Structure via PubChem · Public domain (PubChem)
irofulven
Sign in to saveAlso known as HMAF, 6-hydroxymethylacylfulvene
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.
Chemical data
- Formula
- C15H18O3
- Molecular weight
- 246.3 g/mol
- IUPAC name
- (5'R)-5'-hydroxy-1'-(hydroxymethyl)-2',5',7'-trimethylspiro[cyclopropane-1,6'-indene]-4'-one
- SMILES
- CC1=C(C2=C(C3(CC3)[C@@](C(=O)C2=C1)(C)O)C)CO
- InChIKey
- NICJCIQSJJKZAH-AWEZNQCLSA-N
- XLogP
- -0.2
- Polar surface area
- 57.5 Ų
- H-bond donors
- 2
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 3
- Molecule type
- Small molecule
- Indications
- pancreatic carcinoma, neoplasm, myelodysplastic syndrome, cutaneous melanoma
via ChEMBL · EBI
Research
119 papers- Morning for Irofulven, What Could be fiNER?Clinical cancer research : an official journal of the American Association for Cancer Research · 2021
- Irofulven (MGI Pharma).Current opinion in investigational drugs (London, England : 2000) · 2002
- Irofulven induces replication-dependent CHK2 activation related to p53 status.Biochemical pharmacology · 2007
- Mapping the immune-genetic architecture of aging: A single-cell causal framework for biomarker discovery and therapeutic targeting.Ageing research reviews · 2025
- Characterizations of irofulven cytotoxicity in combination with cisplatin and oxaliplatin in human colon, breast, and ovarian cancer cells.Cancer chemotherapy and pharmacology · 2006
via PubMed
Wikidata facts
- Mass
- 246.125594
- Has use
- medication
Show 4 more facts
- subject has role
- alkylating antineoplastic agent
- chemical formula
- C₁₅H₁₈O₃
- isomeric SMILES
- CC1=C(C2=C(C3(CC3)[C@@](C(=O)C2=C1)(C)O)C)CO
- canonical SMILES
- CC1=C(C2=C(C3(CC3)C(C(=O)C2=C1)(C)O)C)CO
Sources (2)
via Wikidata · CC0
~4 min read
Encyclopedic overview
4 sectionsContents
- Licensing and Clinical development
- Synthesis
- Mechanism
- 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.
Excerpted from Wikipedia’s “irofulven” article, available under the CC BY-SA 4.0 licence.