| Stereochemistry | ABSOLUTE |
| Molecular Formula | C15H18O3 |
| Molecular Weight | 246.3016 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1=C(CO)C2=C(C)C3(CC3)[C@@](C)(O)C(=O)C2=C1
InChI
InChIKey=NICJCIQSJJKZAH-AWEZNQCLSA-N
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
| Molecular Formula | C15H18O3 |
| Molecular Weight | 246.3016 |
| Charge | 0 |
| Count |
MOL RATIO
1 MOL RATIO (average) |
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
IROFULVEN is a semisynthetic derivative of a natural sesquiterpene toxin illudin S, isolated from the fungus Omphalotus illudens. It alkylates DNA and protein macromolecules, forms adducts, and arrests cells in the S-phase of the cell cycle. It 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 P-glycoprotein than other alkylating agents. IROFULVEN has been evaluated in 19 clinical trials, predominantly in refractory prostate and ovarian cancer patients. Results were positive, including a 10% response rate in patients with prostate cancer previously treated with docetaxel and 13% in ovarian cancer patients relapsing between 6 and 12 months after standard treatment with carboplatin and paclitaxel.
