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Drug ReportsBupivacaine
Bupivacaine hydrochloride, Exparel liposomal(bupivacaine)
Bupivacaine, Duocaine, Exparel, Marcaine, Sensorcaine, Vivacaine, 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, A-type voltage-gated potassium channel KCND3, potassium voltage-gated channel subfamily A member 5, and sodium channel protein type 5 subunit alpha.
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1M
3M
6M
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2Y
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EMA approval date
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Study first post date
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Commercial
Therapeutic Areas
Therapeutic Area
MeSH
signs and symptoms pathological conditionsD013568
Trade Name
FDA
EMA
Bupivacaine, Exparel, Marcaine, Sensorcaine (discontinued: Bupivacaine, Bupivacaine liposome, Posimir, Sensorcaine, Xaracoll)
Combinations
Bupivacaine epinephrine, Marcaine w/ epinephrine, Sensorcaine, Vivacaine, Zynrelef (discontinued: Bupivacaine epinephrine, Duocaine, Zynrelef)
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
EXPARELPacira BioSciencesN-022496 RX2011-10-28
2 products, RLD, RS
Show 1 discontinued
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
Show 3 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
0.25% bupivacaine hcl bupivacaine hydrochlorideANDA2024-06-20
blt-25 kitunapproved drug other2024-09-11
bupivacaineANDA2024-10-25
bupivacaine hciANDA2024-01-22
bupivacaine hci and epinephrineANDA2024-01-30
bupivacaine hclNew Drug Application2024-01-27
bupivacaine hcl bupivacine hclANDA2023-06-09
bupivacaine hydrochlorideANDA2025-10-03
bupivacaine hydrochloride and epinephrineANDA2024-10-14
bupivacaine hydrochloride bupivacaine hydrochloride and epinephrineANDA2024-10-15
Show 56 more
Indications
FDA
EMA
Indication
Ontology
MeSH
ICD-10
postoperative pain—D010149G89.18
rheumatoid arthritisEFO_0000685D001172M06.9
osteoarthritisEFO_0002506D010003M15-M19
septic shock—D012772A48.3
hypotensionEFO_0005251D007022I95
ventricular tachycardia—D017180I47.2
anaphylaxis—D000707T78.2
bradycardia—D001919R00.1
heart arrestEFO_0009492D006323I46
open-angle glaucomaEFO_0004190D005902H40.1
Show 11 more
Agency Specific
FDA
EMA
Expiration
Code
BUPIVACAINE, EXPAREL, PACIRA PHARMS INC
2026-11-09I-929
2024-03-22NPP
BUPIVACAINE / MELOXICAM, ZYNRELEF KIT, HERON THERAPS INC
2024-05-12NP
BUPIVACAINE, POSIMIR, INNOCOLL
2024-02-01NP
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
118195742041-01-22DPU-3250
118195752041-01-22DPU-3250
Bupivacaine, Posimir, Innocoll
114000192041-01-12DP
117716242041-01-12U-3724
81531492025-09-15DP
81536612025-09-15U-3074
87536652025-09-15DPU-3074
88460722025-09-15DPU-3074
Bupivacaine / Meloxicam, Zynrelef Kit, Heron Theraps Inc
118448372036-04-21U-3417
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
117461412033-01-09DP
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
C9144
Injection, bupivacaine (posimir), 1 mg
C9290
Injection, bupivacaine liposome, 1 mg
Clinical
Clinical Trials
4217 clinical trials
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Indications Phases 4
Indication
MeSH
Ontology
ICD-10
Ph 1
Ph 2
Ph 3
Ph 4
Other
Total
Postoperative painD010149—G89.1859710331
PainD010146EFO_0003843R522—37—12
Pain managementD059408——1—1215
AgnosiaD000377EFO_0007136F881—31—5
Intestinal obstructionD007415—K56.60———4—4
HerniaD006547—K40-K46—2—2—4
MammaplastyD016462————12—3
AnalgesiaD000698————1113
Rotator cuff injuriesD000070636—M75.1———3—3
Cesarean sectionD002585—————2—2
Show 18 more
Indications Phases 3
Indication
MeSH
Ontology
ICD-10
Ph 1
Ph 2
Ph 3
Ph 4
Other
Total
BunionD000071378—M21.611—4——5
Hallux valgusD006215———12——3
HemorrhoidsD006484EFO_0009552K64——2——2
Knee osteoarthritisD020370EFO_0004616M17——2——2
OsteoarthritisD010003EFO_0002506M15-M19——2——2
Dental pinsD003772————1——1
ToothacheD014098—K08.89——1——1
Coronary artery diseaseD003324—I25.1——1——1
Coronary stenosisD023921EFO_1000882———1——1
Mitral valve insufficiencyD008944————1——1
Show 7 more
Indications Phases 2
Indication
MeSH
Ontology
ICD-10
Ph 1
Ph 2
Ph 3
Ph 4
Other
Total
Inguinal herniaD006552HP_0000023K40—2———2
Dupuytren contractureD004387EFO_0004229M72.0—1———1
ContractureD003286EFO_0003899M62.4—1———1
Indications Phases 1
Indication
MeSH
Ontology
ICD-10
Ph 1
Ph 2
Ph 3
Ph 4
Other
Total
Healthy volunteers/patients———4————4
Breast implantationD019928——1————1
Spinal fusionD013123——1————1
Liver diseasesD008107EFO_0001421K70-K771————1
Hepatic insufficiencyD048550——1————1
Indications Without Phase
Indication
MeSH
Ontology
ICD-10
Ph 1
Ph 2
Ph 3
Ph 4
Other
Total
EstheticsD004954——————11
Shoulder injuriesD000070599——————11
Anterior cruciate ligament injuriesD000070598——————11
Replacement arthroplasty kneeD019645——————11
Low back painD017116—M54.5————11
Bronchiolitis obliterans syndromeD000092122—D89.811————11
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)Loading
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
KCND3
KCND3
Organism
Homo sapiens
Gene name
KCND3
Gene synonyms
NCBI Gene ID
3752
Protein name
potassium voltage-gated channel subfamily D member 3
Protein synonyms
potassium channel, voltage gated Shal related subfamily D, member 3, potassium ionic channel Kv4.3, potassium voltage-gated channel long, potassium voltage-gated channel, Shal-related subfamily, member 3, sha1-related potassium channel Kv4.3, voltage-gated K+ channel, Voltage-gated potassium channel subunit Kv4.3
Uniprot ID
Q9UK17
Mouse ortholog
Kcnd3 (56543)
potassium voltage-gated channel subfamily D member 3 (Q9Z0V1)
Variants
No data
Financial
Revenue by drug
$
€
£
₣
Exparel – Pacira BioSciences
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Bupivacaine – Pacira BioSciences
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Zynrelef – Heron Therapeutics /de/
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Estimated US medical usage
Bupivacaine
Total medical expenditures per year (USD, in millions)
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Number of persons purchased
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Number of purchases
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Refill frequency
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Price per prescription (USD)
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Trends
PubMed Central
Top Terms for Disease or Syndrome:
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Additional graphs summarizing 30,202 documents
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Safety
Black-box Warning
Black-box warning for: 0.25% bupivacaine hcl bupivacaine hydrochloride, Blt-25 kit, Bupivacaine hci, Bupivacaine hcl, Bupivacaine hcl bupivacine hcl, Bupivacaine hydrochloride, Bupivacaine hydrochloride and epinephrine, Bupivacaine hydrochloride bupivacaine hydrochloride and epinephrine, Bupivacaine hydrochloride injection, solution, Bupivilog kit, Dexlido-m kit, Dyural 40 kit, Dyural 80 kit, Dyural 80-lm, Dyural lm kit, Ketorocaine lm kit, Marbeta 25 kit, Marbeta l kit, Marcaine, Marcaine marcaine with epinephrine, Marcaine with epinephrine, Mardex 25 kit, Marlido 25 kit, Marlido kit, Marvona suik, Mlk f1 kit, Mlk f3 kit, Mlk f4 kit, Mlk kit f2, Physicians ez use m-pred, Posimir, Sensorcaine mpf, Sensorcaine sensorcaine, Sensorcaine sensorcaine-mpf sensorcaine-mpf, Sensorcaine(r) (bupivacaine hci and epinephrine), Sensorcaine-mpf, Zynrelef
Adverse Events
Top Adverse Reactions
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16,031 adverse events reported
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