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MedKoo Cat#: 584388 | Name: Erbstatin
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Erbstatin is a tyrosine protein kinase inhibitor that when combined with foroxymithine has been shown to have antineoplastic activity against L-1210 leukemia.

Chemical Structure

Erbstatin
Erbstatin
CAS#100827-28-9

Theoretical Analysis

MedKoo Cat#: 584388

Name: Erbstatin

CAS#: 100827-28-9

Chemical Formula: C9H9NO3

Exact Mass: 179.0582

Molecular Weight: 179.18

Elemental Analysis: C, 60.33; H, 5.06; N, 7.82; O, 26.79

Price and Availability

Size Price Availability Quantity
1mg USD 850.00 2 Weeks
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Related CAS #
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Synonym
Erbstatin; Antibiotic MH 435A; NSC 610187; NSC610187; NSC-610187; NSC606641; NSC 606641; NSC-606641
IUPAC/Chemical Name
Formamide, N-(2-(2,5-dihydroxyphenyl)ethenyl)-, (E)-
InChi Key
SIHZWGODIRRSRA-ONEGZZNKSA-N
InChi Code
InChI=1S/C9H9NO3/c11-6-10-4-3-7-5-8(12)1-2-9(7)13/h1-6,12-13H,(H,10,11)/b4-3+
SMILES Code
O=CN/C=C/C1=CC(O)=CC=C1O
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
>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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 179.18 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.

Recalculate based on batch purity %
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: Imoto M, Umezawa K, Komuro K, Sawa T, Takeuchi T, Umezawa H. Antitumor activity of erbstatin, a tyrosine protein kinase inhibitor. Jpn J Cancer Res. 1987 Apr;78(4):329-32. PubMed PMID: 3108212. 2: Zhang ZH, Rhodes KJ, Childers WE, Argentieri TM, Wang Q. Disinactivation of N-type inactivation of voltage-gated K channels by an erbstatin analogue. J Biol Chem. 2004 Jul 9;279(28):29226-30. Epub 2004 May 10. PubMed PMID: 15136567. 3: McIntyre BS, Sylvester PW. Genistein and erbstatin inhibition of normal mammary epithelial cell proliferation is associated with EGF-receptor down-regulation. Cell Prolif. 1998 Feb;31(1):35-46. PubMed PMID: 9666817. 4: Stanwell C, Ye B, Yuspa SH, Burke TR Jr. Cell protein cross-linking by erbstatin and related compounds. Biochem Pharmacol. 1996 Aug 9;52(3):475-80. PubMed PMID: 8687502. 5: Naccache PH, Gilbert C, Caon AC, Gaudry M, Huang CK, Bonak VA, Umezawa K, McColl SR. Selective inhibition of human neutrophil functional responsiveness by erbstatin, an inhibitor of tyrosine protein kinase. Blood. 1990 Nov 15;76(10):2098-104. PubMed PMID: 2173635. 6: Bishop WR, Petrin J, Wang L, Ramesh U, Doll RJ. Inhibition of protein kinase C by the tyrosine kinase inhibitor erbstatin. Biochem Pharmacol. 1990 Nov 1;40(9):2129-35. PubMed PMID: 2242040. 7: Treuner M, Böhmer FD, Schulze W, Petuchov SP, Grosse R. Limited selectivity of a synthetic erbstatin derivative for tyrosine kinase and cell growth inhibition. Biochem Int. 1992 Mar;26(4):617-25. PubMed PMID: 1319149. 8: Takekura N, Yasui W, Kyo E, Yoshida K, Kameda T, Kitadai Y, Abe K, Umezawa K, Tahara E. Effects of tyrosine kinase inhibitor, erbstatin, on cell growth and growth-factor/receptor gene expression in human gastric carcinoma cells. Int J Cancer. 1991 Apr 1;47(6):938-42. PubMed PMID: 1849125. 9: Sugata D, Yamashita K, Umezawa K. Inhibition of serum-induced M-phase progression by a tyrosine kinase inhibitor, erbstatin. Biochem Biophys Res Commun. 1993 Jul 15;194(1):239-45. PubMed PMID: 8333839. 10: Markovits J, Larsen AK, Ségal-Bendirdjian E, Fossé P, Saucier JM, Gazit A, Levitzki A, Umezawa K, Jacquemin-Sablon A. Inhibition of DNA topoisomerases I and II and induction of apoptosis by erbstatin and tyrphostin derivatives. Biochem Pharmacol. 1994 Aug 3;48(3):549-60. PubMed PMID: 8068042. 11: Kawada M, Tawara J, Tsuji T, Honma Y, Hozumi M, Wang JY, Umezawa K. Inhibition of Abelson oncogene function by erbstatin analogues. Drugs Exp Clin Res. 1993;19(6):235-41. Review. PubMed PMID: 8013266. 12: Imoto M, Umezawa K, Sawa T, Takeuchi T, Umezawa H. In situ inhibition of tyrosine protein kinase by erbstatin. Biochem Int. 1987 Nov;15(5):989-95. PubMed PMID: 3501720. 13: Kryukova Y, Rybin VO, Qu J, Steinberg SF, Robinson RB. Age-dependent differences in the inhibition of HCN2 current in rat ventricular myocytes by the tyrosine kinase inhibitor erbstatin. Pflugers Arch. 2009 Feb;457(4):821-30. doi: 10.1007/s00424-008-0565-7. Epub 2008 Aug 12. PubMed PMID: 18696104; PubMed Central PMCID: PMC2701652. 14: Isshiki K, Imoto M, Sawa T, Umezawa K, Takeuchi T, Umezawa H, Tsuchida T, Yoshioka T, Tatsuta K. Inhibition of tyrosine protein kinase by synthetic erbstatin analogs. J Antibiot (Tokyo). 1987 Aug;40(8):1209-10. PubMed PMID: 3680036. 15: Watanabe Y, Kakeya H, Ikoma E, Umezawa K. Induction of morphological and enzymic differentiation in rat pheochromocytoma PC12h cells by stable erbstatin analogues. Drugs Exp Clin Res. 1993;19(1):1-6. PubMed PMID: 8223134. 16: Isshiki K, Imoto M, Takeuchi T, Umezawa H, Tsuchida T, Yoshioka T, Tatsuta K. Effective synthesis of erbstatin and its analogs. J Antibiot (Tokyo). 1987 Aug;40(8):1207-8. PubMed PMID: 3680035. 17: Salari H, Duronio V, Howard SL, Demos M, Jones K, Reany A, Hudson AT, Pelech SL. Erbstatin blocks platelet activating factor-induced protein-tyrosine phosphorylation, polyphosphoinositide hydrolysis, protein kinase C activation, serotonin secretion and aggregation of rabbit platelets. FEBS Lett. 1990 Apr 9;263(1):104-8. PubMed PMID: 1691984. 18: Toi M, Mukaida H, Wada T, Hirabayashi N, Toge T, Hori T, Umezawa K. Antineoplastic effect of erbstatin on human mammary and esophageal tumors in athymic nude mice. Eur J Cancer. 1990;26(6):722-4. PubMed PMID: 2144161. 19: Simizu S, Imoto M, Masuda N, Takada M, Umezawa K. Involvement of hydrogen peroxide production in erbstatin-induced apoptosis in human small cell lung carcinoma cells. Cancer Res. 1996 Nov 1;56(21):4978-82. PubMed PMID: 8895753. 20: Umezawa H, Imoto M, Sawa T, Isshiki K, Matsuda N, Uchida T, Iinuma H, Hamada M, Takeuchi T. Studies on a new epidermal growth factor-receptor kinase inhibitor, erbstatin, produced by MH435-hF3. J Antibiot (Tokyo). 1986 Jan;39(1):170-3. PubMed PMID: 3005217.