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Details

Stereochemistry RACEMIC
Molecular Formula C18H28N2O.ClH.H2O
Molecular Weight 342.904
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BUPIVACAINE HYDROCHLORIDE

SMILES

O.Cl.CCCCN1CCCCC1C(=O)NC2=C(C)C=CC=C2C

InChI

InChIKey=HUCIWBPMHXGLFM-UHFFFAOYSA-N
InChI=1S/C18H28N2O.ClH.H2O/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;1H2

HIDE SMILES / InChI

Molecular Formula C18H28N2O
Molecular Weight 288.4277
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Bupivacaine is a widely used local anesthetic agent. Bupivacaine is often administered by spinal injection prior to total hip arthroplasty. It is also commonly injected into surgical wound sites to reduce pain for up to 20 hours after surgery. In comparison to other local anesthetics it has a long duration of action. It is also the most toxic to the heart when administered in large doses. Bupivacaine blocks 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 binds to the intracellular portion of sodium channels and blocks sodium influx into nerve cells, which prevents depolarization. In general, the progression of anesthesia is related to the diameter, myelination and conduction velocity of affected nerve fibers. 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. Bupivacaine sometimes used in combination with epinephrine to prevent systemic absorption and extend the duration of action.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
EXPAREL

Cmax

ValueDoseCo-administeredAnalytePopulation
952 ng/mL
75 mg single, epidural
BUPIVACAINE plasma
Homo sapiens
810 ng/mL
75 mg single, epidural
BUPIVACAINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
3868 ng × h/mL
75 mg single, epidural
BUPIVACAINE plasma
Homo sapiens
4096 ng × h/mL
75 mg single, epidural
BUPIVACAINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
3.9 h
75 mg single, epidural
BUPIVACAINE plasma
Homo sapiens
2.7 h
75 mg single, epidural
BUPIVACAINE plasma
Homo sapiens
7.7 h
2.5 mg/kg single, caudal
BUPIVACAINE blood
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
16%
2.5 mg/kg single, caudal
BUPIVACAINE blood
Homo sapiens

Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as victim

Tox targets

PubMed

Sample Use Guides

In Vivo Use Guide
single-dose administration only. maximum dosage of EXPAREL ((Bupivacaine Liposome Injectable Suspension) should not exceed 266 mg (20 mL, 1.3% of undiluted drug).
Route of Administration: Intravascular
In Vitro Use Guide
Bupivacaine increased the phosphorylation of GSK-3β(Tyr216) in ovarian carcinoma (SKOV-3) but without measurable effect in prostate carcinoma (PC3). GSK-3β inhibition and siRNA gene knockdown decreased bupivacaine induced cell death in SKOV-3 but not in PC3.
Substance Class Chemical
Record UNII
7TQO7W3VT8
Record Status Validated (UNII)
Record Version