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Details

Stereochemistry ABSOLUTE
Molecular Formula C8H8O3
Molecular Weight 152.1476
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MANDELIC ACID, (S)-

SMILES

c1ccc(cc1)[C@@]([H])(C(=O)O)O

InChI

InChIKey=IWYDHOAUDWTVEP-ZETCQYMHSA-N
InChI=1S/C8H8O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7,9H,(H,10,11)/t7-/m0/s1

HIDE SMILES / InChI

Molecular Formula C8H8O3
Molecular Weight 152.1476
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment:: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/23608509 | https://www.ncbi.nlm.nih.gov/pubmed/11459664 | http://eci2012.net/wp-content/uploads/2015/03/Mandelamine-PM-En-100446.02-11Mar2015.pdf

(S)-Mandelic acid (L-Mandelic acid) is an enantiomer of the aromatic alpha hydroxy acid that is used in the production of pharmaceuticals for its antibacterial activity and administered as an oral antibiotic or a treatment for urinary tract infections. Well-known ester drugs, such as cyclandelate and homatropine, are derived from L-mandelic acid. Because of its antibacterial properties, L-mandelic acid is an alternative to α-hydroxy acids in skin care products. Among the most popular ingredients in both skin care and anti-aging products, L-mandelic acid now represents a multi-billion dollar industry.

Originator

Sources: Zeitschrift fuer Physikalische Chemie, Stoechiometrie und Verwandtschaftslehre (1903), 46, 30.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
4900.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Mandelamine

Approved Use

For the suppression or elimination of bacteriuria associated with pyelonephritis, cystitis and other urinary tract infections.
PubMed

PubMed

TitleDatePubMed
Patents

Patents

Sample Use Guides

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 Jun 26 10:46:56 UTC 2021
Edited
by admin
on Sat Jun 26 10:46:56 UTC 2021
Record UNII
L0UMW58G3T
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MANDELIC ACID, (S)-
Common Name English
(+)-.ALPHA.-HYDROXYPHENYLACETIC ACID
Systematic Name English
L-MANDELIC ACID
Common Name English
MANDELIC ACID, L-
Common Name English
L-(+)-MANDELIC ACID
Common Name English
(+)-(S)-MANDELIC ACID
Common Name English
BENZENEACETIC ACID, .ALPHA.-HYDROXY-, (.ALPHA.S)-
Systematic Name English
(S)-MANDELIC ACID
Common Name English
Code System Code Type Description
FDA UNII
L0UMW58G3T
Created by admin on Sat Jun 26 10:46:56 UTC 2021 , Edited by admin on Sat Jun 26 10:46:56 UTC 2021
PRIMARY
DRUG BANK
DB03357
Created by admin on Sat Jun 26 10:46:56 UTC 2021 , Edited by admin on Sat Jun 26 10:46:56 UTC 2021
PRIMARY
CAS
17199-29-0
Created by admin on Sat Jun 26 10:46:56 UTC 2021 , Edited by admin on Sat Jun 26 10:46:56 UTC 2021
PRIMARY
PUBCHEM
439616
Created by admin on Sat Jun 26 10:46:56 UTC 2021 , Edited by admin on Sat Jun 26 10:46:56 UTC 2021
PRIMARY
ECHA (EC/EINECS)
241-240-8
Created by admin on Sat Jun 26 10:46:56 UTC 2021 , Edited by admin on Sat Jun 26 10:46:56 UTC 2021
PRIMARY
Related Record Type Details
RACEMATE -> ENANTIOMER