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    Irofulven

    ACTIVE PHARMA INGREDIENTS

    DEVELOPMENTS

    PharmaCompass
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    2D Structure
    Also known as: Hmaf, Mgi 114, 158440-71-2, 6-hydroxymethylacylfulvene, (-)-irofulven, Mgi-114
    Molecular Formula
    C15H18O3
    Molecular Weight
    246.30  g/mol
    InChI Key
    NICJCIQSJJKZAH-AWEZNQCLSA-N
    FDA UNII
    6B799IH05A
    A novel anti-cancer compound synthesized by scientists at the University of California, San Diego more than a decade ago from toxins of the poisonous jack-o-lantern mushroom, has been granted fast track status by the U.S. Food and Drug Administration (FDA) after demonstrating promise against one of the most deadly cancers. MGI-114 (Irofulven) is currently being developed by MGI PHARMA, Inc., an emerging oncology-focused pharmaceutical company based in Minneapolis. Phase III clinical trials involving the drug have been underway since early 2001 at sites in the U.S. and Europe.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (5'R)-5'-hydroxy-1'-(hydroxymethyl)-2',5',7'-trimethylspiro[cyclopropane-1,6'-indene]-4'-one
    2.1.2 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
    2.1.3 InChI Key
    NICJCIQSJJKZAH-AWEZNQCLSA-N
    2.1.4 Canonical SMILES
    CC1=C(C2=C(C3(CC3)C(C(=O)C2=C1)(C)O)C)CO
    2.1.5 Isomeric SMILES
    CC1=C(C2=C(C3(CC3)[C@@](C(=O)C2=C1)(C)O)C)CO
    2.2 Other Identifiers
    2.2.1 UNII
    6B799IH05A
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 6-(hydroxymethyl)acylfulvene

    2. 6-hydroxymethylacylfulvene

    3. Hmaf Cpd

    4. Mgi 114

    5. Mgi-114

    6. Mgi.114

    2.3.2 Depositor-Supplied Synonyms

    1. Hmaf

    2. Mgi 114

    3. 158440-71-2

    4. 6-hydroxymethylacylfulvene

    5. (-)-irofulven

    6. Mgi-114

    7. Nsc 683863

    8. (hydroxymethyl)acylfulvene

    9. Nsc-683863

    10. (5'r)-5'-hydroxy-1'-(hydroxymethyl)-2',5',7'-trimethylspiro[cyclopropane-1,6'-indene]-4'-one

    11. 6b799ih05a

    12. Lp-100

    13. (r)-6'-hydroxy-3'-(hydroxymethyl)-2',4',6'-trimethylspiro(cyclopropane-1,5'-(5h)inden)-7'(6'h)-one

    14. 6-(hydroxymethyl)acylfulvene

    15. Acylfulvene, 6-(hydroxymethyl)-

    16. Irofulven [usan:inn]

    17. Unii-6b799ih05a

    18. Mgi.114

    19. Irofulven [inn]

    20. Irofulven [mi]

    21. Irofulven (usan/inn)

    22. Irofulven [usan]

    23. Irofulven [who-dd]

    24. Schembl8800

    25. Chembl118218

    26. Dtxsid50166423

    27. Chebi:135002

    28. Zinc3916310

    29. Bdbm50410835

    30. Nsc683863

    31. Akos027256650

    32. Db05786

    33. (r)-6'-hydroxy-3'-(hydroxymethyl)-2',4',6'-trimethylspiro[cyclopropane-1,5'-inden]-7'(6'h)-one

    34. Hy-14429

    35. Nci60_030149

    36. Spiro(cyclopropane-1,5'(5h)-inden)-7'(6'h)-one, 6'-hydroxy-3'-(hydroxymethyl)-2',4',6'-trimethyl-, (r)-

    37. Cs-0003353

    38. D04614

    39. Q6072197

    2.4 Create Date
    2005-03-26
    3 Chemical and Physical Properties
    Molecular Weight 246.30 g/mol
    Molecular Formula C15H18O3
    XLogP3-0.2
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count3
    Rotatable Bond Count1
    Exact Mass246.125594432 g/mol
    Monoisotopic Mass246.125594432 g/mol
    Topological Polar Surface Area57.5 Ų
    Heavy Atom Count18
    Formal Charge0
    Complexity558
    Isotope Atom Count0
    Defined Atom Stereocenter Count1
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Investigated for use/treatment in brain cancer, breast cancer, endometrial cancer, liver cancer, lung cancer, ovarian cancer, pancreatic cancer, pediatric indications, prostate cancer, and sarcoma.

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Antineoplastic Agents, Alkylating

    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) (See all compounds classified as Antineoplastic Agents, Alkylating.)

    Radiation-Sensitizing Agents

    Drugs used to potentiate the effectiveness of radiation therapy in destroying unwanted cells. (See all compounds classified as Radiation-Sensitizing Agents.)

    5.2 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.