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2D Structure
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 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

2D Structure

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.)