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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

1976
PubMed

PubMed

TitleDatePubMed
[Occupational chronic exposure to organic solvents. III. Gas-chromatographic determination of hippuric acid in serum (author's transl)].
1975
Final report on the safety assessment of Benzyl Alcohol, Benzoic Acid, and Sodium Benzoate.
2001
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
Short-term oral toxicity of gasohol in female rats.
2001 Nov-Dec
Methenamine hippurate for preventing urinary tract infections.
2002
Mapping of local renal blood flow with PET and H(2)(15)O.
2002 Apr
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
Analytical reproducibility in (1)H NMR-based metabonomic urinalysis.
2002 Nov
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
Acid-base status of critically ill patients with acute renal failure: analysis based on Stewart-Figge methodology.
2003 Aug
Determination of urinary hippuric acid by micellar electrokinetic capillary chromatography.
2003 Aug 15
Role of angiotensin II in L-NAME-induced systemic and renal hemodynamic effects in hydrochlorothiazide-pretreated hypertensive subjects.
2003 Feb
Glycine conjugation of para-aminobenzoic acid (PABA): a pilot study of a novel prognostic test in acute liver failure in children.
2003 Jan
Rapid detection and identification of Brachyspira aalborgi from rectal biopsies and faeces of a patient.
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 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
  • Download
Name Type Language
HIPPURIC ACID
INCI   MI  
INCI  
Official Name English
HIPPURICUM ACIDUM
HPUS  
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
Created by admin on Mon Mar 31 18:50:52 GMT 2025 , Edited by admin on Mon Mar 31 18:50:52 GMT 2025
LOINC 75069-5
Created by admin on Mon Mar 31 18:50:52 GMT 2025 , Edited by admin on Mon Mar 31 18:50:52 GMT 2025
Code System Code Type Description
CHEBI
606565
Created by admin on Mon Mar 31 18:50:52 GMT 2025 , Edited by admin on Mon Mar 31 18:50:52 GMT 2025
PRIMARY
FDA UNII
TE0865N2ET
Created by admin on Mon Mar 31 18:50:52 GMT 2025 , Edited by admin on Mon Mar 31 18:50:52 GMT 2025
PRIMARY
MERCK INDEX
m6023
Created by admin on Mon Mar 31 18:50:52 GMT 2025 , Edited by admin on Mon Mar 31 18:50:52 GMT 2025
PRIMARY Merck Index
ECHA (EC/EINECS)
207-806-3
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PRIMARY
EPA CompTox
DTXSID9046073
Created by admin on Mon Mar 31 18:50:52 GMT 2025 , Edited by admin on Mon Mar 31 18:50:52 GMT 2025
PRIMARY
PUBCHEM
464
Created by admin on Mon Mar 31 18:50:52 GMT 2025 , Edited by admin on Mon Mar 31 18:50:52 GMT 2025
PRIMARY
CAS
495-69-2
Created by admin on Mon Mar 31 18:50:52 GMT 2025 , Edited by admin on Mon Mar 31 18:50:52 GMT 2025
PRIMARY
NSC
9982
Created by admin on Mon Mar 31 18:50:52 GMT 2025 , Edited by admin on Mon Mar 31 18:50:52 GMT 2025
PRIMARY
CHEBI
18089
Created by admin on Mon Mar 31 18:50:52 GMT 2025 , Edited by admin on Mon Mar 31 18:50:52 GMT 2025
PRIMARY
NCI_THESAURUS
C87277
Created by admin on Mon Mar 31 18:50:52 GMT 2025 , Edited by admin on Mon Mar 31 18:50:52 GMT 2025
PRIMARY
SMS_ID
100000125975
Created by admin on Mon Mar 31 18:50:52 GMT 2025 , Edited by admin on Mon Mar 31 18:50:52 GMT 2025
PRIMARY
EVMPD
SUB33142
Created by admin on Mon Mar 31 18:50:52 GMT 2025 , Edited by admin on Mon Mar 31 18:50:52 GMT 2025
PRIMARY
RXCUI
1923619
Created by admin on Mon Mar 31 18:50:52 GMT 2025 , Edited by admin on Mon Mar 31 18:50:52 GMT 2025
PRIMARY
MESH
C030514
Created by admin on Mon Mar 31 18:50:52 GMT 2025 , Edited by admin on Mon Mar 31 18:50:52 GMT 2025
PRIMARY
WIKIPEDIA
HIPPURIC ACID
Created by admin on Mon Mar 31 18:50:52 GMT 2025 , Edited by admin on Mon Mar 31 18:50:52 GMT 2025
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
TRANSPORTER -> INHIBITOR
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
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PARENT -> METABOLITE
PARENT -> METABOLITE INACTIVE
PARENT -> METABOLITE
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PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY