General
Preferred name
BUPIVACAINE
Synonyms
BUPIVACAINE HYDROCHLORIDE ()
levobupivacaine ()
Bupivacaine HCl ()
Vivacaine ()
Bupivacaine hydrochloride ()
bupivacaine, Durect-2 ()
Bupivacaine (hydrochloride) ()
Bupivacaine-d9 ()
Bupivacaine hydrochloride preservative free ()
Bupivacaine Hydrochloride Kit ()
Marcaine hydrochloride preservative free ()
Carbostesin ()
Bupivacaine hydrochloride rs ()
WIN 11,318 ()
NSC-758631 ()
Bupivacaine hydrochloride monohydrate ()
Bupivac HCl ()
Marcaine ()
Xaracoll ()
AH-2250 ()
Bupivacaini hydrochloridum ()
Marcain ()
WIN-11318 ()
LAC-43 ()
Sensorcaine ()
Marcaine hydrochloride ()
Bupivacaine hydrochloride hydrate ()
Exparel liposomal ()
Ropivacaine hydrochloride impurity, bupivacaine- ()
Bupivacaine liposome ()
SKY-0402 ()
LIQ865 ()
LIQ-865 ()
Bucaine ()
Liposomal bupivacaine ()
SKY0402 ()
Posimir ()
Anekain ()
Exparel ()
P&D ID
PD010116
CAS
14252-80-3
18010-40-7
38396-39-3
2180-92-9
15233-43-9
119427-31-5
474668-57-0
Tags
natural product
drug
available
Approved by
FDA
First approval
1972
Drug indication
Pain
Anesthetic (local)
Anaesthesia
Drug Status
investigational
vet_approved
approved
Max Phase
4.0
Structure
Probe scores
P&D probe-likeness score
[[ v.score ]]%
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
MOA Local anesthetics such as bupivacaine block the generation and the conduction of nerve impulses, presumably by increasing the threshold for electrical excitation in the nerve, by slowing the propagation of the nerve impulse, and by reducing the rate of rise of the action potential. Bupivacaine prevents depolarization by bindng to the intracellular portion of sodium channels and blocking sodium ion influx into neurons. In general, the progression of anesthesia is related to the diameter, myelination and conduction velocity of affected nerve fibers. Clinically, the order of loss of nerve function is as follows: (1) pain, (2) temperature, (3) touch, (4) proprioception, and (5) skeletal muscle tone. The analgesic effects of Bupivicaine are thought to potentially be due to its binding to the prostaglandin E2 receptors, subtype EP1 (PGE2EP1), which inhibits the production of prostaglandins, thereby reducing fever, inflammation, and hyperalgesia.
ABSORPTION Systemic absorption of local anesthetics is dose- and concentration-dependendent on the total drug administered. Other factors that affect the rate of systemic absorption include the route of administration, blood flow at the administration site, and the presence or absence of epinephrine in the anesthetic solution.
DESCRIPTION The isomer is also an approved drug but has a longer duration of action and produces less vasodilation. (GtoPdb)
Cell lines
1
Organisms
0
Compound Sets
25
AdooQ Bioactive Compound Library
A10168
Cayman Chemical Bioactives
31718
18246
16618
ChEMBL Approved Drugs
CHEMBL1200396
CHEMBL1098
ChEMBL Drugs
CHEMBL1200396
CHEMBL1098
DrugBank
DB00297
DrugBank Approved Drugs
DB00297
DrugCentral
432
DrugCentral Approved Drugs
432
DrugMAP
DM4PRFC
DrugMAP Approved Drugs
DM4PRFC
DrugMatrix
Enamine BioReference Compounds
Guide to Pharmacology
2397
LSP-MoA library (Laboratory of Systems Pharmacology)
CHEMBL1200396
CHEMBL1098
MedChem Express Bioactive Compound Library
HY-B0405A
HY-B0405
NCATS Inxight Approved Drugs
Y8335394RO
Novartis Chemogenetic Library (NIBR MoA Box)
NPC Screening Collection
Other bioactive compounds
Prestwick Chemical Library
ReFrame library
Selleckchem Bioactive Compound Library
Bupivacaine-hydrochloride(Marcain)
TargetMol Bioactive Compound Library
T0030
The Spectrum Collection
VGSC-DB
NA5920
External IDs
89
Properties
(calculated by RDKit )
Molecular Weight
288.22
Hydrogen Bond Acceptors
2
Hydrogen Bond Donors
1
Rotatable Bonds
5
Ring Count
2
Aromatic Ring Count
1
cLogP
3.9
TPSA
32.34
Fraction CSP3
0.61
Chiral centers
1.0
Largest ring
6.0
QED
0.89
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Pathway
Membrane Transporter/Ion Channel
Neuronal Signaling
Target
Sodium Channel
Calcium Channel
iGluR
Potassium Channel
Member status
member
MOA
"Sodium Channel Blocker
anaesthetic"
"""Sodium Channel Blocker
anaesthetic"""
Therapeutic Class
Anesthetics
VGSC Target
Nav1.9
Source data