Irofulven

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Irofulven
200px
IUPAC name (5'R)-5'-hydroxy-1'-(hydroxymethyl)-2',5',7'-trimethyl-
spiro[cyclopropane-1,6'-indene]-4'-one
Identifiers
CAS number
PubChem 148189
SMILES C[C@@]1(O)[C@]2(CC2)C(C)=C3C(C1=O)=CC(C)=C3CO
Properties
Molecular formula C15H18O3
Molar mass 246.302 g/mol
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

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Overview

Irofulven or 6-hydroxymethylacylfulvene (also known as HMAF of MGI-114) is a substance that is used in the treatment of cancer. It belongs to the family of drugs called alkylating agents.

Irofulven is an analogue of illudin S, a sesquiterpene toxin found in mushrooms of the genus Omphalotus. The compound was oringally synthesized by Dr. Trevor McMorris (UCSD) and found to have anticancer properties by Dr. Michael J Kelner (UCSD).[1]

References

Kelner MJ, McMorris TC, Estes L, Wang W, Samson KM, Taetle R. Efficacy of HMAF (MGI-114) in the MV522 metastatic lung carcinoma xenograft model nonresponsive to traditional anticancer agents. Invest New Drugs 14(2) 161-167, 1996

  1. MacDonald JR, Muscoplat CC, Dexter DL, Mangold GL, Chen SF, Kelner MJ, McMorris TC, Von Hoff DD (1997). "Preclinical antitumor activity of 6-hydroxymethylacylfulvene, a semisynthetic derivative of the mushroom toxin illudin S". Cancer Res. 57 (2): 279–83. PMID 9000568.  Free full text

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