LOMIBUVIR

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Search structure


Synonyms	Lomibuvir VX-222 Vch-222
Status
Molecule Category	UNKNOWN
UNII	37L2LF4A2D


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

Structure


InChI Key	WPMJNLCLKAKMLA-VVPTUSLJSA-N
Smiles	CC(C)(C)C#Cc1cc(N(C(=O)[C@H]2CC[C@H](C)CC2)[C@H]2CC[C@H](O)CC2)c(C(=O)O)s1
InChI	InChI=1S/C25H35NO4S/c1-16-5-7-17(8-6-16)23(28)26(18-9-11-19(27)12-10-18)21-15-20(13-14-25(2,3)4)31-22(21)24(29)30/h15-19,27H,5-12H2,1-4H3,(H,29,30)/t16-,17-,18-,19-

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C25H35NO4S
Molecular Weight	445.63
AlogP	5.31
Hydrogen Bond Acceptor	4.0
Hydrogen Bond Donor	2.0
Number of Rotational Bond	4.0
Polar Surface Area	77.84
Molecular species	ACID
Aromatic Rings	1.0
Heavy Atoms	31.0

Bioactivity

Mechanism of Action	Action	Reference
Hepatitis C virus NS5B RNA-dependent RNA polymerase negative allosteric modulator	NEGATIVE ALLOSTERIC MODULATOR	PubMed PubMed

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Enzyme Transferase	30-320	-	-	-	-
Unclassified protein	7-8100	-	-	-	-

Assay Description	Organism	Bioactivity	Reference
Antiviral activity against Hepatitis C virus genotype 1b infected in human HuH7.5 cells after 3 days by luciferase reporter gene assay	Hepatitis C virus subtype 1b	23.0 nM
Antiviral activity against Hepatitis C virus genotype 1a infected in human HuH7.5 cells after 3 days by luciferase reporter gene assay	Hepatitis C virus subtype 1a	15.0 nM
Antiviral activity against Hepatitis C virus H77 genotype 1a infected in human HuH7 cells assessed as intrinsic antiviral potency after 72 hrs by luciferase reporter gene assay	Hepatitis C virus (isolate H77)	2.8 nM
Antiviral activity against Hepatitis C virus H77 genotype 1a infected in human HuH7 cells assessed as observed antiviral potency after 72 hrs by luciferase reporter gene assay	Hepatitis C virus (isolate H77)	13.0 nM
Antiviral activity against Hepatitis C virus Con1 genotype 1b infected in human HuH7 cells after 72 hrs by luciferase reporter gene assay	Hepatitis C virus (isolate Con1)	6.0 nM
Allosteric inhibition of HCV genotype 1b NS5A infected in human l389lucubi- neo/NS3-375.1-containing Huh7ET cells assessed as RNA replication/translation after 4 days by luciferase reporter gene assay	Hepatitis C virus subtype 1b	7.0 nM
Allosteric inhibition of HCV genotype 1a NS5A infected in human W11.8 cells assessed as reduction in viral RNA replication after 4 days by ELISA	Hepatitis C virus subtype 1a	53.0 nM
Allosteric inhibition of HCV genotype 1b NS5A infected in human l389lucubi- neo/NS3-375.1-containing Huh7ET cells assessed as RNA replication/translation after 4 days in presence of 40% human serum by luciferase reporter gene assay	Hepatitis C virus subtype 1b	66.0 nM
Inhibition of HCV genotype 1a NS5B L419M mutant	Hepatitis C virus subtype 1a	320.0 nM
Inhibition of HCV genotype 1a NS5B L419I mutant	Hepatitis C virus subtype 1a	320.0 nM
Inhibition of HCV genotype 1a NS5B M423I mutant	Hepatitis C virus subtype 1a	30.0 nM
Inhibition of HCV genotype 1a NS5B M423T mutant	Hepatitis C virus subtype 1a	310.0 nM
Inhibition of HCV genotype 1a NS5B M423V mutant	Hepatitis C virus subtype 1a	65.0 nM

Related Entries

Cross References

Resources	Reference
ChEMBL	CHEMBL3039503
DrugBank	DB11954
FDA SRS	37L2LF4A2D
SureChEMBL	SCHEMBL134631

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).