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
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 |
|---|---|---|
| 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 |
|
| Inter- and intra-individual sources of variation in levels of urinary styrene metabolites. | 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 |
|
| Enantiomer separation of mandelates and their analogs on cyclodextrin derivative chiral stationary phases by capillary GC. | 2001 Oct |
|
| Polymorphism of xenobiotic-metabolizing enzymes and excretion of styrene-specific mercapturic acids. | 2001 Oct |
|
| Bioavailability and pharmacokinetics of magnesium after administration of magnesium salts to humans. | 2001 Sep-Oct |
|
| GSTM1 polymorphism and styrene metabolism: insights from an acute accidental exposure. | 2002 Aug 5 |
|
| 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 |
|
| Assessment of sperm DNA integrity in workers exposed to styrene. | 2002 Nov |
|
| Fluorescent sensors for the enantioselective recognition of mandelic acid: signal amplification by dendritic branching. | 2002 Nov 27 |
|
| A highly selective aerobic oxidation process catalyzed by electron-deficient nitroarenes via single electron transfer processes. | 2002 Oct 18 |
|
| The role of various biomarkers in the evaluation of styrene genotoxicity. | 2003 |
|
| Nonlinear amplification of circular dichroism activity upon cyclodimerization of a chiral saddle-shaped porphyrin. | 2003 Jan 7 |
|
| Solvent ototoxicity in the rat and guinea pig. | 2003 Jan-Feb |
|
| Inhibition of mandelate racemase by alpha-fluorobenzylphosphonates. | 2003 Jun 16 |
|
| Sperm-FISH analysis and human monitoring: a study on workers occupationally exposed to styrene. | 2003 Jun 6 |
|
| 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 |
|
| 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 |
|
| C4'-spiroalkylated nucleosides having sulfur incorporated at the apex position. | 2003 Oct 31 |
|
| 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 |
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.
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PARENT (SALT/SOLVATE)
SUBSTANCE RECORD
