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

Details

Stereochemistry ABSOLUTE
Molecular Formula C15H15NO2S
Molecular Weight 273.3517
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ARMODAFINIL

SMILES

c1ccc(cc1)C(c2ccccc2)[S@](=O)CC(=N)O

InChI

InChIKey=YFGHCGITMMYXAQ-LJQANCHMSA-N
InChI=1S/C15H15NO2S/c16-14(17)11-19(18)15(12-7-3-1-4-8-12)13-9-5-2-6-10-13/h1-10,15H,11H2,(H2,16,17)/t19-/m1/s1

HIDE SMILES / InChI

Description
Curator's Comment:: Description was created based on several sources, including https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/021875s023lbl.pdf | https://www.drugs.com/pro/armodafinil.html

Armodafinil is the R-enantiomer of modafinil, a wake-promoting agent, that primarily affects areas of the brain involved in controlling wakefulness. Armodafinil is an indirect dopamine receptor agonist; both armodafinil and modafinil bind in vitro to the dopamine transporter and inhibit dopamine reuptake. Armodafinil tablets are indicated to improve wakefulness in adult patients with excessive sleepiness associated with obstructive sleep apnea (OSA), narcolepsy, or shift work disorder (SWD). Once-daily armodafinil was generally well tolerated in adult patients with excessive sleepiness associated with OSA (despite treatment of the underlying condition), narcolepsy or SWSD.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
51.79 µM [IC50]
51.79 µM [IC50]
13.0 µM [Ki]
4.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PROVIGIL

Approved Use

Provigil is indicated to improve wakefulness in adult patients with excessive sleepiness associated with narcolepsy, obstructive sleep apnea (OSA), or shift work disorder (SWD).

Launch Date

9.1437118E11
Primary
PROVIGIL

Approved Use

Provigil is indicated to improve wakefulness in adult patients with excessive sleepiness associated with narcolepsy, obstructive sleep apnea (OSA), or shift work disorder (SWD).

Launch Date

9.1437118E11
Primary
NUVIGIL

Approved Use

NUVIGIL is indicated to improve wakefulness in patients with excessive sleepiness associated with obstructive sleep apnea, narcolepsy and shift work disorder. In OSA, NUVIGIL is indicated as an adjunct to standard treatment(s) for the underlying obstruction. If continuous positive airway pressure (CPAP) is the treatment of choice for a patient, a maximal effort to treat with CPAP for an adequate period of time should be made prior to initiating NUVIGIL. If NUVIGIL is used adjunctively with CPAP, the encouragement of and periodic assessment of CPAP compliance is necessary. In all cases, careful attention to the diagnosis and treatment of the underlying sleep disorder(s) is of utmost importance. Prescribers should be aware that some patients may have more than one sleep disorder contributing to their excessive sleepiness. The effectiveness of NUVIGIL in long-term use (greater than 12 weeks) has not been systematically evaluated in placebo-controlled trials. The physician who elects to prescribe NUVIGIL for an extended time in patients should periodically re-evaluate long-term usefulness for the individual patient.

Launch Date

1.18186561E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
7.4 μg/mL
200 mg 1 times / day multiple, oral
dose: 200 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ARMODAFINIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
10.5 μg/mL
250 mg 1 times / day multiple, oral
dose: 250 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ARMODAFINIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
10 μg/mL
300 mg 1 times / day multiple, oral
dose: 300 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ARMODAFINIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
13.4 μg/mL
400 mg 1 times / day multiple, oral
dose: 400 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ARMODAFINIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
1.8 μg/mL
50 mg 1 times / day multiple, oral
dose: 50 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ARMODAFINIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
4 μg/mL
100 mg 1 times / day multiple, oral
dose: 100 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ARMODAFINIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
6.9 μg/mL
400 mg single, oral
dose: 400 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ARMODAFINIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
7 μg/mL
300 mg single, oral
dose: 300 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ARMODAFINIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
1.1 μg/mL
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ARMODAFINIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
2.4 μg/mL
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ARMODAFINIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
2.2 μg/mL
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ARMODAFINIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: HIGH-FAT
4.1 μg/mL
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ARMODAFINIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
105.9 μg × h/mL
200 mg 1 times / day multiple, oral
dose: 200 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ARMODAFINIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
136.1 μg × h/mL
250 mg 1 times / day multiple, oral
dose: 250 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ARMODAFINIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
150.4 μg × h/mL
300 mg 1 times / day multiple, oral
dose: 300 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ARMODAFINIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
189.5 μg × h/mL
400 mg 1 times / day multiple, oral
dose: 400 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ARMODAFINIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
23.4 μg × h/mL
50 mg 1 times / day multiple, oral
dose: 50 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ARMODAFINIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
56.2 μg × h/mL
100 mg 1 times / day multiple, oral
dose: 100 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ARMODAFINIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
142.9 μg × h/mL
400 mg single, oral
dose: 400 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ARMODAFINIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
146 μg × h/mL
300 mg single, oral
dose: 300 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ARMODAFINIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
15.9 μg × h/mL
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ARMODAFINIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
40.6 μg × h/mL
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ARMODAFINIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
43.8 μg × h/mL
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ARMODAFINIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: HIGH-FAT
75.9 μg × h/mL
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ARMODAFINIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
13.8 h
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ARMODAFINIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
150 mg 1 times / day steady, oral
Recommended
Dose: 150 mg, 1 times / day
Route: oral
Route: steady
Dose: 150 mg, 1 times / day
Sources:
unhealthy, 21 years
n = 1
Health Status: unhealthy
Condition: idiopathic hypersomnia
Age Group: 21 years
Sex: F
Population Size: 1
Sources:
Disc. AE: Stevens-Johnson syndrome...
AEs leading to
discontinuation/dose reduction:
Stevens-Johnson syndrome (1 patient)
Sources:
400 mg single, oral
Highest studied dose
Dose: 400 mg
Route: oral
Route: single
Dose: 400 mg
Sources:
healthy, 21–40 years
n = 6
Health Status: healthy
Age Group: 21–40 years
Sex: M
Population Size: 6
Sources:
400 mg 1 times / day steady, oral
Highest studied dose
Dose: 400 mg, 1 times / day
Route: oral
Route: steady
Dose: 400 mg, 1 times / day
Sources:
healthy, 21–40 years
n = 4
Health Status: healthy
Age Group: 21–40 years
Sex: M
Population Size: 4
Sources:
Disc. AE: Adverse event...
AEs leading to
discontinuation/dose reduction:
Adverse event
Sources:
150 mg 1 times / day steady, oral
Recommended
Dose: 150 mg, 1 times / day
Route: oral
Route: steady
Dose: 150 mg, 1 times / day
Sources:
unhealthy
n = 645
Health Status: unhealthy
Population Size: 645
Sources:
Disc. AE: Headache...
AEs leading to
discontinuation/dose reduction:
Headache (1%)
Sources:
150 mg 1 times / day steady, oral
Recommended
Dose: 150 mg, 1 times / day
Route: oral
Route: steady
Dose: 150 mg, 1 times / day
Sources: Page: p.6
unhealthy
n = 645
Health Status: unhealthy
Population Size: 645
Sources: Page: p.6
Disc. AE: Rash, Angioneurotic edema...
AEs leading to
discontinuation/dose reduction:
Rash (2%)
Angioneurotic edema (1%)
Hyperhidrosis (1%)
Rash papular (1%)
Sources: Page: p.6
AEs

AEs

AESignificanceDosePopulation
Stevens-Johnson syndrome 1 patient
Disc. AE
150 mg 1 times / day steady, oral
Recommended
Dose: 150 mg, 1 times / day
Route: oral
Route: steady
Dose: 150 mg, 1 times / day
Sources:
unhealthy, 21 years
n = 1
Health Status: unhealthy
Condition: idiopathic hypersomnia
Age Group: 21 years
Sex: F
Population Size: 1
Sources:
Adverse event Disc. AE
400 mg 1 times / day steady, oral
Highest studied dose
Dose: 400 mg, 1 times / day
Route: oral
Route: steady
Dose: 400 mg, 1 times / day
Sources:
healthy, 21–40 years
n = 4
Health Status: healthy
Age Group: 21–40 years
Sex: M
Population Size: 4
Sources:
Headache 1%
Disc. AE
150 mg 1 times / day steady, oral
Recommended
Dose: 150 mg, 1 times / day
Route: oral
Route: steady
Dose: 150 mg, 1 times / day
Sources:
unhealthy
n = 645
Health Status: unhealthy
Population Size: 645
Sources:
Angioneurotic edema 1%
Disc. AE
150 mg 1 times / day steady, oral
Recommended
Dose: 150 mg, 1 times / day
Route: oral
Route: steady
Dose: 150 mg, 1 times / day
Sources: Page: p.6
unhealthy
n = 645
Health Status: unhealthy
Population Size: 645
Sources: Page: p.6
Hyperhidrosis 1%
Disc. AE
150 mg 1 times / day steady, oral
Recommended
Dose: 150 mg, 1 times / day
Route: oral
Route: steady
Dose: 150 mg, 1 times / day
Sources: Page: p.6
unhealthy
n = 645
Health Status: unhealthy
Population Size: 645
Sources: Page: p.6
Rash papular 1%
Disc. AE
150 mg 1 times / day steady, oral
Recommended
Dose: 150 mg, 1 times / day
Route: oral
Route: steady
Dose: 150 mg, 1 times / day
Sources: Page: p.6
unhealthy
n = 645
Health Status: unhealthy
Population Size: 645
Sources: Page: p.6
Rash 2%
Disc. AE
150 mg 1 times / day steady, oral
Recommended
Dose: 150 mg, 1 times / day
Route: oral
Route: steady
Dose: 150 mg, 1 times / day
Sources: Page: p.6
unhealthy
n = 645
Health Status: unhealthy
Population Size: 645
Sources: Page: p.6
PubMed

PubMed

TitleDatePubMed
Sleep disorders.
2001 Feb
Successful treatment of excessive daytime sleepiness in Parkinson's disease with modafinil.
2001 Jul
Randomized, double-blind, placebo-controlled crossover trial of modafinil in the treatment of residual excessive daytime sleepiness in the sleep apnea/hypopnea syndrome.
2001 Mar
Dopaminergic role in stimulant-induced wakefulness.
2001 Mar 1
Benefits and risks of pharmacotherapy for narcolepsy.
2002
Differential enhancement of dialysate serotonin levels in distinct brain regions of the awake rat by modafinil: possible relevance for wakefulness and depression.
2002 Apr 1
Modafinil reduces excessive somnolence and enhances mood in patients with myotonic dystrophy.
2002 Dec 24
Efficacy and safety of modafinil (Provigil) for the treatment of fatigue in multiple sclerosis: a two centre phase 2 study.
2002 Feb
Determination of modafinil, modafinil acid and modafinil sulfone in human plasma utilizing liquid-liquid extraction and high-performance liquid chromatography.
2002 Feb 15
Maintaining alertness and performance during sleep deprivation: modafinil versus caffeine.
2002 Jan
Reduction of daytime sleepiness in a depressive patient during adjunct treatment with modafinil.
2002 Jan-Feb
Comparison of the effects of modafinil and sleep deprivation on sleep and cortical EEG spectra in mice.
2002 Jul
Gateways to clinical trials.
2002 Jul-Aug
Gateways to Clinical Trials. June 2002.
2002 Jun
Acute behavioral and physiological effects of modafinil in drug abusers.
2002 Mar
Is psychosis exacerbated by modafinil?
2002 Mar
Use of modafinil in spastic cerebral palsy.
2002 Mar
Treatment of excessive daytime sleepiness in patients with Parkinson's disease with modafinil.
2002 Mar-Apr
Modafinil monotherapy in depression.
2002 May
Stress-induced subsensitivity to modafinil and its prevention by corticosteroids.
2002 Nov
Temporal pattern of hippocampal high-frequency oscillations during sleep after stimulant-evoked waking.
2003
Modafinil in children with attention-deficit hyperactivity disorder.
2003 Aug
TetraTab--cognitive enhancement gone wrong.
2003 Aug
Cognitive enhancing effects of modafinil in healthy volunteers.
2003 Jan
Should a pharmaceutical be approved for the broad indication of excessive sleepiness?
2003 Jan 15
Modafinil maintains waking in the fruit fly drosophila melanogaster.
2003 Mar 15
The safety and efficacy of modafinil in multiple sclerosis-related fatigue.
2003 Oct
The quest for a smart pill.
2003 Sep
Anti-narcoleptic agent modafinil and its sulfone: a novel facile synthesis and potential anti-epileptic activity.
2004 Aug
Piperidine-based nocaine/modafinil hybrid ligands as highly potent monoamine transporter inhibitors: efficient drug discovery by rational lead hybridization.
2004 Nov 18
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Psychostimulants and military operations.
2007 Apr
Acute chorea and hyperthermia after concurrent use of modafinil and tranylcypromine.
2007 Apr
Mechanisms of modafinil: A review of current research.
2007 Jun
Symptoms and sleep patterns during inpatient treatment of methamphetamine withdrawal: a comparison of mirtazapine and modafinil with treatment as usual.
2008 Oct
Effects of the atypical stimulant modafinil on a brief gambling episode in pathological gamblers with high vs. low impulsivity.
2009 Aug
Modafinil for the treatment of cocaine dependence.
2009 Sep 1
[Modafinil in psychiatric disorders: the promising state reconsidered].
2010
Effects of modafinil on the sleep EEG depend on Val158Met genotype of COMT.
2010 Aug
Armodafinil in the treatment of sleep/wake disorders.
2010 Sep 7
Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis.
2015 May 18
Patents

Sample Use Guides

In Vivo Use Guide
Dosage in Narcolepsy and Obstructive Sleep Apnea (OSA) The recommended dosage of PROVIGIL (Modafinil ) for patients with narcolepsy or OSA is 200 mg taken orally once a day as a single dose in the morning.
Route of Administration: Oral
At high concentrations of modafinil (>/=100 uM), the mean activity of CYP2C9 in pooled human liver microsomes was decreased (up to 60%) relative to that in the solvent controls.
Name Type Language
ARMODAFINIL
INN   MART.   ORANGE BOOK   USAN   VANDF   WHO-DD  
INN   USAN  
Official Name English
ACETAMIDE, 2-((R)-(DIPHENYLMETHYL)SULFINYL)-
Systematic Name English
CEP-10953
Code English
ARMODAFINIL [WHO-DD]
Common Name English
NSC-751850
Code English
CEP-10952
Code English
CRL-40982
Code English
NUVIGIL
Brand Name English
ARMODAFINIL [USP-RS]
Common Name English
MODAFINIL, (R)-
Common Name English
(-)-2-((R)-(DIPHENYLMETHYL)SULFINYL)ACETAMIDE
Systematic Name English
NSC-758711
Code English
ARMODAFINIL [MART.]
Common Name English
R-(-)-MODAFINIL
Common Name English
ARMODAFINIL [INN]
Common Name English
ARMODAFINIL [ORANGE BOOK]
Common Name English
ARMODAFINIL [USAN]
Common Name English
ACETAMIDE, 2-((DIPHENYLMETHYL)SULFINYL)-, (-)-
Systematic Name English
ARMODAFINIL [VANDF]
Common Name English
Classification Tree Code System Code
WHO-ATC N06BA13
Created by admin on Fri Jun 25 22:02:33 UTC 2021 , Edited by admin on Fri Jun 25 22:02:33 UTC 2021
NCI_THESAURUS C47795
Created by admin on Fri Jun 25 22:02:33 UTC 2021 , Edited by admin on Fri Jun 25 22:02:33 UTC 2021
LIVERTOX 63
Created by admin on Fri Jun 25 22:02:33 UTC 2021 , Edited by admin on Fri Jun 25 22:02:33 UTC 2021
Code System Code Type Description
CAS
112111-43-0
Created by admin on Fri Jun 25 22:02:33 UTC 2021 , Edited by admin on Fri Jun 25 22:02:33 UTC 2021
PRIMARY
PUBCHEM
9690109
Created by admin on Fri Jun 25 22:02:33 UTC 2021 , Edited by admin on Fri Jun 25 22:02:33 UTC 2021
PRIMARY
DRUG CENTRAL
4501
Created by admin on Fri Jun 25 22:02:33 UTC 2021 , Edited by admin on Fri Jun 25 22:02:33 UTC 2021
PRIMARY
INN
8474
Created by admin on Fri Jun 25 22:02:33 UTC 2021 , Edited by admin on Fri Jun 25 22:02:33 UTC 2021
PRIMARY
DRUG BANK
DB06413
Created by admin on Fri Jun 25 22:02:33 UTC 2021 , Edited by admin on Fri Jun 25 22:02:33 UTC 2021
PRIMARY
LACTMED
Armodafinil
Created by admin on Fri Jun 25 22:02:33 UTC 2021 , Edited by admin on Fri Jun 25 22:02:33 UTC 2021
PRIMARY
RXCUI
641465
Created by admin on Fri Jun 25 22:02:33 UTC 2021 , Edited by admin on Fri Jun 25 22:02:33 UTC 2021
PRIMARY RxNorm
NCI_THESAURUS
C65241
Created by admin on Fri Jun 25 22:02:33 UTC 2021 , Edited by admin on Fri Jun 25 22:02:33 UTC 2021
PRIMARY
ChEMBL
CHEMBL1201192
Created by admin on Fri Jun 25 22:02:33 UTC 2021 , Edited by admin on Fri Jun 25 22:02:33 UTC 2021
PRIMARY
WIKIPEDIA
ARMODAFINIL
Created by admin on Fri Jun 25 22:02:33 UTC 2021 , Edited by admin on Fri Jun 25 22:02:33 UTC 2021
PRIMARY
USP_CATALOG
1042758
Created by admin on Fri Jun 25 22:02:33 UTC 2021 , Edited by admin on Fri Jun 25 22:02:33 UTC 2021
PRIMARY USP-RS
FDA UNII
V63XWA605I
Created by admin on Fri Jun 25 22:02:33 UTC 2021 , Edited by admin on Fri Jun 25 22:02:33 UTC 2021
PRIMARY
EVMPD
SUB32249
Created by admin on Fri Jun 25 22:02:33 UTC 2021 , Edited by admin on Fri Jun 25 22:02:33 UTC 2021
PRIMARY