MANDELIC ACID

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 207 Sources: http://eci2012.net/wp-content/uploads/2015/03/Mandelamine-PM-En-100446.02-11Mar2015.pdf	Curative		Approved 8583	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 Health Status: unhealthy Age Group: 19.4 Sex: M+F 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 Sources: https://pubmed.ncbi.nlm.nih.gov/31190944/	unhealthy Health Status: unhealthy Sex: M+F 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 Health Status: unhealthy Age Group: 19.4 Sex: M+F 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 Health Status: unhealthy Age Group: 19.4 Sex: M+F 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 Sources: https://pubmed.ncbi.nlm.nih.gov/31190944/	unhealthy Health Status: unhealthy Sex: M+F 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
Histidine-functionalized silica and its copper complex as stationary phases for capillary electrochromatography.	2001 Aug	11519966
Fitting adsorption isotherms to the distribution data determined using packed micro-columns for high-performance liquid chromatography.	2001 Aug 3	11519805
Stereochemical metabolism of styrene in volunteers.	2001 Jul	11516070
Inter- and intra-individual sources of variation in levels of urinary styrene metabolites.	2001 Jul	11516068
Intervention study on acquired color vision deficiencies in styrene-exposed workers.	2001 May	11382185
Polymorphism of xenobiotic-metabolizing enzymes and excretion of styrene-specific mercapturic acids.	2001 Oct	11599931
An enzyme library approach to biocatalysis: development of nitrilases for enantioselective production of carboxylic acid derivatives.	2002 Aug 7	12148986
A practical enantioselective fluorescent sensor for mandelic acid.	2002 Mar 13	11878942
Assessment of sperm DNA integrity in workers exposed to styrene.	2002 Nov	12407048
A highly selective aerobic oxidation process catalyzed by electron-deficient nitroarenes via single electron transfer processes.	2002 Oct 18	12375984
Audiometric findings in workers exposed to low levels of styrene and noise.	2002 Sep	12227672
Absolute configuration of tert-butyl-1-(2-methylnaphthyl)phosphine oxide.	2002 Sep 6	12201778
Exceptional chiral recognition of racemic carboxylic acids by calix[4]arenes bearing optically pure alpha,beta-amino alcohol groups.	2004 Apr 15	15070294
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
Determination of urinary styrene metabolites in the general Italian population by liquid chromatography-tandem mass spectrometry.	2004 Aug	15205964
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
High resolution structures of an oxidized and reduced flavoprotein. The water switch in a soluble form of (S)-mandelate dehydrogenase.	2004 Jan 30	14604988
Altered substrate specificity in flavocytochrome b2: structural insights into the mechanism of L-lactate dehydrogenation.	2004 Jul 27	15260495
Cytogenetic markers, DNA single-strand breaks, urinary metabolites, and DNA repair rates in styrene-exposed lamination workers.	2004 Jun	15175174
Mandelamide hydrolase from Pseudomonas putida: characterization of a new member of the amidase signature family.	2004 Jun 22	15196015
Chiral synthesis of (2S,3S)-2-(2-morpholin-2-yl-2-phenylmethoxy)phenol.	2004 Mar	14770413
Current trends in quantitative structure activity relationships on FXa inhibitors: evaluation and comparative analysis.	2004 Nov	15250038
Prevalence of varicose veins and venous anatomy in patients without truncal saphenous reflux.	2004 Oct	15350560

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 `Mon Mar 31 19:38:44 GMT 2025` Edited by `admin` on `Mon Mar 31 19:38:44 GMT 2025`
Record UNII	NH496X0UJX
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-7925

Preferred Name

English

MANDELIC ACID

Official Name

English

PARAMANDELIC ACID

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

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