HIPPURIC ACID

Possibly Marketed Outside US

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 8504	20.0 µM [IC50]
Solute carrier family 22 member 8 17 Target ID: CHEMBL1641348 Sources: http://www.ncbi.nlm.nih.gov/pubmed/14675047	Inhibitor 8504	30.8 µM [Ki]
Bacterial growth 6 Target ID: Bacterial growth Sources: http://www.ncbi.nlm.nih.gov/pubmed/3895402	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Urinary tract infections 207 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/17681s014lbl.pdf	Curative		Approved 8583	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
Human urine certified reference material CZ 6009: creatinine, styrene metabolites (mandelic acid and phenylglyoxylic acid).	2004-03	14551662
Comparison of the BAX System with a multiplex PCR method for simultaneous detection and identification of Campylobacter jejuni and Campylobacter coli in environmental samples.	2003-11-01	14527799
Determination of urinary hippuric acid by micellar electrokinetic capillary chromatography.	2003-08-15	12906897
Acid-base status of critically ill patients with acute renal failure: analysis based on Stewart-Figge methodology.	2003-08	12930557
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.	2003-08	12867486
Carboxymethyl benzylamide dextran inhibits angiogenesis and growth of VEGF-overexpressing human epidermoid carcinoma xenograft in nude mice.	2003-07-07	12838326
Inhibition of epidermoid carcinoma A431 cell growth and angiogenesis in nude mice by early and late treatment with a novel dextran derivative.	2003-06-16	12799647
Biological monitoring of low level occupational xylene exposure and the role of recent exposure.	2003-06	12765874
Determination of urinary hippuric acid and o-cresol levels as biological indicators of toluene exposure in shoe-workers and glue sniffers.	2003-05-31	12775497
Enterococcus phoeniculicola sp. nov., a novel member of the enterococci isolated from the uropygial gland of the Red-billed Woodhoopoe, Phoeniculus purpureus.	2003-05	12807187
Hippuric acid and methyl hippuric acid in rat hair: possible monitoring of xylene and toluene exposure.	2003-04-23	12742703
Palladium-catalyzed asymmetric addition of pronucleophiles to allenes.	2003-04-16	12683811
Gender differences in the metabolism of benzene, toluene and trichloroethylene in rat with special reference to certain biochemical parameters.	2003-04	12974453
Moment analysis of metabolic heterogeneity: conjugation of benzoate with glycine in rat liver studied by multiple indicator dilution technique.	2003-04	12649380
Studies on dialysate mixing in the Genius single-pass batch system for hemodialysis therapy.	2003-04	12631371
Solvent ototoxicity in the rat and guinea pig.	2003-03-14	12633735
Rapid detection and identification of Brachyspira aalborgi from rectal biopsies and faeces of a patient.	2003-03	12648729
Alteration of local ACE activity and vascular responsiveness during development of 2K1C renovascular hypertension.	2003-03	12591015
Oxygen and hydrogen isotope effects in an active site tyrosine to phenylalanine mutant of peptidylglycine alpha-hydroxylating monooxygenase: mechanistic implications.	2003-02-25	12590568
Kinetic study of angiotensin converting enzyme activity by capillary electrophoresis after in-line reaction at the capillary inlet.	2003-02-07	12597637
Role of angiotensin II in L-NAME-induced systemic and renal hemodynamic effects in hydrochlorothiazide-pretreated hypertensive subjects.	2003-02	12569265
Analysis method of the angiotensin-I converting enzyme inhibitory activity based on micellar electrokinetic chromatography.	2003-01	12558042
Expression and characterization of frog peptidylglycine alpha-hydroxylating monooxygenase.	2003-01	12509982
Glycine conjugation of para-aminobenzoic acid (PABA): a pilot study of a novel prognostic test in acute liver failure in children.	2003-01	12499998
Hippuric acid in urine: reference values.	2002-12	12488939
Peptides with angiotensin I-converting enzyme (ACE) inhibitory activity from defibrinated, hydrolyzed bovine plasma.	2002-11-20	12428947
A study on human urine in a high-selenium area of China by 1H-NMR spectroscopy.	2002-11	12449239
Simultaneous determination of metabolites of trimethylbenzenes, dimethylbenzylmercapturicacid and dimethylhippuric acid, in human urine by solid-phase extraction followed by liquid chromatography tandem mass spectrometry.	2002-11	12447892
Analytical reproducibility in (1)H NMR-based metabonomic urinalysis.	2002-11	12437328
Renal disposition of a furan dicarboxylic acid and other uremic toxins in the rat.	2002-11	12388676
Physiological variation in metabolic phenotyping and functional genomic studies: use of orthogonal signal correction and PLS-DA.	2002-10-23	12387891
Simultaneous determination of styrene, toluene, and xylene metabolites in urine by gas chromatography/mass spectrometry.	2002-10	12373452
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.	2002-10	12358729
Simultaneous detection of hippuric acid and methylhippuric acid in urine by Empore disk and gas chromatography-mass spectrometry.	2002-09-05	12191723
High levels of hippuric acid in the urine of Thai press workers.	2002-09	12693601
Effect of intestinal microflora on the urinary metabolic profile of rats: a (1)H-nuclear magnetic resonance spectroscopy study.	2002-09	12396275
Bioactivation of benzylamine to reactive intermediates in rodents: formation of glutathione, glutamate, and peptide conjugates.	2002-09	12230413
Metabolite ratio of toluene-exposed rotogravure printing plant workers reflects individual mutagenic risk by sister chromatid exchanges.	2002-08-26	12160902
Value of urinary prophylaxis with methenamine in gynecologic surgery.	2002-08	12174159
Behavior of non-protein-bound and protein-bound uremic solutes during daily hemodialysis.	2002-08	12148107
Validated method for quantitation of biomarkers for benzene and its alkylated analogues in urine.	2002-07-15	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.	2002-07-10	12101634
Improved paclitaxel and baccatin III production in suspension cultures of Taxus media.	2002-06-08	12052053
The effect of cigarette smoking on urinary hippuric acid concentration in Thai workers with occupational exposure to toluene.	2002-06	12188417
[Generalized muscle weakness mimicking periodic paralysis in a patient with toluene abuse].	2002-05	12058413
Short-term moderate sodium restriction induces relative hyperfiltration in normotensive normoalbuminuric Type I diabetes mellitus.	2002-04	12032630
Helicobacter muricola sp. nov., a novel Helicobacter species isolated from the ceca and feces of Korean wild mouse (Mus musculus molossinus).	2002-03-19	12007652
Biochemical function of the donor liver in living related liver transplantation.	2002-03	12009642
Profile of solvent abusers (glue sniffers) in East Malaysia.	2001-12	12166590
Organic acids in urine from human newborns.	1976-01	1245060

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 `Mon Mar 31 18:50:52 GMT 2025` Edited by `admin` on `Mon Mar 31 18:50:52 GMT 2025`
Record UNII	TE0865N2ET
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

HIPPURIC ACID

Official Name

English

HIPPURICUM ACIDUM

Preferred 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 [MI]

Common Name

English

BENZOYLAMINOACETIC ACID

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C255