Levobupivacaine
Chirocaine (levobupivacaine) is a small molecule pharmaceutical. Levobupivacaine was first approved as Chirocaine on 1999-08-05. It is used to treat pain in the USA.
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Levobupivacaine hydrochloride
Tradename | Company | Number | Date | Products |
|---|---|---|---|---|
| CHIROCAINE | Purdue Pharma | N-020997 DISCN | 1999-08-05 | 3 products, RLD |
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EMA
Brand Name | Status | Last Update |
|---|---|---|
| 0.25% bupivacaine hcl bupivacaine hydrochloride | ANDA | 2024-06-20 |
| blt-25 kit | unapproved drug other | 2026-01-07 |
| bupivacaine | ANDA | 2026-04-07 |
| bupivacaine hci | ANDA | 2024-01-22 |
| bupivacaine hci and epinephrine | ANDA | 2024-01-30 |
| bupivacaine hcl | New Drug Application | 2026-06-22 |
| bupivacaine hcl bupivacine hcl | ANDA | 2023-06-09 |
| bupivacaine hydrochloride | ANDA | 2026-07-20 |
| bupivacaine hydrochloride and epinephrine | ANDA | 2025-10-27 |
| bupivacaine hydrochloride bupivacaine hydrochloride and epinephrine | ANDA | 2026-03-09 |
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Indications
FDA
EMA
Indication | Ontology | MeSH | ICD-10 |
|---|---|---|---|
| pain | EFO_0003843 | D010146 | R52 |
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Clinical Trials
607 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 | — | 7 | 11 | 34 | 100 | 148 |
| Analgesia | D000698 | — | — | — | 2 | 2 | 7 | 25 | 36 |
| Pain | D010146 | EFO_0003843 | R52 | 1 | — | 3 | 17 | 13 | 34 |
| Anesthesia | D000758 | — | — | 1 | 3 | 2 | 8 | 15 | 27 |
| Agnosia | D000377 | EFO_0007136 | F88 | — | 2 | 3 | 5 | 16 | 26 |
| Breast neoplasms | D001943 | EFO_0003869 | C50 | — | 1 | — | 4 | 17 | 22 |
| Acute pain | D059787 | — | R52 | 1 | 3 | 2 | 2 | 11 | 17 |
| Local anesthesia | D000772 | — | — | — | — | 1 | 4 | 11 | 16 |
| Hip fractures | D006620 | EFO_0003964 | S72.00 | — | — | — | 7 | 8 | 15 |
| Nerve block | D009407 | — | — | — | — | 1 | 4 | 9 | 14 |
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Indications Phases 3
Indication | MeSH | Ontology | ICD-10 | Ph 1 | Ph 2 | Ph 3 | Ph 4 | Other | Total |
|---|---|---|---|---|---|---|---|---|---|
| Paralysis | D010243 | — | — | — | — | 1 | — | 4 | 5 |
| Syndrome | D013577 | — | — | — | — | 1 | — | 4 | 5 |
| Respiratory paralysis | D012133 | EFO_1001840 | — | — | — | 1 | — | 3 | 4 |
| Brachial plexus block | D065527 | — | — | — | — | 1 | — | 3 | 4 |
| Cleft palate | D002972 | EFO_0003920 | Q35 | — | 1 | 1 | — | 2 | 3 |
| Abdominal pain | D015746 | EFO_0003766 | R10.9 | — | 1 | 1 | — | 2 | 3 |
| Complex regional pain syndromes | D020918 | EFO_1001998 | — | — | — | 1 | — | 2 | 3 |
| Reflex sympathetic dystrophy | D012019 | EFO_1001147 | G90.5 | — | — | 1 | — | 2 | 3 |
| Neoplasms | D009369 | — | C80 | — | 1 | 1 | — | 1 | 2 |
| Spinal diseases | D013122 | — | M45-M49 | — | — | 1 | — | 1 | 2 |
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Indications Phases 2
Indication | MeSH | Ontology | ICD-10 | Ph 1 | Ph 2 | Ph 3 | Ph 4 | Other | Total |
|---|---|---|---|---|---|---|---|---|---|
| Laryngismus | D007826 | — | J38.5 | 1 | 1 | — | — | — | 1 |
| Cryptorchidism | D003456 | EFO_0004562 | Q53.1 | — | 1 | — | — | — | 1 |
| Postoperative cognitive complications | D000079690 | — | — | — | 1 | — | — | — | 1 |
Indications Phases 1
Indication | MeSH | Ontology | ICD-10 | Ph 1 | Ph 2 | Ph 3 | Ph 4 | Other | Total |
|---|---|---|---|---|---|---|---|---|---|
| Obstetric labor complications | D007744 | — | — | 1 | — | — | — | 2 | 3 |
| Kidney neoplasms | D007680 | EFO_0003865 | C64 | 1 | — | — | — | 1 | 2 |
| Morton neuroma | D000070607 | — | G57.6 | 1 | — | — | — | — | 1 |
Indications Without Phase
Indication | MeSH | Ontology | ICD-10 | Ph 1 | Ph 2 | Ph 3 | Ph 4 | Other | Total |
|---|---|---|---|---|---|---|---|---|---|
| Video-assisted thoracic surgery | D020775 | — | — | — | — | — | — | 8 | 8 |
| Neuralgia | D009437 | EFO_0009430 | — | — | — | — | — | 5 | 5 |
| Aortic dissection | D000784 | — | I71.0 | — | — | — | — | 4 | 4 |
| Emergence delirium | D000071257 | — | — | — | — | — | — | 3 | 3 |
| Arm injuries | D001134 | — | — | — | — | — | — | 3 | 3 |
| Headache | D006261 | — | R51 | — | — | — | — | 3 | 3 |
| Lung neoplasms | D008175 | — | C34.90 | — | — | — | — | 3 | 3 |
| Strabismus | D013285 | — | H50.2 | — | — | — | — | 2 | 2 |
| Pelvic organ prolapse | D056887 | EFO_0004710 | — | — | — | — | — | 2 | 2 |
| Prolapse | D011391 | — | — | — | — | — | — | 2 | 2 |
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Epidemiology
Epidemiological information for investigational and approved indications
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Drug
General
| Drug common name | Levobupivacaine |
| INN | levobupivacaine |
| Description | Levobupivacaine is the (S)-(-)-enantiomer of bupivacaine. It has a role as a local anaesthetic, an adrenergic antagonist, an amphiphile, an EC 3.1.1.8 (cholinesterase) inhibitor and an EC 3.6.3.8 (Ca(2+)-transporting ATPase) inhibitor. It is a conjugate base of a levobupivacaine(1+). It is an enantiomer of a dextrobupivacaine. |
| Classification | Small molecule |
| Drug class | local anesthetics |
| Image (chem structure or protein) |  |
| Structure (InChI/SMILES or Protein Sequence) | CCCCN1CCCC[C@H]1C(=O)Nc1c(C)cccc1C |
Identifiers
| PDB | — |
| CAS-ID | 27262-47-1 |
| RxCUI | — |
| ChEMBL ID | CHEMBL1201193 |
| ChEBI ID | 6149 |
| PubChem CID | 92253 |
| DrugBank | DB01002 |
| UNII ID | A5H73K9U3W (ChemIDplus, GSRS) |
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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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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, Marvona-25 suik, Mlk f1 kit, Mlk f3 kit, Mlk f4 kit, Mlk kit f2, Posimir, Sensorcaine, Sensorcaine mpf, Sensorcaine sensorcaine, Sensorcaine sensorcaine-mpf sensorcaine-mpf, Sensorcaine(r) (bupivacaine hci and epinephrine), Sensorcaine-mpf, Zynrelef
Adverse Events
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532 adverse events reported
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