Irofulven

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Irofulven
IUPAC name	(5'R)-5'-hydroxy-1'-(hydroxymethyl)-2',5',7'-trimethyl- spiro[cyclopropane-1,6'-indene]-4'-one
Identifiers
CAS number
PubChem	148189
SMILES	C[C@@]1(O)[C@]2(CC2)C(C)=C3C(C1=O)=CC(C)=C3CO
Properties
Molecular formula	C15H18O3
Molar mass	246.302 g/mol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Irofulven or 6-hydroxymethylacylfulvene (also known as HMAF of MGI-114) is a substance that is used in the treatment of cancer. It belongs to the family of drugs called alkylating agents.

Irofulven is an analogue of illudin S, a sesquiterpene toxin found in mushrooms of the genus Omphalotus. The compound was oringally synthesized by Dr. Trevor McMorris (UCSD) and found to have anticancer properties by Dr. Michael J Kelner (UCSD).^[1]

[edit] References

1. ^ MacDonald JR, Muscoplat CC, Dexter DL, Mangold GL, Chen SF, Kelner MJ, McMorris TC, Von Hoff DD (1997). "Preclinical antitumor activity of 6-hydroxymethylacylfulvene, a semisynthetic derivative of the mushroom toxin illudin S". Cancer Res. 57 (2): 279–83. PMID 9000568.  Free full text

Kelner MJ, McMorris TC, Estes L, Wang W, Samson KM, Taetle R. Efficacy of HMAF (MGI-114) in the MV522 metastatic lung carcinoma xenograft model nonresponsive to traditional anticancer agents. Invest New Drugs 14(2) 161-167, 1996

v • d • e Chemotherapeutic agents/Antineoplastic agents (L01) Alkylating and alkylating-like agents Nitrogen mustards: (Chlorambucil, Chlormethine, Cyclophosphamide, Ifosfamide, Melphalan, Bendamustine, Uramustine) Nitrosoureas:(Carmustine, Fotemustine, Lomustine, Streptozocin) Platinum (alkylating-like): (Carboplatin, Cisplatin, Oxaliplatin, Triplatin tetranitrate, Satraplatin) Alkyl sulfonates:(Busulfan, Treosulfan) Hydrazines:(Procarbazine, Dacarbazine, Temozolomide) Aziridines:(ThioTEPA) Antimetabolites Folic acid: (Aminopterin, Methotrexate, Pemetrexed, Raltitrexed). Purine:(Cladribine, Clofarabine, Fludarabine, Mercaptopurine, Pentostatin, Thioguanine) Pyrimidine:(Capecitabine, Cytarabine, Decitabine, Fluorouracil, Floxuridine, Gemcitabine) Spindle poison/mitotic inhibitor Taxane: (Docetaxel, Larotaxel, Paclitaxel). Vinca: (Vinblastine, Vincristine, Vindesine, Vinorelbine). Cytotoxic/antitumor antibiotics Anthracycline family: (Daunorubicin, Doxorubicin, Epirubicin, Idarubicin, Mitoxantrone, Pixantrone, Valrubicin) streptomyces (Actinomycin, Bleomycin, Mitomycin, Plicamycin) - Hydroxyurea Topoisomerase inhibitors Camptotheca: (Camptothecin, Topotecan, Irinotecan, Rubitecan), Podophyllum:(Etoposide, Teniposide) CI monoclonal antibodies Receptor tyrosine kinase (Cetuximab, Panitumumab, Trastuzumab) - CD20 (Rituximab, Tositumomab) - other (Alemtuzumab, Bevacizumab, Gemtuzumab) Photosensitizers Aminolevulinic acid, Methyl aminolevulinate, Porfimer sodium, Verteporfin Tyrosine kinase inhibitors Axitinib, Bosutinib, Cediranib, Dasatinib, Erlotinib, Gefitinib, Imatinib, Lapatinib, Lestaurtinib, Nilotinib, Semaxanib, Sorafenib, Sunitinib, Vandetanib Cyclin-dependent kinase inhibitor Seliciclib Other retinoids (Alitretinoin, Tretinoin), Fusion protein (Aflibercept) - Altretamine, Amsacrine, Anagrelide, Arsenic trioxide, Asparaginase (Pegaspargase), Bexarotene, Bortezomib, Celecoxib, Denileukin diftitox, Elesclomol, Estramustine, Irofulven, Ixabepilone, Masoprocol, Mitotane, Oblimersen, Testolactone, Tipifarnib, Trabectedin