Cilengitide

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
PubChem	176873
ChemSpider	154046^Y
KEGG	D03497^Y
MeSH	Cilengitide
ChEMBL	CHEMBL429876
Jmol-3D images	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
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 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). Hence, it is under investigation for the treatment of glioblastoma by inhibiting angiogenesis.^[1]^[2]

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

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" (in German). Österreichische Apothekerzeitung (22/2008): 1136–7.