AMMONIUM HIPPURATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C9H8NO3.H4N
Molecular Weight	196.2032
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[NH4+].[O-]C(=O)CNC(=O)C1=CC=CC=C1

InChI

InChIKey=RXBWNIYFOFYPJR-UHFFFAOYSA-N

InChI=1S/C9H9NO3.H3N/c11-8(12)6-10-9(13)7-4-2-1-3-5-7;/h1-5H,6H2,(H,10,13)(H,11,12);1H3

HIDE SMILES / InChI

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
Organic acids in urine from human newborns.	1976 Jan	1245060
Profile of solvent abusers (glue sniffers) in East Malaysia.	2001 Dec	12166590
Short-term moderate sodium restriction induces relative hyperfiltration in normotensive normoalbuminuric Type I diabetes mellitus.	2002 Apr	12032630
Value of urinary prophylaxis with methenamine in gynecologic surgery.	2002 Aug	12174159
Behavior of non-protein-bound and protein-bound uremic solutes during daily hemodialysis.	2002 Aug	12148107
Metabolite ratio of toluene-exposed rotogravure printing plant workers reflects individual mutagenic risk by sister chromatid exchanges.	2002 Aug 26	12160902
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
The effect of cigarette smoking on urinary hippuric acid concentration in Thai workers with occupational exposure to toluene.	2002 Jun	12188417
Biochemical function of the donor liver in living related liver transplantation.	2002 Mar	12009642
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
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
Improved paclitaxel and baccatin III production in suspension cultures of Taxus media.	2002 May-Jun	12052053
A study on human urine in a high-selenium area of China by 1H-NMR spectroscopy.	2002 Nov	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 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
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
Hippuric acid and methyl hippuric acid in rat hair: possible monitoring of xylene and toluene exposure.	2003 Apr 23	12742703
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
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
Oxygen and hydrogen isotope effects in an active site tyrosine to phenylalanine mutant of peptidylglycine alpha-hydroxylating monooxygenase: mechanistic implications.	2003 Feb 25	12590568
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
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
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
Determination of urinary hippuric acid and o-cresol levels as biological indicators of toluene exposure in shoe-workers and glue sniffers.	2003 Mar-Apr	12775497
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
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

Name

Type

Language

AMMONIUM HIPPURATE

Systematic Name

English

GLYCINE, N-BENZOYL-, AMMONIUM SALT (1:1)

Common Name

English

HIPPURIC ACID AMMONIUM SALT [MI]

Common Name

English

HIPPURIC ACID, MONOAMMONIUM SALT

Common Name

English

HIPPURIC ACID AMMONIUM SALT

Common Name

English

Code System Code Type Description

ECHA (EC/EINECS)

208-547-9