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Incyclinide
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    Incyclinide

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    Incyclinide
    Incyclinide skeletal.svg
    Clinical data
    Trade names Metastat (proposed)
    ATC code
    • none
    Legal status
    Legal status
    • Abandoned?
    Identifiers
    • (4aS,5aR,12aS)-3,10,12,12a-Tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydronaphthacen-2-carboxamide
    CAS Number
    PubChem CID
    ChemSpider
    UNII
    KEGG
    ChEMBL
    Chemical and physical data
    Formula C19H17NO7
    Molar mass 371.345 g·mol−1
    3D model (JSmol)
    • c1cc2c(c(c1)O)C(=O)C3=C([C@]4([C@@H](C[C@@H]3C2)CC(=C(C4=O)C(=O)N)O)O)O
    • InChI=1S/C19H17NO7/c20-18(26)14-11(22)6-9-5-8-4-7-2-1-3-10(21)12(7)15(23)13(8)16(24)19(9,27)17(14)25/h1-3,8-9,21-22,24,27H,4-6H2,(H2,20,26)/t8-,9-,19-/m0/s1
    • Key:ZXFCRFYULUUSDW-OWXODZSWSA-N

    Incyclinide (proposed trade name Metastat) is a chemically modified tetracycline antibiotic that was investigated in clinical trials for the treatment of rosacea, various tumours, allergic and inflammatory diseases and a number of other conditions.

    Data from animal studies suggest that centrally infused incyclinide attenuates microglial mediated neuroinflammation in the paraventricular nucleus of the hypothalamus and sympathetic activation in angiotensin II-induced hypertension. This was also associated with unique changes in gut microbial communities and profound attenuation of gut pathology in animal models of hypertension.

    Mechanism of action

    Like other tetracyclines, incyclinide inhibits matrix metalloproteinases. In contrast to traditional tetracyclines, it lacks antibiotic properties.



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