Armodafinil

HCID 9690109CAS 112111-43-0

Grundinformationen

Standard-SMILES
NC(=O)C[S@@](=O)C(c1ccccc1)c1ccccc1
InChIKey
YFGHCGITMMYXAQ-LJQANCHMSA-N
Summenformel
C15H15NO2S
Durchschnittliche Molmasse
273,4 g/mol
Monoisotopische Masse
273,08234972

Überblick

Armodafinil is a 2-[(diphenylmethyl)sulfinyl]acetamide that has R configuration at the sulfur atom. Like its racemate, modafinil, it is used for the treatment of sleeping disorders such as narcolepsy, obstructive sleep apnoea, and shift-work sleep disorder. Peak concentration in the blood later occurs later following administration than with modafinil, so it is thought that armodafinil may be more effective than modafinil in treating people with excessive daytime sleepiness. It has a role as a central nervous system stimulant and a eugeroic. It is an enantiomer of a (S)-modafinil.

Namen und Bezeichner

Bevorzugter Name
Armodafinil
IUPAC
2-[(R)-benzhydrylsulfinyl]acetamide

Namen und Synonyme

Armodafinil112111-43-0Nuvigil(R)-Modafinil(-)-Modafinil(R)-(-)-ModafinilarmodafiniloCEP-109532-[(R)-(Diphenylmethyl)sulfinyl]acetamideModafinil, (r)-R-(-)-Modafinilarmodafinilum
Weitere Namen anzeigen
(-)-(R)-modafinilCEP 10953CEP-10952CRL-40982V63XWA605INSC-751850NSC-758711CHEBI:77590

Datenbank-Bezeichner

CAS
112111-43-0
PubChem CID
9690109
DTXSID
DTXSID90920667
ChEMBL
CHEMBL1201192
ChEBI
CHEBI:77590
UNII
V63XWA605I
EC Number
682-508-8

Eigenschaften

Berechnete Struktureigenschaften

XLogP
1,7
Polarare Oberfläche (TPSA)
79,4 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
3
Frei drehbare Bindungen
5
Schwere Atome
19

Experimentelle und physikochemische Eigenschaften

Drugs · 2 Einträge

DEA NFLIS-Drug Category -> Stimulants

Pharmaceuticals -> Listed in ZINC15

Human Drugs · 3 Einträge

Breast Feeding; Lactation; Milk, Human; Central Nervous System Stimulants; Wakefulness-Promoting Agents

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Collision Cross Section157.93 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

Danger

H318 (90.5%): Causes serious eye damage [Danger Serious eye damage/eye irritation]

P264+P265, P280, P305+P354+P338, and P317 (click each P-code to see the statement)

Aggregated GHS information provided per 42 reports by companies from 5 notifications to the ECHA C&L Inventory.

Gefahrenhinweise

Hazard Classes and CategoriesEye Dam. 1 (90.5%)

Toxikologische Informationen

Drug Induced Liver Injury · 6 Einträge

Drug Induced Liver Injury Rank (DILIrank 2.0)

Armodafinil

Ambiguous-DILI-concern

3

Warnings & precautions

DOI:10.1016/j.drudis.2016.02.015

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 2 Einträge

N - Nervous system

QN - Nervous system

Protein BindingSpecific data unavailable. Similar to modafinil: approximately 60%, primarily to albumin.
Mechanism of Action · 1 Eintrag

Nuvigil (armodafinil) is a single-isomer of modafini. The exact mechanism of action is unknown. Armodafinil belongs to a class of drugs known as eugeroics, which are stimulants that provide long-lasting mental arousal. Pharmacologically, armodafinil does not bind to or inhibit several receptors and enzymes potentially relevant for sleep/wake regulation. Armodafinil is not a direct- or indirect-acting dopamine receptor agonist. However, in vitro, both armodafinil and modafinil bind to the dopamine transporter and inhibit dopamine reuptake. [Medilexicon]

Biological Half-LifeTerminal half-life is approximately 15 hours.
Metabolism/Metabolites · 1 Eintrag

In vitro and in vivo data show that armodafinil undergoes hydrolytic deamidation, S-oxidation, and aromatic ring hydroxylation, with subsequent glucuronide conjugation of the hydroxylated products. Amide hydrolysis is the single most prominent metabolic pathway, with sulfone formation by cytochrome P450 (CYP) 3A4/5 being next in importance. The other oxidative products are formed too slowly in vitro to enable identification of the enzyme(s) responsible. Only two metabolites reach appreciable concentrations in plasma (i.e., R-modafinil acid and modafinil sulfone). Data specific to armodafinil disposition are not available.

MeSH Pharmacological Classification · 3 Einträge

A loosely defined group of drugs that tend to increase behavioral alertness, agitation, or excitation. They work by a variety of mechanisms, but usually not by direct excitation of neurons. The many drugs that have such actions as side effects to their main therapeutic use are not included here.

A specific category of drugs that prevent sleepiness by specifically targeting sleep-mechanisms in the brain. They are used to treat DISORDERS OF EXCESSIVE SOMNOLENCE such as NARCOLEPSY. Note that this drug category does not include broadly-acting central nervous system stimulants such as AMPHETAMINES.

Drugs and compounds that induce the synthesis of CYTOCHROME P-450 CYP3A.

Zugehörige Reaktionen

3

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