bupivacaine   Click here for help

GtoPdb Ligand ID: 2397

Synonyms: DL-Bupivacaine | Exparel® | Marcain® | Posimir® | Sensorcaine® | W-7 | Xaracoll®
Approved drug
bupivacaine is an approved drug (FDA (1972), EMA (2020))
Compound class: Synthetic organic
Comment: The isomer levobupivacaine is also an approved drug but has a longer duration of action and produces less vasodilation.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 6
Topological polar surface area 32.34
Molecular weight 288.22
XLogP 3.57
No. Lipinski's rules broken 0
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Canonical SMILES CCCCN1CCCCC1C(=O)Nc1c(C)cccc1C
Isomeric 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)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1972), EMA (2020))
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
International Nonproprietary Names Click here for help
INN number INN
2279 bupivacaine
Synonyms Click here for help
DL-Bupivacaine | Exparel® | Marcain® | Posimir® | Sensorcaine® | W-7 | Xaracoll®
Database Links Click here for help
BindingDB Ligand 50017664
CAS Registry No. 38396-39-3
ChEMBL Ligand CHEMBL1098
DrugBank Ligand DB00297
DrugCentral Ligand 432
GtoPdb PubChem SID 135650032
PubChem CID 2474
Search Google for chemical match using the InChIKey LEBVLXFERQHONN-UHFFFAOYSA-N
Search Google for chemicals with the same backbone LEBVLXFERQHONN
Search PubMed clinical trials bupivacaine
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UniChem Compound Search for chemical match using the InChIKey LEBVLXFERQHONN-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey LEBVLXFERQHONN-UHFFFAOYSA-N
Wikipedia Bupivacaine