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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
Structure of MANDELIC ACID

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)

HIDE SMILES / InChI

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 ( + / - )

Description
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.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Mandelamine

Approved Use

For the suppression or elimination of bacteriuria associated with pyelonephritis, cystitis and other urinary tract infections.
Doses

Doses

DosePopulationAdverse 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)
Erythema (2 patients)
Sources:
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)
lactobionic acid(1%; 2/day)
sulfate zinc(1%; 2/day)
Sources:
unhealthy
n = 20
Health Status: unhealthy
Condition: facial acne
Sex: M+F
Population Size: 20
Sources:
Other AEs: Skin erythema desquamative...
Other AEs:
Skin erythema desquamative (5%)
Sources:
AEs

AEs

AESignificanceDosePopulation
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)
lactobionic acid(1%; 2/day)
sulfate zinc(1%; 2/day)
Sources:
unhealthy
n = 20
Health Status: unhealthy
Condition: facial acne
Sex: M+F
Population Size: 20
Sources:
PubMed

PubMed

TitleDatePubMed
[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
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 Thu Jul 06 02:21:32 UTC 2023
Edited
by admin
on Thu Jul 06 02:21:32 UTC 2023
Record UNII
NH496X0UJX
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MANDELIC ACID
INCI   MART.   MI   USP-RS   WHO-DD  
INCI  
Official Name English
PARAMANDELIC ACID
Common Name English
MANDELIC ACID [INCI]
Common Name English
HOMATROPINE HYDROBROMIDE IMPURITY C [EP IMPURITY]
Common Name English
PHENYLACETIC ACID, .ALPHA.--HYDROXY-
Common Name English
RACEMIC MANDELIC ACID
Common Name English
MANDELIC ACID [USP-RS]
Common Name English
Mandelic acid [WHO-DD]
Common Name English
MANDELIC ACID [MART.]
Common Name English
NSC-7925
Code English
MANDELIC ACID [MI]
Common Name English
GLYCOPYRRONIUM BROMIDE IMPURITY C [EP IMPURITY]
Common Name English
.ALPHA.-HYDROXYPHENYLACETIC ACID
Systematic Name English
DL-MANDELIC ACID
Common Name English
HOMATROPINE METHYLBROMIDE IMPURITY C [EP IMPURITY]
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
MERCK INDEX
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
CHEBI
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
SMS_ID
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
NCI_THESAURUS
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
WIKIPEDIA
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
RS_ITEM_NUM
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
DRUG CENTRAL
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
CAS
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
RXCUI
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
DAILYMED
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
DRUG BANK
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
EVMPD
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
EPA CompTox
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
MESH
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
ECHA (EC/EINECS)
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
ChEMBL
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
FDA UNII
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
PUBCHEM
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
NSC
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
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