LEVOBUPIVACAINE


Synonyms	(-)-bupivacaine (s)-bupivacaine Bupivacaine (-)-form Bupivacaine, (-)- Bupivacaine, (s)- L-bupivacaine Levobupivacaine Novabupi
Status
Molecule Category	Free-form
ATC	N01BB10
UNII	A5H73K9U3W
EPA CompTox	DTXSID8048496


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

Structure


InChI Key	LEBVLXFERQHONN-INIZCTEOSA-N
Smiles	CCCCN1CCCC[C@H]1C(=O)Nc1c(C)cccc1C
InChI	InChI=1S/C18H28N2O/c1-4-5-12-20-13-7-6-11-16(20)18(21)19-17-14(2)9-8-10-15(17)3/h8-10,16H,4-7,11-13H2,1-3H3,(H,19,21)/t16-/m0/s1

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C18H28N2O
Molecular Weight	288.44
AlogP	3.9
Hydrogen Bond Acceptor	2.0
Hydrogen Bond Donor	1.0
Number of Rotational Bond	5.0
Polar Surface Area	32.34
Molecular species	NEUTRAL
Aromatic Rings	1.0
Heavy Atoms	21.0

Assay Description	Organism	Bioactivity
DRUGMATRIX: CYP450, 2D6 enzyme inhibition (substrate: 3-Cyano-7-ethoxycoumarin)	None	196.4 nM
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	8.67 %
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	-0.2 %	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	-0.2 %

Related Entries

Cross References

Resources	Reference
ChEBI	6149
ChEMBL	CHEMBL1201193
DrugBank	DB01002
DrugCentral	4
FDA SRS	A5H73K9U3W
Human Metabolome Database	HMDB0015137
Guide to Pharmacology	7211
KEGG	C07887
PharmGKB	PA164754741
PubChem	92253
SureChEMBL	SCHEMBL34537
ZINC	ZINC000001530812

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).

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).