Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C9H9NO3 |
| Molecular Weight | 179.1727 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)CNC(=O)C1=CC=CC=C1
InChI
InChIKey=QIAFMBKCNZACKA-UHFFFAOYSA-N
InChI=1S/C9H9NO3/c11-8(12)6-10-9(13)7-4-2-1-3-5-7/h1-5H,6H2,(H,10,13)(H,11,12)
DescriptionCurator's Comment: Description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/19891605 and https://www.medicines.org.uk/emc/medicine/7597
Curator's Comment: Description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/19891605 and https://www.medicines.org.uk/emc/medicine/7597
Hippuric Acid is an acyl glycine produced by the conjugation of benzoic acid and glycine, found as a normal component in urine as a metabolite of aromatic compounds from food. Increased urine hippuric acid content may have antibacterial effects. Hippuric Acid is used therapeutically in the form of its salts (hippurates of calcium and ammonium). It is an ingredient of FDA-approved drug Hiprex (methenamine hippurate tablets USP). Each yellow capsule-shaped tablet of Hiprex contains 1 g Methenamine Hippurate which is the Hippuric Acid Salt of Methenamine (hexamethylene tetramine). The tablet also contains inactive ingredients. Hiprex (methenamine hippurate tablets USP) has antibacterial activity because the methenamine component is hydrolyzed to formaldehyde in acid urine. Hippuric acid has some antibacterial activity and also acts to keep the urine acid. The drug is generally active against E. coli, enterococci and staphylococci. Enterobacter aerogenes is generally resistant. The urine must be kept sufficiently acid for urea-splitting organisms such as Proteus and Pseudomonas to be inhibited. Hiprex is indicated for prophylactic or suppressive treatment of frequently recurring urinary tract infections when long-term therapy is considered necessary.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL1641347 |
20.0 µM [IC50] | ||
Target ID: CHEMBL1641348 |
30.8 µM [Ki] | ||
Target ID: Bacterial growth |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Curative | HIPREX Approved UseHIPREX is indicated for prophylactic or suppressive treatment of frequently recurring urinary
tract infections when long-term therapy is considered necessary. This drug should only be used
after eradication of the infection by other appropriate antimicrobial agents. Launch Date1976 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Profile of solvent abusers (glue sniffers) in East Malaysia. | 2001 Dec |
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| Effect of anticoagulants in colorimetric assay for basic carboxypeptidases. | 2002 |
|
| Proton nuclear magnetic resonance spectral profiles of urine from children and adolescents with type 1 diabetes. | 2002 |
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| Methenamine hippurate for preventing urinary tract infections. | 2002 |
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| Short-term moderate sodium restriction induces relative hyperfiltration in normotensive normoalbuminuric Type I diabetes mellitus. | 2002 Apr |
|
| Aponecrotic, antiangiogenic and antiproliferative effects of a novel dextran derivative on breast cancer growth in vitro and in vivo. | 2002 Apr |
|
| Sister chromatid exchanges and micronuclei in peripheral lymphocytes of shoe factory workers exposed to solvents. | 2002 Apr |
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| Mapping of local renal blood flow with PET and H(2)(15)O. | 2002 Apr |
|
| Effect of protein-bound uraemic toxins on the thermodynamic characteristics of human albumin. | 2002 Apr 1 |
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| Value of urinary prophylaxis with methenamine in gynecologic surgery. | 2002 Aug |
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| Behavior of non-protein-bound and protein-bound uremic solutes during daily hemodialysis. | 2002 Aug |
|
| Metabolite ratio of toluene-exposed rotogravure printing plant workers reflects individual mutagenic risk by sister chromatid exchanges. | 2002 Aug 26 |
|
| Validated method for quantitation of biomarkers for benzene and its alkylated analogues in urine. | 2002 Jul 15 |
|
| The effect of cigarette smoking on urinary hippuric acid concentration in Thai workers with occupational exposure to toluene. | 2002 Jun |
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| Urinary benzylmercapturic acid as a marker of occupational exposure to toluene. | 2002 Jun |
|
| Biochemical function of the donor liver in living related liver transplantation. | 2002 Mar |
|
| Improved method for direct high-performance liquid chromatography assay of angiotensin-converting enzyme-catalyzed reactions. | 2002 Mar 15 |
|
| Helicobacter muricola sp. nov., a novel Helicobacter species isolated from the ceca and feces of Korean wild mouse (Mus musculus molossinus). | 2002 Mar 19 |
|
| Toluene metabolites as biological indicators of exposure. | 2002 Mar 24 |
|
| Cytogenetic analysis of buccal cells from shoe-workers and pathology and anatomy laboratory workers exposed to n-hexane, toluene, methyl ethyl ketone and formaldehyde. | 2002 Mar-Apr |
|
| [Generalized muscle weakness mimicking periodic paralysis in a patient with toluene abuse]. | 2002 May |
|
| Major role of organic anion transporter 3 in the transport of indoxyl sulfate in the kidney. | 2002 May |
|
| Improved paclitaxel and baccatin III production in suspension cultures of Taxus media. | 2002 May-Jun |
|
| Analytical reproducibility in (1)H NMR-based metabonomic urinalysis. | 2002 Nov |
|
| Renal disposition of a furan dicarboxylic acid and other uremic toxins in the rat. | 2002 Nov |
|
| Peptides with angiotensin I-converting enzyme (ACE) inhibitory activity from defibrinated, hydrolyzed bovine plasma. | 2002 Nov 20 |
|
| Simultaneous determination of styrene, toluene, and xylene metabolites in urine by gas chromatography/mass spectrometry. | 2002 Oct |
|
| Role of blood-brain barrier organic anion transporter 3 (OAT3) in the efflux of indoxyl sulfate, a uremic toxin: its involvement in neurotransmitter metabolite clearance from the brain. | 2002 Oct |
|
| Physiological variation in metabolic phenotyping and functional genomic studies: use of orthogonal signal correction and PLS-DA. | 2002 Oct 23 |
|
| High levels of hippuric acid in the urine of Thai press workers. | 2002 Sep |
|
| Effect of intestinal microflora on the urinary metabolic profile of rats: a (1)H-nuclear magnetic resonance spectroscopy study. | 2002 Sep |
|
| Bioactivation of benzylamine to reactive intermediates in rodents: formation of glutathione, glutamate, and peptide conjugates. | 2002 Sep |
|
| Simultaneous detection of hippuric acid and methylhippuric acid in urine by Empore disk and gas chromatography-mass spectrometry. | 2002 Sep 5 |
|
| Gender differences in the metabolism of benzene, toluene and trichloroethylene in rat with special reference to certain biochemical parameters. | 2003 Apr |
|
| Moment analysis of metabolic heterogeneity: conjugation of benzoate with glycine in rat liver studied by multiple indicator dilution technique. | 2003 Apr |
|
| Palladium-catalyzed asymmetric addition of pronucleophiles to allenes. | 2003 Apr 16 |
|
| Hippuric acid and methyl hippuric acid in rat hair: possible monitoring of xylene and toluene exposure. | 2003 Apr 23 |
|
| Acid-base status of critically ill patients with acute renal failure: analysis based on Stewart-Figge methodology. | 2003 Aug |
|
| Detection of carboxylic acids and inhibition of hippuric acid formation in rats treated with 3-butene-1,2-diol, a major metabolite of 1,3-butadiene. | 2003 Aug |
|
| Determination of urinary hippuric acid by micellar electrokinetic capillary chromatography. | 2003 Aug 15 |
|
| Role of angiotensin II in L-NAME-induced systemic and renal hemodynamic effects in hydrochlorothiazide-pretreated hypertensive subjects. | 2003 Feb |
|
| Analysis method of the angiotensin-I converting enzyme inhibitory activity based on micellar electrokinetic chromatography. | 2003 Jan |
|
| Carboxymethyl benzylamide dextran inhibits angiogenesis and growth of VEGF-overexpressing human epidermoid carcinoma xenograft in nude mice. | 2003 Jul 7 |
|
| Biological monitoring of low level occupational xylene exposure and the role of recent exposure. | 2003 Jun |
|
| Inhibition of epidermoid carcinoma A431 cell growth and angiogenesis in nude mice by early and late treatment with a novel dextran derivative. | 2003 Jun 16 |
|
| Rapid detection and identification of Brachyspira aalborgi from rectal biopsies and faeces of a patient. | 2003 Mar |
|
| Determination of urinary hippuric acid and o-cresol levels as biological indicators of toluene exposure in shoe-workers and glue sniffers. | 2003 Mar-Apr |
|
| Enterococcus phoeniculicola sp. nov., a novel member of the enterococci isolated from the uropygial gland of the Red-billed Woodhoopoe, Phoeniculus purpureus. | 2003 May |
|
| Comparison of the BAX System with a multiplex PCR method for simultaneous detection and identification of Campylobacter jejuni and Campylobacter coli in environmental samples. | 2003 Nov 1 |
|
| Human urine certified reference material CZ 6009: creatinine, styrene metabolites (mandelic acid and phenylglyoxylic acid). | 2004 Mar |
Sample Use Guides
1 tablet (1.0 g) twice daily (morning and night) for adults and pediatric patients over 12 years of age. 1/2 to 1 tablet (0.5 to 1.0 g) twice daily (morning and night) for pediatric patients 6 to 12 years of age. Since the antibacterial activity of Hiprex is greater in acid urine, restriction of alkalinizing foods and medications is desirable.
Route of Administration:
Oral
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NCI_THESAURUS |
C255
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LOINC |
75069-5
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TE0865N2ET
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m6023
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207-806-3
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DTXSID9046073
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464
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18089
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C87277
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100000125975
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C030514
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HIPPURIC ACID
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ACTIVE MOIETY
PARENT (METABOLITE INACTIVE)
PARENT (METABOLITE)
PARENT (METABOLITE)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
