DIBUCAINE

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Search structure


Synonyms	Cinchocaine Dibucaine NSC-159055 Nupercainal
Status
Molecule Category	UNKNOWN
UNII	L6JW2TJG99
EPA CompTox	DTXSID3045271


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

Structure


InChI Key	PUFQVTATUTYEAL-UHFFFAOYSA-N
Smiles	CCCCOc1cc(C(=O)NCCN(CC)CC)c2ccccc2n1
InChI	InChI=1S/C20H29N3O2/c1-4-7-14-25-19-15-17(16-10-8-9-11-18(16)22-19)20(24)21-12-13-23(5-2)6-3/h8-11,15H,4-7,12-14H2,1-3H3,(H,21,24)

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C20H29N3O2
Molecular Weight	343.47
AlogP	3.49
Hydrogen Bond Acceptor	4.0
Hydrogen Bond Donor	1.0
Number of Rotational Bond	10.0
Polar Surface Area	54.46
Molecular species	BASE
Aromatic Rings	2.0
Heavy Atoms	25.0

Assay Description	Organism	Bioactivity	Reference
Inhibition of binding of Batrachotoxinin [3H]BTX-B to high affinity sites on voltage dependent sodium channels in a vesicular preparation from guinea pig cerebral cortex at 10 uM	Cavia porcellus	77.4 %
Displacement of [3H]Batrachotoxin from sodium channel site 2 in Wistar rat brain after 60 mins	Rattus norvegicus	550.0 nM		Displacement of [3H]Batrachotoxin from sodium channel site 2 in Wistar rat brain after 60 mins	Rattus norvegicus	610.0 nM
Displacement of [3H]Batrachotoxin from sodium channel site 2 in Wistar rat brain at 10 uM after 60 mins relative to control	Rattus norvegicus	10.0 %
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	-13.31 %
Inhibition of 2C protein in Enterovirus D68 US/KY/14-18953 infected in human RD cells assessed as reduction of viral RNA level at 3 uM measured at 9 hrs post infection by RT-qPCR method relative to control	Homo sapiens	80.0 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	31.42 %
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	-0.16 %		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	-0.16 %

Cross References

Resources	Reference
ChEBI	247956
ChEMBL	CHEMBL1086
DrugBank	DB00527
DrugCentral	859
FDA SRS	L6JW2TJG99
Human Metabolome Database	HMDB0014668
Guide to Pharmacology	7159
KEGG	C07879
PharmGKB	PA449286
PubChem	3025
SureChEMBL	SCHEMBL34473
ZINC	ZINC000001530939

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).