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
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
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 | ( + / - ) |
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 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) Sources: Erythema (2 patients) |
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) Sources: lactobionic acid(1%; 2/day) sulfate zinc(1%; 2/day) |
unhealthy n = 20 Health Status: unhealthy Condition: facial acne Sex: M+F Population Size: 20 Sources: |
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 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) Sources: lactobionic acid(1%; 2/day) sulfate zinc(1%; 2/day) |
unhealthy n = 20 Health Status: unhealthy Condition: facial acne Sex: M+F Population Size: 20 Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
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
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
by
admin
on
Edited
Thu Jul 06 01:56:23 UTC 2023
by
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Record UNII |
6PGE18556E
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Record Status |
Validated (UNII)
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Record Version |
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M1799
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