NAV

Adrafinil

Identification

Generic Name
Adrafinil
DrugBank Accession Number
DB08925
Background

Adrafinil is a mild central nervous system stimulating drug typically employed to relieve excessive sleepiness and inattention in geriatric patients. It is also been used off-label to prevent fatigue or falling asleep for extended periods of time. Adrafinil does not currently have FDA approval and is thus unregulated in the United States. It was marketed in France and elsewhere in Europe under the trade name Olmifon until September 2011 when France's FDA equivalent reassessed the drug and withdrew marketing permission. Adrafinil is metabolized to modafinil.

Type
Small Molecule
Groups
Withdrawn
Structure
3D
Similar Structures
Weight
Average: 289.35
Monoisotopic: 289.077264521
Chemical Formula
C15H15NO3S
Synonyms
  • Adrafinil
  • Adrafinilum
External IDs
  • CRL 40028
  • CRL-40028
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Pharmacology

Indication

Used to relieve excessive sleepiness and inattention in elderly patients.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Adrafinil is a prodrug; it is primarily metabolized in vivo to modafinil, resulting in nearly identical pharmacological effects. Unlike modafinil, the active metabolite must accumulate before the drug is able to act. Oral adrafinil without food usually begins to act within 45 minutes to 1 hour.

Mechanism of action
Not Available
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
Integrate drug-drug
interactions in your software
AcebutololThe therapeutic efficacy of Adrafinil can be decreased when used in combination with Acebutolol.
AceclofenacThe risk or severity of hypertension can be increased when Aceclofenac is combined with Adrafinil.
AcemetacinThe risk or severity of hypertension can be increased when Adrafinil is combined with Acemetacin.
Acetylsalicylic acidThe risk or severity of hypertension can be increased when Acetylsalicylic acid is combined with Adrafinil.
AclidiniumThe risk or severity of Tachycardia can be increased when Aclidinium is combined with Adrafinil.
Food Interactions
Not Available

Products

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Active Moieties
NameKindUNIICASInChI Key
ModafinilprodrugR3UK8X3U3D68693-11-8YFGHCGITMMYXAQ-UHFFFAOYSA-N
International/Other Brands
Olmifon (Cephalon)

Categories

ATC Codes
N06BX17 — Adrafinil
Drug Categories
Classification
Not classified
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
BI81Z4542G
CAS number
63547-13-7
InChI Key
CGNMLOKEMNBUAI-UHFFFAOYSA-N
InChI
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)
IUPAC Name
2-diphenylmethanesulfinyl-N-hydroxyacetamide
SMILES
ONC(=O)CS(=O)C(C1=CC=CC=C1)C1=CC=CC=C1

References

General References
Not Available
KEGG Drug
D07348
PubChem Substance
347910387
ChemSpider
2297976
RxNav
45938
ChEBI
135200
ChEMBL
CHEMBL93077
Wikipedia
Adrafinil

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.758 mg/mLALOGPS
logP2.19ALOGPS
logP1.53Chemaxon
logS-2.6ALOGPS
pKa (Strongest Acidic)8.1Chemaxon
pKa (Strongest Basic)-5.5Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area66.4 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity79.15 m3·mol-1Chemaxon
Polarizability29.63 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-0910000000-4db08b8651ab7a028701
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-02t9-0950000000-43943da43cf37b5382a6
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-0910000000-9bcc3b631e813f2ec891
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-5900000000-c0fcf30f54146f5318fb
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-0930000000-11b7f2cacd665dfff214
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-2900000000-b36b95b5c3a8aee2ce6b
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-157.47717
predicted
DeepCCS 1.0 (2019)
[M+H]+159.83516
predicted
DeepCCS 1.0 (2019)
[M+Na]+165.92833
predicted
DeepCCS 1.0 (2019)

Drug created at October 08, 2013 20:30 / Updated at May 14, 2021 01:05