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Compound Detail

CHEMBL207197

OLCEGEPANT
🧪 Phase II
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🧪 Phase II
NCCCC[C@H](NC(=O)[C@@H](Cc1cc(Br)c(O)c(Br)c1)NC(=O)N1CCC(N2Cc3ccccc3NC2=O)CC1)C(=O)N1CCN(c2ccncc2)CC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL207197
Name OLCEGEPANT
Phase Phase II
Structure Type MOL
InChI Key ITIXDWVDFFXNEG-JHOUSYSJSA-N

Known Names

Bibn 4096 bs BIBN-4096 BS Bibn-4096bs Olcegepant
5
Targets
20
Activities
4
Assay Types
13
PK Parameters
20
Publications
4
Known Names
1
Indications
1
Mechanisms

Molecular Properties

869.7
MW (Da)
4.41
ALogP
8
HBA
5
HBD
176.5
PSA (Ų)
0.17
QED
1
Ro5 Violations
12
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product
USAN Stem -gepant

Extended Properties

Molecular Formula C38H47Br2N9O5
MW 869.66
Aromatic Rings 3
Heavy Atoms 54
NP-Likeness -0.61

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

Ki 11 meas. best 11.0
IC50 6 meas. best 10.7
Kd 2 meas. best 10.4
EC50 1 meas. best 10.59

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Calcitonin gene-related peptide type 1 receptor
CHEMBL3798
 Ki 11.0 10.94 0.0 5
Unchecked
CHEMBL612545
 Ki 11.0 11.0 0.0 1
Calcitonin gene-related peptide 1
CHEMBL5293
 Ki 10.85 10.85 0.0 1
Calcitonin gene-related peptide type 1 receptor
CHEMBL3798
 IC50 10.7 9.8733 0.0 3
Calcitonin gene-related peptide type 1 receptor
CHEMBL3798
 EC50 10.59 10.59 0.0 1
Calcitonin-gene-related peptide receptor, CALCRL/RAMP1
CHEMBL2107838
 IC50 10.52 10.26 0.0 2
Calcitonin-gene-related peptide receptor, CALCRL/RAMP1
CHEMBL2107838
 Ki 10.5 10.5 0.0 1
Calcitonin gene-related peptide type 1 receptor
CHEMBL3798
 Kd 10.4 10.25 0.0 2
Calcitonin gene-related peptide type 1 receptor
CHEMBL4755
 Ki 8.47 8.47 3.4 2
Unchecked
CHEMBL612545
 IC50 8.19 8.19 6.4 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 260000.0 ng.hr.mL-1 Rattus norvegicus
CL 2.6 mL.min-1.kg-1 Homo sapiens
CL 65.0 mL.min-1.kg-1 Rattus norvegicus
CL 12.0 L/hr Homo sapiens
CL 38.0 mL.min-1.kg-1 Rattus norvegicus
Cmax 1000390.96 nM Rattus norvegicus
Cmax 240.0 nM Homo sapiens
F 1.0 % Rattus norvegicus
F 1.0 % Canis lupus familiaris
F 1.0 % Rattus norvegicus
MRT 1.9 hr Homo sapiens
T1/2 2.5 hr Homo sapiens
T1/2 2.5 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked Ki = 0.01 nM 11.0 Binding affinity to CGRP (unknown origin) 31740056
Calcitonin gene-related peptide type 1 receptor Ki = 0.01 nM 11.0 Displacement of [125I]CGRP from CGRP receptor in human SK-N-MC cell membranes pr... 24405707
Calcitonin gene-related peptide type 1 receptor Ki = 0.01 nM 11.0 Antagonist activity at human CGRP receptor 23632269
Calcitonin gene-related peptide type 1 receptor Ki = 0.01 nM 11.0 Displacement of [125I]-CGRP from CGRP receptor in human SK-N-MC cells 24900474
Calcitonin gene-related peptide type 1 receptor Ki = 0.014 nM 10.85 Binding affinity to human CGRP receptor 24960305
Calcitonin gene-related peptide type 1 receptor Ki = 0.014 nM 10.85 Displacement of [125I]CGRP from CGRP receptor in human SK-N-MC cells after 180 m... 22607672
Calcitonin gene-related peptide 1 Ki = 0.014 nM 10.85 Displacement of [125I]adrenomedullin form CGRP receptor in human SK-N-MC cell me... 21982500
Calcitonin gene-related peptide type 1 receptor IC50 = 0.02 nM 10.7 Displacement of [125I]CGRP from CGRP receptor in human SK-N-MC cells 22732695
Calcitonin gene-related peptide type 1 receptor EC50 = 0.026 nM 10.59 Antagonist activity at CGRP receptor in human SK-N-MC cells assessed as inhibiti... 24794104
Calcitonin-gene-related peptide receptor, CALCRL/RAMP1 IC50 = 0.03 nM 10.52 Inhibition of human CLR/RAMP1 32058712
Calcitonin gene-related peptide type 1 receptor IC50 = 0.03 nM 10.52 Antagonist activity against human CGRP receptor 24960305
Calcitonin-gene-related peptide receptor, CALCRL/RAMP1 Ki = 0.03162 nM 10.5 Displacement of [3H]telcagepant from recombinant human CLR/RAMP1 expressed in Sf... 32558564
Calcitonin gene-related peptide type 1 receptor Kd = 0.03981 nM 10.4 Antagonist activity against CGRP receptor assessed as inhibition of CGRP-mediate... 24960305
Calcitonin gene-related peptide type 1 receptor Kd = 0.07943 nM 10.1 Antagonist activity against CGRP receptor assessed as inhibition of CGRP-mediate... 24960305
Calcitonin-gene-related peptide receptor, CALCRL/RAMP1 IC50 = 0.1 nM 10.0 Antagonist activity at human cloned CLR/RAMP1 receptor expressed in E10 cells me... 16527483
Calcitonin gene-related peptide type 1 receptor Ki = 3.4 nM 8.47 Displacement of [125I]CGRP from CGRP receptor in rat spleen homogenate after 180... 22607672
Calcitonin gene-related peptide type 1 receptor Ki = 3.4 nM 8.47 Binding affinity to rat CGRP receptor 24960305
Calcitonin gene-related peptide type 1 receptor IC50 = 4.0 nM 8.4 Antagonist activity at CGRP receptor in human SK-N-MC cells assessed as inhibiti... 24405707
Unchecked IC50 = 6.4 nM 8.19 Inhibition of rat CGRP receptor 32058712

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL4495565 SARS-CoV-2 6
24960305 10.1021/jm500364u Homo sapiens 6
24960305 10.1021/jm500364u Calcitonin gene-related peptide type 1 receptor 5
18426954 10.1124/dmd.108.020479 ADMET 4
24405707 10.1016/j.bmcl.2013.12.089 Rattus norvegicus 4
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 3
32558564 10.1021/acs.jmedchem.0c01003 Calcitonin-gene-related peptide receptor, CALCRL/RAMP1 2
16527483 10.1016/j.bmcl.2006.02.051 Calcitonin-gene-related peptide receptor, CALCRL/RAMP1 2
32558564 10.1021/acs.jmedchem.0c01003 No relevant target 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
24794104 10.1016/j.bmcl.2014.04.033 Calcitonin gene-related peptide type 1 receptor 2
24405707 10.1016/j.bmcl.2013.12.089 Calcitonin gene-related peptide type 1 receptor 2
22607672 10.1016/j.bmcl.2012.04.105 Calcitonin gene-related peptide type 1 receptor 2
24960305 10.1021/jm500364u Canis familiaris 1
24405707 10.1016/j.bmcl.2013.12.089 Nucleic Acid 1
23632269 10.1016/j.bmcl.2013.04.012 Calcitonin gene-related peptide type 1 receptor 1
24900474 10.1021/ml300021s Calcitonin gene-related peptide type 1 receptor 1
22732695 10.1016/j.bmcl.2012.05.118 Calcitonin gene-related peptide type 1 receptor 1
22607672 10.1016/j.bmcl.2012.04.105 Unchecked 1

Data from ChEMBL 36 via Core Engine