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Compound Detail

CHEMBL429876

CILENGITIDE
🧪 Phase III
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🧪 Phase III
CC(C)[C@H]1C(=O)N[C@@H](CCCNC(=N)N)C(=O)NCC(=O)N[C@@H](CC(=O)O)C(=O)N[C@H](Cc2ccccc2)C(=O)N1C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL429876
Name CILENGITIDE
Phase Phase III
Structure Type BOTH
InChI Key AMLYAMJWYAIXIA-VWNVYAMZSA-N

Known Names

Cilengitida Cilengitide EMD 121974 EMD-12192 EMD-121974
8
Targets
61
Activities
2
Assay Types
0
PK Parameters
20
Publications
5
Known Names
20
Indications
2
Mechanisms

Molecular Properties

588.7
MW (Da)
-1.97
ALogP
7
HBA
8
HBD
235.9
PSA (Ų)
0.09
QED
2
Ro5 Violations
9
Rot. Bonds

Drug Information

Molecule Type Protein
Chirality Single Enantiomer

Flags

Natural Product
USAN Stem -tide
USAN Year 2001

Extended Properties

Molecular Formula C27H40N8O7
MW 588.67
Aromatic Rings 1
Heavy Atoms 42
NP-Likeness 1.05

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Integrin alpha-V/beta-3 antagonist ANTAGONIST Integrin alpha-V/beta-3 ✓ ✓
Integrin alpha-V/beta-5 antagonist ANTAGONIST Integrin alpha-V/beta-5 ✓ ✓

Indications

Glioblastoma Glioblastoma Astrocytoma Astrocytoma Brain Neoplasms Carcinoma, Non-Small-Cell Lung Gliosarcoma Melanoma Oligodendroglioma Paraganglioma Prostatic Neoplasms, Castration-Resistant Breast Neoplasms, Male Carcinoma, Squamous Cell Central Nervous System Neoplasms Diffuse Intrinsic Pontine Glioma Kidney Diseases Leukemia Multiple Myeloma Myelodysplastic Syndromes Myeloproliferative Disorders

Activity Summary

IC50 60 meas. best 9.89
Ki 1 meas. best 9.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Integrin alpha-V/beta-5
CHEMBL2096675
 IC50 9.89 7.8193 0.1 14
Integrin alpha-V/alpha-5
CHEMBL3430893
 IC50 9.89 9.89 0.1 1
Integrin alpha-V/beta-3
CHEMBL1907598
 IC50 9.29 8.0268 0.5 25
Integrin alpha-V/beta-3
CHEMBL1907598
 Ki 9.0 9.0 1.0 1
Integrin alpha-5/beta-1
CHEMBL2095226
 IC50 7.88 6.951 13.2 10
Unchecked
CHEMBL612545
 IC50 7.85 7.85 14.0 1
Integrin alpha-V/beta-3/alpha-V/beta-5
CHEMBL4106150
 IC50 6.43 6.43 370.0 1
Integrin alpha-V/beta-6
CHEMBL2111416
 IC50 6.33 5.7033 470.0 3
Integrin alpha-IIb/beta-3
CHEMBL2093869
 IC50 6.23 5.805 590.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Integrin alpha-V/beta-5 IC50 = 0.13 nM 9.89 Displacement of [125I]echistatin from AlphaV-beta-5 integrin receptor 16509596
Integrin alpha-V/beta-5 IC50 = 0.13 nM 9.89 Displacement of [125I]echistatin from human integrin alpha-V-beta-5 receptor by ... 18303826
Integrin alpha-V/beta-5 IC50 = 0.13 nM 9.89 Displacement of [125I]Echistatin from human placental integrin alpha-V-beta-5 re... 18343671
Integrin alpha-V/alpha-5 IC50 = 0.13 nM 9.89 Displacement of [125I]echistatin from integrin alphaVbeta5 receptor in human pla... 19195898
Integrin alpha-V/beta-5 IC50 = 0.13 nM 9.89 Displacement of [125I]-echistatin from alpha-v-beta-5 integrin receptor 16302808
Integrin alpha-V/beta-3 IC50 = 0.51 nM 9.29 Binding affinity to soluble truncated human recombinant Fc-tagged alphaVbeta3 an... 24095096
Integrin alpha-V/beta-3 IC50 = 0.54 nM 9.27 Inhibition of vitronectin binding to recombinant human integrin alphaV (Phe31 to... 32094009
Integrin alpha-V/beta-3 IC50 = 0.54 nM 9.27 Binding affinity to human integrin alphaVbeta3 incubated for 1 hr by ELISA based... 33356253
Integrin alpha-V/beta-3 IC50 = 0.54 nM 9.27 Inhibition of human vitronectin binding to human integrin alphavbeta3 receptor a... 31306009
Integrin alpha-V/beta-3 IC50 = 0.54 nM 9.27 Inhibition of vitronectin binding to human alphaVbeta3 integrin after 1 hr by EL... 29775303
Integrin alpha-V/beta-3 IC50 = 0.54 nM 9.27 Inhibition of vitronectin binding to human alphavbeta3 integrin receptor after 1... 24654918
Integrin alpha-V/beta-3 IC50 = 0.54 nM 9.27 Inhibition of vitronectin binding to Integrin alphaVbeta3 receptor (unknown orig... 23362923
Integrin alpha-V/beta-3 IC50 = 0.58 nM 9.24 Displacement of biotinylated ECM from human placental integrin alphavbeta3 recep... 26818999
Integrin alpha-V/beta-3 IC50 = 0.6 nM 9.22 Inhibition of integrin alphaVbeta3 20218623
Integrin alpha-V/beta-3 IC50 = 0.65 nM 9.19 Antagonist activity at alphavbeta3 integrin receptor (unknown origin) by cell-fr... 24568695
Integrin alpha-V/beta-3 IC50 = 0.86 nM 9.07 Binding affinity to Integrin alpha-v-beta-3 receptor by ELISA assay 17184884
Integrin alpha-V/beta-3 Ki = 1.0 nM 9.0 Binding affinity to human integrin alphaVbeta3 receptor using acetyl-CisoDGRCGVR... 29883545
Integrin alpha-V/beta-5 IC50 = 2.1 nM 8.68 Binding affinity to Integrin alpha-v-beta-5 receptor by ELISA assay 17184884
Integrin alpha-V/beta-3 IC50 = 3.0 nM 8.52 Inhibition of vitronectin binding to recombinant human alphaV-beta3 integrin 11855984
Integrin alpha-V/beta-5 IC50 = 7.6 nM 8.12 Inhibition of vitronectin binding to Integrin alphaVbeta5 receptor (unknown orig... 23362923

Literature References

PubMed DOI Target Context # Activities
29775303 10.1021/acs.jmedchem.8b00004 Integrin alpha-V/beta-3 10
29775303 10.1021/acs.jmedchem.8b00004 U-87 MG 6
24949551 10.1021/jm5004478 Integrin alpha-V/beta-3 4
33961417 10.1021/acs.jmedchem.1c00533 Human alphaherpesvirus 1 4
29883545 10.1021/acs.jmedchem.8b00745 Integrin alpha-V/beta-3 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
17184884 10.1016/j.ejmech.2006.10.015 Unchecked 2
24095096 10.1016/j.bmcl.2013.09.031 Integrin alpha-V/beta-3 2
31306009 10.1021/acs.jmedchem.9b00360 Integrin alpha-V/beta-3 2
24949551 10.1021/jm5004478 Integrin alpha-V/beta-5 2
29775303 10.1021/acs.jmedchem.8b00004 E3 ubiquitin-protein ligase Mdm2 2
35839966 10.1016/j.bmcl.2022.128888 Integrin alpha-V/beta-3 2
11855984 10.1021/jm0102598 Integrin alpha-V/beta-6 2
33479689 10.1039/d0md00098a Integrin alpha-V/beta-3 2
24949551 10.1021/jm5004478 Integrin alpha-5/beta-1 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
24949551 10.1021/jm5004478 Integrin alpha-IIb/beta-3 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
11855984 10.1021/jm0102598 Integrin alpha-V/beta-3 2
11855984 10.1021/jm0102598 Integrin alpha-V/beta-5 2

Data from ChEMBL 36 via Core Engine