Irofulven

Irofulven
Names
Preferred IUPAC name
(6′R)-6′-Hydroxy-3′-(hydroxymethyl)-2′,4′,6′-trimethylspiro[cyclopropane-1,5′-inden]-7′(6′H)-one
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
KEGG
UNII
  • 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 Y
    Key: NICJCIQSJJKZAH-AWEZNQCLSA-N Y
  • InChI=1/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
    Key: NICJCIQSJJKZAH-AWEZNQCLBL
  • O=C1C/3=C/C(=C(C\3=C(/C2([C@]1(O)C)CC2)C)CO)C
Properties
C15H18O3
Molar mass 246.302 g/mol
Density 1.285 g/mL
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references

Irofulven or 6-hydroxymethylacylfulvene (also known as HMAF and MGI-114) is an experimental cancer drug. It belongs to the family of drugs called alkylating agents.

It inhibits the DNA replication of cultured cells deficient in the nucleotide excision repair pathway.

Irofulven is an analogue of illudin S, a sesquiterpene toxin found in the Jack 'o' Lantern mushroom (Omphalotus illudens). The compound was originally synthesized by Dr. Trevor McMorris and found to have anticancer properties in mice by Dr. Michael J Kelner.