Bupivacaine - PharmaKB

Sensorcaine, 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, 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

Clinical

Drug

Target

Variants

Financial

Trends

Safety

Events Timeline

YTD

Max

Events

FDA approval date

EMA approval date

Patent expiration date

Study first post date

Last update post date

Start date

Primary completion date

Completion date

Results first post date

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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)

Combinations

Sensorcaine, Zynrelef (generic drugs available since 1986-02-17, discontinued: Duocaine)

Drug Products

FDA

EMA

New Drug Application (NDA)

Abbreviated New Drug Application (ANDA)

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

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

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Labels

FDA

EMA

Brand Name	Status	Last Update
0.25% bupivacaine hcl bupivacaine hydrochloride	ANDA	2024-01-28
bupivacaine	ANDA	2023-12-20
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	2024-01-02
bupivacaine hydrochloride and epinephrine	ANDA	2023-10-12
bupivacaine hydrochloride bupivacaine hydrochloride and epinephrine	ANDA	2024-02-15
bupivacaine hydrochloride bupivacaine hydrochloride with epinephrine		2008-08-14

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Indications

FDA

EMA

Indication	Ontology	MeSH	ICD-10
postoperative pain	—	D010149	G89.18

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

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

3351 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	39	106	70	187	380	744
Pain	D010146	EFO_0003843	R52	7	17	14	63	81	179
Analgesia	D000698	—	—	6	7	11	29	100	150
Anesthesia	D000758	—	—	4	9	7	21	71	108
Acute pain	D059787	—	R52	4	10	8	22	35	72
Spinal anesthesia	D000775	—	—	—	3	6	22	39	69
Local anesthesia	D000772	—	—	3	6	4	9	45	66
Replacement arthroplasty knee	D019645	—	—	1	4	—	29	32	66
Labor pain	D048949	—	—	2	4	4	14	28	50
Cesarean section	D002585	—	—	—	1	2	15	33	50

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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	—	8	12
Abdominal pain	D015746	HP_0002027	R10.9	—	2	1	—	7	9
Chronic pancreatitis	D050500	EFO_0000342	K86.1	1	—	2	—	5	8
Coronary artery disease	D003324	—	I25.1	1	1	2	—	3	7
Musculoskeletal diseases	D009140	—	—	—	1	1	—	4	6
Epidural anesthesia	D000767	—	—	—	1	1	—	4	6
Cleft palate	D002972	HP_0000175	Q35	—	1	1	—	2	4
Kidney calculi	D007669	EFO_0004253	N20	—	—	1	—	2	3
Visceral pain	D059265	—	—	—	—	1	—	2	3
Infratentorial neoplasms	D015192	—	C71.7	1	1	1	—	—	3

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Indications Phases 2

Indication	MeSH	Ontology	ICD-10	Ph 1	Ph 2	Ph 3	Ph 4	Other	Total
Postoperative complications	D011183	—	—	1	2	—	—	11	13
Herniorrhaphy	D059685	—	—	1	3	—	—	—	4
Postherpetic neuralgia	D051474	—	—	1	1	—	—	1	3
Thyroid diseases	D013959	HP_0000820	E00-E07	—	1	—	—	2	3
Bariatric surgery	D050110	—	—	1	1	—	—	2	3
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
Subarachnoid hemorrhage	D013345	EFO_0000713	I60	1	1	—	—	—	2
Laparoscopy	D010535	—	—	—	1	—	—	1	2

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Indications Phases 1

Indication	MeSH	Ontology	ICD-10	Ph 1	Ph 2	Ph 3	Ph 4	Other	Total
Urinary bladder neoplasms	D001749	—	C67	1	—	—	—	5	6
Hiv infections	D015658	EFO_0000764	B20	4	—	—	—	—	4
Spinal fusion	D013123	—	—	2	—	—	—	1	3
Emergence delirium	D000071257	—	—	1	—	—	—	2	3
Anxiety	D001007	EFO_0005230	F41.1	1	—	—	—	2	3
Vaginismus	D052065	—	N94.2	1	—	—	—	1	2
Covid-19	D000086382	—	U07.1	1	—	—	—	1	2
Hepatic insufficiency	D048550	—	—	1	—	—	—	1	2
Adenomyosis	D062788	EFO_1001757	N80.0	1	—	—	—	1	2
Primary dysautonomias	D054969	—	—	2	—	—	—	—	2

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Indications Without Phase

Indication	MeSH	Ontology	ICD-10	Ph 1	Ph 2	Ph 3	Ph 4	Other	Total
Thoracotomy	D013908	—	—	—	—	—	—	9	9
Cholecystitis	D002764	HP_0001082	K81	—	—	—	—	8	8
Arthroscopy	D001182	—	—	—	—	—	—	7	7
Nephrectomy	D009392	—	—	—	—	—	—	5	5
Pre-eclampsia	D011225	EFO_0000668	O14	—	—	—	—	4	4
Urinary retention	D016055	HP_0000016	R33	—	—	—	—	4	4
Ultrasonography	D014463	—	—	—	—	—	—	4	4
Arm injuries	D001134	—	—	—	—	—	—	4	4
Esthetics	D004954	—	—	—	—	—	—	3	3
Breast diseases	D001941	—	N60-N65	—	—	—	—	3	3

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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

KCND3

KCNA5

SCN5A

Organism

Homo sapiens

Gene name

KCNJ6

Gene synonyms

GIRK2, KATP2, KCNJ7

NCBI Gene ID

3763

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

Q53WW6

Mouse ortholog

Kcnj6 (16522)

G protein-activated inward rectifier potassium channel 2 (P48542)

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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Refill frequency

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Price per prescription (USD)

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Trends

PubMed Central

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Additional graphs summarizing 25,484 documents

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Safety

Black-box Warning

Black-box warning for: 0.25% bupivacaine hcl bupivacaine hydrochloride, 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 sensorcaine, Sensorcaine sensorcaine-mpf sensorcaine-mpf, Sensorcaine(r) (bupivacaine hci and epinephrine), Sensorcaine-mpf, Zynrelef

Adverse Events

Top Adverse Reactions

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12,130 adverse events reported

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