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Details

Stereochemistry RACEMIC
Molecular Formula C8H7O3.H4N
Molecular Weight 169.1778
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AMMONIUM MANDELATE

SMILES

[NH4+].OC(C([O-])=O)C1=CC=CC=C1

InChI

InChIKey=BDEXTKUJIZCFST-UHFFFAOYSA-N
InChI=1S/C8H8O3.H3N/c9-7(8(10)11)6-4-2-1-3-5-6;/h1-5,7,9H,(H,10,11);1H3

HIDE SMILES / InChI

Molecular Formula H3N
Molecular Weight 17.0305
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
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
Toxicity and biodegradation of products from polyester hydrolysis.
2001
Cumulative exposure to styrene and visual functions.
2001 Apr
Simultaneous high-performance liquid chromatographic determination of urinary mandelic and phenylglyoxylic acids as indirect evaluation of styrene exposure.
2001 Apr 5
Histidine-functionalized silica and its copper complex as stationary phases for capillary electrochromatography.
2001 Aug
Identification of 1-adenine DNA adducts in workers occupationally exposed to styrene.
2001 Aug
Metabolism of the styrene metabolite 4-vinylphenol by rat and mouse liver and lung.
2001 Aug 10
Structure of an active soluble mutant of the membrane-associated (S)-mandelate dehydrogenase.
2001 Aug 21
Coupling of simulated moving bed chromatography and fractional crystallisation for efficient enantioseparation.
2001 Jan 26
A QM/MM study of the racemization of vinylglycolate catalyzed by mandelate racemase enzyme.
2001 Jan 31
Oxidation-active flavin models: oxidation of alpha-hydroxy acids by benzo-dipteridine bearing metal-binding site in the presence of divalent metal ion and base in organic solvents.
2001 Mar 21
Intervention study on acquired color vision deficiencies in styrene-exposed workers.
2001 May
Discrimination in resolving systems. VI. Comparison of the diastereomers of deoxyephedrinium and ephedrinium 4'-fluoromandelates.
2001 May 15
Trifluoromethyl ketone-based inhibitors of apoptosis in cerebellar granule neurons.
2001 Nov
Polymorphism of xenobiotic-metabolizing enzymes and excretion of styrene-specific mercapturic acids.
2001 Oct
DNA single strand breaks induced by low levels of occupational exposure to styrene: the gap between standards and reality.
2002
Asymmetric intramolecular [2 + 2] photocycloadditions: alpha- and beta-hydroxy acids as chiral tether groups.
2002 Feb 22
Evaluation of genotoxic effects in a group of workers exposed to low levels of styrene.
2002 Feb 28
Impact of adsorption isotherm parameters on the performance of enantioseparation using simulated moving bed chromatography.
2002 Jan 25
Analysis of styrene and its metabolites in blood and urine of workers exposed to both styrene and acetone.
2002 Jan-Feb
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
A practical enantioselective fluorescent sensor for mandelic acid.
2002 Mar 13
Kinetics and thermodynamics of mandelate racemase catalysis.
2002 Mar 26
Fluorescent sensors for the enantioselective recognition of mandelic acid: signal amplification by dendritic branching.
2002 Nov 27
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
A highly selective aerobic oxidation process catalyzed by electron-deficient nitroarenes via single electron transfer processes.
2002 Oct 18
Finnish quality assurance programme for biological monitoring of organic solvents.
2002 Oct 5
The role of various biomarkers in the evaluation of styrene genotoxicity.
2003
Structural and kinetic analysis of catalysis by a thiamin diphosphate-dependent enzyme, benzoylformate decarboxylase.
2003 Feb 25
A glycopeptide antibiotic chiral stationary phase for the enantiomer resolution of hydroxy acid derivatives by capillary electrochromatography.
2003 Mar
Asymmetric environments in encapsulation complexes.
2003 May 21
C4'-spiroalkylated nucleosides having sulfur incorporated at the apex position.
2003 Oct 31
[Experimental study on the in vitro resistance to Toxoplasma gondii by murine lymphocyte].
2003 Sep
Nitration of endogenous para-hydroxyphenylacetic acid and the metabolism of nitrotyrosine.
2003 Sep 1
Exceptional chiral recognition of racemic carboxylic acids by calix[4]arenes bearing optically pure alpha,beta-amino alcohol groups.
2004 Apr 15
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
Quininium (R)-mandelate, a structure with large Z' described as an incommensurately modulated structure in (3+1)-dimensional superspace.
2004 Feb
Esters of mandelic acid as substrates for (S)-mandelate dehydrogenase from Pseudomonas putida: implications for the reaction mechanism.
2004 Feb 24
Synthesis and antibiotic activity of the tricyclic furo[3,2-c] isochromen-2-trione unit of the pyranonaphthoquinones.
2004 Feb 9
Construction of an electro-enzymatic bioreactor for the production of (R)-mandelate from benzoylformate.
2004 Jan
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
Evaluation of the efficiency of respiratory protective equipment based on the biological monitoring of styrene in fibreglass reinforced plastics industries.
2004 Mar
Chiral synthesis of (2S,3S)-2-(2-morpholin-2-yl-2-phenylmethoxy)phenol.
2004 Mar
Human urine certified reference material CZ 6009: creatinine, styrene metabolites (mandelic acid and phenylglyoxylic acid).
2004 Mar
Hydrophobic nature of the active site of mandelate racemase.
2004 Mar 9
Current trends in quantitative structure activity relationships on FXa inhibitors: evaluation and comparative analysis.
2004 Nov
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 Thu Jul 06 01:56:23 UTC 2023
Edited
by admin
on Thu Jul 06 01:56:23 UTC 2023
Record UNII
6PGE18556E
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AMMONIUM MANDELATE
MI  
Common Name English
MANDELIC ACID AMMONIUM SALT
Common Name English
AMMONIUM MANDELATE [MI]
Common Name English
.ALPHA.-HYDROXYBENZENEACETIC ACID AMMONIUM SALT (1:1)
Common Name English
Code System Code Type Description
EPA CompTox
DTXSID30967475
Created by admin on Thu Jul 06 01:56:23 UTC 2023 , Edited by admin on Thu Jul 06 01:56:23 UTC 2023
PRIMARY
MERCK INDEX
M1799
Created by admin on Thu Jul 06 01:56:23 UTC 2023 , Edited by admin on Thu Jul 06 01:56:23 UTC 2023
PRIMARY Merck Index
ECHA (EC/EINECS)
208-475-8
Created by admin on Thu Jul 06 01:56:23 UTC 2023 , Edited by admin on Thu Jul 06 01:56:23 UTC 2023
PRIMARY
CAS
530-31-4
Created by admin on Thu Jul 06 01:56:23 UTC 2023 , Edited by admin on Thu Jul 06 01:56:23 UTC 2023
PRIMARY
ChEMBL
CHEMBL2105969
Created by admin on Thu Jul 06 01:56:23 UTC 2023 , Edited by admin on Thu Jul 06 01:56:23 UTC 2023
PRIMARY
FDA UNII
6PGE18556E
Created by admin on Thu Jul 06 01:56:23 UTC 2023 , Edited by admin on Thu Jul 06 01:56:23 UTC 2023
PRIMARY
PUBCHEM
10732
Created by admin on Thu Jul 06 01:56:23 UTC 2023 , Edited by admin on Thu Jul 06 01:56:23 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE