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    Also known as: 5714-73-8, Hiprex, Hexamine hippurate, Hexamethylenetetramine monohippurate, Hexamethylenetetramine hippurate, 1,3,5,7-tetraazaadamantane benzoylglycinate
    Molecular Formula
    C15H21N5O3
    Molecular Weight
    319.36  g/mol
    InChI Key
    ROAIXOJGRFKICW-UHFFFAOYSA-N
    FDA UNII
    M329791L57
    Methenamine Hippurate
    Methenamine Hippurate is the hippurate salt form of methenamine, a prodrug and inactive weak base that slowly hydrolyzes in acidic urine to ammonia and the effective, urinary tract antiseptic formaldehyde. Formaldehyde probably exerts its antibacterial effect by denaturation of protein. Depending on the urinary concentrations, formaldehyde is either bactericidal or bacteriostatic. Formaldehyde urinary concentrations are dependent on urine pH, volume, and flow rate. Formaldehyde acts as an antibacterial agent against gram-positive and gram-negative organisms.
    1 2D Structure

    Methenamine Hippurate

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    2-benzamidoacetic acid;1,3,5,7-tetrazatricyclo[3.3.1.13,7]decane
    2.1.2 InChI
    InChI=1S/C9H9NO3.C6H12N4/c11-8(12)6-10-9(13)7-4-2-1-3-5-7;1-7-2-9-4-8(1)5-10(3-7)6-9/h1-5H,6H2,(H,10,13)(H,11,12);1-6H2
    2.1.3 InChI Key
    ROAIXOJGRFKICW-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    C1N2CN3CN1CN(C2)C3.C1=CC=C(C=C1)C(=O)NCC(=O)O
    2.2 Other Identifiers
    2.2.1 UNII
    M329791L57
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Hexamine Hippurate

    2. Hip-rex

    3. Hiprex

    4. Urex

    5. Urotractan

    2.3.2 Depositor-Supplied Synonyms

    1. 5714-73-8

    2. Hiprex

    3. Hexamine Hippurate

    4. Hexamethylenetetramine Monohippurate

    5. Hexamethylenetetramine Hippurate

    6. 1,3,5,7-tetraazaadamantane Benzoylglycinate

    7. Methenamine (hippurate)

    8. Hippramine

    9. Haiprex

    10. Viapta

    11. 2-benzamidoacetic Acid;1,3,5,7-tetrazatricyclo[3.3.1.13,7]decane

    12. M329791l57

    13. Glycine, N-benzoyl, Compd. With 1,3,5,7-tetraazatricyclo(3.3.1.1(sup 3,7))decane (1:1)

    14. Hexamethylenetetramine Monohippurate;hexamethylenetetramine Monohippurate

    15. Methenamine Hippurate [usan]

    16. R-657

    17. Einecs 227-206-5

    18. Hexamethylene Tetramine Hippurate

    19. Unii-m329791l57

    20. Hiprex (tn)

    21. Urex (tn)

    22. Hippuric Acid, Compd. With Hexamethylenetetramine (1:1)

    23. Methenamine Hippurate [usan:usp:inn:ban]

    24. Schembl3029

    25. Chebi:6825

    26. Chembl1201104

    27. Dtxsid10972603

    28. Methenamine Hippurate (jan/usp)

    29. Methenamine Hippurate [jan]

    30. Hy-b1691

    31. Methenamine Hippurate [vandf]

    32. Mfcd00072147

    33. S9466

    34. Methenamine Hippurate [mart.]

    35. Akos037645132

    36. Methenamine Hippurate [usp-rs]

    37. Methenamine Hippurate [who-dd]

    38. N-benzoylglycine, Compound With 1,3,5,7-tetraazatricyclo(3.3.1.13,7)decane (1:1)

    39. Methenamine Hippurate (200 Mg)

    40. As-57463

    41. Methenamine Hippurate [orange Book]

    42. Methenamine Hippurate [usp Impurity]

    43. Cs-0013675

    44. Ft-0671059

    45. Methenamine Hippurate [usp Monograph]

    46. D00855

    47. D81437

    48. 714m738

    49. Q27283414

    50. 1,3,5,7-tetraazatricyclo[3.3.1.1(3),?]decane; 2-(phenylformamido)acetic Acid

    51. N-[hydroxy(phenyl)methylidene]glycine--1,3,5,7-tetraazatricyclo[3.3.1.1~3,7~]decane (1/1)

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 319.36 g/mol
    Molecular Formula C15H21N5O3
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count7
    Rotatable Bond Count3
    Exact Mass319.16443955 g/mol
    Monoisotopic Mass319.16443955 g/mol
    Topological Polar Surface Area79.4 Ų
    Heavy Atom Count23
    Formal Charge0
    Complexity282
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 4  
    Drug NameHiprex
    Drug LabelEach yellow capsule-shaped tablet contains 1 g Methenamine Hippurate which is the Hippuric Acid Salt of Methenamine (hexamethylene tetramine). The tablet also contains inactive ingredients. FD&C Yellow No. 5 (tartrazine, see PRECAUTIONS), Magnesium S.
    Active IngredientMethenamine hippurate
    Dosage FormTablet
    RouteOral
    Strength1gm
    Market StatusPrescription
    CompanySanofi Aventis Us

    2 of 4  
    Drug NameMethenamine hippurate
    PubMed HealthMethenamine (By mouth)
    Drug ClassesAntiseptic
    Drug LabelMethenamine Hippurate Tablets are a urinary tract antiseptic drug. Each white, scored tablet contains methenamine hippurate 1g (see HOW SUPPLIED). Methenamine Hippurate Tablets also contain: magnesium stearate, povidone and saccharin sodium. Chemical...
    Active IngredientMethenamine hippurate
    Dosage FormTablet
    RouteOral
    Strength1gm
    Market StatusPrescription
    CompanyCorepharma

    3 of 4  
    Drug NameHiprex
    Drug LabelEach yellow capsule-shaped tablet contains 1 g Methenamine Hippurate which is the Hippuric Acid Salt of Methenamine (hexamethylene tetramine). The tablet also contains inactive ingredients. FD&C Yellow No. 5 (tartrazine, see PRECAUTIONS), Magnesium S.
    Active IngredientMethenamine hippurate
    Dosage FormTablet
    RouteOral
    Strength1gm
    Market StatusPrescription
    CompanySanofi Aventis Us

    4 of 4  
    Drug NameMethenamine hippurate
    PubMed HealthMethenamine (By mouth)
    Drug ClassesAntiseptic
    Drug LabelMethenamine Hippurate Tablets are a urinary tract antiseptic drug. Each white, scored tablet contains methenamine hippurate 1g (see HOW SUPPLIED). Methenamine Hippurate Tablets also contain: magnesium stearate, povidone and saccharin sodium. Chemical...
    Active IngredientMethenamine hippurate
    Dosage FormTablet
    RouteOral
    Strength1gm
    Market StatusPrescription
    CompanyCorepharma

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Anti-Bacterial Agents

    Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

    Anti-Infective Agents, Urinary

    Substances capable of killing agents causing urinary tract infections or of preventing them from spreading. (See all compounds classified as Anti-Infective Agents, Urinary.)

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    22-Jan-2021
    03-Sep-2024
    KGS
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