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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 painD010149G89.18
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 kneeD01964513221440
Spinal anesthesiaD00077514161839
Acute painD059787R5237620738
AnesthesiaD000758253111837
Local anesthesiaD00077235262136
Labor painD048949213101126
Cesarean sectionD0025851101526
Show 185 more
Indications Phases 3
Indication
MeSH
Ontology
ICD-10
Ph 1
Ph 2
Ph 3
Ph 4
Other
Total
Video-assisted thoracic surgeryD0207751135
Musculoskeletal diseasesD0091401135
Laparoscopic cholecystectomyD017081134
Coronary artery diseaseD003324I25.11124
Pancreatic neoplasmsD010190EFO_0003860C251124
Chronic pancreatitisD050500EFO_0000342K86.11113
Thoracic diseasesD0138961213
Intraoperative complicationsD007431123
Female genital neoplasmsD005833123
Femoral fracturesD005264S721113
Show 39 more
Indications Phases 2
Indication
MeSH
Ontology
ICD-10
Ph 1
Ph 2
Ph 3
Ph 4
Other
Total
HerniorrhaphyD059685134
Thyroid diseasesD013959HP_0000820E00-E07123
Myofascial pain syndromesD009209EFO_1001054112
PhimosisD010688EFO_1001104N47.1112
ParaphimosisD010263EFO_1001086N47.2112
BalanitisD001446EFO_1000833N48.1112
Thyroid noduleD016606EFO_1001436112
Postherpetic neuralgiaD051474112
Referred painD05359111
Lacrimal apparatus diseasesD007766HP_0009926H0411
Show 18 more
Indications Phases 1
Indication
MeSH
Ontology
ICD-10
Ph 1
Ph 2
Ph 3
Ph 4
Other
Total
Healthy volunteers/patients55
Spinal fusionD013123213
Lung diseasesD008171EFO_0003818J98.4123
SternotomyD05634622
AdenomyosisD062788EFO_1001757N80.0112
Primary dysautonomiasD05496922
Emergence deliriumD000071257112
Post-dural puncture headacheD051299112
Sphenopalatine ganglion blockD059387112
Hiv infectionsD015658EFO_0000764B2022
Show 13 more
Indications Without Phase
Indication
MeSH
Ontology
ICD-10
Ph 1
Ph 2
Ph 3
Ph 4
Other
Total
EstheticsD00495433
Congenital hip dislocationD006618HP_0001385Q65.233
Postoperative complicationsD01118333
Renal insufficiencyD051437HP_0000083N1933
Pre-eclampsiaD011225EFO_0000668O1422
HyperparathyroidismD006961EFO_0008506E21.322
BradycardiaD001919HP_0001662R00.122
Liver neoplasmsD008113EFO_1001513C22.022
NephrectomyD00939222
UltrasonographyD01446322
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
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
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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