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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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 | 2025-01-10 |
| bupivacaine hydrochloride and epinephrine | ANDA | 2024-10-14 |
| bupivacaine hydrochloride bupivacaine hydrochloride and epinephrine | ANDA | 2024-10-15 |
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Indications
FDA
EMA
Indication | Ontology | MeSH | ICD-10 |
|---|---|---|---|
| pain | EFO_0003843 | D010146 | R52 |
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4059 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 | 49 | 132 | 107 | 263 | 682 | 1184 |
| Pain | D010146 | EFO_0003843 | R52 | 7 | 17 | 17 | 73 | 92 | 203 |
| Analgesia | D000698 | — | — | 6 | 8 | 14 | 36 | 138 | 199 |
| Anesthesia | D000758 | — | — | 4 | 10 | 9 | 26 | 90 | 134 |
| Bone fractures | D050723 | EFO_0003931 | T14.8 | 7 | 7 | 8 | 26 | 74 | 119 |
| Acute pain | D059787 | — | R52 | 4 | 12 | 9 | 27 | 66 | 111 |
| Local anesthesia | D000772 | — | — | 7 | 7 | 6 | 17 | 68 | 103 |
| Hernia | D006547 | — | K40-K46 | 4 | 10 | 9 | 15 | 60 | 94 |
| Replacement arthroplasty knee | D019645 | — | — | 2 | 5 | 2 | 41 | 43 | 92 |
| Spinal anesthesia | D000775 | — | — | 2 | 3 | 6 | 27 | 55 | 92 |
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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 | — | 24 | 28 |
| Kidney calculi | D007669 | EFO_0004253 | N20 | — | 1 | 2 | — | 10 | 13 |
| Nephrolithiasis | D053040 | — | N20.0 | — | 1 | 1 | — | 10 | 12 |
| Cholecystitis | D002764 | — | K81 | — | — | 1 | — | 11 | 12 |
| Shoulder injuries | D000070599 | — | — | — | 1 | 1 | — | 10 | 12 |
| Abdominal pain | D015746 | EFO_0003766 | R10.9 | — | 3 | 2 | — | 8 | 11 |
| Coronary artery disease | D003324 | — | I25.1 | 1 | 1 | 2 | — | 6 | 10 |
| Pancreatitis | D010195 | EFO_0000278 | K85 | 1 | — | 2 | — | 7 | 10 |
| Thyroid diseases | D013959 | — | E00-E07 | — | 3 | 2 | — | 6 | 10 |
| Nephrectomy | D009392 | — | — | — | 1 | 1 | — | 7 | 8 |
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Indications Phases 2
Indication | MeSH | Ontology | ICD-10 | Ph 1 | Ph 2 | Ph 3 | Ph 4 | Other | Total |
|---|---|---|---|---|---|---|---|---|---|
| Herniorrhaphy | D059685 | — | — | 1 | 3 | — | — | 3 | 7 |
| Postherpetic neuralgia | D051474 | — | — | 1 | 1 | — | — | 3 | 5 |
| Laminectomy | D007796 | — | — | — | 1 | — | — | 3 | 4 |
| Post-traumatic headache | D051298 | — | G44.3 | 1 | 1 | — | — | 2 | 4 |
| Rhinosinusitis | D000096825 | — | — | 1 | 2 | — | — | 1 | 3 |
| Postoperative cognitive complications | D000079690 | — | — | — | 1 | — | — | 2 | 3 |
| Headache disorders | D020773 | EFO_0009550 | G44 | — | 1 | — | — | 2 | 3 |
| Cluster headache | D003027 | — | G44.00 | — | 1 | — | — | 2 | 3 |
| Radical mastectomy | D015409 | — | — | 1 | 1 | — | — | 2 | 3 |
| Nasal polyps | D009298 | — | J33 | — | 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 | — | — | — | 7 | 8 |
| Respiratory insufficiency | D012131 | — | J96.9 | 1 | — | — | — | 4 | 5 |
| Hiv infections | D015658 | EFO_0000764 | B20 | 4 | — | — | — | — | 4 |
| 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 | — | U07.1 | 2 | — | — | — | — | 2 |
| Breast implantation | D019928 | — | — | 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 | — | — | — | — | — | — | 13 | 13 |
| Ischemia | D007511 | EFO_0000556 | — | — | — | — | — | 6 | 6 |
| Acalculous cholecystitis | D042101 | EFO_1000790 | — | — | — | — | — | 6 | 6 |
| Aortic valve stenosis | D001024 | EFO_0000266 | — | — | — | — | — | 5 | 5 |
| Acute cholecystitis | D041881 | EFO_1001289 | K81.0 | — | — | — | — | 5 | 5 |
| Congenital abnormalities | D000013 | EFO_0003915 | Q89.9 | — | — | — | — | 4 | 4 |
| Kidney diseases | D007674 | EFO_0003086 | N08 | — | — | — | — | 4 | 4 |
| Breast diseases | D001941 | — | N60-N65 | — | — | — | — | 4 | 4 |
| Rheumatoid arthritis | D001172 | EFO_0000685 | M06.9 | — | — | — | — | 4 | 4 |
| Diabetic foot | D017719 | EFO_1001459 | — | — | — | — | — | 4 | 4 |
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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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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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13,773 adverse events reported
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