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 | ( + / - ) |
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 |
|
| Toxicity and biodegradation of products from polyester hydrolysis. | 2001 |
|
| Structure of an active soluble mutant of the membrane-associated (S)-mandelate dehydrogenase. | 2001 Aug 21 |
|
| Biological monitoring of workers exposed to ethylbenzene and co-exposed to xylene. | 2001 Jan |
|
| Effects of low-level occupational exposure to styrene on color vision: dose relation with a urinary metabolite. | 2001 Jan |
|
| A QM/MM study of the racemization of vinylglycolate catalyzed by mandelate racemase enzyme. | 2001 Jan 31 |
|
| Stereochemical metabolism of styrene in volunteers. | 2001 Jul |
|
| 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 |
|
| Discrimination in resolving systems. VI. Comparison of the diastereomers of deoxyephedrinium and ephedrinium 4'-fluoromandelates. | 2001 May 15 |
|
| Bioavailability and pharmacokinetics of magnesium after administration of magnesium salts to humans. | 2001 Sep-Oct |
|
| 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 |
|
| An enzyme library approach to biocatalysis: development of nitrilases for enantioselective production of carboxylic acid derivatives. | 2002 Aug 7 |
|
| 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 |
|
| 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 |
|
| Mandelic acid condensation polymer: novel candidate microbicide for prevention of human immunodeficiency virus and herpes simplex virus entry. | 2002 Nov |
|
| 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 |
|
| Absolute configuration of tert-butyl-1-(2-methylnaphthyl)phosphine oxide. | 2002 Sep 6 |
|
| Structural and kinetic analysis of catalysis by a thiamin diphosphate-dependent enzyme, benzoylformate decarboxylase. | 2003 Feb 25 |
|
| Solvent ototoxicity in the rat and guinea pig. | 2003 Jan-Feb |
|
| A glycopeptide antibiotic chiral stationary phase for the enantiomer resolution of hydroxy acid derivatives by capillary electrochromatography. | 2003 Mar |
|
| 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 |
|
| 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 |
|
| [Experimental study on the in vitro resistance to Toxoplasma gondii by murine lymphocyte]. | 2003 Sep |
|
| 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 |
|
| Influence of (hydroxy)alkylamino substituents on enantioseparation ability of single-isomer amino-beta-cyclodextrin derivatives in chiral capillary electrophoresis. | 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 |
|
| A rapid HPLC method for the determination of carboxylic acids in human urine using a monolithic column. | 2004 Jan |
|
| 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
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 18:45:00 GMT 2023
by
admin
on
Fri Dec 15 18:45:00 GMT 2023
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| Record UNII |
6PGE18556E
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
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m1799
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6PGE18556E
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PARENT -> SALT/SOLVATE |
