Bupivacaine hydrochloride, Zynrelef(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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Commercial
Therapeutic Areas
Therapeutic Area | MeSH |
|---|---|
| signs and symptoms pathological conditions | D013568 |
Trade Name
FDA
EMA
Bupivacaine, Bupivacaine liposome, Exparel, Marcaine, Sensorcaine (discontinued: Bupivacaine, Posimir, Sensorcaine, Xaracoll)
CombinationsBupivacaine 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 hydrochloride
Tradename | Company | Number | Date | Products |
|---|---|---|---|---|
| SENSORCAINE | Fresenius Kabi | N-018304 RX | 1982-01-01 | 3 products, RLD |
| MARCAINE HYDROCHLORIDE | Hospira | N-016964 RX | 1982-01-01 | 1 products, RLD, RS |
| MARCAINE HYDROCHLORIDE PRESERVATIVE FREE | Hospira | N-016964 RX | 1982-01-01 | 1 products, RLD, RS |
| MARCAINE HYDROCHLORIDE | Hospira | N-016964 RX | 1982-01-01 | 1 products, RLD, RS |
| MARCAINE HYDROCHLORIDE PRESERVATIVE FREE | Hospira | N-016964 RX | 1982-01-01 | 2 products, RLD, RS |
| MARCAINE | Hospira | N-018692 RX | 1984-05-04 | 1 products, RLD, RS |
Show 3 discontinued
Bupivacaine
Tradename | Company | Number | Date | Products |
|---|---|---|---|---|
| EXPAREL | Pacira BioSciences | N-022496 RX | 2011-10-28 | 2 products, RLD, RS |
Show 1 discontinued
Bupivacaine hydrochloride
+
Epinephrine bitartrate
Tradename | Company | Number | Date | Products |
|---|---|---|---|---|
| SENSORCAINE | Fresenius Kabi | N-018304 RX | 1983-09-02 | 2 products, RLD |
| MARCAINE HYDROCHLORIDE W/ EPINEPHRINE | Hospira | N-016964 RX | 1982-01-01 | 1 products, RLD, RS |
| MARCAINE HYDROCHLORIDE W/ EPINEPHRINE PRESERVATIVE FREE | Hospira | N-016964 RX | 1982-01-01 | 1 products, RLD, RS |
| MARCAINE HYDROCHLORIDE W/ EPINEPHRINE | Hospira | N-016964 RX | 1982-01-01 | 1 products, RLD, RS |
| MARCAINE HYDROCHLORIDE W/ EPINEPHRINE PRESERVATIVE FREE | Hospira | N-016964 RX | 1982-01-01 | 2 products, RLD, RS |
Show 1 discontinued
Bupivacaine hydrochloride
+
Lidocaine hydrochloride
Tradename | Company | Number | Date | Products |
|---|---|---|---|---|
| DUOCAINE | Amphastar Pharmaceuticals | N-021496 DISCN | 2003-05-23 | 1 products |
Hide discontinued
Bupivacaine
+
Meloxicam
Tradename | Company | Number | Date | Products |
|---|---|---|---|---|
| ZYNRELEF KIT | Heron Therapeutics | N-211988 RX | 2021-05-12 | 2 products, RLD, RS |
Show 1 discontinued
Labels
FDA
EMA
Brand Name | Status | Last Update |
|---|---|---|
| 0.25% bupivacaine hcl bupivacaine hydrochloride | ANDA | 2024-06-20 |
| blt-25 kit | unapproved drug other | 2024-09-11 |
| bupivacaine | ANDA | 2024-10-25 |
| bupivacaine hci | ANDA | 2024-01-22 |
| bupivacaine hci and epinephrine | ANDA | 2024-01-30 |
| bupivacaine hcl | New Drug Application | 2024-01-27 |
| bupivacaine hcl bupivacine hcl | ANDA | 2023-06-09 |
| bupivacaine hydrochloride | ANDA | 2025-01-10 |
| bupivacaine hydrochloride and epinephrine | ANDA | 2024-10-14 |
| bupivacaine hydrochloride bupivacaine hydrochloride and epinephrine | ANDA | 2024-10-15 |
Show 56 more
Indications
FDA
EMA
Show 11 more
Agency Specific
FDA
EMA
Expiration | Code | ||
|---|---|---|---|
BUPIVACAINE, EXPAREL, PACIRA PHARMS INC | |||
| 2026-11-09 | I-929 | ||
| 2024-03-22 | NPP | ||
BUPIVACAINE / MELOXICAM, ZYNRELEF KIT, HERON THERAPS INC | |||
| 2024-05-12 | NP | ||
BUPIVACAINE, POSIMIR, INNOCOLL | |||
| 2024-02-01 | NP | ||
Patent Expiration
Patent | Expires | Flag | FDA Information |
|---|---|---|---|
| Bupivacaine, Exparel, Pacira Pharms Inc | |||
| 11033495 | 2041-01-22 | DP | U-3182 |
| 11179336 | 2041-01-22 | DP | U-3250 |
| 11278494 | 2041-01-22 | DP | U-3250 |
| 11304904 | 2041-01-22 | DP | U-3346 |
| 11311486 | 2041-01-22 | DP | U-3250 |
| 11357727 | 2041-01-22 | DP | U-3380 |
| 11426348 | 2041-01-22 | DP | U-3380 |
| 11452691 | 2041-01-22 | DP | U-3439 |
| 11819574 | 2041-01-22 | DP | U-3250 |
| 11819575 | 2041-01-22 | DP | U-3250 |
| Bupivacaine, Posimir, Innocoll | |||
| 11400019 | 2041-01-12 | DP | |
| 11771624 | 2041-01-12 | U-3724 | |
| 8153149 | 2025-09-15 | DP | |
| 8153661 | 2025-09-15 | U-3074 | |
| 8753665 | 2025-09-15 | DP | U-3074 |
| 8846072 | 2025-09-15 | DP | U-3074 |
| Bupivacaine / Meloxicam, Zynrelef Kit, Heron Theraps Inc | |||
| 11844837 | 2036-04-21 | U-3417 | |
| 9694079 | 2035-04-20 | DP | U-3118 |
| 9801945 | 2035-04-20 | DP | U-3118 |
| 10098957 | 2035-04-20 | U-3118 | |
| 10213510 | 2035-04-20 | DP | U-3118 |
| 10632199 | 2035-04-20 | DP | U-3118 |
| 10898575 | 2035-04-20 | DP | U-3118 |
| 10980886 | 2035-04-20 | DP | |
| 11083730 | 2035-04-20 | DP | U-3118 |
| 11083797 | 2035-04-20 | DP | U-3118 |
| 11413350 | 2035-04-20 | U-3417 | |
| 9592227 | 2034-03-13 | DP | U-3118 |
| 9744163 | 2034-03-13 | DP | |
| 9913909 | 2034-03-13 | U-3118 | |
| 10398686 | 2034-03-13 | DP | |
| 11253504 | 2034-03-13 | U-3118 | |
| Bupivacaine Hydrochloride, Xaracoll, Innocoll Pharms | |||
| 11746141 | 2033-01-09 | DP | |
| RE47826 | 2029-05-20 | U-2949 | |
Clinical
Clinical Trials
3843 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 pain | D010149 | — | G89.18 | 5 | 9 | 6 | 10 | 3 | 30 |
| Pain | D010146 | EFO_0003843 | R52 | 1 | — | 3 | 7 | — | 11 |
| Pain management | D059408 | — | — | 1 | — | 1 | 2 | 1 | 5 |
| Hernia | D006547 | — | K40-K46 | — | 2 | — | 3 | — | 5 |
| Intestinal obstruction | D007415 | — | K56.60 | — | — | — | 4 | — | 4 |
| Mammaplasty | D016462 | — | — | — | — | 1 | 2 | — | 3 |
| Analgesia | D000698 | — | — | — | — | 1 | 1 | 1 | 3 |
| Rotator cuff injuries | D000070636 | — | M75.1 | — | — | — | 3 | — | 3 |
| Cesarean section | D002585 | — | — | — | — | — | 2 | — | 2 |
| Abdominal hernia | D046449 | — | K46 | — | — | — | 2 | — | 2 |
Show 17 more
Indications Phases 3
Indication | MeSH | Ontology | ICD-10 | Ph 1 | Ph 2 | Ph 3 | Ph 4 | Other | Total |
|---|---|---|---|---|---|---|---|---|---|
| Bunion | D000071378 | — | M21.61 | 1 | — | 4 | — | — | 5 |
| Hallux valgus | D006215 | — | — | — | 1 | 2 | — | — | 3 |
| Hemorrhoids | D006484 | EFO_0009552 | K64 | — | — | 2 | — | — | 2 |
| Dental pins | D003772 | — | — | — | — | 1 | — | — | 1 |
| Toothache | D014098 | — | K08.89 | — | — | 1 | — | — | 1 |
| Knee osteoarthritis | D020370 | EFO_0004616 | M17 | — | — | 1 | — | — | 1 |
| Osteoarthritis | D010003 | EFO_0002506 | M15-M19 | — | — | 1 | — | — | 1 |
| Agnosia | D000377 | EFO_0007136 | F88 | — | — | 1 | — | — | 1 |
| Coronary artery disease | D003324 | — | I25.1 | — | — | 1 | — | — | 1 |
| Coronary stenosis | D023921 | EFO_1000882 | — | — | — | 1 | — | — | 1 |
Show 8 more
Indications Phases 2
Indication | MeSH | Ontology | ICD-10 | Ph 1 | Ph 2 | Ph 3 | Ph 4 | Other | Total |
|---|---|---|---|---|---|---|---|---|---|
| Inguinal hernia | D006552 | HP_0000023 | K40 | — | 2 | — | — | — | 2 |
| Dupuytren contracture | D004387 | EFO_0004229 | M72.0 | — | 1 | — | — | — | 1 |
| Contracture | D003286 | EFO_0003899 | M62.4 | — | 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 implantation | D019928 | — | — | 1 | — | — | — | — | 1 |
| Spinal fusion | D013123 | — | — | 1 | — | — | — | — | 1 |
| Liver diseases | D008107 | EFO_0001421 | K70-K77 | 1 | — | — | — | — | 1 |
| Hepatic insufficiency | D048550 | — | — | 1 | — | — | — | — | 1 |
Indications Without Phase
Indication | MeSH | Ontology | ICD-10 | Ph 1 | Ph 2 | Ph 3 | Ph 4 | Other | Total |
|---|---|---|---|---|---|---|---|---|---|
| Esthetics | D004954 | — | — | — | — | — | — | 1 | 1 |
| Shoulder injuries | D000070599 | — | — | — | — | — | — | 1 | 1 |
| Anterior cruciate ligament injuries | D000070598 | — | — | — | — | — | — | 1 | 1 |
Epidemiology
Epidemiological information for investigational and approved indications
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Drug
General
| Drug common name | Bupivacaine |
| INN | bupivacaine |
| 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 class | local anesthetics |
| Image (chem structure or protein) |  |
| Structure (InChI/SMILES or Protein Sequence) | CCCCN1CCCCC1C(=O)Nc1c(C)cccc1C |
Identifiers
| PDB | — |
| CAS-ID | 38396-39-3 |
| RxCUI | — |
| ChEMBL ID | CHEMBL1098 |
| ChEBI ID | 77431 |
| PubChem CID | 2474 |
| DrugBank | DB00297 |
| UNII ID | Y8335394RO (ChemIDplus, GSRS) |
Target
Agency Approved
No data
Alternate
KCND3
KCND3
Organism
Homo sapiens
Gene name
KCND3
Gene synonyms
NCBI Gene ID
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
Mouse ortholog
Kcnd3 (56543)
potassium voltage-gated channel subfamily D member 3 (Q9Z0V1)
Variants
No data
Financial
Revenue by drug
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Zynrelef – Heron Therapeutics /de/
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Bupivacaine – Pacira BioSciences
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Exparel – Pacira BioSciences
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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 28,214 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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15,382 adverse events reported
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