AMMONIUM MANDELATE

Possibly Marketed Outside US

Details

Stereochemistry	RACEMIC
Molecular Formula	C8H7O3.H4N
Molecular Weight	169.1778
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[NH4+].OC(C([O-])=O)C1=CC=CC=C1

InChI

InChIKey=BDEXTKUJIZCFST-UHFFFAOYSA-N

InChI=1S/C8H8O3.H3N/c9-7(8(10)11)6-4-2-1-3-5-6;/h1-5,7,9H,(H,10,11);1H3

HIDE SMILES / InChI

Molecular Formula	H3N
Molecular Weight	17.0305
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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
Toxicity and biodegradation of products from polyester hydrolysis.	2001	11413830
Cumulative exposure to styrene and visual functions.	2001 Apr	11323784
Simultaneous high-performance liquid chromatographic determination of urinary mandelic and phenylglyoxylic acids as indirect evaluation of styrene exposure.	2001 Apr 5	11334354
Histidine-functionalized silica and its copper complex as stationary phases for capillary electrochromatography.	2001 Aug	11519966
Identification of 1-adenine DNA adducts in workers occupationally exposed to styrene.	2001 Aug	11515252
Metabolism of the styrene metabolite 4-vinylphenol by rat and mouse liver and lung.	2001 Aug 10	11497334
Structure of an active soluble mutant of the membrane-associated (S)-mandelate dehydrogenase.	2001 Aug 21	11502180
Coupling of simulated moving bed chromatography and fractional crystallisation for efficient enantioseparation.	2001 Jan 26	11218123
A QM/MM study of the racemization of vinylglycolate catalyzed by mandelate racemase enzyme.	2001 Jan 31	11456585
Oxidation-active flavin models: oxidation of alpha-hydroxy acids by benzo-dipteridine bearing metal-binding site in the presence of divalent metal ion and base in organic solvents.	2001 Mar 21	11456915
Intervention study on acquired color vision deficiencies in styrene-exposed workers.	2001 May	11382185
Discrimination in resolving systems. VI. Comparison of the diastereomers of deoxyephedrinium and ephedrinium 4'-fluoromandelates.	2001 May 15	11317345
Trifluoromethyl ketone-based inhibitors of apoptosis in cerebellar granule neurons.	2001 Nov	11725976
Polymorphism of xenobiotic-metabolizing enzymes and excretion of styrene-specific mercapturic acids.	2001 Oct	11599931
DNA single strand breaks induced by low levels of occupational exposure to styrene: the gap between standards and reality.	2002	11934013
Asymmetric intramolecular [2 + 2] photocycloadditions: alpha- and beta-hydroxy acids as chiral tether groups.	2002 Feb 22	11846645
Evaluation of genotoxic effects in a group of workers exposed to low levels of styrene.	2002 Feb 28	11836023
Impact of adsorption isotherm parameters on the performance of enantioseparation using simulated moving bed chromatography.	2002 Jan 25	11831760
Analysis of styrene and its metabolites in blood and urine of workers exposed to both styrene and acetone.	2002 Jan-Feb	11888014
Validated method for quantitation of biomarkers for benzene and its alkylated analogues in urine.	2002 Jul 15	12076687
Hydroxamates as substrates and inhibitors for FMN-dependent 2-hydroxy acid dehydrogenases.	2002 Jun	12406701
A practical enantioselective fluorescent sensor for mandelic acid.	2002 Mar 13	11878942
Kinetics and thermodynamics of mandelate racemase catalysis.	2002 Mar 26	11900548
Fluorescent sensors for the enantioselective recognition of mandelic acid: signal amplification by dendritic branching.	2002 Nov 27	12440923
Simultaneous determination of styrene, toluene, and xylene metabolites in urine by gas chromatography/mass spectrometry.	2002 Oct	12373452
(R)-mandelic acid (S)-alanine hemihydrate.	2002 Oct	12359945
Arginine 165/arginine 277 pair in (S)-mandelate dehydrogenase from Pseudomonas putida: role in catalysis and substrate binding.	2002 Oct 15	12369819
A highly selective aerobic oxidation process catalyzed by electron-deficient nitroarenes via single electron transfer processes.	2002 Oct 18	12375984
Finnish quality assurance programme for biological monitoring of organic solvents.	2002 Oct 5	12376146
The role of various biomarkers in the evaluation of styrene genotoxicity.	2003	12893075
Structural and kinetic analysis of catalysis by a thiamin diphosphate-dependent enzyme, benzoylformate decarboxylase.	2003 Feb 25	12590569
A glycopeptide antibiotic chiral stationary phase for the enantiomer resolution of hydroxy acid derivatives by capillary electrochromatography.	2003 Mar	12627454
Asymmetric environments in encapsulation complexes.	2003 May 21	12785856
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
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
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
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

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 01:56:23 UTC 2023` Edited by `admin` on `Thu Jul 06 01:56:23 UTC 2023`
Record UNII	6PGE18556E
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

AMMONIUM MANDELATE

Common Name

English

MANDELIC ACID AMMONIUM SALT

Common Name

English

AMMONIUM MANDELATE [MI]

Common Name

English

.ALPHA.-HYDROXYBENZENEACETIC ACID AMMONIUM SALT (1:1)

Common Name

English

Code System Code Type Description

EPA CompTox

DTXSID30967475