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- Withdrawn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
Structure for Adrafinil (DB08925)
- Weight
- Average: 289.35
Monoisotopic: 289.077264521 - Chemical Formula
- C15H15NO3S
- Synonyms
- Adrafinil
- Adrafinilum
- External IDs
- CRL 40028
- CRL-40028
Pharmacology
- Indication
Used to relieve excessive sleepiness and inattention in elderly patients.
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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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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.
Drug Interaction Integrate drug-drug
interactions in your softwareAcebutolol The therapeutic efficacy of Adrafinil can be decreased when used in combination with Acebutolol. Aceclofenac The risk or severity of hypertension can be increased when Aceclofenac is combined with Adrafinil. Acemetacin The risk or severity of hypertension can be increased when Adrafinil is combined with Acemetacin. Acetylsalicylic acid The risk or severity of hypertension can be increased when Acetylsalicylic acid is combined with Adrafinil. Aclidinium The risk or severity of Tachycardia can be increased when Aclidinium is combined with Adrafinil. Adenosine The risk or severity of Tachycardia can be increased when Adenosine is combined with Adrafinil. Alclofenac The risk or severity of hypertension can be increased when Adrafinil is combined with Alclofenac. Alfentanil The risk or severity of hypertension can be increased when Alfentanil is combined with Adrafinil. Alfuzosin The therapeutic efficacy of Adrafinil can be decreased when used in combination with Alfuzosin. Aliskiren Adrafinil may decrease the antihypertensive activities of Aliskiren. 
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- Not Available
Products
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Name Kind UNII CAS InChI Key Modafinil prodrug R3UK8X3U3D 68693-11-8 YFGHCGITMMYXAQ-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
- External Links
Clinical Trials
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
Property Value Source Water Solubility 0.758 mg/mL ALOGPS logP 2.19 ALOGPS logP 1.53 Chemaxon logS -2.6 ALOGPS pKa (Strongest Acidic) 8.1 Chemaxon pKa (Strongest Basic) -5.5 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 66.4 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 79.15 m3·mol-1 Chemaxon Polarizability 29.63 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Not Available
Drug created at October 08, 2013 20:30 / Updated at May 14, 2021 01:05