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    Larazotide Acetate

    ACTIVE PHARMA INGREDIENTS

    DEVELOPMENTS

    DIGITAL CONTENT

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    2D Structure
    Also known as: 258818-34-7, 258818-34-7 (free base), At-2347, 2-[[(2s)-1-[(2s)-5-amino-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[2-[(2-aminoacetyl)amino]acetyl]amino]-3-methylbutanoyl]amino]-4-methylpentanoyl]amino]-3-methylbutanoyl]amino]-5-oxopentanoyl]pyrrolidine-2-carbonyl]amino]acetic acid, Glycylglycyl-l-valyl-l-leucyl-l-valyl-l-glutaminyl-l-prolylglycine, Larazotide [usan:inn]
    Molecular Formula
    C32H55N9O10
    Molecular Weight
    725.8  g/mol
    InChI Key
    ORFLZNAGUTZRLQ-ZMBVWFSWSA-N
    An octapeptide inhibitor of paracellular permeability whose structure is derived from a protein (zonula occludens toxin) secreted by Vibrio cholerae for treatment of Coeliac disease.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    2-[[(2S)-1-[(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[2-[(2-aminoacetyl)amino]acetyl]amino]-3-methylbutanoyl]amino]-4-methylpentanoyl]amino]-3-methylbutanoyl]amino]-5-oxopentanoyl]pyrrolidine-2-carbonyl]amino]acetic acid
    2.1.2 InChI
    InChI=1S/C32H55N9O10/c1-16(2)12-20(38-30(49)26(17(3)4)39-24(44)14-35-23(43)13-33)28(47)40-27(18(5)6)31(50)37-19(9-10-22(34)42)32(51)41-11-7-8-21(41)29(48)36-15-25(45)46/h16-21,26-27H,7-15,33H2,1-6H3,(H2,34,42)(H,35,43)(H,36,48)(H,37,50)(H,38,49)(H,39,44)(H,40,47)(H,45,46)/t19-,20-,21-,26-,27-/m0/s1
    2.1.3 InChI Key
    ORFLZNAGUTZRLQ-ZMBVWFSWSA-N
    2.1.4 Canonical SMILES
    CC(C)CC(C(=O)NC(C(C)C)C(=O)NC(CCC(=O)N)C(=O)N1CCCC1C(=O)NCC(=O)O)NC(=O)C(C(C)C)NC(=O)CNC(=O)CN
    2.1.5 Isomeric SMILES
    CC(C)C[C@@H](C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCC(=O)N)C(=O)N1CCC[C@H]1C(=O)NCC(=O)O)NC(=O)[C@H](C(C)C)NC(=O)CNC(=O)CN
    2.2 Synonyms
    2.2.1 Depositor-Supplied Synonyms

    1. 258818-34-7

    2. 258818-34-7 (free Base)

    3. At-2347

    4. 2-[[(2s)-1-[(2s)-5-amino-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[2-[(2-aminoacetyl)amino]acetyl]amino]-3-methylbutanoyl]amino]-4-methylpentanoyl]amino]-3-methylbutanoyl]amino]-5-oxopentanoyl]pyrrolidine-2-carbonyl]amino]acetic Acid

    5. Glycylglycyl-l-valyl-l-leucyl-l-valyl-l-glutaminyl-l-prolylglycine

    6. Larazotide [usan:inn]

    7. Unii-zn3r5560zv

    8. Larazotide-acetate

    9. At 2347

    10. Larazotide (usan/inn)

    11. Zn3r5560zv

    12. Chembl2105646

    13. Dtxsid30180526

    14. Chebi:177799

    15. Zinc68009799

    16. Db05645

    17. H-gly-gly-val-leu-val-gln-pro-gly-oh

    18. Hy-106268

    19. Cs-0025478

    20. D09351

    21. 818l347

    22. Q27295752

    2.3 Create Date
    2006-10-25
    3 Chemical and Physical Properties
    Molecular Weight 725.8 g/mol
    Molecular Formula C32H55N9O10
    XLogP3-3.6
    Hydrogen Bond Donor Count9
    Hydrogen Bond Acceptor Count11
    Rotatable Bond Count21
    Exact Mass725.40718899 g/mol
    Monoisotopic Mass725.40718899 g/mol
    Topological Polar Surface Area301 Ų
    Heavy Atom Count51
    Formal Charge0
    Complexity1290
    Isotope Atom Count0
    Defined Atom Stereocenter Count5
    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 autoimmune diseases, diabetes mellitus type 1, and gastrointestinal diseases and disorders (miscellaneous).

    5 Pharmacology and Biochemistry
    5.1 Mechanism of Action

    AT-1001 is an orally administered octapeptide zonulin receptor antagonist that appears to exert its inhibitory effect on gliadin-induced tight junction disassembly by blocking putative zonulin receptors on the luminal surface of the small intestine.