Details
Stereochemistry | RACEMIC |
Molecular Formula | C18H28N2O |
Molecular Weight | 288.4277 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCN1CCCCC1C(=O)NC2=C(C)C=CC=C2C
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)
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 Date1.31976004E12 |
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 |
---|---|---|
The influence of baricity on the haemodynamic effects of intrathecal bupivacaine 0.5%. | 1999 May |
|
Combined spinal epidural for labour analgesia--duration, efficacy and side effects of adding sufentanil or fentanyl to bupivacaine intrathecally vs plain bupivacaine. | 1999 Oct |
|
More Horner's than meets the eye. | 2000 |
|
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 |
|
Bupivacaine-induced myocardial depression and pulmonary edema: a case report. | 2000 Jul |
|
Nitric oxide modulation affects the tissue distribution and toxicity of bupivacaine. | 2000 Jul |
|
Phantom pain and regional anaesthesia. | 2000 Jun |
|
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 |
|
[Acute toxic accident following lumbar plexus block with bupivacaine]. | 2000 May |
|
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 |
|
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 |
|
Bilateral paravertebral block: a satisfactory alternative for labour analgesia. | 2001 Feb |
|
Subarachnoid sufentanil for early postoperative pain management in orthopedic patients: a placebo-controlled, double-blind study using spinal microcatheters. | 2001 Feb |
|
Effects of bupivacaine and a novel local anesthetic, IQB-9302, on human cardiac K+ channels. | 2001 Feb |
|
Direct cardiac effects of intracoronary bupivacaine, levobupivacaine and ropivacaine in the sheep. | 2001 Feb |
|
Extended femoral nerve sheath block after total hip arthroplasty: continuous versus patient-controlled techniques. | 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 |
|
Evidence that postoperative pain is a mediator of the tumor-promoting effects of surgery in rats. | 2001 Feb 1 |
|
[Practice and complications of spinal anesthesia in African tropical countries]. | 2001 Jan |
|
Epidural naloxone reduces intestinal hypomotility but not analgesia of epidural morphine. | 2001 Jan |
|
Survey of 1057 patients receiving postoperative patient-controlled epidural analgesia. | 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 |
|
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 |
|
Minimum local anesthetic volume blocking the femoral nerve in 50% of cases: a double-blinded comparison between 0.5% ropivacaine and 0.5% bupivacaine. | 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 |
|
An accidental ringblock of the great toe? | 2001 Jan |
|
Morphine with or without a local anaesthetic for postoperative intrathecal pain treatment after selective dorsal rhizotomy in children. | 2001 Jan |
|
Spinal anesthesia with hypobaric bupivacaine for knee arthroscopies: effect of posture on motor block. | 2001 Jan-Feb |
|
Comparison of technical and block characteristics of different combined spinal and epidural anesthesia techniques. | 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 |
|
Epidural analgesia in the dog and cat. | 2001 Mar |
|
Continuous epidural infusion: human vigilance is essential. | 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 |
|
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 |
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.
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Classification Tree | Code System | Code | ||
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N0000007681
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N0000175976
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FDA ORPHAN DRUG |
237207
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WHO-VATC |
QN01BB01
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QN01BB51
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N0000175682
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NCI_THESAURUS |
C245
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WHO-ATC |
N01BB51
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WHO-ATC |
N01BB01
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WHO-ESSENTIAL MEDICINES LIST |
1.2
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218-553-3
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2180-92-9
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2474
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m2769
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1815
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Bupivacaine
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253-911-2
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Y8335394RO
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D002045
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ZZ-05
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CHEMBL1098
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7790
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DB00297
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77431
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BUPIVACAINE
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100000088449
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DTXSID2022703
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432
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SUB05983MIG
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ACTIVE MOIETY
METABOLITE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)