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
1. Goodman SL, Hölzemann G, Sulyok GA, Kessler H. (2002)
Nanomolar small molecule inhibitors for alphav(beta)6, alphav(beta)5, and alphav(beta)3 integrins.
J Med Chem, 45 (5): 1045-51. [PMID:11855984]
2. Kim KB, Prieto V, Joseph RW, Diwan AH, Gallick GE, Papadopoulos NE, Bedikian AY, Camacho LH, Hwu P, Ng CS et al.. (2012)
A randomized phase II study of cilengitide (EMD 121974) in patients with metastatic melanoma.
Melanoma Res, 22 (4): 294-301. [PMID:22668797]
3. MacDonald TJ, Taga T, Shimada H, Tabrizi P, Zlokovic BV, Cheresh DA, Laug WE. (2001)
Preferential susceptibility of brain tumors to the antiangiogenic effects of an alpha(v) integrin antagonist.
Neurosurgery, 48 (1): 151-7. [PMID:11152340]
4. Mikkelsen T, Brodie C, Finniss S, Berens ME, Rennert JL, Nelson K, Lemke N, Brown SL, Hahn D, Neuteboom B et al.. (2009)
Radiation sensitization of glioblastoma by cilengitide has unanticipated schedule-dependency.
Int J Cancer, 124 (11): 2719-27. [PMID:19199360]
5. Stupp R, Hegi ME, Gorlia T, Erridge SC, Perry J, Hong YK, Aldape KD, Lhermitte B, Pietsch T, Grujicic D et al.. (2014)
Cilengitide combined with standard treatment for patients with newly diagnosed glioblastoma with methylated MGMT promoter (CENTRIC EORTC 26071-22072 study): a multicentre, randomised, open-label, phase 3 trial.
Lancet Oncol, 15 (10): 1100-8. [PMID:25163906]
6. Weller M, Nabors LB, Gorlia T, Leske H, Rushing E, Bady P, Hicking C, Perry J, Hong YK, Roth P et al.. (2016)
Cilengitide in newly diagnosed glioblastoma: biomarker expression and outcome.
Oncotarget, 7 (12): 15018-32. [PMID:26918452]
7. Yamada S, Bu XY, Khankaldyyan V, Gonzales-Gomez I, McComb JG, Laug WE. (2006)
Effect of the angiogenesis inhibitor Cilengitide (EMD 121974) on glioblastoma growth in nude mice.
Neurosurgery, 59 (6): 1304-12; discussion 1312. [PMID:17277694]