	DMS0ZBI	Moderate	Decreased clearance of Rimegepant due to the transporter inhibition by Ag-221.	BCR-ABL1-negative chronic myeloid leukaemia [2A41]	[12]
Pexidartinib	DMS2J0Z	Major	Increased metabolism of Rimegepant caused by Pexidartinib mediated induction of CYP450 enzyme.	Bone/articular cartilage neoplasm [2F7B]	[13]
Eslicarbazepine	DMZREFQ	Major	Increased metabolism of Rimegepant caused by Eslicarbazepine mediated induction of CYP450 enzyme.	Epilepsy/seizure [8A61-8A6Z]	[13]
Berotralstat	DMWA2DZ	Moderate	Decreased metabolism of Rimegepant caused by Berotralstat mediated inhibition of CYP450 enzyme.	Innate/adaptive immunodeficiency [4A00]	[14]
Selpercatinib	DMZR15V	Moderate	Decreased metabolism of Rimegepant caused by Selpercatinib mediated inhibition of CYP450 enzyme.	Lung cancer [2C25]	[15]
Fedratinib	DM4ZBK6	Moderate	Decreased metabolism of Rimegepant caused by Fedratinib mediated inhibition of CYP450 enzyme.	Myeloproliferative neoplasm [2A20]	[13]
Darolutamide	DMV7YFT	Moderate	Decreased clearance of Rimegepant due to the transporter inhibition by Darolutamide.	Prostate cancer [2C82]	[13]
Voxelotor	DMCS6M5	Moderate	Decreased metabolism of Rimegepant caused by Voxelotor mediated inhibition of CYP450 enzyme.	Sickle-cell disorder [3A51]	[13]
Tedizolid	DMG2SKR	Moderate	Decreased clearance of Rimegepant due to the transporter inhibition by Tedizolid.	Skin and skin-structure infection [1F28-1G0Z]	[13]
Larotrectinib	DM26CQR	Moderate	Decreased metabolism of Rimegepant caused by Larotrectinib mediated inhibition of CYP450 enzyme.	Solid tumour/cancer [2A00-2F9Z]	[12]
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Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Benzyl alcohol	E00010	244	Antimicrobial preservative; Solvent
Mannitol	E00103	6251	Diluent; Flavoring agent; Lyophilization aid; Plasticizing agent; Tonicity agent
Menthol	E00050	1254	Flavoring agent
Sucralose	E00370	71485	Flavoring agent
Vanillin	E00049	1183	Flavoring agent
Eucalyptol	E00063	2758	Flavoring agent
Gelatin	E00630	Not Available	Other agent
Limonene	E00705	22311	Flavoring agent
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⏷ Show the Full List of 8 Pharmaceutical Excipients of This Drug

Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Rimegepant eq 75mg base Orally Disintegrating tablet	eq 75mg base	Orally Disintegrating Tablet	Sublingual; Oral

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References

1	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health Human Services. 2020
2	Metabolism and excretion of the once-daily human glucagon-like peptide-1 analog liraglutide in healthy male subjects and its in vitro degradation by dipeptidyl peptidase IV and neutral endopeptidase. Drug Metab Dispos. 2010 Nov;38(11):1944-53. doi: 10.1124/dmd.110.034066. Epub 2010 Aug 13.
3	FDA Approved Drug Products: Nurtec ODT (rimegepant) orally disintegrating tablets
4	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health Human Services. 2019
5	2018 FDA drug approvals.Nat Rev Drug Discov. 2019 Feb;18(2):85-89.
6	Pharmacological properties of MK-3207, a potent and orally active calcitonin gene-related peptide receptor antagonist. J Pharmacol Exp Ther. 2010 Apr;333(1):152-60.
7	EHMTI-0315. AMG 334, the first potent and selective human monoclonal antibody antagonist against the CGRP receptor. J Headache Pain. 2014; 15(Suppl 1): G43.
8	CGRP antagonists: novel concept for treatment of migraine. Med Monatsschr Pharm. 2009 May;32(5):182-5.
9	Olcegepant, a non-peptide CGRP1 antagonist for migraine treatment. IDrugs. 2007 Aug;10(8):566-74.
10	BI 44370 TA, an oral CGRP antagonist for the treatment of acute migraine attacks: results from a phase II study. Cephalalgia. 2011 Apr;31(5):573-84.
11	Safety and tolerability of LBR-101, a humanized monoclonal antibody that blocks the binding of CGRP to its receptor: Results of the Phase 1 program. Cephalalgia. 2013 Dec 23;34(7):483-492.
12	Cerner Multum, Inc. "Australian Product Information.".
13	Product Information. Nurtec ODT (rimegepant). Biohaven Pharmaceuticals, New Haven, CT.
14	Product Information. Orladeyo (berotralstat). BioCryst Pharmaceuticals Inc, Durham, NC.
15	Cerner Multum, Inc. "UK Summary of Product Characteristics.".