cilengitide   Click here for help

GtoPdb Ligand ID: 6597

Synonyms: EMD-12192 | EMD-121974
Comment: Cilengitide is a cyclic RGD pentapeptide, first-in-class integrin inhibitor. It inhibits integrin αv-induced angiogenesis. It was investigated for anti-tumour activity. Glioblastoma was one of the cancers investigated [6], based on encouraging preclinical studies in animals [3-4,7].
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2D Structure
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Canonical SMILES OC(=O)CC1NC(=O)CNC(=O)C(CCCNC(=N)N)NC(=O)C(N(C(=O)C(NC1=O)Cc1ccccc1)C)C(C)C
Isomeric SMILES OC(=O)C[C@@H]1NC(=O)CNC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](N(C(=O)[C@H](NC1=O)Cc1ccccc1)C)C(C)C
InChI InChI=1S/C27H40N8O7/c1-15(2)22-25(41)33-17(10-7-11-30-27(28)29)23(39)31-14-20(36)32-18(13-21(37)38)24(40)34-19(26(42)35(22)3)12-16-8-5-4-6-9-16/h4-6,8-9,15,17-19,22H,7,10-14H2,1-3H3,(H,31,39)(H,32,36)(H,33,41)(H,34,40)(H,37,38)(H4,28,29,30)/t17-,18-,19+,22-/m0/s1
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Summary of Clinical Use Click here for help
Phase 2 clinical trial results indicate little clinical efficacy as a single-agent therapy for metastatic melanoma, despite treatment being well tolerated [2]. Phase 3 in glioblastoma has been completed (NCT00689221), but the drug showed no improved clinical efficacy when added to standard temozolomide chemoradiotherapy, and development was terminated as a result [5]. Orphan designation for glioma granted by the European Medicines Agency in 2004, was withdrawn at the request of the sponsor in 2013.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Cilengitide inhibits integrin αv-induced angiogenesis.
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT00689221 Cilengitide, Temozolomide, and Radiation Therapy in Treating Patients With Newly Diagnosed Glioblastoma and Methylated Gene Promoter Status Phase 3 Interventional EMD Serono