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
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
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 | ( + / - ) |
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/11895133
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
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2072 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12761351 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | EXPAREL Approved UseBupivacaine 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 Date2011 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
952 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25776489/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25776489/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3868 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25776489/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25776489/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25776489/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25776489/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3344993/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
16% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3344993/ |
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
Dose | Population | Adverse 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... |
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
AE | Significance | Dose | Population |
---|---|---|---|
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: |
PubMed
Title | Date | PubMed |
---|---|---|
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 |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27195613
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
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Edited
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Record UNII |
AKA908P8J1
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Record Status |
Validated (UNII)
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Record Version |
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Related Record | Type | Details | ||
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ENANTIOMER -> RACEMATE | |||
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SOLVATE->ANHYDROUS | |||
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PARENT -> SALT/SOLVATE |
Related Record | Type | Details | ||
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ACTIVE MOIETY |