ARMODAFINIL

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C15H15NO2S
Molecular Weight	273.35
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC(=O)C[S@@+]([O-])C(C1=CC=CC=C1)C2=CC=CC=C2

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

Molecular Formula	C15H15NO2S
Molecular Weight	273.35
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.drugbank.ca/drugs/DB00745https://www.ncbi.nlm.nih.gov/pubmed/19689169
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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Cytochrome P450 2C19 51 Target ID: CHEMBL3622 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26338061	Inhibitor 8504	51.79 µM [IC50]
Cytochrome P450 2C19 51 Target ID: CHEMBL3622 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26338061	Inhibitor 8504	51.79 µM [IC50]
Dopamine transporter 183 Target ID: CHEMBL238 Sources: http://www.drugbank.ca/drugs/DB00745	Inhibitor 8504	13.0 µM [Ki]
Dopamine transporter 183 Target ID: CHEMBL238 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/021875s023lbl.pdf	Inhibitor 8504	4.0 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Narcolepsy 20 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/nda/98/020717A_Provigil_prntlbl.pdf	Primary	Approved 8583	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 1998
Obstructive sleep apnea 6 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/nda/98/020717A_Provigil_prntlbl.pdf	Primary	Approved 8583	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 1998
Sleep disorder 25 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19689169	Primary	Approved 8583	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 2007

C_max

Value	Dose	Analyte	Population
1.1 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19133704	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19133704	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
4.1 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19133704	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
7 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19133704	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
6.9 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19133704	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
1.8 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19133704	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19133704	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
7.4 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19133704	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19133704	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19133704	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19133704	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
2.2 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19133704	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

AUC

Value	Dose	Analyte	Population
15.9 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19133704	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19133704	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
75.9 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19133704	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
146 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19133704	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
142.9 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19133704	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
23.4 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19133704	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19133704	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
105.9 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19133704	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19133704	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19133704	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19133704	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
43.8 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19133704	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
13.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19133704	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

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:77590	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:77590
ZINC	ZINC000003831139	http://zinc15.docking.org/substances/ZINC000003831139

PubMed

Title	Date	PubMed
Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis.	2015-05-18	25811541
Armodafinil in the treatment of sleep/wake disorders.	2010-09-07	20856606
A retrospective review of supratherapeutic modafinil exposures.	2010-09	20358418
Effects of modafinil on the sleep EEG depend on Val158Met genotype of COMT.	2010-08	20815183
Modafinil effects on reinstatement of methamphetamine seeking in a rat model of relapse.	2010-06	20352413
A cost-effectiveness analysis of modafinil therapy for psychostimulant dependence.	2010-05	20565514
Normalizing effects of modafinil on sleep in chronic cocaine users.	2010-03	20080983
Modafinil for bipolar depression with comorbid methamphetamine abuse.	2010-02-19	20163392
[Modafinil in psychiatric disorders: the promising state reconsidered].	2010	21064019
Open-label pilot study of modafinil for methamphetamine dependence.	2009-10	19745650
Modafinil for the treatment of cocaine dependence.	2009-09-01	19560290
Effects of the atypical stimulant modafinil on a brief gambling episode in pathological gamblers with high vs. low impulsivity.	2009-08	18583430
How to keep the brain awake? The complex molecular pharmacogenetics of wake promotion.	2009-06	19194377
Modafinil treatment of amphetamine abuse in adult ADHD.	2009-06	18562425
Evidence for the involvement of dopamine transporters in behavioral stimulant effects of modafinil.	2009-05	19197004
A double-blind, placebo-controlled trial of modafinil (200 mg/day) for methamphetamine dependence.	2009-02	19149817
Symptoms and sleep patterns during inpatient treatment of methamphetamine withdrawal: a comparison of mirtazapine and modafinil with treatment as usual.	2008-10	18329221
Modafinil: a review of neurochemical actions and effects on cognition.	2008-06	17712350
Chest tightness and palpitations associated with modafinil and consumption of free glutamate.	2008-04	18381922
Smoked cocaine self-administration is decreased by modafinil.	2008-03	17568397
Hyperprolactinemia and galactorrhea induced by serotonin and norepinephrine reuptake inhibiting antidepressants.	2007-07	17606668
Mechanisms of modafinil: A review of current research.	2007-06	19300566
Psychostimulants and military operations.	2007-04	17484308
Acute chorea and hyperthermia after concurrent use of modafinil and tranylcypromine.	2007-04	17403991
Modafinil for excessive sleepiness associated with chronic shift work sleep disorder: effects on patient functioning and health-related quality of life.	2007	17632651
Use of modafinil for the treatment of attention deficit/hyperactivity disorder.	2006-10	16954326
Modafinil augmentation of SSRI therapy in patients with major depressive disorder and excessive sleepiness and fatigue: a 12-week, open-label, extension study.	2006-02	16520686
[Effect of diazepam and modafinil on acute hepatic failure in mice].	2005-06	16045030
Prediction of genotoxicity of chemical compounds by statistical learning methods.	2005-06	15962942
A double-blind, placebo-controlled trial of modafinil for cocaine dependence.	2005-01	15525998
Modafinil influences the pharmacokinetics of intravenous cocaine in healthy cocaine-dependent volunteers.	2005	15966757
Piperidine-based nocaine/modafinil hybrid ligands as highly potent monoamine transporter inhibitors: efficient drug discovery by rational lead hybridization.	2004-11-18	15537337
Anti-narcoleptic agent modafinil and its sulfone: a novel facile synthesis and potential anti-epileptic activity.	2004-08	15260124
Modafinil treatment of excessive sedation associated with divalproex sodium.	2004-01	14763681
Narcolepsy drug could be approved for wider use.	2003-10-04	14558511
Dosing regimen effects of modafinil for improving daytime wakefulness in patients with narcolepsy.	2003-10-02	14520165
The safety and efficacy of modafinil in multiple sclerosis-related fatigue.	2003-10	13678557
You'll lose sleep over this pill.	2003-09-29	14521093
Modafinil in children with attention-deficit hyperactivity disorder.	2003-08	14580657
Modafinil for treatment of cognitive side effects of antiepileptic drugs in a patient with seizures and stroke.	2003-06	12791341
Modafinil and cocaine: a double-blind, placebo-controlled drug interaction study.	2003-05-01	12681523
Chiral analysis of d- and l-modafinil in human serum: application to human pharmacokinetic studies.	2003-04	12657914
Modafinil increases histamine release in the anterior hypothalamus of rats.	2003-03-20	12614915
Temporal pattern of hippocampal high-frequency oscillations during sleep after stimulant-evoked waking.	2003	14568034
Modafinil for social phobia and amphetamine dependence.	2002-11	12411237
Narcolepsy and psychopathology: is there an association?	2002-07	14592199
Acute behavioral and physiological effects of modafinil in drug abusers.	2002-03	11981223
Is psychosis exacerbated by modafinil?	2002-03	11879175
Dopaminergic role in stimulant-induced wakefulness.	2001-03-01	11222668
Non-amphetaminic mechanism of stimulant locomotor effect of modafinil in mice.	1995-12	8998404

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

In Vitro Use Guide

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:01:50 GMT 2025` Edited by `admin` on `Mon Mar 31 18:01:50 GMT 2025`
Record UNII	V63XWA605I
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NUVIGIL

Preferred Name

English

ARMODAFINIL

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

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

2-[(R)-(Diphenylmethyl)sulfinyl]acetamide

Systematic 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