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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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

(+)-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.

CNS Activity

Originator

Approval Year

Targets

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

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PROVIGIL

PubMed

Sample Use Guides

In Vivo Use Guide
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
Record UNII
152JRG3T0U
Record Status Validated (UNII)
Record Version