Modafinil

Modafinil
Clinical data
(R)-(−)-modafinil (armodafinil; top) (S)-(+)-modafinil (bottom)
Trade names	Provigil, others (see below)
AHFS/Drugs.com	Monograph
MedlinePlus	a602016
License data	US FDA: Modafinil
Pregnancy category	AU: B3 US: C (Risk not ruled out)
Dependence liability	Psychological: Very low Physical: Negligible
Addiction liability	Very low to low
Routes of administration	Oral (tablets)
ATC code	N06BA07 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) CA: Schedule F UK: POM (Prescription only) US: Schedule IV
Pharmacokinetic data
Bioavailability	Not determined due to the aqueous insolubility
Protein binding	62%
Metabolism	Hepatic (primarily via amide hydrolysis;CYP1A2, CYP2B6, CYP2C9, CYP2C19, CYP3A4, CYP3A5 involved
Biological half-life	15 hours (R-enantiomer), 4 hours (S-enantiomer)
Excretion	Urine (80%)
Identifiers
IUPAC name 2-[(diphenylmethyl)sulfinul]acetamide
Synonyms	CRL-40476; Diphenylmethylsulfinylacetamide
CAS Number	68693-11-8^Y
PubChem (CID)	4236
IUPHAR/BPS	7555
DrugBank	DB00745^Y
ChemSpider	4088^Y
UNII	R3UK8X3U3D^Y
KEGG	D01832^Y
ChEBI	CHEBI:31859^N
ChEMBL	CHEMBL1373^Y
ECHA InfoCard	100.168.719
Chemical and physical data
Formula	C₁₅H₁₅NO₂S
Molar mass	273.35 g/mol
3D model (Jmol)	Interactive image
SMILES O=S(C(c1ccccc1)c2ccccc2)CC(=O)N
InChI 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)^Y Key:YFGHCGITMMYXAQ-UHFFFAOYSA-N^Y
^NY (what is this?)

Modafinil (INN,USAN, BAN, JAN) is a wakefulness-promoting agent (or eugeroic) used for treatment of disorders such as narcolepsy, shift work sleep disorder, and excessive daytime sleepiness associated with obstructive sleep apnea. It has also seen widespread off-label use as a purported cognition-enhancing agent. In English-speaking countries it is sold under the brand names Alertec, Modavigil, and Provigil. In the United States modafinil is classified as a schedule IV controlled substance and restricted in availability and usage, due to concerns about possible addiction potential. In most other countries it is a prescription drug but not otherwise legally restricted.

Although the mechanism of action of modafinil was initially unknown, it now appears that the drug acts as a selective, relatively weak, atypical dopamine reuptake inhibitor. However, it appears that other additional mechanisms may also be at play.

Modafinil is a wakefulness-promoting agent (or eugeroic) used for treatment of narcolepsy, shift work sleep disorder, and excessive daytime sleepiness associated with obstructive sleep apnea.

Because of the risk for development of skin or hypersensitivity reactions and serious adverse psychiatric reactions, the European Medicines Agency has recommended that new patient prescriptions should only be to treat sleepiness associated with narcolepsy.

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Wikipedia