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Details

Stereochemistry RACEMIC
Molecular Formula C18H28N2O.ClH
Molecular Weight 324.889
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BUPIVACAINE HYDROCHLORIDE ANHYDROUS

SMILES

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

InChI

InChIKey=SIEYLFHKZGLBNX-UHFFFAOYSA-N
InChI=1S/C18H28N2O.ClH/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

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

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

2011
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
Etidocaine, bupivacaine, and lidocaine seizure thresholds in monkeys.
1975 Apr
Side-effects of epidural infusions of opioid bupivacaine mixtures.
1998 Dec
Incidence of bradycardia during recovery from spinal anaesthesia: influence of patient position.
1998 Nov
Combined spinal epidural for labour analgesia--duration, efficacy and side effects of adding sufentanil or fentanyl to bupivacaine intrathecally vs plain bupivacaine.
1999 Oct
Brain stem stroke associated with bupivacaine injection for adenotonsillectomy.
2000 Apr
Low-dose clonidine and neostigmine prolong the duration of intrathecal bupivacaine-fentanyl for labor analgesia.
2000 Feb
A direct search procedure to optimize combinations of epidural bupivacaine, fentanyl, and clonidine for postoperative analgesia.
2000 Feb
Minidose bupivacaine-fentanyl spinal anesthesia for surgical repair of hip fracture in the aged.
2000 Jan
Mental status change and aphasia after labor analgesia with intrathecal sufentanil/bupivacaine.
2000 May
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
Can anesthesiologic strategies for caesarean section influence newborn jaundice? A retrospective and prospective study.
2001 Feb
Timing of pre-emptive tenoxicam is important for postoperative analgesia.
2001 Feb
Subarachnoid sufentanil for early postoperative pain management in orthopedic patients: a placebo-controlled, double-blind study using spinal microcatheters.
2001 Feb
Levobupivacaine for epidural analgesia in labor: the sparing effect of epidural fentanyl.
2001 Feb
Postoperative sleep disturbance: influences of opioids and pain in humans.
2001 Feb 1
Evidence that postoperative pain is a mediator of the tumor-promoting effects of surgery in rats.
2001 Feb 1
A randomised controlled trial of epidural compared with non-epidural analgesia in labour.
2001 Jan
[Low concentration/high volume is more effective than high concentration/low volume for postoperative continuous epidural analgesia with the combination of bupivacaine and fentanyl].
2001 Jan
Neurologic sequelae after caesarean section.
2001 Jan
Nerve control of type 2A MHC isoform expression in regenerating slow skeletal muscle.
2001 Jan
Anesthetic management of a parturient with superior vena cava obstruction for cesarean section.
2001 Jan
Potencies and probabilities: one-sided P values suggest a one-sided story!
2001 Jan
An accidental ringblock of the great toe?
2001 Jan
Spinal anesthesia with hypobaric bupivacaine for knee arthroscopies: effect of posture on motor block.
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
A comparison of ropivacaine and bupivacaine for cervical plexus block.
2001 Mar
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 18:51:46 GMT 2023
Edited
by admin
on Fri Dec 15 18:51:46 GMT 2023
Record UNII
AKA908P8J1
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BUPIVACAINE HYDROCHLORIDE ANHYDROUS
Common Name English
LAC-43
Code English
(±)-1-BUTYL-2',6'-PIPECOLOXYLIDIDE MONOHYDROCHLORIDE
Common Name English
NSC-758631
Code English
CARBOSTESIN
Brand Name English
ANHYDROUS BUPIVACAINE HYDROCHLORIDE
Common Name English
AH-2250
Code English
Bupivacaine hydrochloride [WHO-DD]
Common Name English
MARCAINE
Brand Name English
BUPIVACAINE HYDROCHLORIDE [USP IMPURITY]
Common Name English
BUPIVACAINE HYDROCHLORIDE, ANHYDROUS
Common Name English
2-PIPERIDINECARBOXAMIDE, 1-BUTYL-N-(2,6-DIMETHYLPHENYL)-, MONOHYDROCHLORIDE
Common Name English
BUPIVACAINE HYDROCHLORIDE [MI]
Common Name English
Code System Code Type Description
CHEBI
3215
Created by admin on Fri Dec 15 18:51:46 GMT 2023 , Edited by admin on Fri Dec 15 18:51:46 GMT 2023
PRIMARY
DRUG BANK
DBSALT000202
Created by admin on Fri Dec 15 18:51:46 GMT 2023 , Edited by admin on Fri Dec 15 18:51:46 GMT 2023
PRIMARY
NSC
758631
Created by admin on Fri Dec 15 18:51:46 GMT 2023 , Edited by admin on Fri Dec 15 18:51:46 GMT 2023
PRIMARY
MERCK INDEX
m2769
Created by admin on Fri Dec 15 18:51:46 GMT 2023 , Edited by admin on Fri Dec 15 18:51:46 GMT 2023
PRIMARY Merck Index
RXCUI
1375412
Created by admin on Fri Dec 15 18:51:46 GMT 2023 , Edited by admin on Fri Dec 15 18:51:46 GMT 2023
PRIMARY RxNorm
DAILYMED
AKA908P8J1
Created by admin on Fri Dec 15 18:51:46 GMT 2023 , Edited by admin on Fri Dec 15 18:51:46 GMT 2023
PRIMARY
CAS
14252-80-3
Created by admin on Fri Dec 15 18:51:46 GMT 2023 , Edited by admin on Fri Dec 15 18:51:46 GMT 2023
SUPERSEDED
EVMPD
SUB71293
Created by admin on Fri Dec 15 18:51:46 GMT 2023 , Edited by admin on Fri Dec 15 18:51:46 GMT 2023
PRIMARY
FDA UNII
AKA908P8J1
Created by admin on Fri Dec 15 18:51:46 GMT 2023 , Edited by admin on Fri Dec 15 18:51:46 GMT 2023
PRIMARY
EPA CompTox
DTXSID0030877
Created by admin on Fri Dec 15 18:51:46 GMT 2023 , Edited by admin on Fri Dec 15 18:51:46 GMT 2023
PRIMARY
CAS
18010-40-7
Created by admin on Fri Dec 15 18:51:46 GMT 2023 , Edited by admin on Fri Dec 15 18:51:46 GMT 2023
PRIMARY
ECHA (EC/EINECS)
241-917-8
Created by admin on Fri Dec 15 18:51:46 GMT 2023 , Edited by admin on Fri Dec 15 18:51:46 GMT 2023
PRIMARY
CHEBI
77431
Created by admin on Fri Dec 15 18:51:46 GMT 2023 , Edited by admin on Fri Dec 15 18:51:46 GMT 2023
PRIMARY
CHEBI
60789
Created by admin on Fri Dec 15 18:51:46 GMT 2023 , Edited by admin on Fri Dec 15 18:51:46 GMT 2023
PRIMARY
PUBCHEM
64737
Created by admin on Fri Dec 15 18:51:46 GMT 2023 , Edited by admin on Fri Dec 15 18:51:46 GMT 2023
PRIMARY
SMS_ID
100000091291
Created by admin on Fri Dec 15 18:51:46 GMT 2023 , Edited by admin on Fri Dec 15 18:51:46 GMT 2023
PRIMARY
Related Record Type Details
ENANTIOMER -> RACEMATE
SOLVATE->ANHYDROUS
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY