Irofulven | CAS#158440-71-2 | antitumor agent

MedKoo Cat#: 562573 | Name: Irofulven

Description:

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

Irofulven is a DNA-damaging and antitumor agent for the treatment of advanced solid tumors, including prostate, ovarian, and pancreatic cancers.

Chemical Structure

Irofulven

CAS#158440-71-2

Theoretical Analysis

MedKoo Cat#: 562573

Name: Irofulven

CAS#: 158440-71-2

Chemical Formula: C15H18O3

Exact Mass: 246.1256

Molecular Weight: 246.30

Elemental Analysis: C, 73.15; H, 7.37; O, 19.49

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 1,250.00	2 Weeks

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Related CAS #

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Synonym

Irofulven; HMAF; MGI 114; NSC-683863; MGI-114; MGI114; NSC 683863; NSC683863;

IUPAC/Chemical Name

(5'R)-5'-Hydroxy-1'-(hydroxymethyl)-2',5',7'-trimethylspiro[cyclopropane-1,6'-indene]-4'-one

InChi Key

NICJCIQSJJKZAH-AWEZNQCLSA-N

InChi Code

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

SMILES Code

O=C([C@@]1(O)C)C2=CC(C)=C(CO)C2=C(C)C31CC3

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 246.30 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: 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. 11: Kelner MJ, McMorris TC, Rojas RJ, Estes LA, Suthipinijtham P. Synergy of irofulven in combination with other DNA damaging agents: synergistic interaction with altretamine, alkylating, and platinum-derived agents in the MV522 lung tumor model. Cancer Chemother Pharmacol. 2008 Dec;63(1):19-26. doi: 10.1007/s00280-008-0703-0. Epub 2008 Feb 28. PubMed PMID: 18305940. 12: Kelner MJ, McMorris TC, Rojas RJ, Estes LA, Suthipinijtham P. Synergy of Irofulven in combination with various anti-metabolites, enzyme inhibitors, and miscellaneous agents in MV522 lung carcinoma cells: marked interaction with gemcitabine and 5-fluorouracil. Invest New Drugs. 2008 Oct;26(5):407-15. doi: 10.1007/s10637-008-9113-8. Epub 2008 Jan 29. PubMed PMID: 18227973. 13: McMorris TC, Chimmani R, Gurram M, Staake MD, Kelner MJ. Synthesis and antitumor activity of amine analogs of irofulven. Bioorg Med Chem Lett. 2007 Dec 15;17(24):6770-2. Epub 2007 Oct 17. PubMed PMID: 17977722. 14: Bayés M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2007 Jul-Aug;29(6):427-37. PubMed PMID: 17922073. 15: Bayés M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2007 Jun;29(5):359-73. PubMed PMID: 17805439. 16: Alexandre J, Kahatt C, Bertheault-Cvitkovic F, Faivre S, Shibata S, Hilgers W, Goldwasser F, Lokiec F, Raymond E, Weems G, Shah A, MacDonald JR, Cvitkovic E. A phase I and pharmacokinetic study of irofulven and capecitabine administered every 2 weeks in patients with advanced solid tumors. Invest New Drugs. 2007 Oct;25(5):453-62. Epub 2007 Jul 13. PubMed PMID: 17628744. 17: Wiltshire T, Senft J, Wang Y, Konat GW, Wenger SL, Reed E, Wang W. BRCA1 contributes to cell cycle arrest and chemoresistance in response to the anticancer agent irofulven. Mol Pharmacol. 2007 Apr;71(4):1051-60. Epub 2007 Jan 17. PubMed PMID: 17229870. 18: Wang Y, Wiltshire T, Senft J, Wenger SL, Reed E, Wang W. Fanconi anemia D2 protein confers chemoresistance in response to the anticancer agent, irofulven. Mol Cancer Ther. 2006 Dec;5(12):3153-61. PubMed PMID: 17172419. 19: Wang Y, Wiltshire T, Senft J, Reed E, Wang W. Irofulven induces replication-dependent CHK2 activation related to p53 status. Biochem Pharmacol. 2007 Feb 15;73(4):469-80. Epub 2006 Oct 27. PubMed PMID: 17118344; PubMed Central PMCID: PMC1800887. 20: Paci A, Rezai K, Deroussent A, De Valeriola D, Re M, Weill S, Cvitkovic E, Kahatt C, Shah A, Waters S, Weems G, Vassal G, Lokiec F. Pharmacokinetics, metabolism, and routes of excretion of intravenous irofulven in patients with advanced solid tumors. Drug Metab Dispos. 2006 Nov;34(11):1918-26. Epub 2006 Aug 8. PubMed PMID: 16896064.