Cilengitide TFA salt
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MedKoo CAT#: 200780A

CAS#: 199807-35-7 (TFA salt)

Description: Cilengitide 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.


Price and Availability

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5mg
USD 150
50mg
USD 750
500mg
USD 2950
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10mg
USD 250
100mg
USD 1250
1g
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25mg
USD 450
200mg
USD 1950
5g
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Cilengitide TFA salt, purity > 98%, is in stock. The same day shipping out after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 200780A
Name: Cilengitide TFA salt
CAS#: 199807-35-7 (TFA salt)
Chemical Formula: C27H40N8O7
Exact Mass:
Molecular Weight: 702.7
Elemental Analysis: C, 55.09; H, 6.85; N, 19.04; O, 19.03


Synonym: EMD 121974;EMD-85189;EMD-121974;NSC-707544;D03497; Cilengitide TFA saltCyclo(L-arginylglycyl-L-aspartyl-D-phenylalanyl-N-methyl-L-valyl)

IUPAC/Chemical Name: 2-((2S,5R,8S,11S)-5-benzyl-11-(3-((diaminomethylene)amino)propyl)-8-isopropyl-7-methyl-3,6,9,12,15-pentaoxo-1,4,7,10,13-pentaazacyclopentadecan-2-yl)acetic acid trifluroacetic acid

InChi Key: WHJCSACXAPYNTG-LOPTWHKWSA-N

InChi Code: InChI=1S/C27H40N8O7.C2HF3O2/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;3-2(4,5)1(6)7/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);(H,6,7)/t17-,18-,19+,22-;/m0./s1

SMILES Code: O=C(O)C[C@@H](C(N[C@H](CC1=CC=CC=C1)C(N(C)[C@@H](C(C)C)C(N[C@@H](CCC/N=C(N)\N)C(NC2)=O)=O)=O)=O)NC2=O.O=C(O)C(F)(F)F


Technical Data

Appearance:
white solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Certificate of Analysis:

Safety Data Sheet (MSDS):

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in water

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in water

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


Additional Information

Related CAS#
199807-35-7 (TFA salt); 188968-51-6 (free base).

Recent publications related to cilengitide supplied by MedKoo
1: Cheshenko N, Trepanier JB, González PA, Eugenin EA, Jacobs WR Jr, Herold BC. Herpes simplex virus type 2 glycoprotein H interacts with integrin αvβ3 to facilitate viral entry and calcium signaling in human genital tract epithelial cells. J Virol. 2014 Sep 1;88(17):10026-38. doi: 10.1128/JVI.00725-14. Epub 2014  Jun 18. PubMed PMID: 24942591; PubMed Central PMCID: PMC4136333.
1: Cheshenko N, Trepanier JB, González PA, Eugenin EA, Jacobs WR Jr, Herold BC. Herpes simplex virus type 2 glycoprotein H interacts with integrin αvβ3 to facilitate viral entry and calcium signaling in human genital tract epithelial cells. J Virol. 2014 Sep 1;88(17):10026-38. doi: 10.1128/JVI.00725-14. Epub 2014  Jun 18. PubMed PMID: 24942591; PubMed Central PMCID: PMC4136333.


References

1: Scaringi C, Minniti G, Caporello P, Enrici RM. Integrin inhibitor cilengitide for the treatment of glioblastoma: a brief overview of current clinical results. Anticancer Res. 2012 Oct;32(10):4213-23. Review. PubMed PMID: 23060541.

2: Kurozumi K, Ichikawa T, Onishi M, Fujii K, Date I. Cilengitide treatment for malignant glioma: current status and future direction. Neurol Med Chir (Tokyo). 2012;52(8):539-47. Review. PubMed PMID: 22976135.

3: Lombardi G, Zustovich F, Farina P, Polo V, Farina M, Puppa AD, Bertorelle R, Gardiman MP, Berti F, Zagonel V. Cilengitide in bevacizumab-refractory high-grade glioma: two case reports and critical review of the literature. Anticancer Drugs. 2012 Aug;23(7):749-53. doi: 10.1097/CAD.0b013e3283520e2c. Review. PubMed PMID: 22382388.

4: Mas-Moruno C, Rechenmacher F, Kessler H. Cilengitide: the first anti-angiogenic small molecule drug candidate design, synthesis and clinical evaluation. Anticancer Agents Med Chem. 2010 Dec;10(10):753-68. Review. PubMed PMID: 21269250; PubMed Central PMCID: PMC3267166.

5: 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. doi: 10.1517/13543784.17.8.1225 . Review. PubMed PMID: 18616418; PubMed Central PMCID: PMC2832832.

6: Smith JW. Cilengitide Merck. Curr Opin Investig Drugs. 2003 Jun;4(6):741-5. Review. PubMed PMID: 12901235.