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Details

Stereochemistry RACEMIC
Molecular Formula C15H14O3S
Molecular Weight 274.3365
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MODAFINIL ACID

SMILES

c1ccc(cc1)C(c2ccccc2)S(=O)CC(=O)O

InChI

InChIKey=QARQPIWTMBRJFX-UHFFFAOYSA-N
InChI=1S/C15H14O3S/c16-14(17)11-19(18)15(12-7-3-1-4-8-12)13-9-5-2-6-10-13/h1-10,15H,11H2,(H,16,17)

HIDE SMILES / InChI

Molecular Formula C15H14O3S
Molecular Weight 274.3365
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Modafinil acid is a metabolite of modafinil, a wake-promoting agent for oral administration. Orally administered modafinil is extensively biotransformed in the liver to the inactive metabolites modafinil acid and modafinil sulphone, before being eliminated primarily in the urine (elimination half-life 9 to 14 hours). Modafinil acid was the major urinary metabolite, which accounted for 35% to 60% of the dose. Two major metabolites of modafinil, modafinil acid, and modafinil sulfone, do not appear to contribute to the CNS-activating properties of modafinil.

Approval Year

PubMed

PubMed

TitleDatePubMed
Single-dose pharmacokinetics of modafinil and methylphenidate given alone or in combination in healthy male volunteers.
1998 Mar
A double-blind, placebo-controlled, ascending-dose evaluation of the pharmacokinetics and tolerability of modafinil tablets in healthy male volunteers.
1999 Jan
Determination of modafinil, modafinil acid and modafinil sulfone in human plasma utilizing liquid-liquid extraction and high-performance liquid chromatography.
2002 Feb 15
Population pharmacokinetics of modafinil and its acid and sulfone metabolites in Chinese males.
2011 Dec
Population pharmacokinetics of modafinil acid and estimation of the metabolic conversion of modafinil into modafinil acid in 5 major ethnic groups of China.
2012 Nov
Patents
Substance Class Chemical
Created
by admin
on Fri Jun 25 20:32:18 UTC 2021
Edited
by admin
on Fri Jun 25 20:32:18 UTC 2021
Record UNII
54N37HN7N4
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MODAFINIL ACID
Common Name English
ACETIC ACID, 2-((DIPHENYLMETHYL)SULFINYL)-
Systematic Name English
MODAFINIL RELATED COMPOUND A
USP-RS  
Common Name English
CRL-40467
Code English
((RS)-(DIPHENYLMETHYL)SULFINYL)ACETIC ACID
Common Name English
CRL 40467
Code English
MODAFINILIC ACID
Common Name English
(+/-)-MODAFINIC ACID
Common Name English
MODAFINIL IMPURITY A [EP]
Common Name English
2-((DIPHENYLMETHYL)SULFINYL)ACETIC ACID
Systematic Name English
MODAFINIL RELATED COMPOUND A [USP-RS]
Common Name English
(BENZHYDRYLSULFINYL)ACETIC ACID
Systematic Name English
Code System Code Type Description
CAS
63547-24-0
Created by admin on Fri Jun 25 20:32:18 UTC 2021 , Edited by admin on Fri Jun 25 20:32:18 UTC 2021
PRIMARY
PUBCHEM
3085267
Created by admin on Fri Jun 25 20:32:18 UTC 2021 , Edited by admin on Fri Jun 25 20:32:18 UTC 2021
PRIMARY
FDA UNII
54N37HN7N4
Created by admin on Fri Jun 25 20:32:18 UTC 2021 , Edited by admin on Fri Jun 25 20:32:18 UTC 2021
PRIMARY
USP_CATALOG
1445346
Created by admin on Fri Jun 25 20:32:18 UTC 2021 , Edited by admin on Fri Jun 25 20:32:18 UTC 2021
PRIMARY USP-RS
Related Record Type Details
ENANTIOMER -> RACEMATE
ENANTIOMER -> RACEMATE
Related Record Type Details
PARENT -> METABOLITE
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP