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Details

Stereochemistry RACEMIC
Molecular Formula C8H8O3
Molecular Weight 152.1473
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MANDELIC ACID

SMILES

OC(C(O)=O)C1=CC=CC=C1

InChI

InChIKey=IWYDHOAUDWTVEP-UHFFFAOYSA-N
InChI=1S/C8H8O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7,9H,(H,10,11)

HIDE SMILES / InChI

Molecular Formula C8H8O3
Molecular Weight 152.1473
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description
Curator's Comment: description was created based on several sources, including, http://dermage.com.br/dermage/paginas/article.pdf

Mandelic acid is an aromatic alpha hydroxy acid that is used for the treatment of urinary tract infections. The drug is marketed in Canada under the name Mandelamine (as a complex with methenamine). Mandelic acid exerts its antibacterial effect mainly by increasing urine acidity. Moreover, mandelic acid is used as a serum for the treatment of wrinkles.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Mandelamine

Approved Use

For the suppression or elimination of bacteriuria associated with pyelonephritis, cystitis and other urinary tract infections.
Doses

Doses

DosePopulationAdverse events​
45 % 1 times / 2 weeks multiple, topical
Dose: 45 %, 1 times / 2 weeks
Route: topical
Route: multiple
Dose: 45 %, 1 times / 2 weeks
Sources:
unhealthy, 19.4
Health Status: unhealthy
Age Group: 19.4
Sex: M+F
Sources:
Other AEs: Burning sensation, Erythema...
Other AEs:
Burning sensation (1 patient)
Erythema (2 patients)
Sources:
1 % 2 times / day multiple, topical
Dose: 1 %, 2 times / day
Route: topical
Route: multiple
Dose: 1 %, 2 times / day
Sources:
unhealthy
Health Status: unhealthy
Sex: M+F
Sources:
Other AEs: Skin erythema desquamative...
Other AEs:
Skin erythema desquamative (5%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Burning sensation 1 patient
45 % 1 times / 2 weeks multiple, topical
Dose: 45 %, 1 times / 2 weeks
Route: topical
Route: multiple
Dose: 45 %, 1 times / 2 weeks
Sources:
unhealthy, 19.4
Health Status: unhealthy
Age Group: 19.4
Sex: M+F
Sources:
Erythema 2 patients
45 % 1 times / 2 weeks multiple, topical
Dose: 45 %, 1 times / 2 weeks
Route: topical
Route: multiple
Dose: 45 %, 1 times / 2 weeks
Sources:
unhealthy, 19.4
Health Status: unhealthy
Age Group: 19.4
Sex: M+F
Sources:
Skin erythema desquamative 5%
1 % 2 times / day multiple, topical
Dose: 1 %, 2 times / day
Route: topical
Route: multiple
Dose: 1 %, 2 times / day
Sources:
unhealthy
Health Status: unhealthy
Sex: M+F
Sources:
PubMed

PubMed

TitleDatePubMed
Histidine-functionalized silica and its copper complex as stationary phases for capillary electrochromatography.
2001 Aug
Fitting adsorption isotherms to the distribution data determined using packed micro-columns for high-performance liquid chromatography.
2001 Aug 3
Stereochemical metabolism of styrene in volunteers.
2001 Jul
Inter- and intra-individual sources of variation in levels of urinary styrene metabolites.
2001 Jul
Intervention study on acquired color vision deficiencies in styrene-exposed workers.
2001 May
Polymorphism of xenobiotic-metabolizing enzymes and excretion of styrene-specific mercapturic acids.
2001 Oct
An enzyme library approach to biocatalysis: development of nitrilases for enantioselective production of carboxylic acid derivatives.
2002 Aug 7
A practical enantioselective fluorescent sensor for mandelic acid.
2002 Mar 13
Assessment of sperm DNA integrity in workers exposed to styrene.
2002 Nov
A highly selective aerobic oxidation process catalyzed by electron-deficient nitroarenes via single electron transfer processes.
2002 Oct 18
Audiometric findings in workers exposed to low levels of styrene and noise.
2002 Sep
Absolute configuration of tert-butyl-1-(2-methylnaphthyl)phosphine oxide.
2002 Sep 6
Exceptional chiral recognition of racemic carboxylic acids by calix[4]arenes bearing optically pure alpha,beta-amino alcohol groups.
2004 Apr 15
Heptakis(6-amino-6-deoxy)-beta-cyclodextrin as a chiral selector for the separation of anionic analyte enantiomers by capillary electrophoresis.
2004 Aug
Influence of (hydroxy)alkylamino substituents on enantioseparation ability of single-isomer amino-beta-cyclodextrin derivatives in chiral capillary electrophoresis.
2004 Aug
Determination of urinary styrene metabolites in the general Italian population by liquid chromatography-tandem mass spectrometry.
2004 Aug
Role of glycine 81 in (S)-mandelate dehydrogenase from Pseudomonas putida in substrate specificity and oxidase activity.
2004 Aug 24
Synthesis and antibiotic activity of the tricyclic furo[3,2-c] isochromen-2-trione unit of the pyranonaphthoquinones.
2004 Feb 9
A rapid HPLC method for the determination of carboxylic acids in human urine using a monolithic column.
2004 Jan
High resolution structures of an oxidized and reduced flavoprotein. The water switch in a soluble form of (S)-mandelate dehydrogenase.
2004 Jan 30
Altered substrate specificity in flavocytochrome b2: structural insights into the mechanism of L-lactate dehydrogenation.
2004 Jul 27
Cytogenetic markers, DNA single-strand breaks, urinary metabolites, and DNA repair rates in styrene-exposed lamination workers.
2004 Jun
Mandelamide hydrolase from Pseudomonas putida: characterization of a new member of the amidase signature family.
2004 Jun 22
Chiral synthesis of (2S,3S)-2-(2-morpholin-2-yl-2-phenylmethoxy)phenol.
2004 Mar
Current trends in quantitative structure activity relationships on FXa inhibitors: evaluation and comparative analysis.
2004 Nov
Prevalence of varicose veins and venous anatomy in patients without truncal saphenous reflux.
2004 Oct
Patents

Sample Use Guides

500 mg - 2 tablets 4 times a day (in the form of (Methenamine Mandelate Tablets U.S.P.).
Route of Administration: Oral
In Vitro Use Guide
Antimicrobal activity of mandelic acid was determined by disc diffusion method. S. aureus type strains (ATCC 700698 and ATCC 25923) and 19 isolates were incubated with 10 ul of 160, 80, 40, 30, 20 and 10 mg/ml of the acid. Concentrations required to inhibit 50 and 90% of the clinical isolates (MIC50 and MIC90) were 20 and 40 (mg/ml) respectively and those required to kill 50 and 90% of the strains (MBC50 and MBC90) were 20 and 80 (mg/ml) respectively.
Substance Class Chemical
Created
by admin
on Mon Mar 31 19:38:44 GMT 2025
Edited
by admin
on Mon Mar 31 19:38:44 GMT 2025
Record UNII
NH496X0UJX
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NSC-7925
Preferred Name English
MANDELIC ACID
INCI   MART.   MI   USP-RS   WHO-DD  
INCI  
Official Name English
PARAMANDELIC ACID
Common Name English
HOMATROPINE HYDROBROMIDE IMPURITY C [EP IMPURITY]
Common Name English
PHENYLACETIC ACID, .ALPHA.--HYDROXY-
Common Name English
RACEMIC MANDELIC ACID
Common Name English
MANDELIC ACID [USP-RS]
Common Name English
Mandelic acid [WHO-DD]
Common Name English
MANDELIC ACID [MART.]
Common Name English
MANDELIC ACID [MI]
Common Name English
GLYCOPYRRONIUM BROMIDE IMPURITY C [EP IMPURITY]
Common Name English
.ALPHA.-HYDROXYPHENYLACETIC ACID
Systematic Name English
DL-MANDELIC ACID
Common Name English
HOMATROPINE METHYLBROMIDE IMPURITY C [EP IMPURITY]
Common Name English
Classification Tree Code System Code
WHO-VATC QB05CA06
Created by admin on Mon Mar 31 19:38:44 GMT 2025 , Edited by admin on Mon Mar 31 19:38:44 GMT 2025
WHO-ATC B05CA06
Created by admin on Mon Mar 31 19:38:44 GMT 2025 , Edited by admin on Mon Mar 31 19:38:44 GMT 2025
WHO-ATC J01XX06
Created by admin on Mon Mar 31 19:38:44 GMT 2025 , Edited by admin on Mon Mar 31 19:38:44 GMT 2025
NCI_THESAURUS C255
Created by admin on Mon Mar 31 19:38:44 GMT 2025 , Edited by admin on Mon Mar 31 19:38:44 GMT 2025
WHO-VATC QJ01XX06
Created by admin on Mon Mar 31 19:38:44 GMT 2025 , Edited by admin on Mon Mar 31 19:38:44 GMT 2025
Code System Code Type Description
MERCK INDEX
m7051
Created by admin on Mon Mar 31 19:38:44 GMT 2025 , Edited by admin on Mon Mar 31 19:38:44 GMT 2025
PRIMARY Merck Index
CHEBI
35825
Created by admin on Mon Mar 31 19:38:44 GMT 2025 , Edited by admin on Mon Mar 31 19:38:44 GMT 2025
PRIMARY
SMS_ID
100000076484
Created by admin on Mon Mar 31 19:38:44 GMT 2025 , Edited by admin on Mon Mar 31 19:38:44 GMT 2025
PRIMARY
NCI_THESAURUS
C61822
Created by admin on Mon Mar 31 19:38:44 GMT 2025 , Edited by admin on Mon Mar 31 19:38:44 GMT 2025
PRIMARY
WIKIPEDIA
MANDELIC ACID
Created by admin on Mon Mar 31 19:38:44 GMT 2025 , Edited by admin on Mon Mar 31 19:38:44 GMT 2025
PRIMARY
RS_ITEM_NUM
1375058
Created by admin on Mon Mar 31 19:38:44 GMT 2025 , Edited by admin on Mon Mar 31 19:38:44 GMT 2025
PRIMARY
DRUG CENTRAL
1629
Created by admin on Mon Mar 31 19:38:44 GMT 2025 , Edited by admin on Mon Mar 31 19:38:44 GMT 2025
PRIMARY
CAS
90-64-2
Created by admin on Mon Mar 31 19:38:44 GMT 2025 , Edited by admin on Mon Mar 31 19:38:44 GMT 2025
PRIMARY
RXCUI
29256
Created by admin on Mon Mar 31 19:38:44 GMT 2025 , Edited by admin on Mon Mar 31 19:38:44 GMT 2025
PRIMARY RxNorm
DAILYMED
NH496X0UJX
Created by admin on Mon Mar 31 19:38:44 GMT 2025 , Edited by admin on Mon Mar 31 19:38:44 GMT 2025
PRIMARY
DRUG BANK
DB13218
Created by admin on Mon Mar 31 19:38:44 GMT 2025 , Edited by admin on Mon Mar 31 19:38:44 GMT 2025
PRIMARY
EVMPD
SUB14462MIG
Created by admin on Mon Mar 31 19:38:44 GMT 2025 , Edited by admin on Mon Mar 31 19:38:44 GMT 2025
PRIMARY
EPA CompTox
DTXSID6023234
Created by admin on Mon Mar 31 19:38:44 GMT 2025 , Edited by admin on Mon Mar 31 19:38:44 GMT 2025
PRIMARY
MESH
C037938
Created by admin on Mon Mar 31 19:38:44 GMT 2025 , Edited by admin on Mon Mar 31 19:38:44 GMT 2025
PRIMARY
ECHA (EC/EINECS)
202-007-6
Created by admin on Mon Mar 31 19:38:44 GMT 2025 , Edited by admin on Mon Mar 31 19:38:44 GMT 2025
PRIMARY
ChEMBL
CHEMBL1609
Created by admin on Mon Mar 31 19:38:44 GMT 2025 , Edited by admin on Mon Mar 31 19:38:44 GMT 2025
PRIMARY
FDA UNII
NH496X0UJX
Created by admin on Mon Mar 31 19:38:44 GMT 2025 , Edited by admin on Mon Mar 31 19:38:44 GMT 2025
PRIMARY
PUBCHEM
1292
Created by admin on Mon Mar 31 19:38:44 GMT 2025 , Edited by admin on Mon Mar 31 19:38:44 GMT 2025
PRIMARY
NSC
7925
Created by admin on Mon Mar 31 19:38:44 GMT 2025 , Edited by admin on Mon Mar 31 19:38:44 GMT 2025
PRIMARY
Related Record Type Details
ENANTIOMER -> RACEMATE
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
ENANTIOMER -> RACEMATE
SALT/SOLVATE -> PARENT
PARENT->INNOVATOR
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
SALT/SOLVATE -> PARENT
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
PARENT -> IMPURITY
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
ACTIVE MOIETY