Details
Stereochemistry | RACEMIC |
Molecular Formula | C15H15NO3S |
Molecular Weight | 289.35 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
ONC(=O)C[S+]([O-])C(C1=CC=CC=C1)C2=CC=CC=C2
InChI
InChIKey=CGNMLOKEMNBUAI-UHFFFAOYSA-N
InChI=1S/C15H15NO3S/c17-14(16-18)11-20(19)15(12-7-3-1-4-8-12)13-9-5-2-6-10-13/h1-10,15,18H,11H2,(H,16,17)
Adrafinil (CRL 40028) was synthesized by Louis Lafon Laboratories. The proprietary name of adrafinil is Olmifon®; its chemical name is (diphenylmethyl )sulfinyl-2-acetohydroxamic acid. Adrafinil is metabolized to modafinil. Adrafinil and modafinil both serve as α1-adrenergic–receptor agonists. The evidence in support of this hypothesis, however, is weak, and other mechanisms of action are probable. Adrafinil may modify the intracerebral release of amino acids (both GABA and glutamate)
and adrafinil may increase cerebral metabolism. Olmifon ® tablets, 300 mg (adrafinil) were indicated for the treatment of disorders of vigilance, attention, and ideo-motor slowing in the elderly. It has been marketed in France since September 19, 1985. Cephalon announced their intent to stop marketing the drug, and has discontinued production and marketing of Olmifon in September 2011. Adrafinil is marketing as nootropic supplement to improve cognitive functions.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2094251 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | OLMIFON Approved UseOlmifon ® tablets, 300 mg (adrafinil) are indicated for the treatment of disorders of vigilance, attention, and ideo-motor slowing in the elderly. Launch Date1981 |
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Primary | OLMIFON Approved UseOlmifon ® tablets, 300 mg (adrafinil) are indicated for the treatment of disorders of vigilance, attention, and ideo-motor slowing in the elderly. Launch Date1981 |
PubMed
Title | Date | PubMed |
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A possibe alpha-adrenergic mechanism for drug (CRL 40028)-induced hyperactivity. | 1979 Oct 26 |
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Pharmacological evidence of the stimulation of central alpha-adrenergic receptors. | 1983 |
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Adrafinil disrupts performance on a delayed nonmatching-to-position task in aged beagle dogs. | 2003 Aug |
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The canine model of human cognitive aging and dementia: pharmacological validity of the model for assessment of human cognitive-enhancing drugs. | 2005 Mar |
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LC-ESI-MS determination and pharmacokinetics of adrafinil in rats. | 2008 Sep 15 |
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Natural non-trasgenic animal models for research in Alzheimer's disease. | 2009 Apr |
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Enantioselective separation and determination of adrafinil and modafinil on Chiralcel OJ-H column in rat serum and urine using solid-phase extraction followed by HPLC. | 2009 Aug |
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Development of a validated LC method for enantiomeric separation and determination of adrafinil and its related substances on a Chiralcel OJ-H column connected to PDA and polarimetric detectors in series. | 2010 Nov |
Patents
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N06BX17
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DSLD |
3424 (Number of products:4)
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ACTIVE MOIETY