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    Darinaparsin

    DEVELOPMENTS

    DIGITAL CONTENT

    PharmaCompass
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    2D Structure
    Also known as: 69819-86-9, Zinapar, Zio-101, Dmas(iii)g, Sp-02l, Zio 101
    Molecular Formula
    C12H22AsN3O6S
    Molecular Weight
    411.31  g/mol
    InChI Key
    JGDXFQORBMPJGR-YUMQZZPRSA-N
    FDA UNII
    9XX54M675G
    Darinaparsin is a small-molecule organic arsenical with potential antineoplastic activity. Although the exact mechanism of action is unclear, darinaparsin, a highly toxic metabolic intermediate of inorganic arsenicals (iAs) that occurs in vivo, appears to generate volatile cytotoxic arsenic compounds when glutathione (GSH) concentrations are low. The arsenic compounds generated from darinaparsin disrupt mitochondrial bioenergetics, producing reactive oxygen species (ROS) and inducing ROS-mediated tumor cell apoptosis; in addition, this agent or its byproducts may initiate cell death by interrupting the G2/M phase of the cell cycle and may exhibit antiangiogenic effects. Compared to inorganic arsenic compounds such as arsenic trioxide (As2O3), darinaparsin appears to exhibit a wide therapeutic window.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (2S)-2-amino-5-[[(2R)-1-(carboxymethylamino)-3-dimethylarsanylsulfanyl-1-oxopropan-2-yl]amino]-5-oxopentanoic acid
    2.1.2 InChI
    InChI=1S/C12H22AsN3O6S/c1-13(2)23-6-8(11(20)15-5-10(18)19)16-9(17)4-3-7(14)12(21)22/h7-8H,3-6,14H2,1-2H3,(H,15,20)(H,16,17)(H,18,19)(H,21,22)/t7-,8-/m0/s1
    2.1.3 InChI Key
    JGDXFQORBMPJGR-YUMQZZPRSA-N
    2.1.4 Canonical SMILES
    C[As](C)SCC(C(=O)NCC(=O)O)NC(=O)CCC(C(=O)O)N
    2.1.5 Isomeric SMILES
    C[As](C)SC[C@@H](C(=O)NCC(=O)O)NC(=O)CC[C@@H](C(=O)O)N
    2.2 Other Identifiers
    2.2.1 UNII
    9XX54M675G
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Clarinaparsin

    2. Dimethylarsinous Glutathione

    3. Dmas(iii)g

    4. Dmas(iii)sg

    5. S-(dimethylarsino)-glutathione

    6. S-(dimethylarsino)glutathione

    7. S-dimethylarsino-glutathione

    8. Zio 101

    9. Zio-101

    10. Zio101

    2.3.2 Depositor-Supplied Synonyms

    1. 69819-86-9

    2. Zinapar

    3. Zio-101

    4. Dmas(iii)g

    5. Sp-02l

    6. Zio 101

    7. 9xx54m675g

    8. Glycine, L-gamma-glutamyl-s-(dimethylarsino)-l-cysteinyl-

    9. Clarinaparsin

    10. (s)-2-amino-5-(((r)-1-((carboxymethyl)amino)-3-((dimethylarsino)thio)-1-oxopropan-2-yl)amino)-5-oxopentanoic Acid

    11. Darinaparsin [usan]

    12. Dmas(iii)sg

    13. Darinaparsin [usan:inn]

    14. Dimethylarsinous Glutathione

    15. S-dimethylarsino-glutathione

    16. S-(dimethylarsino)glutathione

    17. S-(dimethylarsino)-glutathione

    18. Unii-9xx54m675g

    19. Zio101

    20. Sglu1

    21. Darinaparsin [mi]

    22. S-dimethylarsinoglutathione

    23. Darinaparsin (jan/usan)

    24. Darinaparsin [inn]

    25. Darinaparsin [jan]

    26. S-dimethylarsino Glutathione

    27. Darinaparsin [who-dd]

    28. Schembl411358

    29. Sp02

    30. Chembl3247378

    31. Chebi:94295

    32. Zio-101-c

    33. Dtxsid80220108

    34. Bcp15637

    35. Db06179

    36. Hy-14943

    37. Zio 101; Zio101; Zio-101

    38. D08898

    39. Brd-k35723520-001-01-0

    40. Q27166111

    41. Glycine, L-gamma-glutamyl-s-(dimethylarsino)-l-cysteinyl

    42. L-gamma-glutamyl-s-(dimethylarsanyl)-l-cysteinylglycine

    43. L-gamma-glutamyl-s-(dimethylarsino)-l-cysteinyl-glycine

    44. Glycine, L-.gamma.-glutamyl-s-(dimethylarsino)-l-cysteinyl-

    45. (2s)-2-amino-5-[[(2r)-1-(carboxymethylamino)-3-dimethylarsanylsulfanyl-1-oxopropan-2-yl]amino]-5-oxopentanoic Acid

    2.4 Create Date
    2006-10-26
    3 Chemical and Physical Properties
    Molecular Weight 411.31 g/mol
    Molecular Formula C12H22AsN3O6S
    Hydrogen Bond Donor Count5
    Hydrogen Bond Acceptor Count8
    Rotatable Bond Count11
    Exact Mass411.044526 g/mol
    Monoisotopic Mass411.044526 g/mol
    Topological Polar Surface Area184 Ų
    Heavy Atom Count23
    Formal Charge0
    Complexity449
    Isotope Atom Count0
    Defined Atom Stereocenter Count2
    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 blood (blood forming organ disorders, unspecified), cancer/tumors (unspecified), solid tumors, multiple myeloma, and liver cancer.