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

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

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
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
[Bupivacaine-induced meningitis].
1999 Aug
The influence of baricity on the haemodynamic effects of intrathecal bupivacaine 0.5%.
1999 May
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
Continuous paravertebral extrapleural infusion for post-thoracotomy pain management.
1999 Oct
Ropivacaine in peribulbar block: a comparative study with bupivacaine.
1999 Sep
Bupivacaine-induced myocardial depression and pulmonary edema: a case report.
2000 Jul
The dose-response of intrathecal sufentanil added to bupivacaine for labor analgesia.
2000 Jun
Lumbar sympathetic block for sympathetically maintained pain: changes in cutaneous temperatures and pain perception.
2000 Jun
Mental status change and aphasia after labor analgesia with intrathecal sufentanil/bupivacaine.
2000 May
Optimal dose of intrathecal clonidine added to sufentanil plus bupivacaine for labour analgesia.
2000 Sep
Stress-induced osteolysis of distal clavicle: imaging patterns and treatment using CT-guided injection.
2001
[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
Subarachnoid sufentanil for early postoperative pain management in orthopedic patients: a placebo-controlled, double-blind study using spinal microcatheters.
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
Epidural naloxone reduces intestinal hypomotility but not analgesia of epidural morphine.
2001 Jan
Stereoselective effects of the enantiomers of a new local anaesthetic, IQB-9302, on a human cardiac potassium channel (Kv1.5).
2001 Jan
Digitally assisted acromioplasty: the effect of interscalene block on this new surgical technique.
2001 Jan
Clonidine combined with a long acting local anesthetic does not prolong postoperative analgesia after brachial plexus block but does induce hemodynamic changes.
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
Intrathecal low-dose bupivacaine versus lidocaine for in vitro fertilization procedures.
2001 Jan-Feb
Combined spinal and epidural anesthesia with low doses of intrathecal bupivacaine in women with severe preeclampsia: a preliminary report.
2001 Jan-Feb
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
Discomfort with fine-needle aspiration cytology of the breast.
2001 Mar 10
Postoperative narcotic requirement after microscopic lumbar discectomy is not affected by intraoperative ketorolac or bupivacaine.
2001 Mar 15
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.
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
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PRIMARY
EPA CompTox
DTXSID501323779
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PRIMARY
PUBCHEM
5282419
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PRIMARY
SMS_ID
100000088212
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PRIMARY
FDA UNII
7TQO7W3VT8
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PRIMARY
NCI_THESAURUS
C28876
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PRIMARY
ChEMBL
CHEMBL1098
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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
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PRIMARY
CHEBI
31322
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PRIMARY
RXCUI
267396
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PRIMARY RxNorm
EVMPD
SUB21381
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PRIMARY
EVMPD
SUB00902MIG
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PRIMARY
CHEBI
60789
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PRIMARY
MERCK INDEX
m2769
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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