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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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 | 2025-10-03 |
| bupivacaine hydrochloride and epinephrine | ANDA | 2024-10-14 |
| bupivacaine hydrochloride bupivacaine hydrochloride and epinephrine | ANDA | 2024-10-15 |
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Indications
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EMA
Indication | Ontology | MeSH | ICD-10 |
|---|---|---|---|
| pain | EFO_0003843 | D010146 | R52 |
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Clinical Trials
560 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 | — | 6 | 10 | 33 | 89 | 135 |
| Analgesia | D000698 | — | — | — | 2 | 2 | 7 | 24 | 35 |
| Pain | D010146 | EFO_0003843 | R52 | 1 | — | 3 | 16 | 9 | 29 |
| Anesthesia | D000758 | — | — | 1 | 3 | 2 | 8 | 15 | 27 |
| 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 |
| Agnosia | D000377 | EFO_0007136 | F88 | — | — | 3 | 4 | 8 | 15 |
| Hip fractures | D006620 | EFO_0003964 | S72.00 | — | — | — | 7 | 7 | 14 |
| Inguinal hernia | D006552 | HP_0000023 | K40 | 1 | 2 | 1 | 2 | 9 | 14 |
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Indications Phases 3
Indication | MeSH | Ontology | ICD-10 | Ph 1 | Ph 2 | Ph 3 | Ph 4 | Other | Total |
|---|---|---|---|---|---|---|---|---|---|
| Back pain | D001416 | — | M54 | — | — | 1 | — | 5 | 6 |
| Paralysis | D010243 | — | — | — | — | 1 | — | 4 | 5 |
| Syndrome | D013577 | — | — | — | — | 1 | — | 4 | 5 |
| Respiratory paralysis | D012133 | EFO_1001840 | — | — | — | 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 |
| Brachial plexus block | D065527 | — | — | — | — | 1 | — | 2 | 3 |
| Neoplasms | D009369 | — | C80 | — | 1 | 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 | — | — | — | — | — | — | 7 | 7 |
| Neuralgia | D009437 | EFO_0009430 | — | — | — | — | — | 5 | 5 |
| Aortic dissection | D000784 | — | I71.0 | — | — | — | — | 4 | 4 |
| Arm injuries | D001134 | — | — | — | — | — | — | 3 | 3 |
| Headache | D006261 | — | R51 | — | — | — | — | 3 | 3 |
| Strabismus | D013285 | — | H50.2 | — | — | — | — | 2 | 2 |
| Pelvic organ prolapse | D056887 | EFO_0004710 | — | — | — | — | — | 2 | 2 |
| Prolapse | D011391 | — | — | — | — | — | — | 2 | 2 |
| Prostatic neoplasms | D011471 | — | C61 | — | — | — | — | 2 | 2 |
| Nausea | D009325 | — | R11.0 | — | — | — | — | 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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Zynrelef – Heron Therapeutics /de/
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Exparel – Pacira BioSciences
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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, 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
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482 adverse events reported
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