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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 of HIPPURIC ACID

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
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
20.0 µM [IC50]
30.8 µM [Ki]
Target ID: Bacterial growth
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
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

PubMed

TitleDatePubMed
Secretory activity and aryl acid content of serum, urine, and cerebrospinal fluid in normal and uremic man.
1975 May
[Quantitative assay of metabolic rate of para-aminobenzoic acid combining glycine for the assessment of rabbit liver function].
2001 Aug
Absorption of benzoic acid in segmental regions of the vascularly perfused rat small intestine preparation.
2001 Dec
Uremic sera contain inhibitors that block digitoxin-valproic acid interaction.
2001 Oct
Gardnerella vaginalis isolated from patients with bacterial vaginosis and from patients with healthy vaginal ecosystems.
2001 Oct 1
Fast homogeneous assay for plasma procarboxypeptidase U.
2001 Sep
Synthesis of some new quinoline derivatives: new routes to synthesize polysubstituted 2(1H)-quinolone derivatives.
2001 Sep-Oct
Effect of anticoagulants in colorimetric assay for basic carboxypeptidases.
2002
Proton nuclear magnetic resonance spectral profiles of urine from children and adolescents with type 1 diabetes.
2002
Short-term moderate sodium restriction induces relative hyperfiltration in normotensive normoalbuminuric Type I diabetes mellitus.
2002 Apr
Aponecrotic, antiangiogenic and antiproliferative effects of a novel dextran derivative on breast cancer growth in vitro and in vivo.
2002 Apr
Sister chromatid exchanges and micronuclei in peripheral lymphocytes of shoe factory workers exposed to solvents.
2002 Apr
Mapping of local renal blood flow with PET and H(2)(15)O.
2002 Apr
Effect of protein-bound uraemic toxins on the thermodynamic characteristics of human albumin.
2002 Apr 1
Behavior of non-protein-bound and protein-bound uremic solutes during daily hemodialysis.
2002 Aug
Validated method for quantitation of biomarkers for benzene and its alkylated analogues in urine.
2002 Jul 15
The effect of cigarette smoking on urinary hippuric acid concentration in Thai workers with occupational exposure to toluene.
2002 Jun
Urinary benzylmercapturic acid as a marker of occupational exposure to toluene.
2002 Jun
Biochemical function of the donor liver in living related liver transplantation.
2002 Mar
Improved method for direct high-performance liquid chromatography assay of angiotensin-converting enzyme-catalyzed reactions.
2002 Mar 15
Helicobacter muricola sp. nov., a novel Helicobacter species isolated from the ceca and feces of Korean wild mouse (Mus musculus molossinus).
2002 Mar 19
Toluene metabolites as biological indicators of exposure.
2002 Mar 24
Major role of organic anion transporter 3 in the transport of indoxyl sulfate in the kidney.
2002 May
Improved paclitaxel and baccatin III production in suspension cultures of Taxus media.
2002 May-Jun
Analytical reproducibility in (1)H NMR-based metabonomic urinalysis.
2002 Nov
Renal disposition of a furan dicarboxylic acid and other uremic toxins in the rat.
2002 Nov
Peptides with angiotensin I-converting enzyme (ACE) inhibitory activity from defibrinated, hydrolyzed bovine plasma.
2002 Nov 20
Simultaneous determination of styrene, toluene, and xylene metabolites in urine by gas chromatography/mass spectrometry.
2002 Oct
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
Physiological variation in metabolic phenotyping and functional genomic studies: use of orthogonal signal correction and PLS-DA.
2002 Oct 23
High levels of hippuric acid in the urine of Thai press workers.
2002 Sep
Effect of intestinal microflora on the urinary metabolic profile of rats: a (1)H-nuclear magnetic resonance spectroscopy study.
2002 Sep
Bioactivation of benzylamine to reactive intermediates in rodents: formation of glutathione, glutamate, and peptide conjugates.
2002 Sep
Simultaneous detection of hippuric acid and methylhippuric acid in urine by Empore disk and gas chromatography-mass spectrometry.
2002 Sep 5
Gender differences in the metabolism of benzene, toluene and trichloroethylene in rat with special reference to certain biochemical parameters.
2003 Apr
Moment analysis of metabolic heterogeneity: conjugation of benzoate with glycine in rat liver studied by multiple indicator dilution technique.
2003 Apr
Studies on dialysate mixing in the Genius single-pass batch system for hemodialysis therapy.
2003 Apr
Palladium-catalyzed asymmetric addition of pronucleophiles to allenes.
2003 Apr 16
Acid-base status of critically ill patients with acute renal failure: analysis based on Stewart-Figge methodology.
2003 Aug
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
Kinetic study of angiotensin converting enzyme activity by capillary electrophoresis after in-line reaction at the capillary inlet.
2003 Feb 7
Analysis method of the angiotensin-I converting enzyme inhibitory activity based on micellar electrokinetic chromatography.
2003 Jan
Expression and characterization of frog peptidylglycine alpha-hydroxylating monooxygenase.
2003 Jan
Glycine conjugation of para-aminobenzoic acid (PABA): a pilot study of a novel prognostic test in acute liver failure in children.
2003 Jan
Solvent ototoxicity in the rat and guinea pig.
2003 Jan-Feb
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
Rapid detection and identification of Brachyspira aalborgi from rectal biopsies and faeces of a patient.
2003 Mar
Alteration of local ACE activity and vascular responsiveness during development of 2K1C renovascular hypertension.
2003 Mar
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
Human urine certified reference material CZ 6009: creatinine, styrene metabolites (mandelic acid and phenylglyoxylic acid).
2004 Mar
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
  • Download
Name Type Language
HIPPURIC ACID
INCI   MI  
INCI  
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
HPUS  
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C255
Created by admin on Sat Jun 26 05:01:02 UTC 2021 , Edited by admin on Sat Jun 26 05:01:02 UTC 2021
LOINC 75069-5
Created by admin on Sat Jun 26 05:01:02 UTC 2021 , Edited by admin on Sat Jun 26 05:01:02 UTC 2021
Code System Code Type Description
FDA UNII
TE0865N2ET
Created by admin on Sat Jun 26 05:01:02 UTC 2021 , Edited by admin on Sat Jun 26 05:01:02 UTC 2021
PRIMARY
MERCK INDEX
M6023
Created by admin on Sat Jun 26 05:01:02 UTC 2021 , Edited by admin on Sat Jun 26 05:01:02 UTC 2021
PRIMARY Merck Index
ECHA (EC/EINECS)
207-806-3
Created by admin on Sat Jun 26 05:01:02 UTC 2021 , Edited by admin on Sat Jun 26 05:01:02 UTC 2021
PRIMARY
EPA CompTox
495-69-2
Created by admin on Sat Jun 26 05:01:02 UTC 2021 , Edited by admin on Sat Jun 26 05:01:02 UTC 2021
PRIMARY
PUBCHEM
464
Created by admin on Sat Jun 26 05:01:02 UTC 2021 , Edited by admin on Sat Jun 26 05:01:02 UTC 2021
PRIMARY
CAS
495-69-2
Created by admin on Sat Jun 26 05:01:02 UTC 2021 , Edited by admin on Sat Jun 26 05:01:02 UTC 2021
PRIMARY
NCI_THESAURUS
C87277
Created by admin on Sat Jun 26 05:01:02 UTC 2021 , Edited by admin on Sat Jun 26 05:01:02 UTC 2021
PRIMARY
EVMPD
SUB33142
Created by admin on Sat Jun 26 05:01:02 UTC 2021 , Edited by admin on Sat Jun 26 05:01:02 UTC 2021
PRIMARY
RXCUI
1923619
Created by admin on Sat Jun 26 05:01:02 UTC 2021 , Edited by admin on Sat Jun 26 05:01:02 UTC 2021
PRIMARY
MESH
C030514
Created by admin on Sat Jun 26 05:01:02 UTC 2021 , Edited by admin on Sat Jun 26 05:01:02 UTC 2021
PRIMARY
WIKIPEDIA
HIPPURIC ACID
Created by admin on Sat Jun 26 05:01:02 UTC 2021 , Edited by admin on Sat Jun 26 05:01:02 UTC 2021
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
TRANSPORTER -> INHIBITOR
SALT/SOLVATE -> PARENT
Related Record Type Details
PARENT -> METABOLITE
PARENT -> METABOLITE INACTIVE
IN-VIVO
URINE
PARENT -> METABOLITE
Related Record Type Details
ACTIVE MOIETY