Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C8H8O3 |
| Molecular Weight | 152.1476 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
c1ccc(cc1)C(C(=O)O)O
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 | 152.1476 |
| Charge | 0 |
| Count |
|
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Optical Activity | ( + / - ) |
DescriptionCurator's Comment:: description was created based on several sources, including, http://dermage.com.br/dermage/paginas/article.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 |
|---|---|---|
| [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 |
|
| DNA single strand breaks induced by low levels of occupational exposure to styrene: the gap between standards and reality. | 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 |
|
| An enzyme library approach to biocatalysis: development of nitrilases for enantioselective production of carboxylic acid derivatives. | 2002 Aug 7 |
|
| Relation between colour vision loss and occupational styrene exposure level. | 2002 Dec |
|
| Interest of genotyping and phenotyping of drug-metabolizing enzymes for the interpretation of biological monitoring of exposure to styrene. | 2002 Dec |
|
| Asymmetric intramolecular [2 + 2] photocycloadditions: alpha- and beta-hydroxy acids as chiral tether groups. | 2002 Feb 22 |
|
| Analysis of styrene and its metabolites in blood and urine of workers exposed to both styrene and acetone. | 2002 Jan-Feb |
|
| Kinetics and thermodynamics of mandelate racemase catalysis. | 2002 Mar 26 |
|
| Stereospecific synthesis of cryptophycin 1. | 2002 May 16 |
|
| Use of mandelic acid condensation polymer (SAMMA), a new antimicrobial contraceptive agent, for vaginal prophylaxis. | 2002 Nov |
|
| Assessment of sperm DNA integrity in workers exposed to styrene. | 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 |
|
| [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 |
|
| Absolute configuration of tert-butyl-1-(2-methylnaphthyl)phosphine oxide. | 2002 Sep 6 |
|
| 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 |
|
| Comparison of isotopic fractionation in lactic acid and ethanol fermentations. | 2003 Jun |
|
| 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 |
|
| 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 |
|
| Heptakis(6-amino-6-deoxy)-beta-cyclodextrin as a chiral selector for the separation of anionic analyte enantiomers by capillary electrophoresis. | 2004 Aug |
|
| Influence of (hydroxy)alkylamino substituents on enantioseparation ability of single-isomer amino-beta-cyclodextrin derivatives in chiral capillary electrophoresis. | 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 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| 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
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
Sat Jun 26 10:46:57 UTC 2021
by
admin
on
Sat Jun 26 10:46:57 UTC 2021
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| Record UNII |
NH496X0UJX
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| Record Status |
Validated (UNII)
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| Record Version |
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-
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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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| Code System | Code | Type | Description | ||
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M7051
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PRIMARY | Merck Index | ||
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C61822
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PRIMARY | |||
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MANDELIC ACID
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PRIMARY | |||
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1629
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PRIMARY | |||
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90-64-2
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PRIMARY | |||
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29256
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DB13218
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SUB14462MIG
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90-64-2
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C037938
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202-007-6
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CHEMBL1609
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NH496X0UJX
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1292
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1375058
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PRIMARY | USP-RS |
| 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 |
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 |
