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)
Molecular Formula | C9H9NO3 |
Molecular Weight | 179.1727 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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 Sources: http://www.ncbi.nlm.nih.gov/pubmed/11815391 |
20.0 µM [IC50] | ||
Target ID: CHEMBL1641348 Sources: http://www.ncbi.nlm.nih.gov/pubmed/14675047 |
30.8 µM [Ki] | ||
Target ID: Bacterial growth Sources: http://www.ncbi.nlm.nih.gov/pubmed/3895402 |
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 |
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[Occupational chronic exposure to organic solvents. III. Gas-chromatographic determination of hippuric acid in serum (author's transl)]. | 1975 |
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Final report on the safety assessment of Benzyl Alcohol, Benzoic Acid, and Sodium Benzoate. | 2001 |
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Detoxification in relation to toxin tolerance in desert woodrats eating creosote bush. | 2001 Dec |
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Absorption of benzoic acid in segmental regions of the vascularly perfused rat small intestine preparation. | 2001 Dec |
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Classification of Brachyspira spp. isolated from Swedish dogs. | 2001 Jun |
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Short-term oral toxicity of gasohol in female rats. | 2001 Nov-Dec |
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Methenamine hippurate for preventing urinary tract infections. | 2002 |
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Mapping of local renal blood flow with PET and H(2)(15)O. | 2002 Apr |
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Uraemic toxins induce proximal tubular injury via organic anion transporter 1-mediated uptake. | 2002 Jan |
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Identification of a new biotype of Actinomyces hyovaginalis in tissues of pigs during diagnostic bacteriological examination. | 2002 Jan 3 |
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Analytical reproducibility in (1)H NMR-based metabonomic urinalysis. | 2002 Nov |
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Gender differences in the metabolism of benzene, toluene and trichloroethylene in rat with special reference to certain biochemical parameters. | 2003 Apr |
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Moment analysis of metabolic heterogeneity: conjugation of benzoate with glycine in rat liver studied by multiple indicator dilution technique. | 2003 Apr |
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Acid-base status of critically ill patients with acute renal failure: analysis based on Stewart-Figge methodology. | 2003 Aug |
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Determination of urinary hippuric acid by micellar electrokinetic capillary chromatography. | 2003 Aug 15 |
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Role of angiotensin II in L-NAME-induced systemic and renal hemodynamic effects in hydrochlorothiazide-pretreated hypertensive subjects. | 2003 Feb |
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Glycine conjugation of para-aminobenzoic acid (PABA): a pilot study of a novel prognostic test in acute liver failure in children. | 2003 Jan |
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Rapid detection and identification of Brachyspira aalborgi from rectal biopsies and faeces of a patient. | 2003 Mar |
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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 |
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Human urine certified reference material CZ 6009: creatinine, styrene metabolites (mandelic acid and phenylglyoxylic acid). | 2004 Mar |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/pro/hiprex.html
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
In Vitro Use Guide
Sources: http://www.ncbi.nlm.nih.gov/pubmed/11815391
Hippuric acid inhibits PAH uptake in OAT1-expressing proximal tubular cells OK cells with IC50 20uM
Substance Class |
Chemical
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TE0865N2ET
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C255
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75069-5
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HIPPURIC ACID
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT |
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TRANSPORTER -> INHIBITOR | |||
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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Related Record | Type | Details | ||
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PARENT -> METABOLITE | |||
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PARENT -> METABOLITE INACTIVE | |||
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PARENT -> METABOLITE |
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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ACTIVE MOIETY |
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