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Substance Name: Irofulven [USAN:INN]
RN: 158440-71-2
UNII: 6B799IH05A
InChIKey: NICJCIQSJJKZAH-AWEZNQCLSA-N

Note

  • NCI: A semisynthetic sesquiterpene derivative of illudin S, a natural toxin isolated from the fungus Omphalotus illudens. Irofulven alkylates DNA and protein macromolecules, forms adducts, and arrests cells in the S-phase of the cell cycle. This agent requires NADPH-dependent metabolism by alkenal/one oxidoreductase for activity. Irofulven is more active in vitro against tumor cells of epithelial origin and is more resistant to deactivation by p53 loss and MDR1 than other alkylating agents. Check for active clinical trials or closed clinical trials using this agent. (NCI Thesaurus)

Molecular Formula

  • C15-H18-O3

Molecular Weight

  • 246.304
 

Classification Codes

  • Alkylating Agents
  • Antineoplastic (DNA Synthesis Inhibitor/Apoptosis Inducer)
  • Antineoplastic Agents
  • Antineoplastic Agents, Alkylating
  • Natural Product
  • Noxae
  • Radiation-Sensitizing Agents
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Names and Synonyms

Name of Substance

  • 6-(Hydroxymethyl)acylfulvene
  • Irofulven [USAN:INN]

Synonyms

  • (R)-6'-Hydroxy-3'-(hydroxymethyl)-2',4',6'-trimethylspiro(cyclopropane-1,5'-(5H)inden)-7'(6'H)-one
  • 6-(Hydroxymethyl)acylfulvene
  • Acylfulvene, 6-(hydroxymethyl)-
  • HMAF
  • Irofulven
  • MGI 114
  • NSC 683863
  • UNII-6B799IH05A

Systematic Name

  • Spiro(cyclopropane-1,5'(5H)-inden)-7'(6'H)-one, 6'-hydroxy-3'-(hydroxymethyl)-2',4',6'-trimethyl-, (R)-

Registry Numbers

CAS Registry Number

  • 158440-71-2

FDA UNII

  • 6B799IH05A

System Generated Number

  • 0158440712

Structure Descriptors

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

Smiles

C12(CC1)C(=C1C(=C(C=C1C([C@]2(C)O)=O)C)CO)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LDLo intravenous 2mg/kg (2mg/kg) BLOOD: CHANGES IN BONE MARROW NOT INCLUDED ABOVE

BLOOD: THROMBOCYTOPENIA

BLOOD: CHANGES IN OTHER CELL COUNT (UNSPECIFIED)
Fundamental and Applied Toxicology. Vol. 36(1,
rat LD intravenous > 6610ug/kg (6.61mg/kg) BLOOD: CHANGES IN BONE MARROW NOT INCLUDED ABOVE

CARDIAC: OTHER CHANGES

BLOOD: CHANGES IN OTHER CELL COUNT (UNSPECIFIED)
Fundamental and Applied Toxicology. Vol. 36(1,