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    Technical details about Prestwick2_001008, learn more about the structure, uses, toxicity, action, side effects and more

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    Prestwick2_001008

    APIs // Active Pharmaceutical Ingredients

    PharmaCompass

    Minakem offers CDMO services for API & HPAPI, generics, regulatory expertise, track record performance & FDA & GMP certifications.

    ChemWerth works in generic API development & supply, non-infringement patent strategy development and regulatory support.

    2D Structure
    Also known as: 39492-01-8, Gabexate [inn], Ethyl 4-[6-(diaminomethylideneamino)hexanoyloxy]benzoate, Chembl87563, Ethyl p-hydroxybenzoate 6-guanidinohexanoate, Gabexate (inn)
    Molecular Formula
    C16H23N3O4
    Molecular Weight
    321.37  g/mol
    InChI Key
    YKGYIDJEEQRWQH-UHFFFAOYSA-N
    FDA UNII
    4V7M9137X9
    A serine proteinase inhibitor used therapeutically in the treatment of pancreatitis, disseminated intravascular coagulation (DIC), and as a regional anticoagulant for hemodialysis. The drug inhibits the hydrolytic effects of thrombin, plasmin, and kallikrein, but not of chymotrypsin and aprotinin.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    ethyl 4-[6-(diaminomethylideneamino)hexanoyloxy]benzoate
    2.1.2 InChI
    InChI=1S/C16H23N3O4/c1-2-22-15(21)12-7-9-13(10-8-12)23-14(20)6-4-3-5-11-19-16(17)18/h7-10H,2-6,11H2,1H3,(H4,17,18,19)
    2.1.3 InChI Key
    YKGYIDJEEQRWQH-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CCOC(=O)C1=CC=C(C=C1)OC(=O)CCCCCN=C(N)N
    2.2 Other Identifiers
    2.2.1 UNII
    4V7M9137X9
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Foy

    2. Gabexate Mesilate

    3. Gabexate Mesylate

    4. Gabexate Methanesulfonate

    5. Gabexate Monomethanesulfonate

    6. Gabexate Monomethanesulfonate, 14c Labeled Cpd

    7. Gabexate Monomethanesulfonate, 14c-labeled Cpd

    8. Mesilate, Gabexate

    9. Mesylate, Gabexate

    10. Methanesulfonate, Gabexate

    11. Monomethanesulfonate, Gabexate

    2.3.2 Depositor-Supplied Synonyms

    1. 39492-01-8

    2. Gabexate [inn]

    3. Ethyl 4-[6-(diaminomethylideneamino)hexanoyloxy]benzoate

    4. Chembl87563

    5. Ethyl P-hydroxybenzoate 6-guanidinohexanoate

    6. Gabexate (inn)

    7. 4v7m9137x9

    8. Gabexato

    9. Gabexatum

    10. Gabexatum [inn-latin]

    11. Gabexato [inn-spanish]

    12. Methanesulfonic Acid Ethyl 4-[(6-carbamimidamidohexanoyl)oxy]benzoate

    13. Unii-4v7m9137x9

    14. Gabexate [jan]

    15. Gabexate [mi]

    16. Prestwick0_001008

    17. Prestwick1_001008

    18. Prestwick2_001008

    19. Prestwick3_001008

    20. Gabexate [who-dd]

    21. Benzoic Acid, 4-((6-((aminoiminomethyl)amino)-1-oxohexyl)oxy)-, Ethyl Ester

    22. Bspbio_001135

    23. Schembl446024

    24. Spbio_003016

    25. Bpbio1_001249

    26. Gtpl7863

    27. Dtxsid9048566

    28. Schembl13287301

    29. Chebi:93036

    30. Zinc2002226

    31. Bdbm50104435

    32. Db12831

    33. Ethyl 4-(6-guanidinohexanoyloxy)benzoate

    34. Ncgc00025297-01

    35. Ncgc00025297-02

    36. Ncgc00025297-10

    37. Ls-14525

    38. Sbi-0207080.p001

    39. Ethyl 4-((6-guanidinohexanoyl)oxy)benzoate

    40. Ethyl-p-(6-guanidinohex-anoyloxy)-benzoate

    41. Ab00513998

    42. D08004

    43. Ab00513998_02

    44. Q5515384

    45. 4-(6-guanidino-hexanoyloxy)-benzoic Acid Ethyl Ester

    46. Brd-k59256312-066-03-3

    47. Ethyl 4-({6-[(diaminomethylidene)amino]hexanoyl}oxy)benzoate

    48. 4-[6-(diaminomethylideneamino)-1-oxohexoxy]benzoic Acid Ethyl Ester

    2.4 Create Date
    2005-03-25
    3 Chemical and Physical Properties
    Molecular Weight 321.37 g/mol
    Molecular Formula C16H23N3O4
    XLogP31.4
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count11
    Exact Mass321.16885622 g/mol
    Monoisotopic Mass321.16885622 g/mol
    Topological Polar Surface Area117 Ų
    Heavy Atom Count23
    Formal Charge0
    Complexity400
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    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

    No approved indication.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Gabexate bind and inhibits serine proteases in the coagulation cascade to prevent blood clotting. It also prevents proteolytic destruction of IkappaB resulting in suppression of the nuclear factor kappa-B signalling pathway. Ultimately this decreases the production of inflammatory cytokines such as tumor necrosis factor alpha which are produced as a result of NFkappaB activation.

    5.2 MeSH Pharmacological Classification

    Anticoagulants

    Agents that prevent BLOOD CLOTTING. (See all compounds classified as Anticoagulants.)

    Serine Proteinase Inhibitors

    Exogenous or endogenous compounds which inhibit SERINE ENDOPEPTIDASES. (See all compounds classified as Serine Proteinase Inhibitors.)

    5.3 Mechanism of Action

    Gabexate inhibits kallikrein, plasmin, and thrombin by binding to their active sites. The inhibition of these components of the coagulation cascade ultimately prevents the formation of fibrin which must be present and polymerized to form a clot. Gabexate decreases the production of inflammatory cytokines by attenuating NFkappaB and c-Jun N-terminal kinase (JNK) pathway activity. The exact mechanism for this is unknown but it is thought that gabexate prevents the proteolyytic destruction of IkappaB which deactivates NFkappaB and interferes with activator protein 1 binding to DNA.

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