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Details

Stereochemistry RACEMIC
Molecular Formula C8H7O3.H4N
Molecular Weight 169.1782
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AMMONIUM MANDELATE

SMILES

c1ccc(cc1)C(C(=O)O)O.N

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 152.1476
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
[Efficacy of mandelic acid in treating acute toxoplasmosis in mice].
2001
Liquid chromatography/electrospray tandem mass spectrometry characterization of styrene metabolism in man and in rat.
2002
Germicidal activities of representatives of five different teat dip classes against three bovine mycoplasma species using a modified excised teat model.
2002 Aug
Electrochemical recognition of chiral species using quaternary ammonium binaphthyl salts.
2002 Aug 15
GSTM1 polymorphism and styrene metabolism: insights from an acute accidental exposure.
2002 Aug 5
Relation between colour vision loss and occupational styrene exposure level.
2002 Dec
High-throughput screening of enantioselective catalysts by immunoassay.
2002 Jan 4
[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
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
Audiometric findings in workers exposed to low levels of styrene and noise.
2002 Sep
The role of various biomarkers in the evaluation of styrene genotoxicity.
2003
Exposure assessment of monoterpenes and styrene: a comparison of air sampling and biomonitoring.
2003 Aug
Synthesis of optically active atropisomeric anilide derivatives through diastereoselective N-allylation with a chiral Pd-pi-allyl catalyst.
2003 Dec 12
Structural and kinetic analysis of catalysis by a thiamin diphosphate-dependent enzyme, benzoylformate decarboxylase.
2003 Feb 25
Chloride present in biological samples as a tool for enhancement of sensitivity in capillary zone electrophoretic analysis of anionic trace analytes.
2003 Jan
Nonlinear amplification of circular dichroism activity upon cyclodimerization of a chiral saddle-shaped porphyrin.
2003 Jan 7
The mandelamide keto-enol system in aqueous solution. Generation of the enol by hydration of phenylcarbamoylcarbene.
2003 Jan 8
Solvent ototoxicity in the rat and guinea pig.
2003 Jan-Feb
Comparison of isotopic fractionation in lactic acid and ethanol fermentations.
2003 Jun
Inhibition of mandelate racemase by alpha-fluorobenzylphosphonates.
2003 Jun 16
Sperm-FISH analysis and human monitoring: a study on workers occupationally exposed to styrene.
2003 Jun 6
A glycopeptide antibiotic chiral stationary phase for the enantiomer resolution of hydroxy acid derivatives by capillary electrochromatography.
2003 Mar
Use of short-end injection capillary packed with a glycopeptide antibiotic stationary phase in electrochromatography and capillary liquid chromatography for the enantiomeric separation of hydroxy acids.
2003 Mar 21
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
Asymmetric environments in encapsulation complexes.
2003 May 21
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
[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
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
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
Human urine certified reference material CZ 6009: creatinine, styrene metabolites (mandelic acid and phenylglyoxylic acid).
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 15:51:39 UTC 2021
Edited
by admin
on Sat Jun 26 15:51:39 UTC 2021
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
MERCK INDEX
M1799
Created by admin on Sat Jun 26 15:51:39 UTC 2021 , Edited by admin on Sat Jun 26 15:51:39 UTC 2021
PRIMARY Merck Index
ECHA (EC/EINECS)
208-475-8
Created by admin on Sat Jun 26 15:51:39 UTC 2021 , Edited by admin on Sat Jun 26 15:51:39 UTC 2021
PRIMARY
CAS
530-31-4
Created by admin on Sat Jun 26 15:51:39 UTC 2021 , Edited by admin on Sat Jun 26 15:51:39 UTC 2021
PRIMARY
ChEMBL
CHEMBL2105969
Created by admin on Sat Jun 26 15:51:39 UTC 2021 , Edited by admin on Sat Jun 26 15:51:39 UTC 2021
PRIMARY
FDA UNII
6PGE18556E
Created by admin on Sat Jun 26 15:51:39 UTC 2021 , Edited by admin on Sat Jun 26 15:51:39 UTC 2021
PRIMARY
PUBCHEM
10732
Created by admin on Sat Jun 26 15:51:39 UTC 2021 , Edited by admin on Sat Jun 26 15:51:39 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE