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Sensorcaine, Zynrelef(bupivacaine)
Duocaine, Exparel, Marcaine, Posimir, Sensorcaine, Xaracoll, Zynrelef (bupivacaine) is a small molecule pharmaceutical. Bupivacaine was first approved as Sensorcaine on 1982-01-01. It is used to treat postoperative pain in the USA. It has been approved in Europe to treat acute pain and postoperative pain. It is known to target G protein-activated inward rectifier potassium channel 2, potassium voltage-gated channel subfamily D member 3, potassium voltage-gated channel subfamily A member 5, and sodium channel protein type 5 subunit alpha.
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Commercial
Therapeutic Areas
Therapeutic Area
MeSH
signs and symptoms pathological conditionsD013568
Trade Name
FDA
EMA
Exparel, Marcaine, Posimir, Sensorcaine, Xaracoll (generic drugs available since 1986-02-17)
Combinations
Sensorcaine, Zynrelef (generic drugs available since 1986-02-17, discontinued: Duocaine)
Drug Products
FDA
EMA
New Drug Application (NDA)
New Drug Application (NDA)
Abbreviated New Drug Application (ANDA)
Abbreviated New Drug Application (ANDA)
Bupivacaine
Tradename
Company
Number
Date
Products
POSIMIRInnocollN-204803 RX2021-02-01
1 products, RLD, RS
EXPARELPacira BioSciencesN-022496 RX2011-10-28
2 products, RLD, RS
Bupivacaine
+
Meloxicam
Tradename
Company
Number
Date
Products
ZYNRELEF KITHeron TherapeuticsN-211988 RX2021-05-12
2 products, RLD, RS
Show 1 discontinued
Bupivacaine hydrochloride
Tradename
Company
Number
Date
Products
SENSORCAINEFresenius KabiN-018304 RX1982-01-01
3 products, RLD
MARCAINE HYDROCHLORIDEHospiraN-016964 RX1982-01-01
1 products, RLD, RS
MARCAINE HYDROCHLORIDE PRESERVATIVE FREEHospiraN-016964 RX1982-01-01
1 products, RLD, RS
MARCAINE HYDROCHLORIDEHospiraN-016964 RX1982-01-01
1 products, RLD, RS
MARCAINE HYDROCHLORIDE PRESERVATIVE FREEHospiraN-016964 RX1982-01-01
2 products, RLD, RS
MARCAINEHospiraN-018692 RX1984-05-04
1 products, RLD, RS
XARACOLLInnocollN-209511 RX2020-08-28
1 products, RLD, RS
Show 2 discontinued
Bupivacaine hydrochloride
+
Epinephrine bitartrate
Tradename
Company
Number
Date
Products
SENSORCAINEFresenius KabiN-018304 RX1983-09-02
2 products, RLD
MARCAINE HYDROCHLORIDE W/ EPINEPHRINEHospiraN-016964 RX1982-01-01
1 products, RLD, RS
MARCAINE HYDROCHLORIDE W/ EPINEPHRINE PRESERVATIVE FREEHospiraN-016964 RX1982-01-01
1 products, RLD, RS
MARCAINE HYDROCHLORIDE W/ EPINEPHRINEHospiraN-016964 RX1982-01-01
1 products, RLD, RS
MARCAINE HYDROCHLORIDE W/ EPINEPHRINE PRESERVATIVE FREEHospiraN-016964 RX1982-01-01
2 products, RLD, RS
Show 1 discontinued
Bupivacaine hydrochloride
+
Lidocaine hydrochloride
Tradename
Company
Number
Date
Products
DUOCAINEAmphastar PharmaceuticalsN-021496 DISCN2003-05-23
1 products
Hide discontinued
Labels
FDA
EMA
Brand Name
Status
Last Update
bupivacaine hcl bupivacine hclANDA2023-06-09
exparelNew Drug Application2021-01-18
mlk kit f2unapproved drug other2023-03-15
posimirNew Drug Application2022-12-13
sensorcaineNew Drug Application2022-12-29
xaracollNew Drug Application2020-09-08
zynrelefNew Drug Application2021-05-21
Indications
FDA
EMA
Indication
Ontology
MeSH
ICD-10
postoperative pain—D010149G89.18
Agency Specific
FDA
EMA
Expiration
Code
BUPIVACAINE / MELOXICAM, ZYNRELEF KIT, HERON THERAPS INC
2024-05-12NP
BUPIVACAINE, EXPAREL, PACIRA PHARMS INC
2024-03-22NPP
BUPIVACAINE, POSIMIR, INNOCOLL
2024-02-01NP
BUPIVACAINE HYDROCHLORIDE, XARACOLL, INNOCOLL PHARMS
2023-08-28NP
Patent Expiration
Patent
Expires
Flag
FDA Information
Bupivacaine, Exparel, Pacira Pharms Inc
110334952041-01-22DPU-3182
111793362041-01-22DPU-3250
112784942041-01-22DPU-3250
113049042041-01-22DPU-3346
113114862041-01-22DPU-3250
113577272041-01-22DPU-3380
114263482041-01-22DPU-3380
114526912041-01-22DPU-3439
Bupivacaine, Posimir, Innocoll
114000192041-01-12DP
81531492025-09-15DP
81536612025-09-15U-3074
87536652025-09-15DPU-3074
88460722025-09-15DPU-3074
Bupivacaine / Meloxicam, Zynrelef Kit, Heron Theraps Inc
96940792035-04-20DPU-3118
98019452035-04-20DPU-3118
100989572035-04-20U-3118
102135102035-04-20DPU-3118
106321992035-04-20DPU-3118
108985752035-04-20DPU-3118
109808862035-04-20DP
110837302035-04-20DPU-3118
110837972035-04-20DPU-3118
114133502035-04-20U-3417
95922272034-03-13DPU-3118
97441632034-03-13DP
99139092034-03-13U-3118
103986862034-03-13DP
112535042034-03-13U-3118
Bupivacaine Hydrochloride, Xaracoll, Innocoll Pharms
RE478262029-05-20U-2949
ATC Codes
N: Nervous system drugs
— N01: Anesthetics
— N01B: Local anesthetics
— N01BB: Amide local anesthetics
— N01BB01: Bupivacaine
— N01BB51: Bupivacaine, combinations
— N01BB59: Bupivacaine and meloxicam
HCPCS
Code
Description
C9088
Instillation, bupivacaine and meloxicam, 1 mg/0.03 mg
C9089
Bupivacaine, collagen-matrix implant, 1 mg
C9290
Injection, bupivacaine liposome, 1 mg
Clinical
Clinical Trials
1544 clinical trials
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Mock data
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Indications Phases 4
Indication
MeSH
Ontology
ICD-10
Ph 1
Ph 2
Ph 3
Ph 4
Other
Total
Postoperative painD010149G89.18277554134127394
PainD010146EFO_0003843R52614134837115
AnalgesiaD000698436132045
Replacement arthroplasty kneeD01964513—221440
Spinal anesthesiaD000775—14161839
Acute painD059787R5237620738
AnesthesiaD000758253111837
Local anesthesiaD00077235262136
Labor painD048949213101126
Cesarean sectionD002585——1101526
Show 185 more
Indications Phases 3
Indication
MeSH
Ontology
ICD-10
Ph 1
Ph 2
Ph 3
Ph 4
Other
Total
Video-assisted thoracic surgeryD020775—11—35
Musculoskeletal diseasesD009140—11—35
Laparoscopic cholecystectomyD017081——1—34
Coronary artery diseaseD003324I25.1112——4
Pancreatic neoplasmsD010190EFO_0003860C251—1—24
Chronic pancreatitisD050500EFO_0000342K86.11—1—13
Thoracic diseasesD013896—12—13
Intraoperative complicationsD007431——1—23
Female genital neoplasmsD005833—12——3
Femoral fracturesD005264S72—11—13
Show 39 more
Indications Phases 2
Indication
MeSH
Ontology
ICD-10
Ph 1
Ph 2
Ph 3
Ph 4
Other
Total
HerniorrhaphyD05968513———4
Thyroid diseasesD013959HP_0000820E00-E07—1——23
Myofascial pain syndromesD009209EFO_1001054—1——12
PhimosisD010688EFO_1001104N47.111———2
ParaphimosisD010263EFO_1001086N47.211———2
BalanitisD001446EFO_1000833N48.111———2
Thyroid noduleD016606EFO_1001436—1——12
Postherpetic neuralgiaD05147411———2
Referred painD053591—1———1
Lacrimal apparatus diseasesD007766HP_0009926H04—1———1
Show 18 more
Indications Phases 1
Indication
MeSH
Ontology
ICD-10
Ph 1
Ph 2
Ph 3
Ph 4
Other
Total
Healthy volunteers/patients—5————5
Spinal fusionD0131232———13
Lung diseasesD008171EFO_0003818J98.41———23
SternotomyD0563462————2
AdenomyosisD062788EFO_1001757N80.01———12
Primary dysautonomiasD0549692————2
Emergence deliriumD0000712571———12
Post-dural puncture headacheD0512991———12
Sphenopalatine ganglion blockD0593871———12
Hiv infectionsD015658EFO_0000764B202————2
Show 13 more
Indications Without Phase
Indication
MeSH
Ontology
ICD-10
Ph 1
Ph 2
Ph 3
Ph 4
Other
Total
EstheticsD004954————33
Congenital hip dislocationD006618HP_0001385Q65.2————33
Postoperative complicationsD011183————33
Renal insufficiencyD051437HP_0000083N19————33
Pre-eclampsiaD011225EFO_0000668O14————22
HyperparathyroidismD006961EFO_0008506E21.3————22
BradycardiaD001919HP_0001662R00.1————22
Liver neoplasmsD008113EFO_1001513C22.0————22
NephrectomyD009392————22
UltrasonographyD014463————22
Show 76 more
Epidemiology
Epidemiological information for investigational and approved indications
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Drug
General
Drug common nameBUPIVACAINE
INNbupivacaine
Description
1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide is a piperidinecarboxamide obtained by formal condensation of the carboxy group of N-butylpipecolic acid with the amino group of 2,6-dimethylaniline. It is a piperidinecarboxamide, an aromatic amide and a tertiary amino compound. It is a conjugate base of a 1-butyl-2-[(2,6-dimethylphenyl)carbamoyl]piperidinium.
Classification
Small molecule
Drug classlocal anesthetics
Image (chem structure or protein)
Structure (InChI/SMILES or Protein Sequence)
CCCCN1CCCCC1C(=O)Nc1c(C)cccc1C
Identifiers
PDB—
CAS-ID38396-39-3
RxCUI—
ChEMBL IDCHEMBL1098
ChEBI ID77431
PubChem CID2474
DrugBankDB00297
UNII IDY8335394RO (ChemIDplus, GSRS)
Target
Agency Approved
No data
Alternate
KCNJ6
KCNJ6
KCND3
KCND3
KCNA5
KCNA5
SCN5A
SCN5A
Organism
Homo sapiens
Gene name
KCNJ6
Gene synonyms
GIRK2, KATP2, KCNJ7
NCBI Gene ID
3763
Protein name
G protein-activated inward rectifier potassium channel 2
Protein synonyms
BIR1, Inward rectifier K(+) channel Kir3.2, inward rectifier potassium channel KIR3.2, KATP-2, Potassium channel, inwardly rectifying subfamily J member 6, potassium channel, inwardly rectifying subfamily J, member 6, potassium voltage-gated channel subfamily J member 6
Uniprot ID
Q53WW6
Mouse ortholog
Kcnj6 (16522)
G protein-activated inward rectifier potassium channel 2 (P48542)
Variants
Clinical Variant
No data
Financial
Bupivacaine - Pacira BioSciences
$
€
£
₣
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Zynrelef - HERON THERAPEUTICS, INC. /DE/
$
€
£
₣
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Exparel - Pacira BioSciences
$
€
£
₣
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Tabular view
Trends
PubMed Central
Top Terms for Disease or Syndrome:
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Additional graphs summarizing 22,775 documents
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Safety
Black-box Warning
Black-box warning for: Bupivacaine hcl bupivacine hcl, Posimir, Zynrelef
Adverse Events
Top Adverse Reactions
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11 adverse events reported
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