HIPPURIC ACID

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

Structure Search

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)

HIDE SMILES / InChI

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

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/17681s014lbl.pdf
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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Solute carrier family 22 member 6 19 Target ID: CHEMBL1641347 Sources: http://www.ncbi.nlm.nih.gov/pubmed/11815391	Inhibitor 8297	20.0 µM [IC50]
Solute carrier family 22 member 8 17 Target ID: CHEMBL1641348 Sources: http://www.ncbi.nlm.nih.gov/pubmed/14675047	Inhibitor 8297	30.8 µM [Ki]
Bacterial growth 6 Target ID: Bacterial growth Sources: http://www.ncbi.nlm.nih.gov/pubmed/3895402	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Urinary tract infections 205 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/17681s014lbl.pdf	Curative		Approved 8429	HIPREX Approved Use HIPREX 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 Date 1976

PubMed

Title	Date	PubMed
Study of the genotoxicity of toluene.	2000 Jul-Aug	11005432
Hippurate metabolism as a hydroxyl radical trapping mechanism in the rat kidney.	2001	11528207
[Quantitative assay of metabolic rate of para-aminobenzoic acid combining glycine for the assessment of rabbit liver function].	2001 Aug	11602060
Metabonomic investigations into hydrazine toxicity in the rat.	2001 Aug	11511171
Detoxification in relation to toxin tolerance in desert woodrats eating creosote bush.	2001 Dec	11789959
Absorption of benzoic acid in segmental regions of the vascularly perfused rat small intestine preparation.	2001 Dec	11717172
Hippurate participates in the correction of metabolic acidosis.	2001 Feb	11169026
Protein-bound uremic solutes: the forgotten toxins.	2001 Feb	11169024
DNA damage of lymphocytes in experimental chronic renal failure: beneficial effects of losartan.	2001 Feb	11169013
Partially reversible renal tubular damage in patients with obstructive jaundice.	2001 Jun	11391524
Hepatic uptake and metabolism of benzoate: a multiple indicator dilution, perfused rat liver study.	2001 Jun	11352805
Hippuric acid as a modifier of calcium oxalate crystallisation.	2001 Mar	11350018
Hippuric acid test using 13C-labelling and NMR spectroscopy.	2001 Mar	11350017
The hippurate ratio as an indicator of functional hepatic reserve for resection of hepatocellular carcinoma in cirrhotic patients.	2001 May-Jun	11360056
Fast homogeneous assay for plasma procarboxypeptidase U.	2001 Sep	11601677
Inhibition of serum angiotensin-converting enzyme in rabbits after intravenous administration of enalaprilat-loaded intact erythrocytes.	2001 Sep	11578111
Sodium phenylacetate enhances the inhibitory effect of dextran derivative on breast cancer cell growth in vitro and in nude mice.	2001 Sep 14	11556846
Synthesis of some new quinoline derivatives: new routes to synthesize polysubstituted 2(1H)-quinolone derivatives.	2001 Sep-Oct	11680080
Proton nuclear magnetic resonance spectral profiles of urine from children and adolescents with type 1 diabetes.	2002	11901070
Short-term moderate sodium restriction induces relative hyperfiltration in normotensive normoalbuminuric Type I diabetes mellitus.	2002 Apr	12032630
Aponecrotic, antiangiogenic and antiproliferative effects of a novel dextran derivative on breast cancer growth in vitro and in vivo.	2002 Apr	11959788
Hippuric acid in urine: reference values.	2002 Dec	12488939
Validated method for quantitation of biomarkers for benzene and its alkylated analogues in urine.	2002 Jul 15	12076687
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	12101634
[Generalized muscle weakness mimicking periodic paralysis in a patient with toluene abuse].	2002 May	12058413
Simultaneous determination of metabolites of trimethylbenzenes, dimethylbenzylmercapturicacid and dimethylhippuric acid, in human urine by solid-phase extraction followed by liquid chromatography tandem mass spectrometry.	2002 Nov	12447892
Analytical reproducibility in (1)H NMR-based metabonomic urinalysis.	2002 Nov	12437328
Renal disposition of a furan dicarboxylic acid and other uremic toxins in the rat.	2002 Nov	12388676
Peptides with angiotensin I-converting enzyme (ACE) inhibitory activity from defibrinated, hydrolyzed bovine plasma.	2002 Nov 20	12428947
Simultaneous determination of styrene, toluene, and xylene metabolites in urine by gas chromatography/mass spectrometry.	2002 Oct	12373452
Physiological variation in metabolic phenotyping and functional genomic studies: use of orthogonal signal correction and PLS-DA.	2002 Oct 23	12387891
High levels of hippuric acid in the urine of Thai press workers.	2002 Sep	12693601
Effect of intestinal microflora on the urinary metabolic profile of rats: a (1)H-nuclear magnetic resonance spectroscopy study.	2002 Sep	12396275
Bioactivation of benzylamine to reactive intermediates in rodents: formation of glutathione, glutamate, and peptide conjugates.	2002 Sep	12230413
Moment analysis of metabolic heterogeneity: conjugation of benzoate with glycine in rat liver studied by multiple indicator dilution technique.	2003 Apr	12649380
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	12867486
Determination of urinary hippuric acid by micellar electrokinetic capillary chromatography.	2003 Aug 15	12906897
Oxygen and hydrogen isotope effects in an active site tyrosine to phenylalanine mutant of peptidylglycine alpha-hydroxylating monooxygenase: mechanistic implications.	2003 Feb 25	12590568
Analysis method of the angiotensin-I converting enzyme inhibitory activity based on micellar electrokinetic chromatography.	2003 Jan	12558042
Glycine conjugation of para-aminobenzoic acid (PABA): a pilot study of a novel prognostic test in acute liver failure in children.	2003 Jan	12499998
Carboxymethyl benzylamide dextran inhibits angiogenesis and growth of VEGF-overexpressing human epidermoid carcinoma xenograft in nude mice.	2003 Jul 7	12838326
Biological monitoring of low level occupational xylene exposure and the role of recent exposure.	2003 Jun	12765874
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	12799647
Enterococcus phoeniculicola sp. nov., a novel member of the enterococci isolated from the uropygial gland of the Red-billed Woodhoopoe, Phoeniculus purpureus.	2003 May	12807187

Patents

Sample Use Guides

In Vivo Use Guide

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

Hippuric acid inhibits PAH uptake in OAT1-expressing proximal tubular cells OK cells with IC50 20uM

Substance Class	Chemical Created by `admin` on `Fri Dec 15 17:43:05 GMT 2023` Edited by `admin` on `Fri Dec 15 17:43:05 GMT 2023`
Record UNII	TE0865N2ET
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

HIPPURIC ACID

Official Name

English

BENZOYLGLYCINE

Systematic Name

English

NSC-9982

Code

English

BENZAMIDOACETIC ACID

Systematic Name

English

N-BENZOYLGLYCINE

Systematic Name

English

METHYLAMINOLEVULINATE HYDROCHLORIDE IMPURITY H [EP IMPURITY]

Common Name

English

HIPPURICUM ACIDUM [HPUS]

Common Name

English

HIPPURIC ACID [INCI]

Common Name

English

HIPPURIC ACID [MI]

Common Name

English

BENZOYLAMINOACETIC ACID

Systematic Name

English

HIPPURICUM ACIDUM

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C255