Bupivacaine chloride |
![]() Last updated: 15/09/2025 |
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(Also known as: marcaine hydrochloride) |
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A veterinary analgesic mainly used for post-operative care | |
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Post-operative pain | |
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Cats; Dogs; Pigs; Horses; Cattle |
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Approved - usually supplied as a prescription only medicine to be authorised by a veterinarian (POM-V) | |
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Approved |
Chemical structure |
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Bupivacaine chloride exhibits optical isomerism due to the presence of a chiral centre in its molecular structure. This chiral carbon allows for two enantiomers: R(+)-bupivacaine and S(–)-bupivacaine. The racemic mixture is commonly used in clinical practice, but the S(–)-enantiomer, known as levobupivacaine, has gained favour due to its lower cardiotoxicity while maintaining effective nerve blockade. Studies have shown that the R(+)-enantiomer is more potent in blocking sodium channels but also more likely to cause adverse effects on the cardiovascular and central nervous systems. | |
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C₁₈H₂₉ClN₂O | |
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CCCCN1CCCCC1C(=O)NC2=C(C=CC=C2C)C.Cl | |
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SIEYLFHKZGLBNX-UHFFFAOYSA-N | |
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InChI=1S/C18H28N2O.ClH/c1-4-5-12-20-13-7-6-11-16(20)18(21)19-17-14(2)9-8-10-15(17)3;/h8-10,16H,4-7,11-13H2,1-3H3,(H,19,21);1H | |
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Yes |
General status |
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Analgesic; Anesthetic; Medicinal drug | |
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Amide drug | |
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Sodium channel inhibitor. Blocks the excitatory conduction of the nerves through the stabilisation of the neuronal membrane | |
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[Sodium channel protein type 10 subunit alpha, Inhibitor] | |
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18010-40-7 | |
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241-917-8 | |
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64737 | |
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Dermatologicals; Anesthetics for topical use; lidocaine, combinations | |
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QD04AB51 | |
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No | |
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324.9 | |
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1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide;hydrochloride | |
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2',6'-pipecoloxylidide, 1-butyl-, monohydrochloride | |
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White crystalline powder when pure. Clear, blue, semi-viscous liquid when formulated |
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1957, discovered; 1965, introduced to the market for clinical use | |||
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Usually supplied as a solution for injection | |||
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The production of bupivacaine chloride involves a multi-step chemical synthesis starting from 2-piperidinecarboxylic acid, which is first reacted with benzyloxycarbonyl chloride (Cbz) in an alkaline aqueous solution to protect the amine group. After extraction and purification, the protected intermediate is coupled with 2,6-dimethylaniline in dimethylformamide using a catalyst to form the amide linkage. The resulting compound undergoes hydrogenation under pressure to remove the Cbz protecting group, yielding bupivacaine base. This base is then reacted with bromo-n-butane to form the quaternary ammonium salt, followed by treatment with diluted hydrochloric acid to produce bupivacaine hydrochloride. | |||
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Published GHG data is not available for most pharmaceuticals. However, according to industry, global averages suggest producing 1 kg of a typical active pharmaceutical ingredient can range from 10 to 100 kg CO₂e for small molecule drugs and potentially up to 1000 kg CO₂e for complex biologicals such as vaccines, depending on the drug type, its formulation, complexity of synthesis, solvent recovery, and energy sources used. |
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107 | F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment ) 4 = Verified data |
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3.31 | Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source |
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No adverse environmental impacts identified or anticipated |
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As this parameter is not normally measured directly, a surrogate measure is used: ‘Photochemical oxidative DT₅₀’. Where data is available, this can be found in the Fate Indices section below. | ||||||||||
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Fate indices |
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Known soil and groundwater metabolites |
None
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2,6-pipecoloxylidine | - | Mammals | - |
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Metabolised in the liver. Aound 1-10% of bupivacaine is excreted unchanged in the urine. | Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source |
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Health issues |
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Possible cardiotoxin |
Handling issues |
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No information available | |||
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bupivacaine chloride | ||
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Record last updated: | 15/09/2025 |
Contact: | aeru@herts.ac.uk |
Please cite as: | Lewis, K.A., Tzilivakis, J., Warner, D. and Green, A. (2016) An international database for pesticide risk assessments and management. Human and Ecological Risk Assessment: An International Journal, 22(4), 1050-1064. DOI: 10.1080/10807039.2015.1133242 |