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MedKoo product information:
Cilengitide
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MedKoo Code#:
20080
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Name:
Cilengitide
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CAS#:
188968-51-6 (free base); 199807-35-7
(as monotrifluoroacetate).; 199807-38-0 (as
monomethanesulfonate).
Synonym: : EMD
121974；EMD-85189；EMD-121974；NSC-707544；D03497；Cyclo(L-arginylglycyl-L-aspartyl-D-phenylalanyl-N-methyl-L-valyl)。
IUPAC/Chemical name:
2-((2S,5S,8S,11S)-5-benzyl-11-(3-guanidinopropyl)-8-isopropyl-7-methyl-3,6,9,12,15-pentaoxo-1,4,7,10,13-pentaazacyclopentadecan-2-yl)acetic
acid
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Chemical structure: |
Theoretical analysis
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Chemical Formula: C27H40N8O7
Exact Mass: 588.30200
Molecular Weight: 588.6
m/z: 588.30200 (100.0%), 589.30535
(29.2%), 590.30871 (4.1%), 589.29903 (3.0%), 590.30624 (1.4%)
Elemental Analysis: C, 55.09; H, 6.85; N,
19.04; O, 19.03
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Availability and price:
This agent is not in stock, which may be available through custom synthesis. To inquire quotation and lead time or to ask questions, please send email to
sales@medkoo.com to describe your needs. A representative
will respond your email shortly. We offer big discount for orders of bulk quantities.
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Quality control
data:
Product will be shipped with
supporting analytical data.
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Information about this agent
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Cilengtidie is a cyclic Arg-Gly-Asp peptide with
potential antineoplastic activity. Cilengitide binds to and inhibits the
activities of the alpha(v)beta(3) and alpha(v)beta(5) integrins, thereby
inhibiting endothelial cell-cell interactions, endothelial cell-matrix
interactions, and angiogenesis. Check for
active clinical trials or
closed clinical trials using this agent. (NCI
Thesaurus).
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 αv integrins, which are important in angiogenesis (forming
new blood vessels). Hence, it is under investigation for the treatment
of glioblastoma by inhibiting angiogenesis. The European Medicines
Agency has granted cilengitide orphan drug status.
Current developer: Merck
1: Stupp R, Hegi ME, Neyns B, Goldbrunner R,
Schlegel U, Clement PM, Grabenbauer GG, Ochsenbein AF, Simon M, Dietrich
PY, Pietsch T, Hicking C, Tonn JC, Diserens AC, Pica A, Hermisson M,
Krueger S, Picard M, Weller M. Phase I/IIa Study of Cilengitide and
Temozolomide With Concomitant Radiotherapy Followed by Cilengitide and
Temozolomide Maintenance Therapy in Patients With Newly Diagnosed
Glioblastoma. J Clin Oncol. 2010 Jun 1;28(16):2712-8. Epub 2010 May 3.
PubMed PMID: 20439646.
2: Bradley DA, Daignault S, Ryan CJ, Dipaola RS, Smith DC, Small E,
Gross ME, Stein MN, Chen A, Hussain M. Cilengitide (EMD 121974, NSC
707544) in asymptomatic metastatic castration resistant prostate cancer
patients: a randomized phase II trial by the prostate cancer clinical
trials consortium. Invest New Drugs. 2010 Mar 25. [Epub ahead of print]
PubMed PMID: 20336348.
3: Chamberlain MC. Cilengitide: does it really represent a new targeted
therapy for recurrent glioblastoma? J Clin Oncol. 2009 Apr
10;27(11):1921; author reply 1922. Epub 2009 Mar 2. PubMed PMID:
19255301.
4: Maurer GD, Tritschler I, Adams B, Tabatabai G, Wick W, Stupp R,
Weller M. Cilengitide modulates attachment and viability of human glioma
cells, but not sensitivity to irradiation or temozolomide in vitro.
Neuro Oncol. 2009 Dec;11(6):747-56. Epub . PubMed PMID: 19221171; PubMed
Central PMCID: PMC2802395.
5: Alghisi GC, Ponsonnet L, Rüegg C. The integrin antagonist cilengitide
activates alphaVbeta3, disrupts VE-cadherin localization at cell
junctions and enhances permeability in endothelial cells. PLoS One.
2009;4(2):e4449. Epub 2009 Feb 12. PubMed PMID: 19212436; PubMed Central
PMCID: PMC2636874.
6: Mikkelsen T, Brodie C, Finniss S, Berens ME, Rennert JL, Nelson K,
Lemke N, Brown SL, Hahn D, Neuteboom B, Goodman SL. Radiation
sensitization of glioblastoma by cilengitide has unanticipated
schedule-dependency. Int J Cancer. 2009 Jun 1;124(11):2719-27. PubMed
PMID: 19199360.
7: Oliveira-Ferrer L, Hauschild J, Fiedler W, Bokemeyer C, Nippgen J,
Celik I, Schuch G. Cilengitide induces cellular detachment and apoptosis
in endothelial and glioma cells mediated by inhibition of FAK/src/AKT
pathway. J Exp Clin Cancer Res. 2008 Dec 29;27:86. PubMed PMID:
19114005; PubMed Central PMCID: PMC2648308.
8: [Cilengitide: a new weapon against glioblastoma?]. Tumori. 2008
Sep-Oct;94(5):suppl 1-2. Italian. PubMed PMID: 19112962.
9: Reardon DA, Fink KL, Mikkelsen T, Cloughesy TF, O'Neill A, Plotkin S,
Glantz M, Ravin P, Raizer JJ, Rich KM, Schiff D, Shapiro WR, Burdette-Radoux
S, Dropcho EJ, Wittemer SM, Nippgen J, Picard M, Nabors LB. Randomized
phase II study of cilengitide, an integrin-targeting arginine-glycine-aspartic
acid peptide, in recurrent glioblastoma multiforme. J Clin Oncol. 2008
Dec 1;26(34):5610-7. Epub 2008 Nov 3. PubMed PMID: 18981465.
10: Reardon DA, Nabors LB, Stupp R, Mikkelsen T. Cilengitide: an
integrin-targeting arginine-glycine-aspartic acid peptide with promising
activity for glioblastoma multiforme. Expert Opin Investig Drugs. 2008
Aug;17(8):1225-35. Review. PubMed PMID: 18616418; PubMed Central PMCID:
PMC2832832.
11: Tentori L, Dorio AS, Muzi A, Lacal PM, Ruffini F, Navarra P,
Graziani G. The integrin antagonist cilengitide increases the antitumor
activity of temozolomide against malignant melanoma. Oncol Rep. 2008
Apr;19(4):1039-43. PubMed PMID: 18357394.
12: MacDonald TJ, Stewart CF, Kocak M, Goldman S, Ellenbogen RG,
Phillips P, Lafond D, Poussaint TY, Kieran MW, Boyett JM, Kun LE. Phase
I clinical trial of cilengitide in children with refractory brain
tumors: Pediatric Brain Tumor Consortium Study PBTC-012. J Clin Oncol.
2008 Feb 20;26(6):919-24. PubMed PMID: 18281665.
13: Hariharan S, Gustafson D, Holden S, McConkey D, Davis D, Morrow M,
Basche M, Gore L, Zang C, O'Bryant CL, Baron A, Gallemann D, Colevas D,
Eckhardt SG. Assessment of the biological and pharmacological effects of
the alpha nu beta3 and alpha nu beta5 integrin receptor antagonist,
cilengitide (EMD 121974), in patients with advanced solid tumors. Ann
Oncol. 2007 Aug;18(8):1400-7. PubMed PMID: 17693653.
14: Nabors LB, Mikkelsen T, Rosenfeld SS, Hochberg F, Akella NS, Fisher
JD, Cloud GA, Zhang Y, Carson K, Wittemer SM, Colevas AD, Grossman SA.
Phase I and correlative biology study of cilengitide in patients with
recurrent malignant glioma. J Clin Oncol. 2007 May 1;25(13):1651-7.
PubMed PMID: 17470857.
15: Loges S, Butzal M, Otten J, Schweizer M, Fischer U, Bokemeyer C,
Hossfeld DK, Schuch G, Fiedler W. Cilengitide inhibits proliferation and
differentiation of human endothelial progenitor cells in vitro. Biochem
Biophys Res Commun. 2007 Jun 15;357(4):1016-20. Epub 2007 Apr 19. PubMed
PMID: 17466276.
16: Yamada S, Bu XY, Khankaldyyan V, Gonzales-Gomez I, McComb JG, Laug
WE. Effect of the angiogenesis inhibitor Cilengitide (EMD 121974) on
glioblastoma growth in nude mice. Neurosurgery. 2006 Dec;59(6):1304-12;
discussion 1312. PubMed PMID: 17277694.
17: Friess H, Langrehr JM, Oettle H, Raedle J, Niedergethmann M,
Dittrich C, Hossfeld DK, Stöger H, Neyns B, Herzog P, Piedbois P,
Dobrowolski F, Scheithauer W, Hawkins R, Katz F, Balcke P, Vermorken J,
van Belle S, Davidson N, Esteve AA, Castellano D, Kleeff J,
Tempia-Caliera AA, Kovar A, Nippgen J. A randomized multi-center phase
II trial of the angiogenesis inhibitor Cilengitide (EMD 121974) and
gemcitabine compared with gemcitabine alone in advanced unresectable
pancreatic cancer. BMC Cancer. 2006 Dec 11;6:285. PubMed PMID: 17156477;
PubMed Central PMCID: PMC1764757.
18: Albert JM, Cao C, Geng L, Leavitt L, Hallahan DE, Lu B. Integrin
alpha v beta 3 antagonist Cilengitide enhances efficacy of radiotherapy
in endothelial cell and non-small-cell lung cancer models. Int J Radiat
Oncol Biol Phys. 2006 Aug 1;65(5):1536-43. PubMed PMID: 16863930.
19: Beekman KW, Colevas AD, Cooney K, Dipaola R, Dunn RL, Gross M,
Keller ET, Pienta KJ, Ryan CJ, Smith D, Hussain M. Phase II evaluations
of cilengitide in asymptomatic patients with androgen-independent
prostate cancer: scientific rationale and study design. Clin Genitourin
Cancer. 2006 Mar;4(4):299-302. PubMed PMID: 16729916.
20: Colevas AD, Scharf O, Schoenfeldt M. Clinical trials referral
resource. Current clinical trials of cilengitide, an alpha(v) antagonist
in clinical development as an anticancer agent. Oncology (Williston
Park). 2004 Dec;18(14):1778, 1781-2, 1784. PubMed PMID: 15700626.
21: Raguse JD, Gath HJ, Bier J, Riess H, Oettle H. Cilengitide (EMD
121974) arrests the growth of a heavily pretreated highly vascularised
head and neck tumour. Oral Oncol. 2004 Feb;40(2):228-30. PubMed PMID:
14693249.
22: Smith JW. Cilengitide Merck. Curr Opin Investig Drugs. 2003
Jun;4(6):741-5. Review. PubMed PMID: 12901235.
23: Eskens FA, Dumez H, Hoekstra R, Perschl A, Brindley C, Böttcher S,
Wynendaele W, Drevs J, Verweij J, van Oosterom AT. Phase I and
pharmacokinetic study of continuous twice weekly intravenous
administration of Cilengitide (EMD 121974), a novel inhibitor of the
integrins alphavbeta3 and alphavbeta5 in patients with advanced solid
tumours. Eur J Cancer. 2003 May;39(7):917-26. PubMed PMID: 12706360.
24: Burke PA, DeNardo SJ, Miers LA, Lamborn KR, Matzku S, DeNardo GL.
Cilengitide targeting of alpha(v)beta(3) integrin receptor synergizes
with radioimmunotherapy to increase efficacy and apoptosis in breast
cancer xenografts. Cancer Res. 2002 Aug 1;62(15):4263-72. PubMed PMID:
12154028.
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