(-)-Irofulven
Basic information
- CAS
158440-71-2- Standard SMILES
CC1=C(CO)C2=C(C)C3(CC3)[C@@](C)(O)C(=O)C2=C1- InChIKey
NICJCIQSJJKZAH-AWEZNQCLSA-N- Molecular formula
- C15H18O3
- Average molar mass
- 246.3 g/mol
- Monoisotopic mass
- 246.12559443
Overview
Irofulven is a member of cyclohexenones.
Names & identifiers
- Preferred name
- (-)-Irofulven
- IUPAC
- (5'R)-5'-hydroxy-1'-(hydroxymethyl)-2',5',7'-trimethylspiro[cyclopropane-1,6'-indene]-4'-one
- English name
- (-)-Irofulven
- Molecular formula
- C15H18O3
- Molecular weight
- 246.3
Names & synonyms
Irofulven158440-71-2(-)-Irofulven6-HydroxymethylacylfulveneMGI-114(hydroxymethyl)acylfulvene6-(Hydroxymethyl)acylfulveneIrofulveneIrofulvenoNSC-683863MGI114MGI.114
Show more names
HMAFMGI 114NSC 683863(R)-Irofulven[14C]-Irofulven()Irofulven,( ) Irofulven(-)-(HydroxyMethyl)acylfulvene(6'R)-6'-Hydroxy-3'-(hydroxyMethyl)-2',4',6'-triMethylspiro[cyclopropane-1,5'-[5H]inden]-7'(6'H)-one
6B799IH05ALP-100DTXSID50166423HMAF cpdirofulvenumRefChem:791295DTXCID5088914(6'R)-6'-hydroxy-3'-(hydroxymethyl)-2',4',6'-trimethyl-6',7'-dihydrospiro(cyclopropane-1,5'-indene)-7'-one
Database identifiers
- CAS
158440-71-2- PubChem CID
- 148189
- DTXSID
DTXSID50166423- ChEMBL
CHEMBL118218- ChEBI
CHEBI:135002- UNII
- 6B799IH05A
- Nikkaji
- J805.233F
Properties
Computed structural properties
- XLogP
- -0.2
- Topological polar surface area
- 57.5 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 1
- Heavy atoms
- 18
- Formal charge
- 0
- Complexity
- 558
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Physicochemical properties
- Melting point
- 127 · 127-129°
- alpha
- 25 · D25 -639° (c = 0.096 in ethanol)
- storage temp.
- -20 °C · -20°C
- solubility
- Chloroform (Slightly), Ethyl Acetate (Slightly)
- form
- Solid
- color
- Orange
- InChI
- 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([C@](O)(C)C(=O)C3C(=C1C)C(CO)=C(C)C=3)CC2
- FDA UNII
- 6 B799IH05A · 6B799IH05A
Chemistry & industry
Pharmacology
Mechanism of Action
MGI-114(Irofulven) has unique mechanism of action as an anti-tumor agent is due to its ability to be rapidly absorbed by tumor cells. Once inside the cells, the compound binds to DNA and protein targets. This binding interferes with DNA replication and cell division of tumor cells, leading to tumor-specific apoptotic cell death, or “cell suicide.” During this process, tumor cells tend to automatically shut themselves down when they sense their function is compromised.
MeSH Pharmacological Classification
Drugs used to potentiate the effectiveness of radiation therapy in destroying unwanted cells.
A class of drugs that differs from other alkylating agents used clinically in that they are monofunctional and thus unable to cross-link cellular macromolecules. Among their common properties are a requirement for metabolic activation to intermediates with antitumor efficacy and the presence in their chemical structures of N-methyl groups, that after metabolism, can covalently modify cellular DNA. The precise mechanisms by which each of these drugs acts to kill tumor cells are not completely understood. (From AMA, Drug Evaluations Annual, 1994, p2026)
Applications
UsesSemi-synrhetic antitumor agent derived from Illudin S. Inhibits DNA synthesis and induces apoptosis in tumor cells. Antineoplastic.
Additional notes
DefinitionChEBI: Irofulven is a member of cyclohexenones.
Related reactions
7 records
Compound notes
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