WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 201090
Description: E7820 is a α2 integrin inhibitor with potential antiangiogenic and antitumor activities. E7820 inhibits angiogenesis by suppressing integrin alpha 2, a cell adhesion molecule expressed on endothelial cells. Inhibition of integrin alpha 2 leads to an inhibition of cell-cell interactions, endothelial cell-matrix interactions, vascular endothelial cell proliferation and angiogenesis.
MedKoo Cat#: 201090
Chemical Formula: C17H12N4O2S
Exact Mass: 336.0681
Molecular Weight: 336.37
Elemental Analysis: C, 60.70; H, 3.60; N, 16.66; O, 9.51; S, 9.53
Synonym: E7820; E-7820; E 7820.
IUPAC/Chemical Name: N-(3-cyano-4-methyl-1H-indol-7-yl)-3-cyanobenzene-sulfonamide
InChi Key: LWGUASZLXHYWIV-UHFFFAOYSA-N
InChi Code: InChI=1S/C17H12N4O2S/c1-11-5-6-15(17-16(11)13(9-19)10-20-17)21-24(22,23)14-4-2-3-12(7-14)8-18/h2-7,10,20-21H,1H3
SMILES Code: O=S(C1=CC=CC(C#N)=C1)(NC2=CC=C(C)C3=C2NC=C3C#N)=O
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, not in water
Shelf Life: >2 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).
HS Tariff Code: 2934.99.9001
The following data is based on the product molecular weight 336.37 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
|Concentration / Solvent Volume / Mass||1 mg||5 mg||10 mg|
|1 mM||1.15 mL||5.76 mL||11.51 mL|
|5 mM||0.23 mL||1.15 mL||2.3 mL|
|10 mM||0.12 mL||0.58 mL||1.15 mL|
|50 mM||0.02 mL||0.12 mL||0.23 mL|
1: Ito K, Semba T, Uenaka T, Wakabayashi T, Asada M, Funahashi Y. Enhanced anti-angiogenic effect of E7820 in combination with erlotinib in epidermal growth factor receptor-tyrosine kinase inhibitor-resistant non-small-cell lung cancer xenograft models. Cancer Sci. 2014 Aug;105(8):1023-31. doi: 10.1111/cas.12450. PubMed PMID: 24841832.
2: Geramizadeh B, Asadian F, Taghavi A. Esophageal melanocytosis in oral opium consumption. Iran Red Crescent Med J. 2014 Jan;16(1):e7820. doi: 10.5812/ircmj.7820. Epub 2014 Jan 5. PubMed PMID: 24719715; PubMed Central PMCID: PMC3964433.
3: Semba T. [Current status of combination therapies of angiogenesis inhibitors: vascular normalization activity of a novel angiogenesis inhibitor E7820]. Nihon Yakurigaku Zasshi. 2013 Jan;141(1):4-8. Review. Japanese. PubMed PMID: 23302941.
4: Davies E. Former Bush adviser is appointed to lead Global Fund. BMJ. 2012 Nov 16;345:e7820. doi: 10.1136/bmj.e7820. PubMed PMID: 23160969.
5: Keizer RJ, Funahashi Y, Semba T, Wanders J, Beijnen JH, Schellens JH, Huitema AD. Evaluation of α2-integrin expression as a biomarker for tumor growth inhibition for the investigational integrin inhibitor E7820 in preclinical and clinical studies. AAPS J. 2011 Jun;13(2):230-9. doi: 10.1208/s12248-011-9260-2. Epub 2011 Mar 9. PubMed PMID: 21387147; PubMed Central PMCID: PMC3085714.
6: Mita M, Kelly KR, Mita A, Ricart AD, Romero O, Tolcher A, Hook L, Okereke C, Krivelevich I, Rossignol DP, Giles FJ, Rowinsky EK, Takimoto C. Phase I study of E7820, an oral inhibitor of integrin alpha-2 expression with antiangiogenic properties, in patients with advanced malignancies. Clin Cancer Res. 2011 Jan 1;17(1):193-200. doi: 10.1158/1078-0432.CCR-10-0010. PubMed PMID: 21208908.
7: Paolillo M, Russo MA, Serra M, Colombo L, Schinelli S. Small molecule integrin antagonists in cancer therapy. Mini Rev Med Chem. 2009 Oct;9(12):1439-46. Review. PubMed PMID: 19929817.
8: Li MY, Lai FJ, Hsu LJ, Lo CP, Cheng CL, Lin SR, Lee MH, Chang JY, Subhan D, Tsai MS, Sze CI, Pugazhenthi S, Chang NS, Chen ST. Dramatic co-activation of WWOX/WOX1 with CREB and NF-kappaB in delayed loss of small dorsal root ganglion neurons upon sciatic nerve transection in rats. PLoS One. 2009 Nov 12;4(11):e7820. doi: 10.1371/journal.pone.0007820. PubMed PMID: 19918364; PubMed Central PMCID: PMC2771921.
9: Keizer RJ, Zamacona MK, Jansen M, Critchley D, Wanders J, Beijnen JH, Schellens JH, Huitema AD. Application of population pharmacokinetic modeling in early clinical development of the anticancer agent E7820. Invest New Drugs. 2009 Apr;27(2):140-52. doi: 10.1007/s10637-008-9164-x. Epub 2008 Aug 20. PubMed PMID: 18712503.
10: Tucker GC. Integrins: molecular targets in cancer therapy. Curr Oncol Rep. 2006 Mar;8(2):96-103. Review. PubMed PMID: 16507218.
11: Semba T, Funahashi Y, Ono N, Yamamoto Y, Sugi NH, Asada M, Yoshimatsu K, Wakabayashi T. An angiogenesis inhibitor E7820 shows broad-spectrum tumor growth inhibition in a xenograft model: possible value of integrin alpha2 on platelets as a biological marker. Clin Cancer Res. 2004 Feb 15;10(4):1430-8. PubMed PMID: 14977846.
12: Funahashi Y, Sugi NH, Semba T, Yamamoto Y, Hamaoka S, Tsukahara-Tamai N, Ozawa Y, Tsuruoka A, Nara K, Takahashi K, Okabe T, Kamata J, Owa T, Ueda N, Haneda T, Yonaga M, Yoshimatsu K, Wakabayashi T. Sulfonamide derivative, E7820, is a unique angiogenesis inhibitor suppressing an expression of integrin alpha2 subunit on endothelium. Cancer Res. 2002 Nov 1;62(21):6116-23. PubMed PMID: 12414636.
Oral administration of E7820 significantly inhibited basic fibroblast growth factor-induced angiogenesis in Matrigel implants and human colon WiDr tumor-induced angiogenesis in a dorsal air sac model. Twice-daily treatment with E7820 clearly inhibited the s.c. tumor growth of seven tumor cell lines derived from human colon, breast, pancreas, and kidney, and completely suppressed the growth of human pancreatic KP-1 and human colon LoVo cell lines. Moreover, E7820 significantly inhibited the growth of KP-1 and human colon tumor Colo320DM cells orthotopically implanted in the pancreas and cecum, respectively. The efficacy of E7820 was comparable in the s.c. and orthotopic transplantation models. Immunohistochemical analyses using anti-CD31 antibody showed that E7820 significantly reduced microvessel density in orthotopically implanted KP-1 tumor. E7820 reduced integrin alpha2 expression on a megakaryocytic cell line, Dami cells, induced by phorbol 12-myristate 13-acetate treatment. It also decreased the expression level of integrin alpha2 on platelets withdrawn from mice bearing s.c. KP-1 tumor at a dosage close to that affording antitumor activity. These data demonstrate that E7820 showed a broad-spectrum antitumor effect in mice through inhibition of angiogenesis and indicate that the decrease of integrin alpha2 on platelets might serve as a biological marker for the antitumor efficacy of E7820. see http://www.ncbi.nlm.nih.gov/pubmed/14977846