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
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)
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 | ( + / - ) |
DescriptionSources: http://eci2012.net/wp-content/uploads/2015/03/Mandelamine-PM-En-100446.02-11Mar2015.pdfCurator's Comment: description was created based on several sources, including, http://dermage.com.br/dermage/paginas/article.pdf
Sources: http://eci2012.net/wp-content/uploads/2015/03/Mandelamine-PM-En-100446.02-11Mar2015.pdf
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.
Originator
Approval Year
Doses
Dose | Population | Adverse 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 |
Other AEs: Burning sensation, Erythema... Other AEs: Burning sensation (1 patient) Sources: Erythema (2 patients) |
1 % 2 times / day multiple, topical Dose: 1 %, 2 times / day Route: topical Route: multiple Dose: 1 %, 2 times / day Sources: |
unhealthy |
Other AEs: Skin erythema desquamative... |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
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 |
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 |
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 |
PubMed
Title | Date | PubMed |
---|---|---|
Histidine-functionalized silica and its copper complex as stationary phases for capillary electrochromatography. | 2001 Aug |
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Fitting adsorption isotherms to the distribution data determined using packed micro-columns for high-performance liquid chromatography. | 2001 Aug 3 |
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Stereochemical metabolism of styrene in volunteers. | 2001 Jul |
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Inter- and intra-individual sources of variation in levels of urinary styrene metabolites. | 2001 Jul |
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Intervention study on acquired color vision deficiencies in styrene-exposed workers. | 2001 May |
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Polymorphism of xenobiotic-metabolizing enzymes and excretion of styrene-specific mercapturic acids. | 2001 Oct |
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An enzyme library approach to biocatalysis: development of nitrilases for enantioselective production of carboxylic acid derivatives. | 2002 Aug 7 |
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A practical enantioselective fluorescent sensor for mandelic acid. | 2002 Mar 13 |
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Assessment of sperm DNA integrity in workers exposed to styrene. | 2002 Nov |
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A highly selective aerobic oxidation process catalyzed by electron-deficient nitroarenes via single electron transfer processes. | 2002 Oct 18 |
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Audiometric findings in workers exposed to low levels of styrene and noise. | 2002 Sep |
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Absolute configuration of tert-butyl-1-(2-methylnaphthyl)phosphine oxide. | 2002 Sep 6 |
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Exceptional chiral recognition of racemic carboxylic acids by calix[4]arenes bearing optically pure alpha,beta-amino alcohol groups. | 2004 Apr 15 |
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Heptakis(6-amino-6-deoxy)-beta-cyclodextrin as a chiral selector for the separation of anionic analyte enantiomers by capillary electrophoresis. | 2004 Aug |
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Influence of (hydroxy)alkylamino substituents on enantioseparation ability of single-isomer amino-beta-cyclodextrin derivatives in chiral capillary electrophoresis. | 2004 Aug |
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Determination of urinary styrene metabolites in the general Italian population by liquid chromatography-tandem mass spectrometry. | 2004 Aug |
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Role of glycine 81 in (S)-mandelate dehydrogenase from Pseudomonas putida in substrate specificity and oxidase activity. | 2004 Aug 24 |
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Synthesis and antibiotic activity of the tricyclic furo[3,2-c] isochromen-2-trione unit of the pyranonaphthoquinones. | 2004 Feb 9 |
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A rapid HPLC method for the determination of carboxylic acids in human urine using a monolithic column. | 2004 Jan |
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High resolution structures of an oxidized and reduced flavoprotein. The water switch in a soluble form of (S)-mandelate dehydrogenase. | 2004 Jan 30 |
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Altered substrate specificity in flavocytochrome b2: structural insights into the mechanism of L-lactate dehydrogenation. | 2004 Jul 27 |
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Cytogenetic markers, DNA single-strand breaks, urinary metabolites, and DNA repair rates in styrene-exposed lamination workers. | 2004 Jun |
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Mandelamide hydrolase from Pseudomonas putida: characterization of a new member of the amidase signature family. | 2004 Jun 22 |
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Chiral synthesis of (2S,3S)-2-(2-morpholin-2-yl-2-phenylmethoxy)phenol. | 2004 Mar |
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Current trends in quantitative structure activity relationships on FXa inhibitors: evaluation and comparative analysis. | 2004 Nov |
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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
Sources: http://idosi.org/wasj/wasj31(5)14/36.pdf
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
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Record UNII |
NH496X0UJX
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Record Status |
Validated (UNII)
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WHO-VATC |
QB05CA06
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WHO-ATC |
B05CA06
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WHO-ATC |
J01XX06
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NCI_THESAURUS |
C255
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WHO-VATC |
QJ01XX06
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m7051
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35825
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100000076484
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C61822
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MANDELIC ACID
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1375058
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29256
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NH496X0UJX
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DB13218
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Related Record | Type | Details | ||
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ENANTIOMER -> RACEMATE | |||
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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ENANTIOMER -> RACEMATE | |||
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SALT/SOLVATE -> PARENT |
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PARENT->INNOVATOR |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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SALT/SOLVATE -> PARENT |
Related Record | Type | Details | ||
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
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PARENT -> IMPURITY |
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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