MANDELIC ACID

Possibly Marketed Outside US

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 Search

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
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

Conditions

Condition	Modality	Targets	Highest Phase	Product
Urinary tract infections 204 Sources: http://eci2012.net/wp-content/uploads/2015/03/Mandelamine-PM-En-100446.02-11Mar2015.pdf	Curative		Approved 8360	Mandelamine Approved Use For the suppression or elimination of bacteriuria associated with pyelonephritis, cystitis and other urinary tract infections.

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: https://pubmed.ncbi.nlm.nih.gov/31553119/	unhealthy, 19.4 n = 25 Health Status: unhealthy Condition: acne vulgaris Age Group: 19.4 Sex: M+F Population Size: 25 Sources: https://pubmed.ncbi.nlm.nih.gov/31553119/	Other AEs: Burning sensation, Erythema... Other AEs: Burning sensation (1 patient) Erythema (2 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/31553119/
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: https://pubmed.ncbi.nlm.nih.gov/31190944/	unhealthy n = 20 Health Status: unhealthy Condition: facial acne Sex: M+F Population Size: 20 Sources: https://pubmed.ncbi.nlm.nih.gov/31190944/	Other AEs: Skin erythema desquamative... Other AEs: Skin erythema desquamative (5%) Sources: https://pubmed.ncbi.nlm.nih.gov/31190944/

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: https://pubmed.ncbi.nlm.nih.gov/31553119/	unhealthy, 19.4 n = 25 Health Status: unhealthy Condition: acne vulgaris Age Group: 19.4 Sex: M+F Population Size: 25 Sources: https://pubmed.ncbi.nlm.nih.gov/31553119/
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: https://pubmed.ncbi.nlm.nih.gov/31553119/	unhealthy, 19.4 n = 25 Health Status: unhealthy Condition: acne vulgaris Age Group: 19.4 Sex: M+F Population Size: 25 Sources: https://pubmed.ncbi.nlm.nih.gov/31553119/
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: https://pubmed.ncbi.nlm.nih.gov/31190944/	unhealthy n = 20 Health Status: unhealthy Condition: facial acne Sex: M+F Population Size: 20 Sources: https://pubmed.ncbi.nlm.nih.gov/31190944/

Sourcing

Vendor/Aggregator	ID	URL
AAA Chemistry	AR-1I1586
ABI Chem	AC1L1RFM
Alfa Chemistry	19944-53-7	https://www.alfa-chemistry.com/cas_19944-53-7.htm
Avantor Inc	101185-706	https://us.vwr.com/store/catalog/product.jsp?catalog_number=101185-706
ChemTik	CTK4B9567
MP Biomedicals	213829
MuseChem	M069232	https://www.musechem.com/product/M069232.html
NovoSeek	8654
PubChem	8654	https://pubchem.ncbi.nlm.nih.gov/compound/8654
Smolecule	S577104	https://www.smolecule.com/products/s577104

PubMed

Title	Date	PubMed
[Efficacy of mandelic acid in treating acute toxoplasmosis in mice].	2001	12572031
Cumulative exposure to styrene and visual functions.	2001 Apr	11323784
Identification of 1-adenine DNA adducts in workers occupationally exposed to styrene.	2001 Aug	11515252
Unique oxidative mechanisms for the reactive nitrogen oxide species, nitroxyl anion.	2001 Jan 19	11042174
Inter- and intra-individual sources of variation in levels of urinary styrene metabolites.	2001 Jul	11516068
Capillary-scale polarimetry for flowing streams.	2001 May	11394312
Discrimination in resolving systems. VI. Comparison of the diastereomers of deoxyephedrinium and ephedrinium 4'-fluoromandelates.	2001 May 15	11317345
Enantiomer separation of mandelates and their analogs on cyclodextrin derivative chiral stationary phases by capillary GC.	2001 Oct	11990593
DNA single strand breaks induced by low levels of occupational exposure to styrene: the gap between standards and reality.	2002	11934013
Relation between colour vision loss and occupational styrene exposure level.	2002 Dec	12468749
Interest of genotyping and phenotyping of drug-metabolizing enzymes for the interpretation of biological monitoring of exposure to styrene.	2002 Dec	12464798
Analysis of styrene and its metabolites in blood and urine of workers exposed to both styrene and acetone.	2002 Jan-Feb	11888014
Kinetics and thermodynamics of mandelate racemase catalysis.	2002 Mar 26	11900548
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	12054463
Stereospecific synthesis of cryptophycin 1.	2002 May 16	12000261
Use of mandelic acid condensation polymer (SAMMA), a new antimicrobial contraceptive agent, for vaginal prophylaxis.	2002 Nov	12414002
Fluorescent sensors for the enantioselective recognition of mandelic acid: signal amplification by dendritic branching.	2002 Nov 27	12440923
A highly selective aerobic oxidation process catalyzed by electron-deficient nitroarenes via single electron transfer processes.	2002 Oct 18	12375984
Structural and kinetic analysis of catalysis by a thiamin diphosphate-dependent enzyme, benzoylformate decarboxylase.	2003 Feb 25	12590569
Chloride present in biological samples as a tool for enhancement of sensitivity in capillary zone electrophoretic analysis of anionic trace analytes.	2003 Jan	12569541
Nonlinear amplification of circular dichroism activity upon cyclodimerization of a chiral saddle-shaped porphyrin.	2003 Jan 7	12610945
The mandelamide keto-enol system in aqueous solution. Generation of the enol by hydration of phenylcarbamoylcarbene.	2003 Jan 8	12515521
Solvent ototoxicity in the rat and guinea pig.	2003 Jan-Feb	12633735
Inhibition of mandelate racemase by alpha-fluorobenzylphosphonates.	2003 Jun 16	12781191
A glycopeptide antibiotic chiral stationary phase for the enantiomer resolution of hydroxy acid derivatives by capillary electrochromatography.	2003 Mar	12627454
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	12685592
Asymmetric environments in encapsulation complexes.	2003 May 21	12785856
A transient intermediate in the reaction catalyzed by (S)-mandelate dehydrogenase from Pseudomonas putida.	2003 Nov 11	14596603
C4'-spiroalkylated nucleosides having sulfur incorporated at the apex position.	2003 Oct 31	14575495
Heptakis(6-amino-6-deoxy)-beta-cyclodextrin as a chiral selector for the separation of anionic analyte enantiomers by capillary electrophoresis.	2004 Aug	15352011
Influence of (hydroxy)alkylamino substituents on enantioseparation ability of single-isomer amino-beta-cyclodextrin derivatives in chiral capillary electrophoresis.	2004 Aug	15351998
Role of glycine 81 in (S)-mandelate dehydrogenase from Pseudomonas putida in substrate specificity and oxidase activity.	2004 Aug 24	15311930
Synthesis and antibiotic activity of the tricyclic furo[3,2-c] isochromen-2-trione unit of the pyranonaphthoquinones.	2004 Feb 9	14741284
A rapid HPLC method for the determination of carboxylic acids in human urine using a monolithic column.	2004 Jan	14598013

Patents

Sample Use Guides

In Vivo Use Guide

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

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