Bupivacaine hydrochloride, Zynrelef(bupivacaine)
Bupivacaine, Duocaine, Exparel, Marcaine, Posimir, Sensorcaine, Vivacaine, 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, 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, Posimir, Sensorcaine, Xaracoll (discontinued: Bupivacaine, Sensorcaine)
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 |
| XARACOLL | Innocoll | N-209511 RX | 2020-08-28 | 1 products, RLD, RS |
Show 2 discontinued
Bupivacaine
Tradename | Company | Number | Date | Products |
|---|---|---|---|---|
| POSIMIR | Innocoll | N-204803 RX | 2021-02-01 | 1 products, RLD, RS |
| EXPAREL | Pacira BioSciences | N-022496 RX | 2011-10-28 | 2 products, RLD, RS |
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 |
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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 | 2024-11-04 |
| bupivacaine hydrochloride and epinephrine | ANDA | 2024-10-14 |
| bupivacaine hydrochloride bupivacaine hydrochloride and epinephrine | ANDA | 2024-10-15 |
Show 63 more
Indications
FDA
EMA
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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
3621 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 | 53 | 128 | 96 | 238 | 626 | 1094 |
| Pain | D010146 | EFO_0003843 | R52 | 7 | 17 | 14 | 63 | 87 | 185 |
| Analgesia | D000698 | — | — | 6 | 6 | 12 | 30 | 122 | 173 |
| Anesthesia | D000758 | — | — | 4 | 10 | 8 | 22 | 83 | 122 |
| Bone fractures | D050723 | EFO_0003931 | T14.8 | 7 | 7 | 8 | 24 | 66 | 109 |
| Acute pain | D059787 | — | R52 | 4 | 11 | 9 | 25 | 59 | 101 |
| Local anesthesia | D000772 | — | — | 6 | 7 | 5 | 14 | 61 | 91 |
| Spinal anesthesia | D000775 | — | — | 2 | 3 | 6 | 24 | 52 | 86 |
| Hernia | D006547 | HP_0100790 | K40-K46 | 4 | 9 | 7 | 14 | 53 | 84 |
| Replacement arthroplasty knee | D019645 | — | — | 1 | 4 | — | 36 | 43 | 84 |
Show 373 more
Indications Phases 3
Indication | MeSH | Ontology | ICD-10 | Ph 1 | Ph 2 | Ph 3 | Ph 4 | Other | Total |
|---|---|---|---|---|---|---|---|---|---|
| Video-assisted thoracic surgery | D020775 | — | — | 2 | 2 | 1 | — | 23 | 27 |
| Kidney calculi | D007669 | EFO_0004253 | N20 | — | 1 | 2 | — | 9 | 12 |
| Cholecystitis | D002764 | HP_0001082 | K81 | — | — | 1 | — | 11 | 12 |
| Nephrolithiasis | D053040 | — | N20.0 | — | 1 | 1 | — | 9 | 11 |
| Coronary artery disease | D003324 | — | I25.1 | 1 | 1 | 2 | — | 6 | 10 |
| Pancreatitis | D010195 | HP_0001733 | K85 | 1 | — | 2 | — | 7 | 10 |
| Abdominal pain | D015746 | HP_0002027 | R10.9 | — | 2 | 1 | — | 8 | 10 |
| Shoulder injuries | D000070599 | — | — | — | 1 | 1 | — | 8 | 10 |
| Thyroid diseases | D013959 | HP_0000820 | E00-E07 | — | 3 | 1 | — | 6 | 9 |
| Chronic pancreatitis | D050500 | EFO_0000342 | K86.1 | 1 | — | 2 | — | 5 | 8 |
Show 71 more
Indications Phases 2
Indication | MeSH | Ontology | ICD-10 | Ph 1 | Ph 2 | Ph 3 | Ph 4 | Other | Total |
|---|---|---|---|---|---|---|---|---|---|
| Laparoscopy | D010535 | — | — | — | 2 | — | — | 7 | 9 |
| Herniorrhaphy | D059685 | — | — | 1 | 3 | — | — | 2 | 6 |
| Laminectomy | D007796 | — | — | — | 1 | — | — | 3 | 4 |
| Postherpetic neuralgia | D051474 | — | — | 1 | 1 | — | — | 2 | 4 |
| Post-traumatic headache | D051298 | — | G44.3 | 1 | 1 | — | — | 2 | 4 |
| Rhinosinusitis | D000096825 | — | — | 1 | 2 | — | — | 1 | 3 |
| Headache disorders | D020773 | EFO_0009550 | G44 | — | 1 | — | — | 2 | 3 |
| Nasal polyps | D009298 | HP_0100582 | J33 | — | 1 | — | — | 1 | 2 |
| Blood coagulation disorders | D001778 | EFO_0009314 | D68.9 | — | 1 | — | — | 1 | 2 |
| Hemostatic disorders | D020141 | — | — | — | 1 | — | — | 1 | 2 |
Show 37 more
Indications Phases 1
Indication | MeSH | Ontology | ICD-10 | Ph 1 | Ph 2 | Ph 3 | Ph 4 | Other | Total |
|---|---|---|---|---|---|---|---|---|---|
| Urinary bladder neoplasms | D001749 | — | C67 | 1 | — | — | — | 6 | 7 |
| Respiratory insufficiency | D012131 | HP_0002093 | J96.9 | 1 | — | — | — | 4 | 5 |
| Hiv infections | D015658 | EFO_0000764 | B20 | 4 | — | — | — | — | 4 |
| Vitreoretinal surgery | D057586 | — | — | 1 | — | — | — | 2 | 3 |
| Infections | D007239 | EFO_0000544 | — | 2 | — | — | — | 1 | 3 |
| Anxiety | D001007 | EFO_0005230 | F41.1 | 1 | — | — | — | 2 | 3 |
| Vaginismus | D052065 | — | N94.2 | 1 | — | — | — | 1 | 2 |
| Covid-19 | D000086382 | — | — | 1 | — | — | — | 1 | 2 |
| Hepatic insufficiency | D048550 | — | — | 1 | — | — | — | 1 | 2 |
| Pudendal neuralgia | D060545 | — | — | 1 | — | — | — | 1 | 2 |
Show 30 more
Indications Without Phase
Indication | MeSH | Ontology | ICD-10 | Ph 1 | Ph 2 | Ph 3 | Ph 4 | Other | Total |
|---|---|---|---|---|---|---|---|---|---|
| Thoracotomy | D013908 | — | — | — | — | — | — | 13 | 13 |
| Ultrasonography | D014463 | — | — | — | — | — | — | 11 | 11 |
| Nephrectomy | D009392 | — | — | — | — | — | — | 7 | 7 |
| Arthroscopy | D001182 | — | — | — | — | — | — | 7 | 7 |
| Ischemia | D007511 | EFO_0000556 | — | — | — | — | — | 6 | 6 |
| Acalculous cholecystitis | D042101 | EFO_1000790 | — | — | — | — | — | 6 | 6 |
| Acute cholecystitis | D041881 | EFO_1001289 | K81.0 | — | — | — | — | 5 | 5 |
| Congenital abnormalities | D000013 | EFO_0003915 | Q89.9 | — | — | — | — | 4 | 4 |
| Pre-eclampsia | D011225 | EFO_0000668 | O14 | — | — | — | — | 4 | 4 |
| Breast diseases | D001941 | — | N60-N65 | — | — | — | — | 4 | 4 |
Show 231 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
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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Exparel – Pacira BioSciences
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Zynrelef – Heron Therapeutics /de/
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Bupivacaine – 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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Trends
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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, Readysharp anesthetics plus ketorolac, 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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14,873 adverse events reported
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