Skip to main content
Free research Free research Free compound review with research home and workspace preview
Quick search ChEMBL 36
Compound Detail

CHEMBL236593

TELCAGEPANT
🧪 Phase III
Enter ChEMBL ID:
Free Research Context This compound will appear in recent viewed items on the research home for this browser.
Research home View demo workspace
🧪 Phase III
O=C(N[C@@H]1CC[C@@H](c2cccc(F)c2F)CN(CC(F)(F)F)C1=O)N1CCC(n2c(=O)[nH]c3ncccc32)CC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL236593
Name TELCAGEPANT
Phase Phase III
Structure Type MOL
InChI Key CGDZXLJGHVKVIE-DNVCBOLYSA-N

Known Names

Mk-0974 MK0974 Telcagepant
6
Targets
26
Activities
4
Assay Types
30
PK Parameters
20
Publications
3
Known Names
1
Indications
1
Mechanisms

Molecular Properties

566.5
MW (Da)
3.69
ALogP
5
HBA
2
HBD
103.3
PSA (Ų)
0.47
QED
1
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer
USAN Stem -gepant
USAN Year 2008

Extended Properties

Molecular Formula C26H27F5N6O3
MW 566.53
Aromatic Rings 3
Heavy Atoms 40
NP-Likeness -1.42

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Calcitonin gene-related peptide type 1 receptor antagonist ANTAGONIST Calcitonin gene-related peptide type 1 receptor ✓ ✓

Indications

Migraine Disorders

Activity Summary

IC50 11 meas. best 8.7
Ki 11 meas. best 9.11
EC50 2 meas. best 6.92
Kd 2 meas. best 8.72

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Calcitonin-gene-related peptide receptor, CALCRL/RAMP1
CHEMBL2107838
 Ki 9.11 9.11 0.8 1
Calcitonin gene-related peptide type 1 receptor
CHEMBL3798
 Ki 9.11 9.1057 0.8 7
Calcitonin gene-related peptide 1
CHEMBL5293
 Ki 9.11 9.11 0.8 1
Unchecked
CHEMBL612545
 Ki 8.92 8.92 1.2 1
Calcitonin gene-related peptide type 1 receptor
CHEMBL3798
 Kd 8.72 8.575 1.9 2
Calcitonin gene-related peptide type 1 receptor
CHEMBL3798
 IC50 8.7 8.314 2.0 10
Calcitonin gene-related peptide 1
CHEMBL5293
 IC50 8.66 8.66 2.2 1
Rhesus monkey
CHEMBL614875
 EC50 6.92 6.91 120.0 2
Calcitonin gene-related peptide 1
CHEMBL5735
 Ki 5.92 5.92 1200.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 3320000.0 ng.hr.mL-1 Rattus norvegicus
CL 9.4 mL.min-1.kg-1 Rattus norvegicus
CL 17.0 mL.min-1.kg-1 Canis lupus familiaris
CL 7.0 mL.min-1.kg-1 Macaca mulatta
CL 27.0 mL.min-1.kg-1 Rattus norvegicus
CL 9.4 mL.min-1.kg-1 Rattus norvegicus
CL 17.0 mL.min-1.kg-1 Canis lupus familiaris
CL 14.0 mL.min-1.kg-1 Macaca mulatta
CL 12.0 L/hr Homo sapiens
Cmax 970822.37 nM Rattus norvegicus
Cmax 1600.0 nM Homo sapiens
Cmax 2.5 mg Homo sapiens
F 20.0 % Rattus norvegicus
F 35.0 % Rattus norvegicus
F 20.0 % Rattus norvegicus
F 45.0 % Rattus norvegicus
F 22.0 % Rattus norvegicus
F 35.0 % Canis lupus familiaris
F 6.0 % Macaca mulatta
F 45.0 % Homo sapiens
F 22.0 % Rattus norvegicus
F 35.0 % Canis lupus familiaris
F 45.0 % Homo sapiens
Fu 0.038 - Macaca mulatta
Fu 0.041 - Homo sapiens
Fu 0.041 - Homo sapiens
T1/2 1.6 hr Rattus norvegicus
T1/2 2.8 hr Macaca mulatta
T1/2 0.02167 hr Homo sapiens
T1/2 1.6 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Calcitonin gene-related peptide type 1 receptor Ki = 0.77 nM 9.11 Displacement of [125I]-hCGRP from human CGRP receptor expressed in HEK293 cells 24900761
Calcitonin gene-related peptide type 1 receptor Ki = 0.77 nM 9.11 Antagonist activity at human CGRP receptor 23632269
Calcitonin gene-related peptide 1 Ki = 0.78 nM 9.11 Displacement of [125I]adrenomedullin form CGRP receptor in human SK-N-MC cell me... 21982500
Calcitonin gene-related peptide type 1 receptor Ki = 0.77 nM 9.11 Displacement of [125I]CGPR from human CL receptor expressed in HEK293 cells 17929795
Calcitonin gene-related peptide type 1 receptor Ki = 0.77 nM 9.11 Binding affinity to human CGRP receptor 24960305
Calcitonin-gene-related peptide receptor, CALCRL/RAMP1 Ki = 0.77 nM 9.11 Inhibition of human CLR/RAMP1 32058712
Calcitonin gene-related peptide type 1 receptor Ki = 0.8 nM 9.1 Displacement of [125I]human CGRP from human CLR expressed in HEK 293 cells coexp... 19818613
Calcitonin gene-related peptide type 1 receptor Ki = 0.8 nM 9.1 Displacement of [125I]human CGRP from human CLR expressed in HEK293 cells coexpr... 19577468
Calcitonin gene-related peptide type 1 receptor Ki = 0.8 nM 9.1 Displacement of [125I]-CGRP from human recombinant CGRP receptor 21251825
Unchecked Ki = 1.2 nM 8.92 Binding affinity to rhesus monkey CGRP receptor 24960305
Calcitonin gene-related peptide type 1 receptor Kd = 1.9 nM 8.72 Reversible saturable binding affinity to human CGRP receptor using [3H]-labeled ... 24960305
Calcitonin gene-related peptide type 1 receptor IC50 = 2.0 nM 8.7 Antagonist activity at CGRP receptor assessed as inhibition of CGRP-stimulated c... 21251825
Calcitonin gene-related peptide type 1 receptor IC50 = 2.0 nM 8.7 Antagonist activity at human CLR expressed in HEK293 cells coexpressing human RA... 19818613
Calcitonin gene-related peptide type 1 receptor IC50 = 2.2 nM 8.66 Antagonist activity against human CGRP receptor by cell based cAMP accumulation ... 24960305
Calcitonin gene-related peptide 1 IC50 = 2.2 nM 8.66 Inhibition of human CGRP receptor expressed in huamn HEK293 cells coexpressing C... 21982500
Calcitonin gene-related peptide type 1 receptor IC50 = 2.2 nM 8.66 Antagonist activity at human CL receptor expressed in E10 cells assessed as CGRP... 17929795
Calcitonin gene-related peptide type 1 receptor IC50 = 2.4 nM 8.62 Antagonist activity at human CLR expressed in HEK293 cells coexpressing human RA... 19577468
Calcitonin gene-related peptide type 1 receptor Kd = 3.715 nM 8.43 Antagonist activity against CGRP receptor assessed as inhibition of CGRP-mediate... 24960305
Calcitonin gene-related peptide type 1 receptor IC50 = 11.0 nM 7.96 Antagonist activity against human CGRP receptor in presence of 50% human serum b... 24960305
Calcitonin gene-related peptide type 1 receptor IC50 = 11.0 nM 7.96 Antagonist activity at CGRP receptor assessed as inhibition of CGRP-stimulated c... 21251825

Literature References

PubMed DOI Target Context # Activities
24960305 10.1021/jm500364u Homo sapiens 23
- 10.6019/CHEMBL5058564 Fibroblast 9
- 10.6019/CHEMBL5209801 Sphingosine 1-phosphate receptor 1 8
- 10.6019/CHEMBL5209801 Free fatty acid receptor 4 8
- 10.6019/CHEMBL5209801 N-formyl peptide receptor 2 8
- 10.6019/CHEMBL5209801 Beta-2 adrenergic receptor 8
- 10.6019/CHEMBL5209801 C5a anaphylatoxin chemotactic receptor 1 8
- 10.6019/CHEMBL5209801 Alpha-2A adrenergic receptor 8
- 10.6019/CHEMBL5209801 Apelin receptor 8
- 10.6019/CHEMBL5209801 Glucose-dependent insulinotropic receptor 8
- 10.6019/CHEMBL5209801 CX3C chemokine receptor 1 8
- 10.6019/CHEMBL5209801 Glucagon-like peptide 1 receptor 8
- 10.6019/CHEMBL5209801 Adhesion G-protein coupled receptor F1 8
32058712 10.1021/acs.jmedchem.9b01810 ADMET 8
- 10.6019/CHEMBL5209801 Type-1 angiotensin II receptor 8
24960305 10.1021/jm500364u Calcitonin gene-related peptide type 1 receptor 7
- 10.6019/CHEMBL5058564 HEK-293T 7
- 10.6019/CHEMBL5058564 U2OS 5
24960305 10.1021/jm500364u Rhesus monkey 5
17929795 10.1021/jm070668p Rattus norvegicus 5

Data from ChEMBL 36 via Core Engine