MANDELIC ACID, (R)-

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C8H8O3
Molecular Weight	152.1473
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O[C@@H](C(O)=O)C1=CC=CC=C1

InChI

InChIKey=IWYDHOAUDWTVEP-SSDOTTSWSA-N

InChI=1S/C8H8O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7,9H,(H,10,11)/t7-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C8H8O3
Molecular Weight	152.1473
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21488105
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/28936681 | https://www.ncbi.nlm.nih.gov/pubmed/21910908 | http://eci2012.net/wp-content/uploads/2015/03/Mandelamine-PM-En-100446.02-11Mar2015.pdf

(R)-Mandelic acid (D-Mandelic acid) is an enantiomer of the aromatic alpha hydroxy acid that is used as a chiral resolving agent, and as a building block to synthesize pharmaceutical drugs such as penicillin and cephalosporin. (R)-(-)-Mandelic acid, is used as an antiseptic ingredient particularly against urinary tract infections.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Protein-tyrosine phosphatase 1B 34 Target ID: CHEMBL335 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11459664	Inhibitor 8297		5500.0 µM [IC50]

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.

PubMed

Title	Date	PubMed
alpha-Ketocarboxylic acid-based inhibitors of protein tyrosine phosphatases.	2001 Jul 23	11459664

Patents

Sample Use Guides

In Vivo Use Guide

500 mg (R/S-Mandelic acid) - 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 `Sat Dec 16 07:58:27 UTC 2023` Edited by `admin` on `Sat Dec 16 07:58:27 UTC 2023`
Record UNII	PPL7YW1M9W
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

MANDELIC ACID, (R)-

Common Name

English

(R)-.ALPHA.-HYDROXYBENZENEACETIC ACID

Systematic Name

English

SERTRALINE HYDROCHLORIDE IMPURITY E [EP IMPURITY]

Common Name

English

BENZENEACETIC ACID, .ALPHA.-HYDROXY-, (.ALPHA.R)-

Systematic Name

English

(R)-MANDELIC ACID

Common Name

English

D-2-PHENYLGLYCOLIC ACID

Common Name

English

(2R)-HYDROXYPHENYLACETIC ACID

Systematic Name

English

(-)-(R)-MANDELIC ACID

Common Name

English

MANDELIC ACID, D-

Common Name

English

(-)-MANDELIC ACID

Common Name

English

(-)-D-MANDELIC ACID

Common Name

English

Code System Code Type Description

FDA UNII

PPL7YW1M9W