UMIFENOVIR

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Search structure


Synonyms	Arbidol Umifenovir
Status
Molecule Category	UNKNOWN
ATC	J05AX13
UNII	93M09WW4RU
EPA CompTox	DTXSID60895015


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

Structure


InChI Key	KCFYEAOKVJSACF-UHFFFAOYSA-N
Smiles	CCOC(=O)c1c(CSc2ccccc2)n(C)c2cc(Br)c(O)c(CN(C)C)c12
InChI	InChI=1S/C22H25BrN2O3S/c1-5-28-22(27)20-18(13-29-14-9-7-6-8-10-14)25(4)17-11-16(23)21(26)15(19(17)20)12-24(2)3/h6-11,26H,5,12-13H2,1-4H3

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C22H25BrN2O3S
Molecular Weight	477.42
AlogP	5.18
Hydrogen Bond Acceptor	6.0
Hydrogen Bond Donor	1.0
Number of Rotational Bond	7.0
Polar Surface Area	54.7
Molecular species	ZWITTERION
Aromatic Rings	3.0
Heavy Atoms	29.0

Bioactivity

Mechanism of Action	Action	Reference
Hemagglutinin negative modulator	NEGATIVE MODULATOR	PubMed PubMed

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Surface antigen	-	-	11100	-	-

Assay Description	Organism	Bioactivity	Reference
Binding affinity to influenza A virus A/WSN/33 (H1N1) Hemagglutinin 1 binding to sialic acid receptor by surface plasmon resonance assay	Influenza A virus (A/WSN/1933(H1N1))	81.0 nM
Binding affinity to Influenza A virus A/WSN/33 (H1N1) HA1 protein assessed as decrease in protein affinity to sialic acid receptor by surface plasmon resonance assay (Rvb = 70 nM)	Influenza A virus (A/WSN/1933(H1N1))	81.0 nM
Binding affinity to Influenza A virus A/WSN/33 (H1N1) HA1 protein assessed as decrease in protein affinity to sialic acid receptor by measuring dissociation constant by surface plasmon resonance assay (Rvb = 0.001473/Ms)	Influenza A virus (A/WSN/1933(H1N1))	0.0009582 1/Ms
Antiviral activity against Chikungunya virus 899 infected in African green monkey Vero A cells assessed as inhibition of viral replication by measuring reduction in intracellular viral RNA treated 2 hrs prior to infection measured after 24 hrs by qRT-PCR analysis	Chikungunya virus	50.0 %
Antiviral activity against Chikungunya virus 899 infected in African green monkey Vero A cells assessed as inhibition of viral replication at post entry step by measuring reduction in intracellular viral RNA treated 2 hrs post infection measured after 24 hrs by qRT-PCR analysis	Chikungunya virus	50.0 %
Antiviral activity against Chikungunya virus assessed as inhibition of virus replication by cell based assay	Chikungunya virus	10.0 ug.mL-1
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	-5.29 %
Inhibition of SARS-CoV-2 pseudoparticle entry in Huh-7 cells, assessed by luciferase assay after 72 hrs	Homo sapiens	5.0 %		Inhibition of SARS-CoV-2 pseudoparticle entry in Huh-7 cells, assessed by luciferase assay after 72 hrs	Homo sapiens	75.0 %
Inhibition of SARS-CoV-2 pseudoparticle entry in human lung Airway Chip at reported drug Cmax, assessed by qRT-PCR after 48 hrs	Homo sapiens	20.0 %
Assessment of cytotoxicity in Huh-7 cells, assessed as % inhibition of cell viability by Celltiter-Glo assay after 48 hrs	Homo sapiens	1.0 %		Assessment of cytotoxicity in Huh-7 cells, assessed as % inhibition of cell viability by Celltiter-Glo assay after 48 hrs	Homo sapiens	10.0 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	17.3 %
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	0.29 %		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	0.29 %
Antiviral activity against Influenza A virus (A/Puerto Rico/8/1934(H1N1)) infected in MDCK cells incubated for 48 hrs by MTT assay	Influenza A virus	460.0 nM
Antiviral activity against Influenza A virus (A/Puerto Rico/8/1934(H1N1)) infected in MDCK cells pre-treated with virus for 30 mins followed by cell infection for 1 hr by MTT assay	Influenza A virus	400.0 nM

Cross References

Resources	Reference
ChEBI	134730
ChEMBL	CHEMBL1214598
DrugBank	DB13609
DrugCentral	4868
FDA SRS	93M09WW4RU
Guide to Pharmacology	11089
PDB	75U
PubChem	131411
SureChEMBL	SCHEMBL1068701
ZINC	ZINC000019907652

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).