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
| 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 |
| Molecular Formula | H2O4S |
| Molecular Weight | 98.078 |
| Charge | 0 |
| Count |
|
| 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 |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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
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
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| no [IC50 6.04 uM] | ||||
| no [IC50 >10 uM] | ||||
| no [IC50 >10 uM] | ||||
| no [IC50 >10 uM] | ||||
| no [IC50 >100 uM] | ||||
| no [IC50 >40 uM] | ||||
| no [IC50 >40 uM] | ||||
| no [IC50 >40 uM] | ||||
| no [IC50 >40 uM] | ||||
| no [IC50 >40 uM] | ||||
| no [IC50 >50 uM] | ||||
| no [Inhibition 5 uM] | ||||
| no [Inhibition 5 uM] | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| weak | ||||
| yes [IC50 1.08 uM] | ||||
| yes [IC50 1.18 uM] |
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 |
|||
| no | ||||
| no | ||||
| yes | ||||
| yes |
Tox targets
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 08:28:39 UTC 2023
by
admin
on
Sat Dec 16 08:28:39 UTC 2023
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| Record UNII |
1383NM3Q0H
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| Record Status |
Validated (UNII)
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| Record Version |
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-
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| Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C241
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CHEMBL2178422
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2282322
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1383NM3Q0H
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DBSALT002938
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1374024-48-2
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m12192
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C152221
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DTXSID60160174
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ZZ-173
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1383NM3Q0H
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300000023334
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ACTIVE MOIETY |
