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 conditions | D013568 |
Trade Name
FDA
EMA
Exparel, Marcaine, Posimir, Sensorcaine, Xaracoll (generic drugs available since 1986-02-17)
CombinationsSensorcaine, 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
Bupivacaine
+
Meloxicam
Tradename | Company | Number | Date | Products |
---|---|---|---|---|
ZYNRELEF KIT | Heron Therapeutics | N-211988 RX | 2021-05-12 | 2 products, RLD, RS |
Show 1 discontinued
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 |
XARACOLL | Innocoll | N-209511 RX | 2020-08-28 | 1 products, RLD, RS |
Show 2 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
Labels
FDA
EMA
Brand Name | Status | Last Update |
---|---|---|
bupivacaine hcl bupivacine hcl | ANDA | 2023-06-09 |
exparel | New Drug Application | 2021-01-18 |
mlk kit f2 | unapproved drug other | 2023-03-15 |
posimir | New Drug Application | 2022-12-13 |
sensorcaine | New Drug Application | 2022-12-29 |
xaracoll | New Drug Application | 2020-09-08 |
zynrelef | New Drug Application | 2021-05-21 |
Agency Specific
FDA
EMA
Expiration | Code | ||
---|---|---|---|
BUPIVACAINE / MELOXICAM, ZYNRELEF KIT, HERON THERAPS INC | |||
2024-05-12 | NP | ||
BUPIVACAINE, EXPAREL, PACIRA PHARMS INC | |||
2024-03-22 | NPP | ||
BUPIVACAINE, POSIMIR, INNOCOLL | |||
2024-02-01 | NP | ||
BUPIVACAINE HYDROCHLORIDE, XARACOLL, INNOCOLL PHARMS | |||
2023-08-28 | 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 |
Bupivacaine, Posimir, Innocoll | |||
11400019 | 2041-01-12 | DP | |
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 | |||
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 | |||
RE47826 | 2029-05-20 | U-2949 |
Clinical
Clinical Trials
1544 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 | 27 | 75 | 54 | 134 | 127 | 394 | |
Pain | D010146 | EFO_0003843 | R52 | 6 | 14 | 13 | 48 | 37 | 115 |
Analgesia | D000698 | 4 | 3 | 6 | 13 | 20 | 45 | ||
Replacement arthroplasty knee | D019645 | 1 | 3 | — | 22 | 14 | 40 | ||
Spinal anesthesia | D000775 | — | 1 | 4 | 16 | 18 | 39 | ||
Acute pain | D059787 | R52 | 3 | 7 | 6 | 20 | 7 | 38 | |
Anesthesia | D000758 | 2 | 5 | 3 | 11 | 18 | 37 | ||
Local anesthesia | D000772 | 3 | 5 | 2 | 6 | 21 | 36 | ||
Labor pain | D048949 | 2 | 1 | 3 | 10 | 11 | 26 | ||
Cesarean section | D002585 | — | — | 1 | 10 | 15 | 26 |
Show 185 more
Indications Phases 3
Indication | MeSH | Ontology | ICD-10 | Ph 1 | Ph 2 | Ph 3 | Ph 4 | Other | Total |
---|---|---|---|---|---|---|---|---|---|
Video-assisted thoracic surgery | D020775 | — | 1 | 1 | — | 3 | 5 | ||
Musculoskeletal diseases | D009140 | — | 1 | 1 | — | 3 | 5 | ||
Laparoscopic cholecystectomy | D017081 | — | — | 1 | — | 3 | 4 | ||
Coronary artery disease | D003324 | I25.1 | 1 | 1 | 2 | — | — | 4 | |
Pancreatic neoplasms | D010190 | EFO_0003860 | C25 | 1 | — | 1 | — | 2 | 4 |
Chronic pancreatitis | D050500 | EFO_0000342 | K86.1 | 1 | — | 1 | — | 1 | 3 |
Thoracic diseases | D013896 | — | 1 | 2 | — | 1 | 3 | ||
Intraoperative complications | D007431 | — | — | 1 | — | 2 | 3 | ||
Female genital neoplasms | D005833 | — | 1 | 2 | — | — | 3 | ||
Femoral fractures | D005264 | S72 | — | 1 | 1 | — | 1 | 3 |
Show 39 more
Indications Phases 2
Indication | MeSH | Ontology | ICD-10 | Ph 1 | Ph 2 | Ph 3 | Ph 4 | Other | Total |
---|---|---|---|---|---|---|---|---|---|
Herniorrhaphy | D059685 | 1 | 3 | — | — | — | 4 | ||
Thyroid diseases | D013959 | HP_0000820 | E00-E07 | — | 1 | — | — | 2 | 3 |
Myofascial pain syndromes | D009209 | EFO_1001054 | — | 1 | — | — | 1 | 2 | |
Phimosis | D010688 | EFO_1001104 | N47.1 | 1 | 1 | — | — | — | 2 |
Paraphimosis | D010263 | EFO_1001086 | N47.2 | 1 | 1 | — | — | — | 2 |
Balanitis | D001446 | EFO_1000833 | N48.1 | 1 | 1 | — | — | — | 2 |
Thyroid nodule | D016606 | EFO_1001436 | — | 1 | — | — | 1 | 2 | |
Postherpetic neuralgia | D051474 | 1 | 1 | — | — | — | 2 | ||
Referred pain | D053591 | — | 1 | — | — | — | 1 | ||
Lacrimal apparatus diseases | D007766 | HP_0009926 | H04 | — | 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 fusion | D013123 | 2 | — | — | — | 1 | 3 | ||
Lung diseases | D008171 | EFO_0003818 | J98.4 | 1 | — | — | — | 2 | 3 |
Sternotomy | D056346 | 2 | — | — | — | — | 2 | ||
Adenomyosis | D062788 | EFO_1001757 | N80.0 | 1 | — | — | — | 1 | 2 |
Primary dysautonomias | D054969 | 2 | — | — | — | — | 2 | ||
Emergence delirium | D000071257 | 1 | — | — | — | 1 | 2 | ||
Post-dural puncture headache | D051299 | 1 | — | — | — | 1 | 2 | ||
Sphenopalatine ganglion block | D059387 | 1 | — | — | — | 1 | 2 | ||
Hiv infections | D015658 | EFO_0000764 | B20 | 2 | — | — | — | — | 2 |
Show 13 more
Indications Without Phase
Indication | MeSH | Ontology | ICD-10 | Ph 1 | Ph 2 | Ph 3 | Ph 4 | Other | Total |
---|---|---|---|---|---|---|---|---|---|
Esthetics | D004954 | — | — | — | — | 3 | 3 | ||
Congenital hip dislocation | D006618 | HP_0001385 | Q65.2 | — | — | — | — | 3 | 3 |
Postoperative complications | D011183 | — | — | — | — | 3 | 3 | ||
Renal insufficiency | D051437 | HP_0000083 | N19 | — | — | — | — | 3 | 3 |
Pre-eclampsia | D011225 | EFO_0000668 | O14 | — | — | — | — | 2 | 2 |
Hyperparathyroidism | D006961 | EFO_0008506 | E21.3 | — | — | — | — | 2 | 2 |
Bradycardia | D001919 | HP_0001662 | R00.1 | — | — | — | — | 2 | 2 |
Liver neoplasms | D008113 | EFO_1001513 | C22.0 | — | — | — | — | 2 | 2 |
Nephrectomy | D009392 | — | — | — | — | 2 | 2 | ||
Ultrasonography | D014463 | — | — | — | — | 2 | 2 |
Show 76 more
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
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
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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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