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Details

Stereochemistry ABSOLUTE
Molecular Formula C15H15NO2S
Molecular Weight 273.35
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MODAFINIL, (S)-

SMILES

NC(=O)C[S@+]([O-])C(C1=CC=CC=C1)C2=CC=CC=C2

InChI

InChIKey=YFGHCGITMMYXAQ-IBGZPJMESA-N
InChI=1S/C15H15NO2S/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,(H2,16,17)/t19-/m0/s1

HIDE SMILES / InChI

Molecular Formula C15H15NO2S
Molecular Weight 273.35
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: Description was created based on several sources, including https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/020717s020s013s018lbl.pdf | https://www.ncbi.nlm.nih.gov/pubmed/22537794

(+)-modafinil is an enantiomer of modafinil, a wake-promoting agent, that primarily affects areas of the brain involved in controlling wakefulness. (+)-enantiomer of modafinil was clarified to be S-configuration. The optical enantiomers of modafinil have similar pharmacological actions. Both modafinil enantiomers bind in vitro to the dopamine transporter and inhibit dopamine reuptake with the R- slightly more potent than the S-enantiomer. As a component of racemic mixture (+)-modafinil is indicated to improve wakefulness in adult patients with excessive sleepiness associated with narcolepsy, obstructive sleep apnea/hypopnea syndrome, and shift work sleep disorder.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
48.62 µM [IC50]
8.7 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PROVIGIL

Approved Use

PROVIGIL (1:1 racemic mixture of S- and R-modafinil enantiomers) is indicated to improve wakefulness in adult patients with excessive sleepiness associated with narcolepsy, obstructive sleep apnea/hypopnea syndrome, and shift work sleep disorder.

Launch Date

9.1437118E11
PubMed

PubMed

TitleDatePubMed
An enantioselective assay for (+/-)-modafinil.
2001 Aug
Crystal and molecular structure of an (S)-(+)-enantiomer of modafinil, a novel wake-promoting agent.
2004 Oct
Dopamine D2High receptors stimulated by phencyclidines, lysergic acid diethylamide, salvinorin A, and modafinil.
2009 Aug
R-modafinil (armodafinil): a unique dopamine uptake inhibitor and potential medication for psychostimulant abuse.
2012 Sep 1
R-modafinil attenuates nicotine-taking and nicotine-seeking behavior in alcohol-preferring rats.
2015 Jun
Patents

Sample Use Guides

The recommended dose of PROVIGIL (1:1 racemic mixture of S- and R-modafinil enantiomers) is 200 mg given once a day.
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Thu Jul 06 16:24:39 UTC 2023
Edited
by admin
on Thu Jul 06 16:24:39 UTC 2023
Record UNII
152JRG3T0U
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MODAFINIL, (S)-
Common Name English
MODAFINIL, (+)-
Common Name English
CRL-40983
Code English
2-((S)-(DIPHENYLMETHYL)SULFINYL)ACETAMIDE
Systematic Name English
CRL 40983
Code English
NH-02D
Code English
(+)-MODAFINIL
Systematic Name English
(S)-(+)-MODAFINIL
Common Name English
NH 02D
Code English
ACETAMIDE, 2-((S)-(DIPHENYLMETHYL)SULFINYL)-
Systematic Name English
Code System Code Type Description
EPA CompTox
DTXSID70457709
Created by admin on Thu Jul 06 16:24:39 UTC 2023 , Edited by admin on Thu Jul 06 16:24:39 UTC 2023
PRIMARY
PUBCHEM
11173366
Created by admin on Thu Jul 06 16:24:39 UTC 2023 , Edited by admin on Thu Jul 06 16:24:39 UTC 2023
PRIMARY
RS_ITEM_NUM
1445415
Created by admin on Thu Jul 06 16:24:39 UTC 2023 , Edited by admin on Thu Jul 06 16:24:39 UTC 2023
PRIMARY
CHEBI
77591
Created by admin on Thu Jul 06 16:24:39 UTC 2023 , Edited by admin on Thu Jul 06 16:24:39 UTC 2023
PRIMARY
CAS
112111-47-4
Created by admin on Thu Jul 06 16:24:39 UTC 2023 , Edited by admin on Thu Jul 06 16:24:39 UTC 2023
PRIMARY
FDA UNII
152JRG3T0U
Created by admin on Thu Jul 06 16:24:39 UTC 2023 , Edited by admin on Thu Jul 06 16:24:39 UTC 2023
PRIMARY
Related Record Type Details
RACEMATE -> ENANTIOMER