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
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
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 |
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 |
---|---|---|
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 |
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A QM/MM study of the racemization of vinylglycolate catalyzed by mandelate racemase enzyme. | 2001 Jan 31 |
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Intervention study on acquired color vision deficiencies in styrene-exposed workers. | 2001 May |
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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 |
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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 |
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Simultaneous determination of styrene, toluene, and xylene metabolites in urine by gas chromatography/mass spectrometry. | 2002 Oct |
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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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Finnish quality assurance programme for biological monitoring of organic solvents. | 2002 Oct 5 |
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Exposure assessment of monoterpenes and styrene: a comparison of air sampling and biomonitoring. | 2003 Aug |
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Chloride present in biological samples as a tool for enhancement of sensitivity in capillary zone electrophoretic analysis of anionic trace analytes. | 2003 Jan |
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The mandelamide keto-enol system in aqueous solution. Generation of the enol by hydration of phenylcarbamoylcarbene. | 2003 Jan 8 |
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Inhibition of mandelate racemase by alpha-fluorobenzylphosphonates. | 2003 Jun 16 |
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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 |
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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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Role of glycine 81 in (S)-mandelate dehydrogenase from Pseudomonas putida in substrate specificity and oxidase activity. | 2004 Aug 24 |
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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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Evaluation of the efficiency of respiratory protective equipment based on the biological monitoring of styrene in fibreglass reinforced plastics industries. | 2004 Mar |
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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
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
Fri Dec 15 15:09:49 GMT 2023
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on
Fri Dec 15 15:09:49 GMT 2023
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Record UNII |
83WBN2F871
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Record Status |
Validated (UNII)
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Record Version |
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