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

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

Description

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	Inhibitor 8,297	51.79 µM [IC50]
Cytochrome P450 2C19 51	Inhibitor 8,297	51.79 µM [IC50]
Dopamine transporter 180	Inhibitor 8,297	13.0 µM [Ki]
Dopamine transporter 180	Inhibitor 8,297	4.0 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Narcolepsy 20	Primary	Approved 8,429	PROVIGIL
Obstructive sleep apnea 6	Primary	Approved 8,429	PROVIGIL
Sleep disorder 20	Primary	Approved 8,429	NUVIGIL

C_max

Value	Dose	Analyte	Population
7.4 μg/mL	200 mg 1 times / day multiple, oral	ARMODAFINIL plasma	Homo sapiens
10.5 μg/mL	250 mg 1 times / day multiple, oral	ARMODAFINIL plasma	Homo sapiens
10 μg/mL	300 mg 1 times / day multiple, oral	ARMODAFINIL plasma	Homo sapiens
13.4 μg/mL	400 mg 1 times / day multiple, oral	ARMODAFINIL plasma	Homo sapiens
1.8 μg/mL	50 mg 1 times / day multiple, oral	ARMODAFINIL plasma	Homo sapiens
4 μg/mL	100 mg 1 times / day multiple, oral	ARMODAFINIL plasma	Homo sapiens
6.9 μg/mL	400 mg single, oral	ARMODAFINIL plasma	Homo sapiens
7 μg/mL	300 mg single, oral	ARMODAFINIL plasma	Homo sapiens
1.1 μg/mL	50 mg single, oral	ARMODAFINIL plasma	Homo sapiens
2.4 μg/mL	100 mg single, oral	ARMODAFINIL plasma	Homo sapiens
2.2 μg/mL	100 mg single, oral	ARMODAFINIL plasma	Homo sapiens
4.1 μg/mL	200 mg single, oral	ARMODAFINIL plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
105.9 μg × h/mL	200 mg 1 times / day multiple, oral	ARMODAFINIL plasma	Homo sapiens
136.1 μg × h/mL	250 mg 1 times / day multiple, oral	ARMODAFINIL plasma	Homo sapiens
150.4 μg × h/mL	300 mg 1 times / day multiple, oral	ARMODAFINIL plasma	Homo sapiens
189.5 μg × h/mL	400 mg 1 times / day multiple, oral	ARMODAFINIL plasma	Homo sapiens
23.4 μg × h/mL	50 mg 1 times / day multiple, oral	ARMODAFINIL plasma	Homo sapiens
56.2 μg × h/mL	100 mg 1 times / day multiple, oral	ARMODAFINIL plasma	Homo sapiens
142.9 μg × h/mL	400 mg single, oral	ARMODAFINIL plasma	Homo sapiens
146 μg × h/mL	300 mg single, oral	ARMODAFINIL plasma	Homo sapiens
15.9 μg × h/mL	50 mg single, oral	ARMODAFINIL plasma	Homo sapiens
40.6 μg × h/mL	100 mg single, oral	ARMODAFINIL plasma	Homo sapiens
43.8 μg × h/mL	100 mg single, oral	ARMODAFINIL plasma	Homo sapiens
75.9 μg × h/mL	200 mg single, oral	ARMODAFINIL plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
13.8 h	50 mg single, oral		ARMODAFINIL plasma	Homo sapiens

Doses

Show entries

Dose	Population	Adverse events
150 mg 1 times / day steady, oral Recommended	unhealthy, 21 years n = 1	Disc. AE: Stevens-Johnson syndrome...
400 mg single, oral Highest studied dose	healthy, 21–40 years n = 6
400 mg 1 times / day steady, oral Highest studied dose	healthy, 21–40 years n = 4	Disc. AE: Adverse event...
150 mg 1 times / day steady, oral Recommended	unhealthy n = 645	Disc. AE: Headache...
150 mg 1 times / day steady, oral Recommended	unhealthy n = 645	Disc. AE: Rash, Angioneurotic edema...

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AEs

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AE	Significance	Dose	Population
Stevens-Johnson syndrome	1 patient Disc. AE	150 mg 1 times / day steady, oral Recommended	unhealthy, 21 years n = 1
Adverse event	Disc. AE	400 mg 1 times / day steady, oral Highest studied dose	healthy, 21–40 years n = 4
Headache	1% Disc. AE	150 mg 1 times / day steady, oral Recommended	unhealthy n = 645
Angioneurotic edema	1% Disc. AE	150 mg 1 times / day steady, oral Recommended	unhealthy n = 645
Hyperhidrosis	1% Disc. AE	150 mg 1 times / day steady, oral Recommended	unhealthy n = 645

Showing 1 to 5 of 7 entries

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Sourcing

Sourcing

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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

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PubMed

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Title	Date	PubMed
Steady-state pharmacokinetics and tolerability of modafinil given alone or in combination with methylphenidate in healthy volunteers.	2001 Aug	11504278
Off-label uses of modafinil.	2001 Aug	11481196
An enantioselective assay for (+/-)-modafinil.	2001 Aug	11451649
Methylphenidate and narcolepsy: new indication. When modafinil fails.	2001 Feb	11503860
Sleep disorders.	2001 Feb	11471763

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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.

Show entries

Name

Type

Language

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

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Classification Tree

Code System

Code

Centrally acting sympathomimetics

WHO-ATC

N06BA13

Agent Affecting Nervous System

NCI_THESAURUS

C47795

Stimulant

LIVERTOX

NBK548274

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Code System

Code

Type

Description

CAS

112111-43-0

PRIMARY

PUBCHEM

9690109

PRIMARY

DRUG CENTRAL

4501

PRIMARY

INN

8474

PRIMARY

CHEBI

77590

PRIMARY

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ACTIVE MOIETY


					V63XWA605I

ARMODAFINIL

SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Doses

AEs

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2