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
[Occupational chronic exposure to organic solvents. III. Gas-chromatographic determination of hippuric acid in serum (author's transl)].	1975	1184200
Final report on the safety assessment of Benzyl Alcohol, Benzoic Acid, and Sodium Benzoate.	2001	11766131
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
Classification of Brachyspira spp. isolated from Swedish dogs.	2001 Jun	11708750
Short-term oral toxicity of gasohol in female rats.	2001 Nov-Dec	11746192
Methenamine hippurate for preventing urinary tract infections.	2002	11869659
Mapping of local renal blood flow with PET and H(2)(15)O.	2002 Apr	11937589
Uraemic toxins induce proximal tubular injury via organic anion transporter 1-mediated uptake.	2002 Jan	11815391
Identification of a new biotype of Actinomyces hyovaginalis in tissues of pigs during diagnostic bacteriological examination.	2002 Jan 3	11731162
Analytical reproducibility in (1)H NMR-based metabonomic urinalysis.	2002 Nov	12437328
Gender differences in the metabolism of benzene, toluene and trichloroethylene in rat with special reference to certain biochemical parameters.	2003 Apr	12974453
Moment analysis of metabolic heterogeneity: conjugation of benzoate with glycine in rat liver studied by multiple indicator dilution technique.	2003 Apr	12649380
Acid-base status of critically ill patients with acute renal failure: analysis based on Stewart-Figge methodology.	2003 Aug	12930557
Determination of urinary hippuric acid by micellar electrokinetic capillary chromatography.	2003 Aug 15	12906897
Role of angiotensin II in L-NAME-induced systemic and renal hemodynamic effects in hydrochlorothiazide-pretreated hypertensive subjects.	2003 Feb	12569265
Glycine conjugation of para-aminobenzoic acid (PABA): a pilot study of a novel prognostic test in acute liver failure in children.	2003 Jan	12499998
Rapid detection and identification of Brachyspira aalborgi from rectal biopsies and faeces of a patient.	2003 Mar	12648729
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	14527799
Human urine certified reference material CZ 6009: creatinine, styrene metabolites (mandelic acid and phenylglyoxylic acid).	2004 Mar	14551662

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