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Antibiotic
Porfiromycin
Другие языки:

    Porfiromycin

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    Porfiromycin
    Porfiromycin.svg
    Clinical data
    Trade names Promycin
    ATC code
    Identifiers
    • [(4S,6S,7R,8S)-11-amino-7-methoxy-5,12-dimethyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.02,7.04,6]trideca-1(9),11-dien-8-yl]methyl carbamate
    CAS Number
    PubChem CID
    DrugBank
    ChemSpider
    KEGG
    ChEMBL
    Chemical and physical data
    Formula C16H20N4O5
    Molar mass 348.359 g·mol−1
    3D model (JSmol)
    • CC1=C(C(=O)C2=C(C1=O)N3C[C@H]4[C@@H]([C@@]3([C@@H]2COC(=O)N)OC)N4C)N
    • InChI=1S/C16H20N4O5/c1-6-10(17)13(22)9-7(5-25-15(18)23)16(24-3)14-8(19(14)2)4-20(16)11(9)12(6)21/h7-8,14H,4-5,17H2,1-3H3,(H2,18,23)/t7-,8+,14+,16-,19?/m1/s1
    • Key:HRHKSTOGXBBQCB-VFWICMBZSA-N

    Porfiromycin is an N-methyl derivative of the antineoplastic antibiotic, mitomycin C, which is isolated from various Streptomyces bacterial species. As an antineoplastic agent, it is under investigation for the treatment of cancer, particularly head and neck cancer.

    Porfiromycin works by generating oxygen radicals and alkylating DNA, resulting in interstrand cross-links and single-strand breaks. This inhibits DNA synthesis and leads to the death of cancer cells. It has a higher toxicity towards hypoxic cells, making it an attractive option for cancer treatment.

    Porfiromycin can increase the risk of methemoglobinemia when taken with certain medications. It belongs to the class of compounds known as mitomycins, which are characterized by their aziridine ring linked to a 7-amino-6-methyl-cyclohexa[b]pyrrolizine-5,8-dione structure.


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