Irofulven
Title: Irofulven
CAS Registry Number: 158440-71-2
CAS Name: (6¢R)-6¢-Hydroxy-3¢-(hydroxymethyl)-2¢,4¢,6¢-trimethylspiro[cyclopropane-1,5¢-[5H]inden]-7¢(6¢H)-one
Additional Names: (hydroxymethyl)acylfulvene; HMAF
Manufacturers' Codes: MGI-114; NSC-683863
Molecular Formula: C15H18O3
Molecular Weight: 246.30
Percent Composition: C 73.15%, H 7.37%, O 19.49%
Literature References: Semi-synthetic antitumor agent derived from illudin S, q.v. Inhibits DNA synthesis and induces apoptosis in tumor cells. Prepn: M. J. Kelner et al., US 5523490 (1996 to Univ. California); T. C. McMorris et al., J. Nat. Prod. 59, 896 (1996). Enantioselective synthesis: idem et al., J. Org. Chem. 69, 619 (2004). Effect on DNA integrity and apoptosis: J. M. Woynarowski et al., Biochem. Pharmacol. 54, 1181 (1997). Clinical pharmacokinetics and toxicology: J. Alexandre et al., Clin. Cancer Res. 10, 3377 (2004). Clinical evaluation in hormone-refractory prostate cancer: N. Senzer et al., Am. J. Clin. Oncol. 28, 36 (2005). Review: M. Baekelandt, Curr. Opin. Invest. Drugs 3, 1517-1526 (2002).
Properties: Crystals from ether, mp 127-129°. [a]D25 -639° (c = 0.096 in ethanol). Crystal density: 1.262 g/cm3. uv max (ethanol): 235, 330 nm (e 15100, 9200) with tailing to 480 nm.
Melting point: mp 127-129°
Optical Rotation: [a]D25 -639° (c = 0.096 in ethanol)
Absorption maximum: Crystal density: 1.262 g/cm3. uv max (ethanol): 235, 330 nm (e 15100, 9200) with tailing to 480 nm
Therap-Cat: Antineoplastic.
Keywords: Antineoplastic; Alkaloids/Natural Products.

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