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
Molecular Formula | C28H28F2N6O3 |
Molecular Weight | 534.5571 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/?term=23965396
Sources: https://www.ncbi.nlm.nih.gov/pubmed/?term=23965396
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
Sources: http://www.bloomberg.com/news/articles/2013-01-07/bristol-meyers-may-sell-experimental-migraine-drug
Curator's Comment: # Bristol-Myers Squibb
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL3798 Sources: https://www.ncbi.nlm.nih.gov/pubmed/?term=23153230 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Dose | Population | Adverse 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%) Sources: Hypersensitivity (<1%) Dyspnea (<1%) Rash (grade 3, <1%) |
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%) Sources: Urinary tract infection (1.5%) Transaminases increased (2.3%) 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 = 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%) Sources: Urinary tract infection (1%) Dizziness (1%) |
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
AE | Significance | Dose | Population |
---|---|---|---|
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: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Drug as victim
Target | Modality | Activity | Metabolite | Clinical 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 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000ClinPharmR.pdf#page=8 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. Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000ClinPharmR.pdf#page=8 Page: 8.0 |
|||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000ClinPharmR.pdf#page=36 Page: 36.0 |
no | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000ClinPharmR.pdf#page=36 Page: 36.0 |
no | |||
yes | ||||
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/212728Orig1s000PharmR.pdf#page=16 Page: 16.0 |
Substance Class |
Chemical
Created
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admin
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Edited
Sat Dec 16 17:33:38 GMT 2023
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Sat Dec 16 17:33:38 GMT 2023
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997WVV895X
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C241
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Related Record | Type | Details | ||
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TARGET -> INHIBITOR |
Ki
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METABOLIC ENZYME -> SUBSTRATE |
MAJOR
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TRANSPORTER -> SUBSTRATE | |||
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BINDER->LIGAND |
BINDING
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EXCRETED UNCHANGED |
AMOUNT EXCRETED
FECAL
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METABOLIC ENZYME -> INHIBITOR |
WEAK
TIME-DEPENDENT INHIBITION
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METABOLIC ENZYME -> SUBSTRATE | |||
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EXCRETED UNCHANGED |
AMOUNT EXCRETED
URINE
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TRANSPORTER -> SUBSTRATE |
Related Record | Type | Details | ||
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT |
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT | |||
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Tmax | PHARMACOKINETIC |
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ORAL ADMINISTRATION |
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ORAL BIOAVAILABILITY | PHARMACOKINETIC |
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Volume of Distribution | PHARMACOKINETIC |
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AT STEADY-STATE |
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Tmax | PHARMACOKINETIC |
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HIGH-FAT MEAL |
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Biological Half-life | PHARMACOKINETIC |
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IN HEALTHY SUBJECTS |
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