U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C18H28N2O
Molecular Weight 288.4284
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BUPIVACAINE

SMILES

CCCCN1CCCCC1C(=Nc2c(C)cccc2C)O

InChI

InChIKey=LEBVLXFERQHONN-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Description
Curator's Comment:: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/11895133

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
EXPAREL

Approved Use

Bupivacaine Hydrochloride is indicated for the production of local or regional anesthesia or analgesia for surgery, dental and oral surgery procedures, diagnostic and therapeutic procedures, and for obstetrical procedures. Only the 0.25% and 0.5% concentrations are indicated for obstetrical anesthesia. (See WARNINGS .) Experience with nonobstetrical surgical procedures in pregnant patients is not sufficient to recommend use of 0.75% concentration of Bupivacaine Hydrochloride in these patients. Bupivacaine Hydrochloride is not recommended for intravenous regional anesthesia (Bier Block). (See WARNINGS .) The routes of administration and indicated Bupivacaine Hydrochloride concentrations are: • local infiltration 0.25% • peripheral nerve block 0.25% and 0.5% • retrobulbar block 0.75% • sympathetic block 0.25% • lumbar epidural 0.25%, 0.5%, and 0.75% (0.75% not for obstetrical anesthesia) • caudal 0.25% and 0.5% • epidural test dose 0.5% with epinephrine 1:200,000 • dental blocks 0.5% with epinephrine 1:200,000 (See DOSAGE AND ADMINISTRATION for additional information.) Standard textbooks should be consulted to determine the accepted procedures and techniques for the administration of Bupivacaine Hydrochloride.

Launch Date

1.31976004E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
952 ng/mL
75 mg single, epidural
dose: 75 mg
route of administration: Epidural
experiment type: SINGLE
co-administered:
BUPIVACAINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
810 ng/mL
75 mg single, epidural
dose: 75 mg
route of administration: Epidural
experiment type: SINGLE
co-administered:
BUPIVACAINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
3868 ng × h/mL
75 mg single, epidural
dose: 75 mg
route of administration: Epidural
experiment type: SINGLE
co-administered:
BUPIVACAINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
4096 ng × h/mL
75 mg single, epidural
dose: 75 mg
route of administration: Epidural
experiment type: SINGLE
co-administered:
BUPIVACAINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
3.9 h
75 mg single, epidural
dose: 75 mg
route of administration: Epidural
experiment type: SINGLE
co-administered:
BUPIVACAINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
2.7 h
75 mg single, epidural
dose: 75 mg
route of administration: Epidural
experiment type: SINGLE
co-administered:
BUPIVACAINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
7.7 h
2.5 mg/kg single, caudal
dose: 2.5 mg/kg
route of administration: Caudal
experiment type: SINGLE
co-administered:
BUPIVACAINE blood
Homo sapiens
population: UNHEALTHY
age: NEWBORN
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
16%
2.5 mg/kg single, caudal
dose: 2.5 mg/kg
route of administration: Caudal
experiment type: SINGLE
co-administered:
BUPIVACAINE blood
Homo sapiens
population: UNHEALTHY
age: NEWBORN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
40 mg 1 times / day single, intramuscular
Studied dose
Dose: 40 mg, 1 times / day
Route: intramuscular
Route: single
Dose: 40 mg, 1 times / day
Sources:
healthy, 11 months
n = 1
Health Status: healthy
Age Group: 11 months
Population Size: 1
Sources:
Other AEs: Ventricular tachycardia...
Other AEs:
Ventricular tachycardia
Sources:
103 mg 1 times / day single, intravenous
MTD
Dose: 103 mg, 1 times / day
Route: intravenous
Route: single
Dose: 103 mg, 1 times / day
Sources:
healthy, mean age 28 years
n = 12
Health Status: healthy
Age Group: mean age 28 years
Sex: M
Population Size: 12
Sources:
AEs

AEs

AESignificanceDosePopulation
Ventricular tachycardia
40 mg 1 times / day single, intramuscular
Studied dose
Dose: 40 mg, 1 times / day
Route: intramuscular
Route: single
Dose: 40 mg, 1 times / day
Sources:
healthy, 11 months
n = 1
Health Status: healthy
Age Group: 11 months
Population Size: 1
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as victimTox targets
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Incidence of bradycardia during recovery from spinal anaesthesia: influence of patient position.
1998 Nov
Spinal cord compression from precipitation of drug solute around an epidural catheter.
1998 Oct
Combined spinal epidural for labour analgesia--duration, efficacy and side effects of adding sufentanil or fentanyl to bupivacaine intrathecally vs plain bupivacaine.
1999 Oct
A multicentre trial of ropivacaine 7.5 mg x ml(-1) vs bupivacaine 5 mg x ml(-1) for supra clavicular brachial plexus anesthesia.
1999 Oct
More Horner's than meets the eye.
2000
Brain stem stroke associated with bupivacaine injection for adenotonsillectomy.
2000 Apr
A direct search procedure to optimize combinations of epidural bupivacaine, fentanyl, and clonidine for postoperative analgesia.
2000 Feb
Bupivacaine inhibits baroreflex control of heart rate in conscious rats.
2000 Jan
The dose-response of intrathecal sufentanil added to bupivacaine for labor analgesia.
2000 Jun
Advantages of intrathecal nalbuphine, compared with intrathecal morphine, after cesarean delivery: an evaluation of postoperative analgesia and adverse effects.
2000 Sep
Patient-controlled spinal analgesia for labour and caesarean delivery.
2001 Feb
Pediatric caudal block with mepivacaine, bupivacaine or a mixture of both drugs: requirement for postoperative analgesia and plasma concentration of local anesthetics.
2001 Feb
[Bupivacaine in continuous epidural infusion using a portable mechanical devise for postoperative analgesia after surgery for hernia of the lumbar disk].
2001 Feb
[A case of cardiac arrest with coronary artery spasm during lumbar epidural anesthesia].
2001 Feb
[Anesthetic management for the correction of pectus excavatum using pectus bar under video-assistance].
2001 Feb
A randomized prospective comparative study of general versus epidural anesthesia for transcervical hysteroscopic endometrial resection.
2001 Feb
Can anesthesiologic strategies for caesarean section influence newborn jaundice? A retrospective and prospective study.
2001 Feb
Bilateral paravertebral block: a satisfactory alternative for labour analgesia.
2001 Feb
Timing of pre-emptive tenoxicam is important for postoperative analgesia.
2001 Feb
Epidural fentanyl markedly improves thoracic epidural analgesia in a low-dose infusion of bupivacaine, adrenaline and fentanyl. A randomized, double-blind crossover study with and without fentanyl.
2001 Feb
Is comparative cardiotoxicity of S(-) and R(+) bupivacaine related to enantiomer-selective inhibition of L-type Ca(2+) channels?
2001 Feb
Extended femoral nerve sheath block after total hip arthroplasty: continuous versus patient-controlled techniques.
2001 Feb
Levobupivacaine for epidural analgesia in labor: the sparing effect of epidural fentanyl.
2001 Feb
Transient neurologic symptoms after spinal anesthesia with lidocaine in obstetric patients.
2001 Feb
Does pregnancy protect against intrathecal lidocaine-induced transient neurologic symptoms?
2001 Feb
[Spinal anesthesia for cesarean section].
2001 Jan
Stereoselective effects of the enantiomers of a new local anaesthetic, IQB-9302, on a human cardiac potassium channel (Kv1.5).
2001 Jan
Bupivacaine wound instillation via an electronic patient-controlled analgesia device and a double-catheter system does not decrease postoperative pain or opioid requirements after major abdominal surgery.
2001 Jan
Dexamethasone facilitates discharge after outpatient anorectal surgery.
2001 Jan
Cardiac resuscitation after incremental overdosage with lidocaine, bupivacaine, levobupivacaine, and ropivacaine in anesthetized dogs.
2001 Jan
Clonidine in preterm-infant caudal anesthesia may be responsible for postoperative apnea.
2001 Jan-Feb
Femoral nerve block with 0.25% or 0.5% bupivacaine improves postoperative analgesia following outpatient arthroscopic anterior cruciate ligament repair.
2001 Jan-Feb
Selective ulnar nerve localization is not essential for axillary brachial plexus block using a multiple nerve stimulation technique.
2001 Jan-Feb
Randomized clinical trial of local bupivacaine perfusion versus parenteral morphine infusion for pain relief after laparotomy.
2001 Mar
Functional characterisation of human TASK-3, an acid-sensitive two-pore domain potassium channel.
2001 Mar
Corneal sensation after topical anesthesia.
2001 Mar
A comparison of ropivacaine and bupivacaine for cervical plexus block.
2001 Mar
The addition of morphine prolongs fentanyl-bupivacaine spinal analgesia for the relief of labor pain.
2001 Mar
Discomfort with fine-needle aspiration cytology of the breast.
2001 Mar 10
Characterization of TASK-4, a novel member of the pH-sensitive, two-pore domain potassium channel family.
2001 Mar 9
Low-dose spinal anesthesia for cesarean delivery: Have we gone too far?
2001 Mar-Apr
Patents

Sample Use Guides

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
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.
Name Type Language
BUPIVACAINE
HSDB   INN   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
USAN   INN  
Official Name English
BUPIVACAINE COMPONENT OF ZYNRELEF
Brand Name English
BUPIVACAINE [GREEN BOOK]
Common Name English
ROPIVACAINE HYDROCHLORIDE IMPURITY, BUPIVACAINE- [USP]
Common Name English
BUPIVACAINE [VANDF]
Common Name English
LIQ-865
Code English
BUPIVACAINE [HSDB]
Common Name English
BUPIVACAINE [WHO-DD]
Common Name English
BUPIVACAINE [ORANGE BOOK]
Common Name English
SKY0402
Code English
BUPIVACAINE [USAN]
Common Name English
BUPIVACAINE [MI]
Common Name English
2-PIPERIDINECARBOXAMIDE, 1-BUTYL-N-(2,6-DIMETHYLPHENYL)-, (+/-)-
Systematic Name English
POSIMIR
Brand Name English
(1)-1-BUTYL-N-(2,6-DIMETHYLPHENYL)PIPERIDINE-2-CARBOXAMIDE
Common Name English
LIQ865
Code English
BUPIVACAINE [INN]
Common Name English
BUCAINE
Brand Name English
SKY-0402
Code English
ZYNRELEF COMPONENT BUPIVACAINE
Brand Name English
Classification Tree Code System Code
NDF-RT N0000007681
Created by admin on Fri Jun 25 21:35:11 UTC 2021 , Edited by admin on Fri Jun 25 21:35:11 UTC 2021
NDF-RT N0000175976
Created by admin on Fri Jun 25 21:35:11 UTC 2021 , Edited by admin on Fri Jun 25 21:35:11 UTC 2021
FDA ORPHAN DRUG 237207
Created by admin on Fri Jun 25 21:35:11 UTC 2021 , Edited by admin on Fri Jun 25 21:35:11 UTC 2021
WHO-VATC QN01BB01
Created by admin on Fri Jun 25 21:35:11 UTC 2021 , Edited by admin on Fri Jun 25 21:35:11 UTC 2021
WHO-VATC QN01BB51
Created by admin on Fri Jun 25 21:35:11 UTC 2021 , Edited by admin on Fri Jun 25 21:35:11 UTC 2021
NDF-RT N0000175682
Created by admin on Fri Jun 25 21:35:11 UTC 2021 , Edited by admin on Fri Jun 25 21:35:11 UTC 2021
NCI_THESAURUS C245
Created by admin on Fri Jun 25 21:35:11 UTC 2021 , Edited by admin on Fri Jun 25 21:35:11 UTC 2021
WHO-ATC N01BB51
Created by admin on Fri Jun 25 21:35:11 UTC 2021 , Edited by admin on Fri Jun 25 21:35:11 UTC 2021
WHO-ATC N01BB01
Created by admin on Fri Jun 25 21:35:11 UTC 2021 , Edited by admin on Fri Jun 25 21:35:11 UTC 2021
WHO-ESSENTIAL MEDICINES LIST 1.2
Created by admin on Fri Jun 25 21:35:11 UTC 2021 , Edited by admin on Fri Jun 25 21:35:11 UTC 2021
Code System Code Type Description
ECHA (EC/EINECS)
218-553-3
Created by admin on Fri Jun 25 21:35:11 UTC 2021 , Edited by admin on Fri Jun 25 21:35:11 UTC 2021
ALTERNATIVE
CAS
2180-92-9
Created by admin on Fri Jun 25 21:35:11 UTC 2021 , Edited by admin on Fri Jun 25 21:35:11 UTC 2021
SUPERSEDED
PUBCHEM
2474
Created by admin on Fri Jun 25 21:35:11 UTC 2021 , Edited by admin on Fri Jun 25 21:35:11 UTC 2021
PRIMARY
MERCK INDEX
M2769
Created by admin on Fri Jun 25 21:35:11 UTC 2021 , Edited by admin on Fri Jun 25 21:35:11 UTC 2021
PRIMARY Merck Index
RXCUI
1815
Created by admin on Fri Jun 25 21:35:11 UTC 2021 , Edited by admin on Fri Jun 25 21:35:11 UTC 2021
PRIMARY
LACTMED
Bupivacaine
Created by admin on Fri Jun 25 21:35:11 UTC 2021 , Edited by admin on Fri Jun 25 21:35:11 UTC 2021
PRIMARY
ECHA (EC/EINECS)
253-911-2
Created by admin on Fri Jun 25 21:35:11 UTC 2021 , Edited by admin on Fri Jun 25 21:35:11 UTC 2021
PRIMARY
NCI_THESAURUS
C62011
Created by admin on Fri Jun 25 21:35:11 UTC 2021 , Edited by admin on Fri Jun 25 21:35:11 UTC 2021
PRIMARY
CAS
38396-39-3
Created by admin on Fri Jun 25 21:35:11 UTC 2021 , Edited by admin on Fri Jun 25 21:35:11 UTC 2021
PRIMARY
FDA UNII
Y8335394RO
Created by admin on Fri Jun 25 21:35:11 UTC 2021 , Edited by admin on Fri Jun 25 21:35:11 UTC 2021
PRIMARY
MESH
D002045
Created by admin on Fri Jun 25 21:35:11 UTC 2021 , Edited by admin on Fri Jun 25 21:35:11 UTC 2021
PRIMARY
ChEMBL
CHEMBL1098
Created by admin on Fri Jun 25 21:35:11 UTC 2021 , Edited by admin on Fri Jun 25 21:35:11 UTC 2021
PRIMARY
HSDB
7790
Created by admin on Fri Jun 25 21:35:11 UTC 2021 , Edited by admin on Fri Jun 25 21:35:11 UTC 2021
PRIMARY
DRUG BANK
DB00297
Created by admin on Fri Jun 25 21:35:11 UTC 2021 , Edited by admin on Fri Jun 25 21:35:11 UTC 2021
PRIMARY
IUPHAR
2397
Created by admin on Fri Jun 25 21:35:11 UTC 2021 , Edited by admin on Fri Jun 25 21:35:11 UTC 2021
PRIMARY
WIKIPEDIA
BUPIVACAINE
Created by admin on Fri Jun 25 21:35:11 UTC 2021 , Edited by admin on Fri Jun 25 21:35:11 UTC 2021
PRIMARY
EPA CompTox
38396-39-3
Created by admin on Fri Jun 25 21:35:11 UTC 2021 , Edited by admin on Fri Jun 25 21:35:11 UTC 2021
PRIMARY
INN
2279
Created by admin on Fri Jun 25 21:35:11 UTC 2021 , Edited by admin on Fri Jun 25 21:35:11 UTC 2021
PRIMARY
DRUG CENTRAL
432
Created by admin on Fri Jun 25 21:35:11 UTC 2021 , Edited by admin on Fri Jun 25 21:35:11 UTC 2021
PRIMARY
EVMPD
SUB05983MIG
Created by admin on Fri Jun 25 21:35:11 UTC 2021 , Edited by admin on Fri Jun 25 21:35:11 UTC 2021
PRIMARY