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 205 Sources: http://eci2012.net/wp-content/uploads/2015/03/Mandelamine-PM-En-100446.02-11Mar2015.pdf	Curative		Approved 8429	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
Liquid chromatography/electrospray tandem mass spectrometry characterization of styrene metabolism in man and in rat.	2002	12478566
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
High-throughput screening of enantioselective catalysts by immunoassay.	2002 Jan 4	12491459
Use of mandelic acid condensation polymer (SAMMA), a new antimicrobial contraceptive agent, for vaginal prophylaxis.	2002 Nov	12414002
Assessment of sperm DNA integrity in workers exposed to styrene.	2002 Nov	12407048
Fluorescent sensors for the enantioselective recognition of mandelic acid: signal amplification by dendritic branching.	2002 Nov 27	12440923
[A study on the adduct characteristics of styrene and DNA].	2002 Oct	14694722
The role of various biomarkers in the evaluation of styrene genotoxicity.	2003	12893075
Exposure assessment of monoterpenes and styrene: a comparison of air sampling and biomonitoring.	2003 Aug	12883022
Synthesis of optically active atropisomeric anilide derivatives through diastereoselective N-allylation with a chiral Pd-pi-allyl catalyst.	2003 Dec 12	14656123
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
Comparison of isotopic fractionation in lactic acid and ethanol fermentations.	2003 Jun	12818232
Inhibition of mandelate racemase by alpha-fluorobenzylphosphonates.	2003 Jun 16	12781191
Sperm-FISH analysis and human monitoring: a study on workers occupationally exposed to styrene.	2003 Jun 6	12787818
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
Use of ionic liquids in a lipase-facilitated supported liquid membrane.	2003 May	12882011
Effects of clay minerals on Cr(VI) reduction by organic compounds.	2003 May	12733805
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
A high-throughput amenable colorimetric assay for enantioselective screening of nitrilase-producing microorganisms using pH sensitive indicators.	2003 Oct	14567783
C4'-spiroalkylated nucleosides having sulfur incorporated at the apex position.	2003 Oct 31	14575495
[Experimental study on the in vitro resistance to Toxoplasma gondii by murine lymphocyte].	2003 Sep	15169667
Nitration of endogenous para-hydroxyphenylacetic acid and the metabolism of nitrotyrosine.	2003 Sep 1	12797864
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
Quininium (R)-mandelate, a structure with large Z' described as an incommensurately modulated structure in (3+1)-dimensional superspace.	2004 Feb	14734850
Esters of mandelic acid as substrates for (S)-mandelate dehydrogenase from Pseudomonas putida: implications for the reaction mechanism.	2004 Feb 24	14967029
Synthesis and antibiotic activity of the tricyclic furo[3,2-c] isochromen-2-trione unit of the pyranonaphthoquinones.	2004 Feb 9	14741284
Construction of an electro-enzymatic bioreactor for the production of (R)-mandelate from benzoylformate.	2004 Jan	15005146
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
Evaluation of the efficiency of respiratory protective equipment based on the biological monitoring of styrene in fibreglass reinforced plastics industries.	2004 Mar	15090688
Chiral synthesis of (2S,3S)-2-(2-morpholin-2-yl-2-phenylmethoxy)phenol.	2004 Mar	14770413
Human urine certified reference material CZ 6009: creatinine, styrene metabolites (mandelic acid and phenylglyoxylic acid).	2004 Mar	14551662
Hydrophobic nature of the active site of mandelate racemase.	2004 Mar 9	14992589
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 `Fri Dec 15 19:13:46 GMT 2023` Edited by `admin` on `Fri Dec 15 19:13:46 GMT 2023`
Record UNII	NH496X0UJX
Record Status	`Validated (UNII)`
Record Version

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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