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 |
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 |
|---|---|---|
| Cumulative exposure to styrene and visual functions. | 2001 Apr |
|
| Identification of 1-adenine DNA adducts in workers occupationally exposed to styrene. | 2001 Aug |
|
| Hydrogen-bonded bilayers in piperazinium(2+) bis(mandelate) bis(methanol) solvate. | 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 |
|
| 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 |
|
| Unique oxidative mechanisms for the reactive nitrogen oxide species, nitroxyl anion. | 2001 Jan 19 |
|
| Coupling of simulated moving bed chromatography and fractional crystallisation for efficient enantioseparation. | 2001 Jan 26 |
|
| Stereochemical metabolism of styrene in volunteers. | 2001 Jul |
|
| Inter- and intra-individual sources of variation in levels of urinary styrene metabolites. | 2001 Jul |
|
| Discrimination in resolving systems. VI. Comparison of the diastereomers of deoxyephedrinium and ephedrinium 4'-fluoromandelates. | 2001 May 15 |
|
| Design and synthesis of glycolic and mandelic acid derivatives as factor Xa inhibitors. | 2001 Sep 3 |
|
| Liquid chromatography/electrospray tandem mass spectrometry characterization of styrene metabolism in man and in rat. | 2002 |
|
| 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 |
|
| A practical enantioselective fluorescent sensor for mandelic acid. | 2002 Mar 13 |
|
| Kinetics and thermodynamics of mandelate racemase catalysis. | 2002 Mar 26 |
|
| 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 |
|
| [A study on the adduct characteristics of styrene and DNA]. | 2002 Oct |
|
| Absolute configuration of tert-butyl-1-(2-methylnaphthyl)phosphine oxide. | 2002 Sep 6 |
|
| The role of various biomarkers in the evaluation of styrene genotoxicity. | 2003 |
|
| Synthesis of optically active atropisomeric anilide derivatives through diastereoselective N-allylation with a chiral Pd-pi-allyl catalyst. | 2003 Dec 12 |
|
| 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 |
|
| 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 |
|
| Mandelamide hydrolase from Pseudomonas putida: characterization of a new member of the amidase signature family. | 2004 Jun 22 |
|
| Chiral synthesis of (2S,3S)-2-(2-morpholin-2-yl-2-phenylmethoxy)phenol. | 2004 Mar |
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
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admin
on
Edited
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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PARENT -> SALT/SOLVATE |
