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

Molecular Formula C15H15NO3S
Molecular Weight 289.35
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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-induced orofacial dyskinesia.
2004 Aug
The canine model of human cognitive aging and dementia: pharmacological validity of the model for assessment of human cognitive-enhancing drugs.
2005 Mar
Effect of noradrenergic system on the anxiolytic-like effect of DOI (5-HT2A/2C agonists) in the four-plate test.
2006 Jan
Drug metabolism and pharmacokinetics.
2008 Oct
A novel study of screening and confirmation of modafinil, adrafinil and their metabolite modafinilic acid under EI-GC-MS and ESI-LC-MS-MS ionization.
2009 Dec
Epidemiological analysis of doping offences in the professional tennis circuit.
2010 Dec 15
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
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:02:50 GMT 2023
Edited
by admin
on Fri Dec 15 15:02:50 GMT 2023
Record UNII
BI81Z4542G
Record Status Validated (UNII)
Record Version
  • Download
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
Created by admin on Fri Dec 15 15:02:50 GMT 2023 , Edited by admin on Fri Dec 15 15:02:50 GMT 2023
NCI_THESAURUS C29709
Created by admin on Fri Dec 15 15:02:50 GMT 2023 , Edited by admin on Fri Dec 15 15:02:50 GMT 2023
WHO-VATC QN06BX17
Created by admin on Fri Dec 15 15:02:50 GMT 2023 , Edited by admin on Fri Dec 15 15:02:50 GMT 2023
DSLD 3424 (Number of products:4)
Created by admin on Fri Dec 15 15:02:50 GMT 2023 , Edited by admin on Fri Dec 15 15:02:50 GMT 2023
Code System Code Type Description
CAS
63547-13-7
Created by admin on Fri Dec 15 15:02:50 GMT 2023 , Edited by admin on Fri Dec 15 15:02:50 GMT 2023
PRIMARY
ChEMBL
CHEMBL93077
Created by admin on Fri Dec 15 15:02:50 GMT 2023 , Edited by admin on Fri Dec 15 15:02:50 GMT 2023
PRIMARY
DRUG CENTRAL
95
Created by admin on Fri Dec 15 15:02:50 GMT 2023 , Edited by admin on Fri Dec 15 15:02:50 GMT 2023
PRIMARY
MERCK INDEX
m1429
Created by admin on Fri Dec 15 15:02:50 GMT 2023 , Edited by admin on Fri Dec 15 15:02:50 GMT 2023
PRIMARY Merck Index
MESH
C022116
Created by admin on Fri Dec 15 15:02:50 GMT 2023 , Edited by admin on Fri Dec 15 15:02:50 GMT 2023
PRIMARY
RXCUI
45938
Created by admin on Fri Dec 15 15:02:50 GMT 2023 , Edited by admin on Fri Dec 15 15:02:50 GMT 2023
PRIMARY RxNorm
DRUG BANK
DB08925
Created by admin on Fri Dec 15 15:02:50 GMT 2023 , Edited by admin on Fri Dec 15 15:02:50 GMT 2023
PRIMARY
WIKIPEDIA
ADRAFINIL
Created by admin on Fri Dec 15 15:02:50 GMT 2023 , Edited by admin on Fri Dec 15 15:02:50 GMT 2023
PRIMARY
SMS_ID
100000087705
Created by admin on Fri Dec 15 15:02:50 GMT 2023 , Edited by admin on Fri Dec 15 15:02:50 GMT 2023
PRIMARY
EPA CompTox
DTXSID4046498
Created by admin on Fri Dec 15 15:02:50 GMT 2023 , Edited by admin on Fri Dec 15 15:02:50 GMT 2023
PRIMARY
EVMPD
SUB05278MIG
Created by admin on Fri Dec 15 15:02:50 GMT 2023 , Edited by admin on Fri Dec 15 15:02:50 GMT 2023
PRIMARY
NCI_THESAURUS
C81369
Created by admin on Fri Dec 15 15:02:50 GMT 2023 , Edited by admin on Fri Dec 15 15:02:50 GMT 2023
PRIMARY
FDA UNII
BI81Z4542G
Created by admin on Fri Dec 15 15:02:50 GMT 2023 , Edited by admin on Fri Dec 15 15:02:50 GMT 2023
PRIMARY
ECHA (EC/EINECS)
264-303-1
Created by admin on Fri Dec 15 15:02:50 GMT 2023 , Edited by admin on Fri Dec 15 15:02:50 GMT 2023
PRIMARY
INN
5110
Created by admin on Fri Dec 15 15:02:50 GMT 2023 , Edited by admin on Fri Dec 15 15:02:50 GMT 2023
PRIMARY
PUBCHEM
3033226
Created by admin on Fri Dec 15 15:02:50 GMT 2023 , Edited by admin on Fri Dec 15 15:02:50 GMT 2023
PRIMARY
Related Record Type Details
ENANTIOMER -> RACEMATE
ENANTIOMER -> RACEMATE
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ACTIVE MOIETY