Cilengitide

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Cilengitide

IUPAC name 2-[(2S,5R,8S,11S)-5-benzyl-11-{3-[(diaminomethylidene)amino]propyl}-7-methyl-3,6,9,12,15-pentaoxo-8-(propan-2-yl)-1,4,7,10,13-pentaazacyclopentadecan-2-yl]acetic acid
Identifiers
CAS number	188968-51-6^N
PubChem	176873
ChemSpider	154046^Y
KEGG	D03497^Y
MeSH	Cilengitide
ChEMBL	CHEMBL429876^Y
Jmol-3D images	{{#if:O=C1N[C@H](C(=O)NCC(=O)N[C@H](C(=O)N[C@@H](C(=O)N(C)[C@H]1C(C)C)Cc2ccccc2)CC(=O)O)CCC/N=C(\N)N\|Image 1
SMILES O=C1N[C@H](C(=O)NCC(=O)N[C@H](C(=O)N[C@@H](C(=O)N(C)[C@H]1C(C)C)Cc2ccccc2)CC(=O)O)CCC/N=C(\N)N
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^Y Key: AMLYAMJWYAIXIA-VWNVYAMZSA-N^Y InChI=1/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 Key: AMLYAMJWYAIXIA-VWNVYAMZBF
Properties
Molecular formula	C₂₇H₄₀N₈O₇
Molar mass	588.66 g mol⁻¹
Density	1.417 g/mL
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Cilengitide is a molecule designed and synthesized at the Technical University Munich in collaboration with Merck KGaA in Darmstadt. It is based on the cyclic peptide cyclo(-RGDfV-), which is selective for α_v integrins, which are important in angiogenesis (forming new blood vessels), and other aspects of tumor biology. Hence, it is under investigation for the treatment of glioblastoma, where it may act by inhibiting angiogenesis, and influencing tumor invasion and proliferation.^[1]^[2]

The European Medicines Agency has granted cilengitide orphan drug status.^[3]

Cilengitide recently (March 2013) failed to achieve its primary endpoint in a pivotal phase 3 clinical trial for glioblastoma (the CENTRIC trial), and despite some encouraging phase 2 data, the clinical development of the drug in oncology has stopped. Details of the trial results are expected during 2014.

References

↑ Burke P, DeNardo S, Miers L, Lamborn K, Matzku S, DeNardo G (2002). "Cilengitide targeting of α_vβ₃ integrin receptor synergizes with radioimmunotherapy to increase efficacy and apoptosis in breast cancer xenografts". Cancer Res 62 (15): 4263–72. PMID 12154028.
↑ Goodman Simon L., Hoelzemann Guenter, Sulyok Gabor A. G., Kessler Horst (2002). "Nanomolar Small Molecule Inhibitors for α_vβ₆, α_vβ₅, and α_vβ₃ Integrins". Journal of Medicinal Chemistry 45 (5): 1045–51. doi:10.1021/jm0102598. PMID 11855984.
↑ H. Spreitzer (October 27, 2008). "Neue Wirkstoffe - Cilengitide". Österreichische Apothekerzeitung (in German) (22/2008): 1136–7.

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