HIPPURIC ACID

Details

Stereochemistry	ACHIRAL
Molecular Formula	C9H9NO3
Molecular Weight	179.173
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

c1ccc(cc1)C(=NCC(=O)O)O

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	179.173
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 7728	20.0 µM [IC50]
Solute carrier family 22 member 8 17 Target ID: CHEMBL1641348 Sources: http://www.ncbi.nlm.nih.gov/pubmed/14675047	Inhibitor 7728	30.8 µM [Ki]
Target ID: Bacterial growth Sources: http://www.ncbi.nlm.nih.gov/pubmed/3895402	Inhibitor 7728

Conditions

Condition	Modality	Targets	Highest Phase	Product
Urinary tract infections 197 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2005/17681s014lbl.pdf	Curative		Approved 8043	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 2.10988794E11

PubMed

Title	Date	PubMed
Secretory activity and aryl acid content of serum, urine, and cerebrospinal fluid in normal and uremic man.	1975 May	1168235
[Quantitative assay of metabolic rate of para-aminobenzoic acid combining glycine for the assessment of rabbit liver function].	2001 Aug	11602060
Absorption of benzoic acid in segmental regions of the vascularly perfused rat small intestine preparation.	2001 Dec	11717172
Uremic sera contain inhibitors that block digitoxin-valproic acid interaction.	2001 Oct	11678517
Gardnerella vaginalis isolated from patients with bacterial vaginosis and from patients with healthy vaginal ecosystems.	2001 Oct 1	11528575
Fast homogeneous assay for plasma procarboxypeptidase U.	2001 Sep	11601677
Synthesis of some new quinoline derivatives: new routes to synthesize polysubstituted 2(1H)-quinolone derivatives.	2001 Sep-Oct	11680080
Effect of anticoagulants in colorimetric assay for basic carboxypeptidases.	2002	11939576
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
Sister chromatid exchanges and micronuclei in peripheral lymphocytes of shoe factory workers exposed to solvents.	2002 Apr	11940458
Mapping of local renal blood flow with PET and H(2)(15)O.	2002 Apr	11937589
Effect of protein-bound uraemic toxins on the thermodynamic characteristics of human albumin.	2002 Apr 1	11960605
Behavior of non-protein-bound and protein-bound uremic solutes during daily hemodialysis.	2002 Aug	12148107
Validated method for quantitation of biomarkers for benzene and its alkylated analogues in urine.	2002 Jul 15	12076687
The effect of cigarette smoking on urinary hippuric acid concentration in Thai workers with occupational exposure to toluene.	2002 Jun	12188417
Urinary benzylmercapturic acid as a marker of occupational exposure to toluene.	2002 Jun	11981673
Biochemical function of the donor liver in living related liver transplantation.	2002 Mar	12009642
Improved method for direct high-performance liquid chromatography assay of angiotensin-converting enzyme-catalyzed reactions.	2002 Mar 15	11990985
Helicobacter muricola sp. nov., a novel Helicobacter species isolated from the ceca and feces of Korean wild mouse (Mus musculus molossinus).	2002 Mar 19	12007652
Toluene metabolites as biological indicators of exposure.	2002 Mar 24	11879975
Major role of organic anion transporter 3 in the transport of indoxyl sulfate in the kidney.	2002 May	11967025
Improved paclitaxel and baccatin III production in suspension cultures of Taxus media.	2002 May-Jun	12052053
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
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	12358729
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
Simultaneous detection of hippuric acid and methylhippuric acid in urine by Empore disk and gas chromatography-mass spectrometry.	2002 Sep 5	12191723
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
Studies on dialysate mixing in the Genius single-pass batch system for hemodialysis therapy.	2003 Apr	12631371
Palladium-catalyzed asymmetric addition of pronucleophiles to allenes.	2003 Apr 16	12683811
Acid-base status of critically ill patients with acute renal failure: analysis based on Stewart-Figge methodology.	2003 Aug	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 Aug	12867486
Kinetic study of angiotensin converting enzyme activity by capillary electrophoresis after in-line reaction at the capillary inlet.	2003 Feb 7	12597637
Analysis method of the angiotensin-I converting enzyme inhibitory activity based on micellar electrokinetic chromatography.	2003 Jan	12558042
Expression and characterization of frog peptidylglycine alpha-hydroxylating monooxygenase.	2003 Jan	12509982
Glycine conjugation of para-aminobenzoic acid (PABA): a pilot study of a novel prognostic test in acute liver failure in children.	2003 Jan	12499998
Solvent ototoxicity in the rat and guinea pig.	2003 Jan-Feb	12633735
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
Rapid detection and identification of Brachyspira aalborgi from rectal biopsies and faeces of a patient.	2003 Mar	12648729
Alteration of local ACE activity and vascular responsiveness during development of 2K1C renovascular hypertension.	2003 Mar	12591015
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 `Sat Jun 26 05:01:02 UTC 2021` Edited by `admin` on `Sat Jun 26 05:01:02 UTC 2021`
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

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