General
Preferred name
BUPIVACAINE
Synonyms
BUPIVACAINE HYDROCHLORIDE ()
levobupivacaine ()
AH 250 ()
AH-250 ()
AH250 ()
Bupivacaina ()
Exparel ()
Anekain ()
Vivacaine ()
Bupivacaine HCl ()
Bupivacaine hydrochloride ()
bupivacaine, Durect-2 ()
Bupivacaine (hydrochloride) ()
Bupivacaine hydrochloride monohydrate ()
Bupivacaine-d9 ()
Bupivacaine Hydrochloride Kit ()
Marcaine hydrochloride ()
Bupivacaine hydrochloride rs ()
Bupivacaine hydrochloride component of duocaine ()
WIN 11,318 ()
AH-2250 ()
Bupivacaine hydrochloride hydrate ()
LAC-43 ()
Bupivacaine hydrochloride preservative free ()
Marcain ()
Bupivacaine hydrochloride component of sensorcaine ()
Bupivac HCl ()
Sensorcaine ()
Marcaine hydrochloride preservative free ()
Bupivacaini hydrochloridum ()
WIN-11318 ()
Carbostesin ()
Marcaine ()
NSC-758631 ()
Xaracoll ()
SKY0402 ()
Posimir ()
Ropivacaine hydrochloride impurity, bupivacaine- ()
Liposomal bupivacaine ()
BR-003 ()
Bupivacaine liposome ()
LIQ865 ()
Exparel liposomal ()
Bucaine ()
LIQ-865 ()
SKY-0402 ()
Bupivacaine component of zynrelef ()
P&D ID
PD010116
CAS
14252-80-3
38396-39-3
2180-92-9
15233-43-9
18010-40-7
119427-31-5
73360-54-0
474668-57-0
Tags
available
drug
Approved by
FDA
First approval
1972
Drug indication
Hypotension
Pain
Anaesthesia
Inguinal hernia
Drug Status
vet_approved
approved
investigational
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)
DESCRIPTION Bupivacaine hydrochloride is a NMDA receptor inhibitor.Bupivacaine can block sodium, L-calcium, and potassium channels.Bupivacaine potently blocks SCN5A channels with the IC50 of 69.5 ¦ÌM. Bupivacaine hydrochloride can be used for the research of chronic pain[1][2][3].
PRICE 29
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)
DESCRIPTION Bupivacaine is a NMDA receptor inhibitor. Bupivacaine can block sodium, L-calcium, and potassium channels.Bupivacaine potently blocks SCN5A channels with the IC50 of 69.5 ¦ÌM. Bupivacaine can be used for the research of chronic pain[1][2][3].
PRICE 29
DESCRIPTION Bupivacaine (AH-250) is a NMDA receptor inhibitor.Bupivacaine can block sodium, L-calcium, and potassium channels.Bupivacaine potently blocks SCN5A channels with the IC50 of 69.5 ??M. Bupivacaine can be used for the research of chronic pain.
PRICE 560
DESCRIPTION Bupivacaine is a sodium channel blocker and local anesthetic. It is used as local anesthetics for surgery, oral surgery, and dental procedures and for anesthetic purposes in research studies using animals. (Enamine Bioactive Compounds)
DESCRIPTION Bupivacaine hydrochloride (Vivacaine) is a long-acting, amide-type local anesthetic. Bupivacaine hydrochloride reversibly binds to specific sodium ion channels in the neuronal membrane, resulting in a decrease in the voltage-dependent membrane permeability to sodium ions and membrane stabilization; inhibition of depolarization and nerve impulse conduction; and a reversible loss of sensation. (TargetMol Bioactive Compound Library)
DESCRIPTION Bupivacaine (AH-250) is a NMDA receptor inhibitor.Bupivacaine can block sodium, L-calcium, and potassium channels.Bupivacaine potently blocks SCN5A channels with the IC50 of 69.5 μM. Bupivacaine can be used for the research of chronic pain. (TargetMol Bioactive Compound Library)
DESCRIPTION Bupivacaine hydrochloride monohydrate is a potent NMDA receptor inhibitor of sodium, L-calcium, and potassium channels.Bupivacaine hydrochloride monohydrate inhibits SCN5A channels and is commonly used in the study of chronic pain. (TargetMol Bioactive Compound Library)
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 Bioactive Compounds
EBC-11134
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
Prestwick Chemical Library
ReFrame library
Selleckchem Bioactive Compound Library
Bupivacaine-hydrochloride(Marcain)
TargetMol Bioactive Compound Library
T0030
T0030L
T80641
The Spectrum Collection
VGSC-DB
NA5920
External IDs
95
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)
Target
NMDA Receptor
Calcium Channel
Sodium Channel
Potassium Channel
iGluR
Member status
member
MOA
"Sodium Channel Blocker
anaesthetic"
"""Sodium Channel Blocker
anaesthetic"""
Pathway
Membrane Transporter/Ion Channel
Metabolism
Neuroscience
Neuronal Signaling
Therapeutic Class
Anesthetics
VGSC Target
Nav1.9
Source data