TELCAGEPANT

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Synonyms
Status
Molecule Category Free-form
UNII D42O649ALL

Structure

InChI Key CGDZXLJGHVKVIE-DNVCBOLYSA-N
Smiles O=C(N[C@@H]1CC[C@@H](c2cccc(F)c2F)CN(CC(F)(F)F)C1=O)N1CCC(n2c(=O)[nH]c3ncccc32)CC1
InChI
InChI=1S/C26H27F5N6O3/c27-18-4-1-3-17(21(18)28)15-6-7-19(23(38)36(13-15)14-26(29,30)31)33-24(39)35-11-8-16(9-12-35)37-20-5-2-10-32-22(20)34-25(37)40/h1-5,10,15-16,19H,6-9,11-14H2,(H,33,39)(H,32,34,40)/t15-,19-/m1/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C26H27F5N6O3
Molecular Weight 566.53
AlogP 4.1
Hydrogen Bond Acceptor 6.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 4.0
Polar Surface Area 103.59
Molecular species NEUTRAL
Aromatic Rings 3.0
Heavy Atoms 40.0

Bioactivity

Mechanism of Action Action Reference
Calcitonin gene-related peptide type 1 receptor antagonist ANTAGONIST PubMed Wikipedia
Protein: Calcitonin gene-related peptide type 1 receptor
Description: Calcitonin gene-related peptide type 1 receptor
Organism : Homo sapiens
Q16602 ENSG00000064989
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Membrane receptor Family B G protein-coupled receptor Peptide receptor (family B GPCR) Calcitonin-like receptor Calcitonin gene-related peptide receptor
- 2-11 2-4 1-1 -
Other membrane protein
- - - 1 -
Secreted protein
- 2 - 1 -
Assay Description Organism Bioactivity Reference
Displacement of [125I]CGPR from human CL receptor expressed in HEK293 cells Homo sapiens 0.77 nM
Antagonist activity at human CL receptor expressed in E10 cells assessed as CGRP-stimulated cAMP production Homo sapiens 2.2 nM
Antagonist activity at human CL receptor expressed in E10 cells assessed as CGRP-stimulated cAMP production in presence of 50% human serum Homo sapiens 11.0 nM
Inhibition of capsaicin-induced increase in dermal blood flow in iv dosed rhesus monkey Macaca mulatta 120.0 nM
Displacement of [125I]human CGRP from human CLR expressed in HEK293 cells coexpressing human RAMP1 Homo sapiens 0.8 nM
Antagonist activity at human CLR expressed in HEK293 cells coexpressing human RAMP1 assessed as inhibition of human CGRPalpha-induced cAMP production after 30 mins by scintillation proximity assay Homo sapiens 2.4 nM
Antagonist activity at human CLR expressed in HEK293 cells coexpressing human RAMP1 assessed as inhibition of human CGRPalpha-induced cAMP production after 30 mins by scintillation proximity assay in presence of 50% human serum Homo sapiens 11.0 nM
Displacement of [125I]human CGRP from human CLR expressed in HEK 293 cells coexpressing human RAMP1 after 3 hrs by scintillation counting Homo sapiens 0.8 nM
Antagonist activity at human CLR expressed in HEK293 cells coexpressing human RAMP1 assessed as inhibition of human CGRPalpha-induced cAMP production after 5 mins by scintillation proximity assay Homo sapiens 2.0 nM
Antagonist activity at human CLR expressed in HEK293 cells coexpressing human RAMP1 assessed as inhibition of human CGRPalpha-induced cAMP production after 5 mins in presence of 50% human serum by scintillation proximity assay Homo sapiens 11.0 nM
Antagonist activity at CGRP receptor assessed as inhibition of CGRP-stimulated cAMP production by cell based assay in presence of 50% human serum None 11.0 nM
Antagonist activity at CGRP receptor assessed as inhibition of CGRP-stimulated cAMP production by cell based assay None 2.0 nM
Displacement of [125I]-CGRP from human recombinant CGRP receptor Homo sapiens 0.8 nM
Displacement of [125I]adrenomedullin form CGRP receptor in human SK-N-MC cell membrane by competitive binding assay Homo sapiens 0.78 nM
Inhibition of human CGRP receptor expressed in huamn HEK293 cells coexpressing CLR/RAMP1 assessed as inhibition of CGRP-stimulated cAMP production after 1 hr Homo sapiens 2.2 nM
Antagonist activity at human CGRP receptor Homo sapiens 0.77 nM
Displacement of [125I]-hCGRP from human CGRP receptor expressed in HEK293 cells Homo sapiens 0.77 nM
Binding affinity to human CGRP receptor Homo sapiens 0.77 nM
Binding affinity to rhesus monkey CGRP receptor Macaca mulatta 1.2 nM
Antagonist activity against human CGRP receptor by cell based cAMP accumulation assay Homo sapiens 2.2 nM
Antagonist activity against human CGRP receptor in presence of 50% human serum by cell based cAMP accumulation assay Homo sapiens 11.0 nM
Reversible saturable binding affinity to human CGRP receptor using [3H]-labeled compound Homo sapiens 1.9 nM
Inhibition of capsaicin-induced dermal vasodilation in rhesus monkey model by laser Doppler imaging method Macaca mulatta 127.0 nM
Antagonist activity against CGRP receptor assessed as inhibition of CGRP-mediated vasorelaxation in human coronary arteries Homo sapiens 3.715 nM
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging Homo sapiens 6.74 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 6.87 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 1.4 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.07 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 1.61 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.07 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 1.61 %
Inhibition of human CLR/RAMP1 Homo sapiens 0.77 nM

Cross References

Resources Reference
ChEMBL CHEMBL236593
DrugBank DB12228
FDA SRS D42O649ALL
Guide to Pharmacology 703
PDB N7R
PubChem 11319053
SureChEMBL SCHEMBL1198535
ZINC ZINC000028827350
CONTENTS