modafinil   Click here for help

GtoPdb Ligand ID: 7555

Synonyms: Provigil®
Approved drug
modafinil is an approved drug (FDA (1998))
Compound class: Synthetic organic
Comment: Modafinil is a eugeroic (wakefulness-promoting) drug with a multi-faceted mechanism of action. In some jurisdictions this drug is classified as a controlled substance due to its possible addiction potential. It has been termed a 'smart' drug, a group of prescription medications, purchased illegally or used off-label, with alleged cognition-enhancing properties [1,4].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 79.37
Molecular weight 273.08
XLogP 0.61
No. Lipinski's rules broken 0
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Canonical SMILES NC(=O)CS(=O)C(c1ccccc1)c1ccccc1
Isomeric SMILES NC(=O)CS(=O)C(c1ccccc1)c1ccccc1
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)
1. Dance A. (2016)
Smart drugs: A dose of intelligence.
Nature, 531 (7592): S2-3. [PMID:26934523]
2. Erman MK, Rosenberg R, Modafinil Shift Work Sleep Disorder Study Group. (2007)
Modafinil for excessive sleepiness associated with chronic shift work sleep disorder: effects on patient functioning and health-related quality of life.
Prim Care Companion J Clin Psychiatry, 9 (3): 188-94. [PMID:17632651]
3. Gerrard P, Malcolm R. (2007)
Mechanisms of modafinil: A review of current research.
Neuropsychiatr Dis Treat, 3 (3): 349-64. [PMID:19300566]
4. Hawkes N. (2015)
Modafinil does enhance cognition, review finds.
BMJ, 351: h4573. [PMID:26296947]
5. Minzenberg MJ, Carter CS. (2008)
Modafinil: a review of neurochemical actions and effects on cognition.
Neuropsychopharmacology, 33 (7): 1477-502. [PMID:17712350]
6. Zhou J, He R, Johnson KM, Ye Y, Kozikowski AP. (2004)
Piperidine-based nocaine/modafinil hybrid ligands as highly potent monoamine transporter inhibitors: efficient drug discovery by rational lead hybridization.
J Med Chem, 47 (24): 5821-4. [PMID:15537337]
7. Zolkowska D, Jain R, Rothman RB, Partilla JS, Roth BL, Setola V, Prisinzano TE, Baumann MH. (2009)
Evidence for the involvement of dopamine transporters in behavioral stimulant effects of modafinil.
J Pharmacol Exp Ther, 329 (2): 738-46. [PMID:19197004]