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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
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

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 H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Horner's syndrome due to epidural analgesia.
1998 Dec
Spinal cord compression from precipitation of drug solute around an epidural catheter.
1998 Oct
Postoperative extradural infusions in children: preliminary data from a comparison of bupivacaine/diamorphine with plain ropivacaine.
1999
The adaptive response of MyoD family proteins in overloaded, regenerating and denervated rat muscles.
1999 Aug 5
The influence of baricity on the haemodynamic effects of intrathecal bupivacaine 0.5%.
1999 May
Ropivacaine in peribulbar block: a comparative study with bupivacaine.
1999 Sep
More Horner's than meets the eye.
2000
[Acute toxic accident following lumbar plexus block with bupivacaine].
2000 May
Optimal dose of intrathecal clonidine added to sufentanil plus bupivacaine for labour analgesia.
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
Can anesthesiologic strategies for caesarean section influence newborn jaundice? A retrospective and prospective study.
2001 Feb
Effects of bupivacaine and a novel local anesthetic, IQB-9302, on human cardiac K+ channels.
2001 Feb
Is comparative cardiotoxicity of S(-) and R(+) bupivacaine related to enantiomer-selective inhibition of L-type Ca(2+) channels?
2001 Feb
Transient neurologic symptoms after spinal anesthesia with lidocaine in obstetric patients.
2001 Feb
Postoperative sleep disturbance: influences of opioids and pain in humans.
2001 Feb 1
[Infiltration of the surgical wound with local anesthetic for postoperative analgesia in patients operated on for lumbar disc herniation. Comparative study of ropivacaine and bupivacaine].
2001 Jan
A randomised controlled trial of epidural compared with non-epidural analgesia in labour.
2001 Jan
Epidural naloxone reduces intestinal hypomotility but not analgesia of epidural morphine.
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
Survey of 1057 patients receiving postoperative patient-controlled epidural analgesia.
2001 Jan
Digitally assisted acromioplasty: the effect of interscalene block on this new surgical technique.
2001 Jan
Plasma concentrations and pharmacokinetics of bupivacaine with and without adrenaline following caudal anaesthesia in infants.
2001 Jan
Neurologic sequelae after caesarean section.
2001 Jan
The dose-range effects of sufentanil added to 0.125% bupivacaine on the quality of patient-controlled epidural analgesia during labor.
2001 Jan
Randomized clinical trial of local bupivacaine perfusion versus parenteral morphine infusion for pain relief after laparotomy.
2001 Mar
Corneal sensation after topical anesthesia.
2001 Mar
Epidural analgesia in the dog and cat.
2001 Mar
Postoperative narcotic requirement after microscopic lumbar discectomy is not affected by intraoperative ketorolac or bupivacaine.
2001 Mar 15
Characterization of TASK-4, a novel member of the pH-sensitive, two-pore domain potassium channel family.
2001 Mar 9
Assessment of wound infiltration with bupivacaine in women undergoing day-case gynecological laparoscopy.
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 18:29:17 GMT 2023
Edited
by admin
on Fri Dec 15 18:29:17 GMT 2023
Record UNII
7TQO7W3VT8
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BUPIVACAINE HYDROCHLORIDE
EP   MART.   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-IP  
USAN  
Official Name English
BUPIVACAINE HYDROCHLORIDE [VANDF]
Common Name English
BUPIVACAINE HYDROCHLORIDE [ORANGE BOOK]
Common Name English
WIN-11318
Code English
BUPIVACAINE HYDROCHLORIDE [EP MONOGRAPH]
Common Name English
2-PIPERIDINECARBOXAMIDE, 1-BUTYL-N-(2,6-DIMETHYLPHENYL)-, MONOHYDROCHLORIDE, MONOHYDRATE
Common Name English
BUPIVACAINE HYDROCHLORIDE MONOHYDRATE
MI   WHO-DD  
Common Name English
BUPIVACAINE HYDROCHLORIDE COMPONENT OF DUOCAINE
Common Name English
SENSORCAINE
Brand Name English
BUPIVACAINE HCL
Common Name English
BUPIVACAINE HYDROCHLORIDE [WHO-IP]
Common Name English
BUPIVACAINE HYDROCHLORIDE HYDRATE
JAN  
Common Name English
BUPIVACAINE HYDROCHLORIDE COMPONENT OF TKAINE
Common Name English
Bupivacaine hydrochloride monohydrate [WHO-DD]
Common Name English
(±)-1-BUTYL-2',6'-PIPECOLOXYLIDIDE MONOHYDROCHLORIDE, MONOHYDRATE
Common Name English
BUPIVACAINE HYDROCHLORIDE MONOHYDRATE [MI]
Common Name English
1-BUTYL-2',6'-PIPECOLOXYLIDIDE MONOHYDROCHLORIDE MONOHYDRATE
Systematic Name English
DUOCAINE COMPONENT BUPIVACAINE HYDROCHLORIDE
Common Name English
BUPIVACAINE HYDROCHLORIDE HYDRATE [JAN]
Common Name English
1-BUTYL-N-(2,6-DIMETHYLPHENYL)-2-PIPERIDINECARBOXAMIDE MONOHYDROCHLORIDE MONOHYDRATE
Systematic Name English
BUPIVACAINE HYDROCHLORIDE [USP-RS]
Common Name English
BUPIVACAINE HYDROCHLORIDE [USAN]
Common Name English
2-PIPERIDINECARBOXAMIDE, 1-BUTYL-N-(2,6-DIMETHYLPHENYL)-, HYDROCHLORIDE, HYDRATE (1:1:1)
Systematic Name English
BUPIVACAINE HYDROCHLORIDE [USP MONOGRAPH]
Common Name English
BUPIVACAINI HYDROCHLORIDUM [WHO-IP LATIN]
Common Name English
BUPIVACAINE HYDROCHLORIDE [MART.]
Common Name English
XARACOLL
Brand Name English
WIN 11,318
Code English
Classification Tree Code System Code
NCI_THESAURUS C245
Created by admin on Fri Dec 15 18:29:17 GMT 2023 , Edited by admin on Fri Dec 15 18:29:17 GMT 2023
FDA ORPHAN DRUG 510515
Created by admin on Fri Dec 15 18:29:17 GMT 2023 , Edited by admin on Fri Dec 15 18:29:17 GMT 2023
Code System Code Type Description
DRUG BANK
DBSALT001512
Created by admin on Fri Dec 15 18:29:17 GMT 2023 , Edited by admin on Fri Dec 15 18:29:17 GMT 2023
PRIMARY
EPA CompTox
DTXSID501323779
Created by admin on Fri Dec 15 18:29:17 GMT 2023 , Edited by admin on Fri Dec 15 18:29:17 GMT 2023
PRIMARY
PUBCHEM
5282419
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PRIMARY
SMS_ID
100000088212
Created by admin on Fri Dec 15 18:29:17 GMT 2023 , Edited by admin on Fri Dec 15 18:29:17 GMT 2023
PRIMARY
FDA UNII
7TQO7W3VT8
Created by admin on Fri Dec 15 18:29:17 GMT 2023 , Edited by admin on Fri Dec 15 18:29:17 GMT 2023
PRIMARY
NCI_THESAURUS
C28876
Created by admin on Fri Dec 15 18:29:17 GMT 2023 , Edited by admin on Fri Dec 15 18:29:17 GMT 2023
PRIMARY
ChEMBL
CHEMBL1098
Created by admin on Fri Dec 15 18:29:17 GMT 2023 , Edited by admin on Fri Dec 15 18:29:17 GMT 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
BUPIVACAINE HYDROCHLORIDE
Created by admin on Fri Dec 15 18:29:17 GMT 2023 , Edited by admin on Fri Dec 15 18:29:17 GMT 2023
PRIMARY Description: A white, crystalline powder; odourless. Solubility: Soluble in 25 parts of water and in 8 parts of ethanol (~750 g/l) TS; slightly soluble in ether R. Category: Local anaesthetic. Storage: Bupivacaine hydrochloride should be kept in a well-closed container. Definition: Bupivacaine hydrochloride contains not less than 98.5% and not more than 101.0% of C18H28N2O,HCl, calculated with reference to the dried substance.
RS_ITEM_NUM
1078507
Created by admin on Fri Dec 15 18:29:17 GMT 2023 , Edited by admin on Fri Dec 15 18:29:17 GMT 2023
PRIMARY
CHEBI
31322
Created by admin on Fri Dec 15 18:29:17 GMT 2023 , Edited by admin on Fri Dec 15 18:29:17 GMT 2023
PRIMARY
RXCUI
267396
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PRIMARY RxNorm
EVMPD
SUB21381
Created by admin on Fri Dec 15 18:29:17 GMT 2023 , Edited by admin on Fri Dec 15 18:29:17 GMT 2023
PRIMARY
EVMPD
SUB00902MIG
Created by admin on Fri Dec 15 18:29:17 GMT 2023 , Edited by admin on Fri Dec 15 18:29:17 GMT 2023
PRIMARY
CHEBI
60789
Created by admin on Fri Dec 15 18:29:17 GMT 2023 , Edited by admin on Fri Dec 15 18:29:17 GMT 2023
PRIMARY
MERCK INDEX
m2769
Created by admin on Fri Dec 15 18:29:17 GMT 2023 , Edited by admin on Fri Dec 15 18:29:17 GMT 2023
PRIMARY
DAILYMED
7TQO7W3VT8
Created by admin on Fri Dec 15 18:29:17 GMT 2023 , Edited by admin on Fri Dec 15 18:29:17 GMT 2023
PRIMARY
CAS
73360-54-0
Created by admin on Fri Dec 15 18:29:17 GMT 2023 , Edited by admin on Fri Dec 15 18:29:17 GMT 2023
PRIMARY
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http://apps.who.int/phint/en/p/docf/