ARMODAFINIL

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Search structure


Trade Names	ARMODAFINIL NUVIGIL
Synonyms	Armodafinil CEP-10952 CEP-10953 CRL-40982 Modafinil, (r)- NSC-751850 NSC-758711 Nuvigil R-(-)-modafinil
Status
Molecule Category	UNKNOWN
ATC	N06BA13
UNII	V63XWA605I


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	YFGHCGITMMYXAQ-LJQANCHMSA-N
Smiles	NC(=O)C[S@@+]([O-])C(c1ccccc1)c1ccccc1
InChI	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

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C15H15NO2S
Molecular Weight	273.36
AlogP	2.01
Hydrogen Bond Acceptor	2.0
Hydrogen Bond Donor	1.0
Number of Rotational Bond	5.0
Polar Surface Area	60.16
Molecular species	NEUTRAL
Aromatic Rings	2.0
Heavy Atoms	19.0

Bioactivity

Mechanism of Action	Action	Reference
Dopamine transporter inhibitor	INHIBITOR	DailyMed PubMed


Protein: Dopamine transporter Description: Sodium-dependent dopamine transporter Organism : Homo sapiens Q01959 ENSG00000142319

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Dopamine receptor	-	2	-	39000	-
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC06 neurotransmitter transporter family	-	6600	-	3050-3260	-

Assay Description	Organism	Bioactivity	Reference
Antagonist activity at DRD2 (unknown origin) expressed in HEK293T cells transfected with Galphai1-RLuc8 and gamma2-GFP10 assessed as inhibition of quinpirole-induced Gi1 activation pre-incubated with quinpirole for 10 mins before compound incubation for 10 mins by BRET assay	Homo sapiens	2.1 nM
Displacement of [3H]WIN35,428 from wild type human DAT expressed in COS7 cell membranes incubated for >90 mins by radioligand binding assay	Homo sapiens	647.0 nM
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging	Homo sapiens	8.19 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	8.232 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.19 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.19 %

Related Entries

Cross References

Resources	Reference
ChEBI	77590
ChEMBL	CHEMBL1201192
DrugBank	DB06413
DrugCentral	4501
FDA SRS	V63XWA605I
KEGG	D03215
PubChem	9690109
SureChEMBL	SCHEMBL34489
ZINC	ZINC000003831139

CONTENTS

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).