U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of ADRAFINIL

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)

HIDE SMILES / InChI
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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
OLMIFON

Approved Use

Olmifon ® tablets, 300 mg (adrafinil) are indicated for the treatment of disorders of vigilance, attention, and ideo-motor slowing in the elderly.

Launch Date

1981
Primary
OLMIFON

Approved Use

Olmifon ® tablets, 300 mg (adrafinil) are indicated for the treatment of disorders of vigilance, attention, and ideo-motor slowing in the elderly.

Launch Date

1981
PubMed

PubMed

TitleDatePubMed
A possibe alpha-adrenergic mechanism for drug (CRL 40028)-induced hyperactivity.
1979 Oct 26
Pharmacological evidence of the stimulation of central alpha-adrenergic receptors.
1983
Adrafinil disrupts performance on a delayed nonmatching-to-position task in aged beagle dogs.
2003 Aug
The canine model of human cognitive aging and dementia: pharmacological validity of the model for assessment of human cognitive-enhancing drugs.
2005 Mar
LC-ESI-MS determination and pharmacokinetics of adrafinil in rats.
2008 Sep 15
Natural non-trasgenic animal models for research in Alzheimer's disease.
2009 Apr
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
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

Patents

Sample Use Guides

Olmifon ® tablets, 300 mg (adrafinil) 2-4 tablets per day
Route of Administration: Oral
In Vitro Use Guide
Unknown
Name Type Language
ADRAFINIL
INN   MART.   MI   WHO-DD  
INN  
Official Name English
Adrafinil [WHO-DD]
Common Name English
ADRAFINIL [MART.]
Common Name English
adrafinil [INN]
Common Name English
OLMIFON
Brand Name English
ADRAFINIL [NFLIS-DRUG]
Common Name English
2-((DIPHENYLMETHYL)SULFINYL)ACETOHYDROXAMIC ACID
Systematic Name English
ADRAFINIL [MI]
Common Name English
Classification Tree Code System Code
WHO-ATC N06BX17
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NCI_THESAURUS C29709
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WHO-VATC QN06BX17
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DSLD 3424 (Number of products:4)
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Code System Code Type Description
CAS
63547-13-7
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PRIMARY
ChEMBL
CHEMBL93077
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DRUG CENTRAL
95
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MERCK INDEX
m1429
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PRIMARY Merck Index
MESH
C022116
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RXCUI
45938
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DRUG BANK
DB08925
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WIKIPEDIA
ADRAFINIL
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SMS_ID
100000087705
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EPA CompTox
DTXSID4046498
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EVMPD
SUB05278MIG
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NCI_THESAURUS
C81369
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FDA UNII
BI81Z4542G
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ECHA (EC/EINECS)
264-303-1
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INN
5110
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PUBCHEM
3033226
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PRIMARY