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Details

Stereochemistry RACEMIC
Molecular Formula C8H7O3.Na
Molecular Weight 174.1291
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SODIUM MANDELATE

SMILES

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

InChI

InChIKey=FWDLHTBMGQEUDU-UHFFFAOYSA-M
InChI=1S/C8H8O3.Na/c9-7(8(10)11)6-4-2-1-3-5-6;/h1-5,7,9H,(H,10,11);/q;+1/p-1

HIDE SMILES / InChI

Molecular Formula C8H7O3
Molecular Weight 151.1394
Charge -1
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
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://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
Biological monitoring of workers exposed to ethylbenzene and co-exposed to xylene.
2001 Jan
Unique oxidative mechanisms for the reactive nitrogen oxide species, nitroxyl anion.
2001 Jan 19
A QM/MM study of the racemization of vinylglycolate catalyzed by mandelate racemase enzyme.
2001 Jan 31
Intervention study on acquired color vision deficiencies in styrene-exposed workers.
2001 May
Trifluoromethyl ketone-based inhibitors of apoptosis in cerebellar granule neurons.
2001 Nov
The catalytic role of tyrosine 254 in flavocytochrome b2 (L-lactate dehydrogenase from baker's yeast). Comparison between the Y254F and Y254L mutant proteins.
2001 Sep
Design and synthesis of glycolic and mandelic acid derivatives as factor Xa inhibitors.
2001 Sep 3
Bioavailability and pharmacokinetics of magnesium after administration of magnesium salts to humans.
2001 Sep-Oct
Interest of genotyping and phenotyping of drug-metabolizing enzymes for the interpretation of biological monitoring of exposure to styrene.
2002 Dec
Hydroxamates as substrates and inhibitors for FMN-dependent 2-hydroxy acid dehydrogenases.
2002 Jun
Further evidence for distinct reactive intermediates from nitroxyl and peroxynitrite: effects of buffer composition on the chemistry of Angeli's salt and synthetic peroxynitrite.
2002 May 15
Use of mandelic acid condensation polymer (SAMMA), a new antimicrobial contraceptive agent, for vaginal prophylaxis.
2002 Nov
Mandelic acid condensation polymer: novel candidate microbicide for prevention of human immunodeficiency virus and herpes simplex virus entry.
2002 Nov
The use of enzyme immunoassays for the detection of abzymatic activities. Application to an enantioselective thioacetal hydrolysis activity.
2002 Nov 1
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
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
Exposure assessment of monoterpenes and styrene: a comparison of air sampling and biomonitoring.
2003 Aug
Chloride present in biological samples as a tool for enhancement of sensitivity in capillary zone electrophoretic analysis of anionic trace analytes.
2003 Jan
The mandelamide keto-enol system in aqueous solution. Generation of the enol by hydration of phenylcarbamoylcarbene.
2003 Jan 8
Inhibition of mandelate racemase by alpha-fluorobenzylphosphonates.
2003 Jun 16
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
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
Heptakis(6-amino-6-deoxy)-beta-cyclodextrin as a chiral selector for the separation of anionic analyte enantiomers by capillary electrophoresis.
2004 Aug
Role of glycine 81 in (S)-mandelate dehydrogenase from Pseudomonas putida in substrate specificity and oxidase activity.
2004 Aug 24
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
Chiral synthesis of (2S,3S)-2-(2-morpholin-2-yl-2-phenylmethoxy)phenol.
2004 Mar
Hydrophobic nature of the active site of mandelate racemase.
2004 Mar 9
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 Fri Dec 15 15:09:49 GMT 2023
Edited
by admin
on Fri Dec 15 15:09:49 GMT 2023
Record UNII
83WBN2F871
Record Status Validated (UNII)
Record Version
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Name Type Language
SODIUM MANDELATE
Common Name English
DL-SODIUM MANDELATE
Common Name English
MANDELIC ACID SODIUM SALT [MI]
Common Name English
MANDELIC ACID, SODIUM SALT
Common Name English
MANDELIC ACID SODIUM SALT
MI  
Common Name English
SODIUM PHENYLGLYCOLATE
Systematic Name English
Code System Code Type Description
MERCK INDEX
m7051
Created by admin on Fri Dec 15 15:09:49 GMT 2023 , Edited by admin on Fri Dec 15 15:09:49 GMT 2023
PRIMARY Merck Index
FDA UNII
83WBN2F871
Created by admin on Fri Dec 15 15:09:49 GMT 2023 , Edited by admin on Fri Dec 15 15:09:49 GMT 2023
PRIMARY
CAS
114-21-6
Created by admin on Fri Dec 15 15:09:49 GMT 2023 , Edited by admin on Fri Dec 15 15:09:49 GMT 2023
PRIMARY
PUBCHEM
23675514
Created by admin on Fri Dec 15 15:09:49 GMT 2023 , Edited by admin on Fri Dec 15 15:09:49 GMT 2023
PRIMARY
ECHA (EC/EINECS)
204-041-7
Created by admin on Fri Dec 15 15:09:49 GMT 2023 , Edited by admin on Fri Dec 15 15:09:49 GMT 2023
PRIMARY
EPA CompTox
DTXSID30921254
Created by admin on Fri Dec 15 15:09:49 GMT 2023 , Edited by admin on Fri Dec 15 15:09:49 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE