158440-71-2|Irofulven|(5'R)-5'-Hydroxy-1'-(hydroxymethyl)-2',5',7'-trimethylspiro[cyclopropane-1,6'-indene]-4'-one|-范德生物科技公司

Irofulven

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names：
(5'R)-5'-Hydroxy-1'-(hydroxymethyl)-2',5',7'-trimethylspiro[cyclopropane-1,6'-indene]-4'-one
CAS号：
158440-71-2
MDL Number：
MF(分子式)： C15H18O3 MW(分子量)： 246.3
EINECS: Reaxys Number:
Pubchem ID: Brand:BIOFOUNT

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中文别名	Irofulven
英文别名	Irofulven; HMAF; MGI 114; NSC-683863; MGI-114; MGI114; NSC 683863; NSC683863;
CAS号	158440-71-2
Inchi	InChI=1S/C15H18O3/c1-8-6-10-12(11(8)7-16)9(2)15(4-5-15)14(3,18)13(10)17/h6,16,18H,4-5,7H2,1-3H3/t14-/m0/s1
InchiKey	NICJCIQSJJKZAH-AWEZNQCLSA-N
分子式 Formula	C15H18O3
分子量 Molecular Weight	246.3
溶解度Solubility
性状	Solid powder
储藏条件 Storage conditions	Dry, dark and store at 0-4℃ for short term (days to weeks) or -20℃ for long term (Store correctly 2-3years).

产品说明	Irofulven(CAS:158440-71-2):仅限应用于工业或者科学研究过程中非医疗目的，不应用于人类或动物的临床诊断以及治过程疗，该产品非药用，非食用。
Introduction	Irofulven is a DNA-damaging and antitumor agent for the treatment of advanced solid tumors, including prostate, ovarian, and pancreatic cancers.
Application1
Application2
Application3

警示图
危险性	Warning
危险性警示
安全声明
安全防护
备注

[1]Staake MD, Kashinatham A, McMorris TC, Estes LA, Kelner MJ. Hydroxyurea derivatives of irofulven with improved antitumor efficacy. Bioorg Med Chem Lett. 2016 Apr 1;26(7):1836-8. doi: 10.1016/j.bmcl.2016.02.028. Epub 2016 Feb 13. PubMed PMID: 26922141.

[2]Tummala H, Kirwan M, Walne AJ, Hossain U, Jackson N, Pondarre C, Plagnol V, Vulliamy T, Dokal I. ERCC6L2 mutations link a distinct bone-marrow-failure syndrome to DNA repair and mitochondrial function. Am J Hum Genet. 2014 Feb 6;94(2):246-56. doi: 10.1016/j.ajhg.2014.01.007. PubMed PMID: 24507776; PubMed Central PMCID: PMC3928664.

[3] Glatt H, Pietsch KE, Sturla SJ, Meinl W. Sulfotransferase-independent genotoxicity of illudin S and its acylfulvene derivatives in bacterial and mammalian cells. Arch Toxicol. 2014 Jan;88(1):161-9. doi: 10.1007/s00204-013-1097-2. Epub 2013 Jul 24. PubMed PMID: 23881331.

[4] Yu X, Erzinger MM, Pietsch KE, Cervoni-Curet FN, Whang J, Niederhuber J, Sturla SJ. Up-regulation of human prostaglandin reductase 1 improves the efficacy of hydroxymethylacylfulvene, an antitumor chemotherapeutic agent. J Pharmacol Exp Ther. 2012 Nov;343(2):426-33. doi: 10.1124/jpet.112.195768. Epub 2012 Aug 15. PubMed PMID: 22895897; PubMed Central PMCID: PMC3477217.

[5] Schilder RJ, Blessing JA, Shahin MS, Miller DS, Tewari KS, Muller CY, Warshal DP, McMeekin S, Rotmensch J. A phase 2 evaluation of irofulven as second-line treatment of recurrent or persistent intermediately platinum-sensitive ovarian or primary peritoneal cancer: a Gynecologic Oncology Group trial. Int J Gynecol Cancer. 2010 Oct;20(7):1137-41. PubMed PMID: 21495215; PubMed Central PMCID: PMC3079178.

6: McMorris TC, Chimmani R, Alisala K, Staake MD, Banda G, Kelner MJ. Structure-activity studies of urea, carbamate, and sulfonamide derivatives of acylfulvene. J Med Chem. 2010 Feb 11;53(3):1109-16. doi: 10.1021/jm901384s. PubMed PMID: 20067264.7: Siegel DS, Piizzi G, Piersanti G, Movassaghi M. Enantioselective total synthesis of (-)-acylfulvene and (-)-irofulven. J Org Chem. 2009 Dec 18;74(24):9292-304. doi: 10.1021/jo901926z. PubMed PMID: 19938810; PubMed Central PMCID: PMC2805080.8: Escargueil AE, Poindessous V, Soares DG, Sarasin A, Cook PR, Larsen AK. Influence of irofulven, a transcription-coupled repair-specific antitumor agent, on RNA polymerase activity, stability and dynamics in living mammalian cells. J Cell Sci. 2008 Apr 15;121(Pt 8):1275-83. doi: 10.1242/jcs.023259. PubMed PMID: 18388315.9: Dings RP, Van Laar ES, Webber J, Zhang Y, Griffin RJ, Waters SJ, MacDonald JR, Mayo KH. Ovarian tumor growth regression using a combination of vascular targeting agents anginex or topomimetic 0118 and the chemotherapeutic irofulven. Cancer Lett. 2008 Jul 8;265(2):270-80. doi: 10.1016/j.canlet.2008.02.048. Epub 2008 Apr 1. PubMed PMID: 18378392; PubMed Central PMCID: PMC3042303.10: Thuret R, Massard C, Gross-Goupil M, Escudier B, Di Palma M, Bossi A, de Crevoisier R, Chauchereau A, Fizazi K. The postchemotherapy PSA surge syndrome. Ann Oncol. 2008 Jul;19(7):1308-11. doi: 10.1093/annonc/mdn062. Epub 2008 Mar 19. PubMed PMID: 18356135.1

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