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Details

Stereochemistry RACEMIC
Molecular Formula C8H8O3
Molecular Weight 152.1476
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MANDELIC ACID

SMILES

c1ccc(cc1)C(C(=O)O)O

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 152.1476
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
n = 25
Health Status: unhealthy
Condition: acne vulgaris
Age Group: 19.4
Sex: M+F
Population Size: 25
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
Co-administed with::
benzoylperoxide(4%; 2/day)
lactobionic acid(1%; 2/day)
sulfate zinc(1%; 2/day)
Sources:
unhealthy
n = 20
Health Status: unhealthy
Condition: facial acne
Sex: M+F
Population Size: 20
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
n = 25
Health Status: unhealthy
Condition: acne vulgaris
Age Group: 19.4
Sex: M+F
Population Size: 25
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
n = 25
Health Status: unhealthy
Condition: acne vulgaris
Age Group: 19.4
Sex: M+F
Population Size: 25
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
Co-administed with::
benzoylperoxide(4%; 2/day)
lactobionic acid(1%; 2/day)
sulfate zinc(1%; 2/day)
Sources:
unhealthy
n = 20
Health Status: unhealthy
Condition: facial acne
Sex: M+F
Population Size: 20
Sources:
PubMed

PubMed

TitleDatePubMed
Metabolism of the styrene metabolite 4-vinylphenol by rat and mouse liver and lung.
2001 Aug 10
Fitting adsorption isotherms to the distribution data determined using packed micro-columns for high-performance liquid chromatography.
2001 Aug 3
A QM/MM study of the racemization of vinylglycolate catalyzed by mandelate racemase enzyme.
2001 Jan 31
Stereochemical metabolism of styrene in volunteers.
2001 Jul
Discrimination in resolving systems. VI. Comparison of the diastereomers of deoxyephedrinium and ephedrinium 4'-fluoromandelates.
2001 May 15
Polymorphism of xenobiotic-metabolizing enzymes and excretion of styrene-specific mercapturic acids.
2001 Oct
Design and synthesis of glycolic and mandelic acid derivatives as factor Xa inhibitors.
2001 Sep 3
Liquid chromatography/electrospray tandem mass spectrometry characterization of styrene metabolism in man and in rat.
2002
An enzyme library approach to biocatalysis: development of nitrilases for enantioselective production of carboxylic acid derivatives.
2002 Aug 7
Relation between colour vision loss and occupational styrene exposure level.
2002 Dec
High-throughput screening of enantioselective catalysts by immunoassay.
2002 Jan 4
Validated method for quantitation of biomarkers for benzene and its alkylated analogues in urine.
2002 Jul 15
Hydroxamates as substrates and inhibitors for FMN-dependent 2-hydroxy acid dehydrogenases.
2002 Jun
Fluorescent sensors for the enantioselective recognition of mandelic acid: signal amplification by dendritic branching.
2002 Nov 27
[A study on the adduct characteristics of styrene and DNA].
2002 Oct
Simultaneous determination of styrene, toluene, and xylene metabolites in urine by gas chromatography/mass spectrometry.
2002 Oct
(R)-mandelic acid (S)-alanine hemihydrate.
2002 Oct
Arginine 165/arginine 277 pair in (S)-mandelate dehydrogenase from Pseudomonas putida: role in catalysis and substrate binding.
2002 Oct 15
Finnish quality assurance programme for biological monitoring of organic solvents.
2002 Oct 5
Audiometric findings in workers exposed to low levels of styrene and noise.
2002 Sep
Synthesis of optically active atropisomeric anilide derivatives through diastereoselective N-allylation with a chiral Pd-pi-allyl catalyst.
2003 Dec 12
Nonlinear amplification of circular dichroism activity upon cyclodimerization of a chiral saddle-shaped porphyrin.
2003 Jan 7
Comparison of isotopic fractionation in lactic acid and ethanol fermentations.
2003 Jun
Use of ionic liquids in a lipase-facilitated supported liquid membrane.
2003 May
Effects of clay minerals on Cr(VI) reduction by organic compounds.
2003 May
A transient intermediate in the reaction catalyzed by (S)-mandelate dehydrogenase from Pseudomonas putida.
2003 Nov 11
A high-throughput amenable colorimetric assay for enantioselective screening of nitrilase-producing microorganisms using pH sensitive indicators.
2003 Oct
C4'-spiroalkylated nucleosides having sulfur incorporated at the apex position.
2003 Oct 31
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
Role of glycine 81 in (S)-mandelate dehydrogenase from Pseudomonas putida in substrate specificity and oxidase activity.
2004 Aug 24
Quininium (R)-mandelate, a structure with large Z' described as an incommensurately modulated structure in (3+1)-dimensional superspace.
2004 Feb
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
Evaluation of the efficiency of respiratory protective equipment based on the biological monitoring of styrene in fibreglass reinforced plastics industries.
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 Sat Jun 26 10:46:57 UTC 2021
Edited
by admin
on Sat Jun 26 10:46:57 UTC 2021
Record UNII
NH496X0UJX
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MANDELIC ACID
INCI   MART.   MI   USP-RS   WHO-DD  
INCI  
Official Name English
PARAMANDELIC ACID
Common Name English
MANDELIC ACID [INCI]
Common Name English
PHENYLACETIC ACID, .ALPHA.--HYDROXY-
Common Name English
RACEMIC MANDELIC ACID
Common Name English
MANDELIC ACID [USP-RS]
Common Name English
HOMATROPINE METHYLBROMIDE IMPURITY C [EP]
Common Name English
HOMATROPINE HYDROBROMIDE IMPURITY C [EP]
Common Name English
MANDELIC ACID [MART.]
Common Name English
MANDELIC ACID [WHO-DD]
Common Name English
GLYCOPYRRONIUM BROMIDE IMPURITY C [EP]
Common Name English
NSC-7925
Code English
MANDELIC ACID [MI]
Common Name English
.ALPHA.-HYDROXYPHENYLACETIC ACID
Systematic Name English
DL-MANDELIC ACID
Common Name English
Classification Tree Code System Code
WHO-VATC QB05CA06
Created by admin on Sat Jun 26 10:46:58 UTC 2021 , Edited by admin on Sat Jun 26 10:46:58 UTC 2021
WHO-ATC B05CA06
Created by admin on Sat Jun 26 10:46:58 UTC 2021 , Edited by admin on Sat Jun 26 10:46:58 UTC 2021
WHO-ATC J01XX06
Created by admin on Sat Jun 26 10:46:58 UTC 2021 , Edited by admin on Sat Jun 26 10:46:58 UTC 2021
NCI_THESAURUS C255
Created by admin on Sat Jun 26 10:46:58 UTC 2021 , Edited by admin on Sat Jun 26 10:46:58 UTC 2021
WHO-VATC QJ01XX06
Created by admin on Sat Jun 26 10:46:58 UTC 2021 , Edited by admin on Sat Jun 26 10:46:58 UTC 2021
Code System Code Type Description
MERCK INDEX
M7051
Created by admin on Sat Jun 26 10:46:58 UTC 2021 , Edited by admin on Sat Jun 26 10:46:58 UTC 2021
PRIMARY Merck Index
NCI_THESAURUS
C61822
Created by admin on Sat Jun 26 10:46:58 UTC 2021 , Edited by admin on Sat Jun 26 10:46:58 UTC 2021
PRIMARY
WIKIPEDIA
MANDELIC ACID
Created by admin on Sat Jun 26 10:46:58 UTC 2021 , Edited by admin on Sat Jun 26 10:46:58 UTC 2021
PRIMARY
DRUG CENTRAL
1629
Created by admin on Sat Jun 26 10:46:58 UTC 2021 , Edited by admin on Sat Jun 26 10:46:58 UTC 2021
PRIMARY
CAS
90-64-2
Created by admin on Sat Jun 26 10:46:58 UTC 2021 , Edited by admin on Sat Jun 26 10:46:58 UTC 2021
PRIMARY
RXCUI
29256
Created by admin on Sat Jun 26 10:46:58 UTC 2021 , Edited by admin on Sat Jun 26 10:46:58 UTC 2021
PRIMARY RxNorm
DRUG BANK
DB13218
Created by admin on Sat Jun 26 10:46:58 UTC 2021 , Edited by admin on Sat Jun 26 10:46:58 UTC 2021
PRIMARY
EVMPD
SUB14462MIG
Created by admin on Sat Jun 26 10:46:58 UTC 2021 , Edited by admin on Sat Jun 26 10:46:58 UTC 2021
PRIMARY
EPA CompTox
90-64-2
Created by admin on Sat Jun 26 10:46:58 UTC 2021 , Edited by admin on Sat Jun 26 10:46:58 UTC 2021
PRIMARY
MESH
C037938
Created by admin on Sat Jun 26 10:46:58 UTC 2021 , Edited by admin on Sat Jun 26 10:46:58 UTC 2021
PRIMARY
ECHA (EC/EINECS)
202-007-6
Created by admin on Sat Jun 26 10:46:58 UTC 2021 , Edited by admin on Sat Jun 26 10:46:58 UTC 2021
PRIMARY
ChEMBL
CHEMBL1609
Created by admin on Sat Jun 26 10:46:58 UTC 2021 , Edited by admin on Sat Jun 26 10:46:58 UTC 2021
PRIMARY
FDA UNII
NH496X0UJX
Created by admin on Sat Jun 26 10:46:58 UTC 2021 , Edited by admin on Sat Jun 26 10:46:58 UTC 2021
PRIMARY
PUBCHEM
1292
Created by admin on Sat Jun 26 10:46:58 UTC 2021 , Edited by admin on Sat Jun 26 10:46:58 UTC 2021
PRIMARY
USP_CATALOG
1375058
Created by admin on Sat Jun 26 10:46:58 UTC 2021 , Edited by admin on Sat Jun 26 10:46:58 UTC 2021
PRIMARY USP-RS
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ENANTIOMER -> RACEMATE
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
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ENANTIOMER -> RACEMATE
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PARENT->INNOVATOR
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