Cilengitide free base
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MedKoo CAT#: 333194

CAS#: 188968-51-6 (free base)

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

Size
Price

25mg
USD 150
200mg
USD 850
2g
USD 4850
Size
Price

50mg
USD 250
500mg
USD 1850
5g
USD 6950
Size
Price

100mg
USD 450
1g
USD 2850

Cilengitide free base, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 333194
Name: Cilengitide free base
CAS#: 188968-51-6 (free base)
Chemical Formula: C27H40N8O7
Exact Mass: 588.302
Molecular Weight: 588.666
Elemental Analysis: C, 55.09; H, 6.85; N, 19.04; O, 19.02


Related CAS #: 199807-35-7 (TFA)   188968-51-6 (free base)    

Synonym: EMD-85189; EMD 85189; EMD85189; EMD-121974; EMD121974; EMD 121974; NSC-707544; D03497; Cilengitide; Cyclo(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

InChi Key: AMLYAMJWYAIXIA-VWNVYAMZSA-N

InChi Code: 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

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


Technical Data

Appearance:
Solid powder

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

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 DMSO

Shelf Life:
>3 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

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

Harmonized System Code:
2934.99.90.01


References

1: Zhang L, Gülses A, Purcz N, Weimer J, Wiltfang J, Açil Y. A comparative assessment of the effects of integrin inhibitor cilengitide on primary culture of head and neck squamous cell carcinoma (HNSCC) and HNSCC cell lines. Clin Transl Oncol. 2019 Jan 10. doi: 10.1007/s12094-018-02025-3. [Epub ahead of print] PubMed PMID: 30632010.

2: Stojanović N, Dekanić A, Paradžik M, Majhen D, Ferenčak K, Ruščić J, Bardak I, Supina C, Tomicic MT, Christmann M, Osmak M, Ambriović-Ristov A. Differential Effects of Integrin αv Knockdown and Cilengitide on Sensitization of Triple-Negative Breast Cancer and Melanoma Cells to Microtubule Poisons. Mol Pharmacol. 2018 Dec;94(6):1334-1351. doi: 10.1124/mol.118.113027. Epub 2018 Sep 27. PubMed PMID: 30262596.

3: Xu HL, Yang JJ, ZhuGe DL, Lin MT, Zhu QY, Jin BH, Tong MQ, Shen BX, Xiao J, Zhao YZ. Glioma-Targeted Delivery of a Theranostic Liposome Integrated with Quantum Dots, Superparamagnetic Iron Oxide, and Cilengitide for Dual-Imaging Guiding Cancer Surgery. Adv Healthc Mater. 2018 May;7(9):e1701130. doi: 10.1002/adhm.201701130. Epub 2018 Jan 19. PubMed PMID: 29350498.

4: Massabeau C, Khalifa J, Filleron T, Modesto A, Bigay-Gamé L, Plat G, Dierickx L, Aziza R, Rouquette I, Gomez-Roca C, Mounier M, Delord JP, Toulas C, Olivier P, Chatelut E, Mazières J, Cohen-Jonathan Moyal E. Continuous Infusion of Cilengitide Plus Chemoradiotherapy for Patients With Stage III Non-Small-cell Lung Cancer: A Phase I Study. Clin Lung Cancer. 2018 May;19(3):e277-e285. doi: 10.1016/j.cllc.2017.11.002. Epub 2017 Nov 21. PubMed PMID: 29221762.

5: Garciarena CD, McHale TM, Martin-Loeches I, Kerrigan SW. Pre-emptive and therapeutic value of blocking bacterial attachment to the endothelial alphaVbeta3 integrin with cilengitide in sepsis. Crit Care. 2017 Sep 26;21(1):246. doi: 10.1186/s13054-017-1838-3. PubMed PMID: 28946901; PubMed Central PMCID: PMC5613315.

6: Cedra S, Wiegand S, Kolb M, Dietz A, Wichmann G. Reduced Cytokine Release in Ex Vivo Response to Cilengitide and Cetuximab Is a Marker for Improved Survival of Head and Neck Cancer Patients. Cancers (Basel). 2017 Sep 5;9(9). pii: E117. doi: 10.3390/cancers9090117. PubMed PMID: 28872582; PubMed Central PMCID: PMC5615332.

7: Jiao Z, Li Y, Pang H, Zheng Y, Zhao Y. Pep-1 peptide-functionalized liposome to enhance the anticancer efficacy of cilengitide in glioma treatment. Colloids Surf B Biointerfaces. 2017 Oct 1;158:68-75. doi: 10.1016/j.colsurfb.2017.03.058. Epub 2017 Apr 13. PubMed PMID: 28672205.

8: Nalkiran HS, McDonald KL. Is neuroglial antigen 2 a potential contributor to cilengitide response in glioblastoma? J Cancer Res Ther. 2017 Apr-Jun;13(2):329-336. doi: 10.4103/0973-1482.188438. PubMed PMID: 28643756.

9: Haddad T, Qin R, Lupu R, Satele D, Eadens M, Goetz MP, Erlichman C, Molina J. A phase I study of cilengitide and paclitaxel in patients with advanced solid tumors. Cancer Chemother Pharmacol. 2017 Jun;79(6):1221-1227. doi: 10.1007/s00280-017-3322-9. Epub 2017 May 5. PubMed PMID: 28477227.

10: Wichmann G, Cedra S, Schlegel D, Kolb M, Wiegand S, Boehm A, Hofer M, Dietz A. Cilengitide and Cetuximab Reduce Cytokine Production and Colony Formation of Head and Neck Squamous Cell Carcinoma Cells Ex Vivo. Anticancer Res. 2017 Feb;37(2):521-527. PubMed PMID: 28179297.

11: Kurozumi K, Ishida J, Ichikawa T, Date I. [Cilengitide]. Nihon Rinsho. 2016 Sep;74 Suppl 7:672-676. Japanese. PubMed PMID: 30634832.

12: Dolgos H, Freisleben A, Wimmer E, Scheible H, Krätzer F, Yamagata T, Gallemann D, Fluck M. In vitro and in vivo drug disposition of cilengitide in animals and human. Pharmacol Res Perspect. 2016 Mar 17;4(2):e00217. doi: 10.1002/prp2.217. eCollection 2016 Apr. PubMed PMID: 27069630; PubMed Central PMCID: PMC4804314.

13: Khasraw M, Lee A, McCowatt S, Kerestes Z, Buyse ME, Back M, Kichenadasse G, Ackland S, Wheeler H. Cilengitide with metronomic temozolomide, procarbazine, and standard radiotherapy in patients with glioblastoma and unmethylated MGMT gene promoter in ExCentric, an open-label phase II trial. J Neurooncol. 2016 May;128(1):163-171. doi: 10.1007/s11060-016-2094-0. Epub 2016 Mar 2. PubMed PMID: 26935578.

14: Weller M, Nabors LB, Gorlia T, Leske H, Rushing E, Bady P, Hicking C, Perry J, Hong YK, Roth P, Wick W, Goodman SL, Hegi ME, Picard M, Moch H, Straub J, Stupp R. Cilengitide in newly diagnosed glioblastoma: biomarker expression and outcome. Oncotarget. 2016 Mar 22;7(12):15018-32. doi: 10.18632/oncotarget.7588. PubMed PMID: 26918452; PubMed Central PMCID: PMC4924768.

15: Lu LQ, Fang T, Zhou D, Tong XX, Wu J, Yi L. [Efficiency of integrin αvβ3 inhibitor Cilengitide in acute cerebral ischemia in rats]. Zhonghua Yi Xue Za Zhi. 2016 Feb 23;96(7):559-64. doi: 10.3760/cma.j.issn.0376-2491.2016.07.015. Chinese. PubMed PMID: 26902199.

16: Zhao YZ, Lin Q, Wong HL, Shen XT, Yang W, Xu HL, Mao KL, Tian FR, Yang JJ, Xu J, Xiao J, Lu CT. Glioma-targeted therapy using Cilengitide nanoparticles combined with UTMD enhanced delivery. J Control Release. 2016 Feb 28;224:112-125. doi: 10.1016/j.jconrel.2016.01.015. Epub 2016 Jan 11. PubMed PMID: 26792571.

17: Tucci M, Stucci S, Felici C, Cafforio P, Resta L, Rossi R, Silvestris F. Cilengitide restrains the osteoclast-like bone resorbing activity of myeloma plasma cells. Br J Haematol. 2016 Apr;173(1):59-69. doi: 10.1111/bjh.13922. Epub 2016 Jan 5. PubMed PMID: 26728969.

18: Chillà A, Bianconi D, Geetha N, Dorda A, Poettler M, Unseld M, Sykoutri D, Redlich K, Zielinski CC, Prager GW. Effects of cilengitide in osteoclast maturation and behavior. Exp Cell Res. 2015 Sep 10;337(1):68-75. doi: 10.1016/j.yexcr.2015.07.018. Epub 2015 Jul 21. PubMed PMID: 26209605.

19: O'Donnell PH, Karovic S, Karrison TG, Janisch L, Levine MR, Harris PJ, Polite BN, Cohen EE, Fleming GF, Ratain MJ, Maitland ML. Serum C-Telopeptide Collagen Crosslinks and Plasma Soluble VEGFR2 as Pharmacodynamic Biomarkers in a Trial of Sequentially Administered Sunitinib and Cilengitide. Clin Cancer Res. 2015 Nov 15;21(22):5092-9. doi: 10.1158/1078-0432.CCR-15-0427. Epub 2015 Jul 21. PubMed PMID: 26199386; PubMed Central PMCID: PMC4677671.

20: Lam S, Li G, Zada G, Pelargos P, Choy W, Yang I, Smith ZA. Neurosurgery Concepts: Key perspectives on quality of life in children with spina bifida, cilengitide for the treatment of newly diagnosed glioblastoma, surgery and stereotactic radiosurgery in the management of intracranial metastasis, Gamma Knife radiosurgery in patients with Neurofibromatosis Type 2, patient misconceptions on the diagnosis and treatment of lumbar spondylosis. Surg Neurol Int. 2015 Jun 18;6:110. doi: 10.4103/2152-7806.159075. eCollection 2015. PubMed PMID: 26167362; PubMed Central PMCID: PMC4483781.