BUPIVACAINE HYDROCHLORIDE

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Search structure


Trade Names	BUPIVACAINE HYDROCHLORIDE BUPIVACAINE HYDROCHLORIDE KIT BUPIVACAINE HYDROCHLORIDE PRESERVATIVE FREE MARCAINE MARCAINE HYDROCHLORIDE MARCAINE HYDROCHLORIDE PRESERVATIVE FREE SENSORCAINE
Synonyms	AH-2250 Bupivac hcl Bupivacaine hcl Bupivacaine hydrochloride Bupivacaine hydrochloride hydrate Bupivacaine hydrochloride kit Bupivacaine hydrochloride monohydrate Bupivacaine hydrochloride preservative free Bupivacaine hydrochloride rs Bupivacaini hydrochloridum Carbostesin LAC-43 Marcain Marcaine Marcaine hydrochloride Marcaine hydrochloride preservative free NSC-758631 Sensorcaine WIN 11,318 WIN-11318
Status
Molecule Category	Salt-form
UNII	AKA908P8J1
EPA CompTox	DTXSID0030877
Parent Compound:	BUPIVACAINE


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

Structure


InChI Key	SIEYLFHKZGLBNX-UHFFFAOYSA-N
Smiles	CCCCN1CCCCC1C(=O)Nc1c(C)cccc1C.Cl
InChI	InChI=1S/C18H28N2O.ClH/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);1H

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C18H29ClN2O
Molecular Weight	324.9
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 Voltage-gated potassium channel	-	22000-95000	-	-	-
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides	-	-	-	-	94

Assay Description	Organism	Bioactivity	Reference
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	97.15 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	94.2 %

Cross References

Resources	Reference
ChEBI	77441
ChEMBL	CHEMBL1200396
FDA SRS	AKA908P8J1
PubChem	5282419
SureChEMBL	SCHEMBL34374
ZINC	ZINC01530814

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).