Details
Stereochemistry | RACEMIC |
Molecular Formula | C8H8O3 |
Molecular Weight | 152.1473 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(C(O)=O)C1=CC=CC=C1
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 | 152.1473 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
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 |
---|---|---|
[Efficacy of mandelic acid in treating acute toxoplasmosis in mice]. | 2001 |
|
Cumulative exposure to styrene and visual functions. | 2001 Apr |
|
Identification of 1-adenine DNA adducts in workers occupationally exposed to styrene. | 2001 Aug |
|
Unique oxidative mechanisms for the reactive nitrogen oxide species, nitroxyl anion. | 2001 Jan 19 |
|
Inter- and intra-individual sources of variation in levels of urinary styrene metabolites. | 2001 Jul |
|
Capillary-scale polarimetry for flowing streams. | 2001 May |
|
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 |
|
DNA single strand breaks induced by low levels of occupational exposure to styrene: the gap between standards and reality. | 2002 |
|
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 |
|
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 |
|
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 |
|
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 |
|
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 |
|
Nonlinear amplification of circular dichroism activity upon cyclodimerization of a chiral saddle-shaped porphyrin. | 2003 Jan 7 |
|
The mandelamide keto-enol system in aqueous solution. Generation of the enol by hydration of phenylcarbamoylcarbene. | 2003 Jan 8 |
|
Solvent ototoxicity in the rat and guinea pig. | 2003 Jan-Feb |
|
Inhibition of mandelate racemase by alpha-fluorobenzylphosphonates. | 2003 Jun 16 |
|
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 |
|
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 |
|
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 |
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
Thu Jul 06 02:21:32 UTC 2023
by
admin
on
Thu Jul 06 02:21:32 UTC 2023
|
Record UNII |
NH496X0UJX
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
WHO-VATC |
QB05CA06
Created by
admin on Thu Jul 06 02:21:33 UTC 2023 , Edited by admin on Thu Jul 06 02:21:33 UTC 2023
|
||
|
WHO-ATC |
B05CA06
Created by
admin on Thu Jul 06 02:21:33 UTC 2023 , Edited by admin on Thu Jul 06 02:21:33 UTC 2023
|
||
|
WHO-ATC |
J01XX06
Created by
admin on Thu Jul 06 02:21:33 UTC 2023 , Edited by admin on Thu Jul 06 02:21:33 UTC 2023
|
||
|
NCI_THESAURUS |
C255
Created by
admin on Thu Jul 06 02:21:33 UTC 2023 , Edited by admin on Thu Jul 06 02:21:33 UTC 2023
|
||
|
WHO-VATC |
QJ01XX06
Created by
admin on Thu Jul 06 02:21:33 UTC 2023 , Edited by admin on Thu Jul 06 02:21:33 UTC 2023
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
M7051
Created by
admin on Thu Jul 06 02:21:33 UTC 2023 , Edited by admin on Thu Jul 06 02:21:33 UTC 2023
|
PRIMARY | Merck Index | ||
|
35825
Created by
admin on Thu Jul 06 02:21:33 UTC 2023 , Edited by admin on Thu Jul 06 02:21:33 UTC 2023
|
PRIMARY | |||
|
100000076484
Created by
admin on Thu Jul 06 02:21:33 UTC 2023 , Edited by admin on Thu Jul 06 02:21:33 UTC 2023
|
PRIMARY | |||
|
C61822
Created by
admin on Thu Jul 06 02:21:33 UTC 2023 , Edited by admin on Thu Jul 06 02:21:33 UTC 2023
|
PRIMARY | |||
|
MANDELIC ACID
Created by
admin on Thu Jul 06 02:21:33 UTC 2023 , Edited by admin on Thu Jul 06 02:21:33 UTC 2023
|
PRIMARY | |||
|
1375058
Created by
admin on Thu Jul 06 02:21:33 UTC 2023 , Edited by admin on Thu Jul 06 02:21:33 UTC 2023
|
PRIMARY | |||
|
1629
Created by
admin on Thu Jul 06 02:21:33 UTC 2023 , Edited by admin on Thu Jul 06 02:21:33 UTC 2023
|
PRIMARY | |||
|
90-64-2
Created by
admin on Thu Jul 06 02:21:33 UTC 2023 , Edited by admin on Thu Jul 06 02:21:33 UTC 2023
|
PRIMARY | |||
|
29256
Created by
admin on Thu Jul 06 02:21:33 UTC 2023 , Edited by admin on Thu Jul 06 02:21:33 UTC 2023
|
PRIMARY | RxNorm | ||
|
NH496X0UJX
Created by
admin on Thu Jul 06 02:21:33 UTC 2023 , Edited by admin on Thu Jul 06 02:21:33 UTC 2023
|
PRIMARY | |||
|
DB13218
Created by
admin on Thu Jul 06 02:21:33 UTC 2023 , Edited by admin on Thu Jul 06 02:21:33 UTC 2023
|
PRIMARY | |||
|
SUB14462MIG
Created by
admin on Thu Jul 06 02:21:33 UTC 2023 , Edited by admin on Thu Jul 06 02:21:33 UTC 2023
|
PRIMARY | |||
|
DTXSID6023234
Created by
admin on Thu Jul 06 02:21:33 UTC 2023 , Edited by admin on Thu Jul 06 02:21:33 UTC 2023
|
PRIMARY | |||
|
C037938
Created by
admin on Thu Jul 06 02:21:33 UTC 2023 , Edited by admin on Thu Jul 06 02:21:33 UTC 2023
|
PRIMARY | |||
|
202-007-6
Created by
admin on Thu Jul 06 02:21:33 UTC 2023 , Edited by admin on Thu Jul 06 02:21:33 UTC 2023
|
PRIMARY | |||
|
CHEMBL1609
Created by
admin on Thu Jul 06 02:21:33 UTC 2023 , Edited by admin on Thu Jul 06 02:21:33 UTC 2023
|
PRIMARY | |||
|
NH496X0UJX
Created by
admin on Thu Jul 06 02:21:33 UTC 2023 , Edited by admin on Thu Jul 06 02:21:33 UTC 2023
|
PRIMARY | |||
|
1292
Created by
admin on Thu Jul 06 02:21:33 UTC 2023 , Edited by admin on Thu Jul 06 02:21:33 UTC 2023
|
PRIMARY | |||
|
7925
Created by
admin on Thu Jul 06 02:21:33 UTC 2023 , Edited by admin on Thu Jul 06 02:21:33 UTC 2023
|
PRIMARY |
Related Record | Type | Details | ||
---|---|---|---|---|
|
ENANTIOMER -> RACEMATE | |||
|
SALT/SOLVATE -> PARENT | |||
|
SALT/SOLVATE -> PARENT | |||
|
SALT/SOLVATE -> PARENT | |||
|
ENANTIOMER -> RACEMATE | |||
|
SALT/SOLVATE -> PARENT | |||
|
PARENT->INNOVATOR |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
SALT/SOLVATE -> PARENT |
Related Record | Type | Details | ||
---|---|---|---|---|
|
PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
|
||
|
PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |