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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 of HIPPURIC ACID

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
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]
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
[Occupational chronic exposure to organic solvents. III. Gas-chromatographic determination of hippuric acid in serum (author's transl)].
1975
Secretory activity and aryl acid content of serum, urine, and cerebrospinal fluid in normal and uremic man.
1975 May
Final report on the safety assessment of Benzyl Alcohol, Benzoic Acid, and Sodium Benzoate.
2001
Hippurate metabolism as a hydroxyl radical trapping mechanism in the rat kidney.
2001
[Quantitative assay of metabolic rate of para-aminobenzoic acid combining glycine for the assessment of rabbit liver function].
2001 Aug
Metabonomic investigations into hydrazine toxicity in the rat.
2001 Aug
Detoxification in relation to toxin tolerance in desert woodrats eating creosote bush.
2001 Dec
Absorption of benzoic acid in segmental regions of the vascularly perfused rat small intestine preparation.
2001 Dec
Classification of Brachyspira spp. isolated from Swedish dogs.
2001 Jun
99mTc-MAG3: review of pharmacokinetics, clinical application to renal diseases and quantification of renal function.
2001 Jun
Short-term oral toxicity of gasohol in female rats.
2001 Nov-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
Vascular endothelial growth factor 165 (VEGF(165)) activities are inhibited by carboxymethyl benzylamide dextran that competes for heparin binding to VEGF(165) and VEGF(165).KDR Complexes.
2001 Oct 26
Fast homogeneous assay for plasma procarboxypeptidase U.
2001 Sep
Inhibition of serum angiotensin-converting enzyme in rabbits after intravenous administration of enalaprilat-loaded intact erythrocytes.
2001 Sep
Sodium phenylacetate enhances the inhibitory effect of dextran derivative on breast cancer cell growth in vitro and in nude mice.
2001 Sep 14
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
Methenamine hippurate for preventing urinary tract infections.
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
Uraemic toxins induce proximal tubular injury via organic anion transporter 1-mediated uptake.
2002 Jan
Identification of a new biotype of Actinomyces hyovaginalis in tissues of pigs during diagnostic bacteriological examination.
2002 Jan 3
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
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
[Generalized muscle weakness mimicking periodic paralysis in a patient with toluene abuse].
2002 May
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
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
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
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
Oxygen and hydrogen isotope effects in an active site tyrosine to phenylalanine mutant of peptidylglycine alpha-hydroxylating monooxygenase: mechanistic implications.
2003 Feb 25
Analysis method of the angiotensin-I converting enzyme inhibitory activity based on micellar electrokinetic chromatography.
2003 Jan
Carboxymethyl benzylamide dextran inhibits angiogenesis and growth of VEGF-overexpressing human epidermoid carcinoma xenograft in nude mice.
2003 Jul 7
Enterococcus phoeniculicola sp. nov., a novel member of the enterococci isolated from the uropygial gland of the Red-billed Woodhoopoe, Phoeniculus purpureus.
2003 May
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 Fri Dec 15 17:43:05 UTC 2023
Edited
by admin
on Fri Dec 15 17:43:05 UTC 2023
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
METHYLAMINOLEVULINATE HYDROCHLORIDE IMPURITY H [EP IMPURITY]
Common 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 Fri Dec 15 17:43:06 UTC 2023 , Edited by admin on Fri Dec 15 17:43:06 UTC 2023
LOINC 75069-5
Created by admin on Fri Dec 15 17:43:06 UTC 2023 , Edited by admin on Fri Dec 15 17:43:06 UTC 2023
Code System Code Type Description
CHEBI
606565
Created by admin on Fri Dec 15 17:43:06 UTC 2023 , Edited by admin on Fri Dec 15 17:43:06 UTC 2023
PRIMARY
FDA UNII
TE0865N2ET
Created by admin on Fri Dec 15 17:43:06 UTC 2023 , Edited by admin on Fri Dec 15 17:43:06 UTC 2023
PRIMARY
MERCK INDEX
m6023
Created by admin on Fri Dec 15 17:43:06 UTC 2023 , Edited by admin on Fri Dec 15 17:43:06 UTC 2023
PRIMARY Merck Index
ECHA (EC/EINECS)
207-806-3
Created by admin on Fri Dec 15 17:43:06 UTC 2023 , Edited by admin on Fri Dec 15 17:43:06 UTC 2023
PRIMARY
EPA CompTox
DTXSID9046073
Created by admin on Fri Dec 15 17:43:06 UTC 2023 , Edited by admin on Fri Dec 15 17:43:06 UTC 2023
PRIMARY
PUBCHEM
464
Created by admin on Fri Dec 15 17:43:06 UTC 2023 , Edited by admin on Fri Dec 15 17:43:06 UTC 2023
PRIMARY
CAS
495-69-2
Created by admin on Fri Dec 15 17:43:06 UTC 2023 , Edited by admin on Fri Dec 15 17:43:06 UTC 2023
PRIMARY
NSC
9982
Created by admin on Fri Dec 15 17:43:06 UTC 2023 , Edited by admin on Fri Dec 15 17:43:06 UTC 2023
PRIMARY
CHEBI
18089
Created by admin on Fri Dec 15 17:43:06 UTC 2023 , Edited by admin on Fri Dec 15 17:43:06 UTC 2023
PRIMARY
NCI_THESAURUS
C87277
Created by admin on Fri Dec 15 17:43:06 UTC 2023 , Edited by admin on Fri Dec 15 17:43:06 UTC 2023
PRIMARY
SMS_ID
100000125975
Created by admin on Fri Dec 15 17:43:06 UTC 2023 , Edited by admin on Fri Dec 15 17:43:06 UTC 2023
PRIMARY
EVMPD
SUB33142
Created by admin on Fri Dec 15 17:43:06 UTC 2023 , Edited by admin on Fri Dec 15 17:43:06 UTC 2023
PRIMARY
RXCUI
1923619
Created by admin on Fri Dec 15 17:43:06 UTC 2023 , Edited by admin on Fri Dec 15 17:43:06 UTC 2023
PRIMARY
MESH
C030514
Created by admin on Fri Dec 15 17:43:06 UTC 2023 , Edited by admin on Fri Dec 15 17:43:06 UTC 2023
PRIMARY
WIKIPEDIA
HIPPURIC ACID
Created by admin on Fri Dec 15 17:43:06 UTC 2023 , Edited by admin on Fri Dec 15 17:43:06 UTC 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
TRANSPORTER -> INHIBITOR
SALT/SOLVATE -> PARENT
Related Record Type Details
PARENT -> METABOLITE INACTIVE
IN-VIVO
URINE
PARENT -> METABOLITE
PARENT -> METABOLITE
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY