BUPIVACAINE

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Search structure


Trade Names	EXPAREL
Synonyms	Anekain Bucaine Bupivacaine Bupivacaine liposome Exparel LIQ-865 LIQ865 Liposomal bupivacaine Marcaine Posimir Ropivacaine hydrochloride impurity, bupivacaine- SKY-0402 SKY0402 Sensorcaine
Status
Molecule Category	Free-form
ATC	N01BB01
UNII	Y8335394RO
EPA CompTox	DTXSID2022703


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

Structure


InChI Key	LEBVLXFERQHONN-UHFFFAOYSA-N
Smiles	CCCCN1CCCCC1C(=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)

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

Bioactivity

Mechanism of Action	Action	Reference
Sodium channel protein type IV alpha subunit blocker	BLOCKER	PubMed


Protein: Sodium channel protein type IV alpha subunit Description: Sodium channel protein type 4 subunit alpha Organism : Homo sapiens P35499 ENSG00000007314

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Ion channel Voltage-gated ion channel Potassium channels Two-pore domain potassium channel	-	100000	-	-	50
Ion channel Voltage-gated ion channel Voltage-gated sodium channel	-	5400	-	-	63

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	63.4 %
Inhibition of human TASK3 expressed in Xenopus oocytes at 100 uM by whole cell patch clamp assay relative to control	Homo sapiens	50.2 %
Inhibition of rat TASK3 expressed in African green monkey COS7 cells at 100 uM by outside-out patches based electrophysiology assay relative to control	Rattus norvegicus	56.0 %

Related Entries

Cross References

Resources	Reference
ChEBI	77431
ChEMBL	CHEMBL1098
DrugBank	DB00297
DrugCentral	432
FDA SRS	Y8335394RO
Human Metabolome Database	HMDB0014442
Guide to Pharmacology	2397
KEGG	C07529
PharmGKB	PA135057240
PubChem	2474
SureChEMBL	SCHEMBL25438

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).