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    Isatidine

    REF. STANDARDS & IMPURITIES

    PharmaCompass
    Xls

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    2D Structure
    Also known as: Retrorsine n-oxide, 15503-86-3, (5r,6s,9a1r,14ar,z)-3-ethylidene-6-hydroxy-6-(hydroxymethyl)-5-methyl-2,7-dioxo-3,4,5,6,7,9,9a1,11,12,13,14,14a-dodecahydro-2h-[1,6]dioxacyclododecino[2,3,4-gh]pyrrolizine 12-oxide, [1,6]dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione, 3-ethylidene-3,4,5,6,9,11,13,14,14a,14b-decahydro-6-hydroxy-6-(hydroxymethyl)-5-methyl-, 12-oxide, (3z,5r,6s,14ar,14br)-, Chebi:5977, Dtxsid4020747
    Molecular Formula
    C18H25NO7
    Molecular Weight
    367.4  g/mol
    InChI Key
    IDIMIWQPUHURPV-WTWIWYCDSA-N
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (1R,4Z,6R,7S,17R)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-14-oxido-2,9-dioxa-14-azoniatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione
    2.1.2 InChI
    InChI=1S/C18H25NO7/c1-3-12-8-11(2)18(23,10-20)17(22)25-9-13-4-6-19(24)7-5-14(15(13)19)26-16(12)21/h3-4,11,14-15,20,23H,5-10H2,1-2H3/b12-3-/t11-,14-,15-,18-,19?/m1/s1
    2.1.3 InChI Key
    IDIMIWQPUHURPV-WTWIWYCDSA-N
    2.1.4 Canonical SMILES
    CC=C1CC(C(C(=O)OCC2=CC[N+]3(C2C(CC3)OC1=O)[O-])(CO)O)C
    2.1.5 Isomeric SMILES
    C/C=C\1/C[C@H]([C@@](C(=O)OCC2=CC[N+]3([C@H]2[C@@H](CC3)OC1=O)[O-])(CO)O)C
    2.2 Synonyms
    2.2.1 MeSH Synonyms

    1. Ret-no

    2. Retrorsine N-oxide

    2.2.2 Depositor-Supplied Synonyms

    1. Retrorsine N-oxide

    2. 15503-86-3

    3. (5r,6s,9a1r,14ar,z)-3-ethylidene-6-hydroxy-6-(hydroxymethyl)-5-methyl-2,7-dioxo-3,4,5,6,7,9,9a1,11,12,13,14,14a-dodecahydro-2h-[1,6]dioxacyclododecino[2,3,4-gh]pyrrolizine 12-oxide

    4. [1,6]dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione, 3-ethylidene-3,4,5,6,9,11,13,14,14a,14b-decahydro-6-hydroxy-6-(hydroxymethyl)-5-methyl-, 12-oxide, (3z,5r,6s,14ar,14br)-

    5. Chebi:5977

    6. Dtxsid4020747

    7. Retrorsine-n-oxide , Hplc Grade

    8. Zinc4098666

    9. Mfcd00074872

    10. Hy-116832

    11. Cs-0066628

    12. Q27106956

    13. (3z,5r,6s,14ar,14br)-3-ethylidene-6-hydroxy-6-(hydroxymethyl)-5-methyl-3,4,5,6,9,11,13,14,14a,14b-decahydro[1,6]dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione 12-oxide

    2.3 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 367.4 g/mol
    Molecular Formula C18H25NO7
    XLogP30
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count7
    Rotatable Bond Count1
    Exact Mass367.16310214 g/mol
    Monoisotopic Mass367.16310214 g/mol
    Topological Polar Surface Area111 Ų
    Heavy Atom Count26
    Formal Charge0
    Complexity673
    Isotope Atom Count0
    Defined Atom Stereocenter Count4
    Undefined Atom Stereocenter Count1
    Defined Bond Stereocenter Count1
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Pharmacology and Biochemistry
    4.1 Metabolism/Metabolites

    Isatidine is not converted into pyrrolic metabolites by isolated rat liver microsomes. It is, However, reduced to retrorsine in the intestinal tract of rats, possibly by the gut flora, thus accounting for the large increase in toxicity when isatidine is administered by mouth rather than parenterally.

    IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V10 272 (1976)

    4.2 Mechanism of Action

    Levels of pyrrolic metabolites bound to liver tissues and responsible for hepatotoxicity in rats given pyrrolizidine alkaloids did not reflect rates of formation of such metabolites measured in vitro. In animals, additional factors could influence formation and tissue binding of pyrrolic metabolites, including detoxication of alkaloids by hydrolysis and chemical reactivity and stability of toxic metabolites.

    PMID:6825198 Mattocks A et al;Chem-Biol Interact 43(2): 209 (1983)