Procaine benzylpenicillin |
![]() Last updated: 16/09/2025 |
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(Also known as: penicillin G procaine) |
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A combination of benzylpenicillin with the local anaesthetic agent procaine used as an anesthetic | |
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Used as a local anaesthetic for minor surgical procedures on a variety of animals | |
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Cattle; Sheep; Goats, Horses; Pigs; Dogs; Cats |
Approval status |
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Approved - usually available as a prescription only medicine to be authorised by a veterinarian (POM-V) | |
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Approved |
Chemical structure |
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Procaine benzylpenicillin exhibits chiral isomerism, due to the presence of multiple asymmetric carbon atoms in the benzylpenicillin portion of the molecule. The penicillin nucleus contains chiral centres at positions 3, 5, and 6, which are essential for its beta-lactam ring structure and antibacterial activity. The procaine component also contains a chiral centre, but in pharmaceutical formulations, procaine is typically used as a racemic mixture. When combined, procaine benzylpenicillin forms an equimolar salt, where the stereochemistry of benzylpenicillin governs the drug’s biological activity. | |
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C₂₉H₃₈N₄O₆S | |
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CCN(CC)CCOC(=O)C1=CC=C(C=C1)N.CC1(C(N2C(S1)C(C2=O)NC(=O)CC3=CC=CC=C3)C(=O)O)C | |
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CCN(CC)CCOC(=O)C1=CC=C(C=C1)N.CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)CC3=CC=CC=C3)C(=O)O)C | |
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WHRVRSCEWKLAHX-LQDWTQKMSA-N | |
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InChI=1S/C16H18N2O4S.C13H20N2O2/c1-16(2)12(15(21)22)18-13(20)11(14(18)23-16)17-10(19)8-9-6-4-3-5-7-9;1-3-15(4-2)9-10-17-13(16)11-5-7-12(14)8-6-11/h3-7,11-12,14H,8H2,1-2H3,(H,17,19)(H,21,22);5-8H,3-4,9-10,14H2,1-2H3/t11-,12+,14-;/m1./s1 | |
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Yes |
General status |
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Anesthetic, Medicinal drug | |
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Aminobenzoate | |
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Synthetic | |
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Sodium channel modulator | |
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[Sodium channel protein type 10 subunit alpha, Antagonist], [Glutamate [NMDA] receptor subunit 3A, Antagonist], [5-hydroxytryptamine 3 receptor, Antagonist], [Sodium-dependent dopamine transporter, Antagonist], [Neuronal acetylcholine receptor subunit alpha-2, Antagonist] | |
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54-35-3 | |
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5903 | |
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Nervous system: Anaesthetic | |
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QN01BA52 | |
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No | |
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Allowed susbstance (Table 1: All food producing species) | |
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570.7 | |
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2-(diethylamino)ethyl 4-aminobenzoate;(2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid | |
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Commercial |
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Current | |||
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1928, penicillin discovered; 1950s, procain salt developed; 1960s, widespread agricultural use | |||
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Usually supplied as a sterile suspension solution for subcutaneous injection | |||
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The production of procaine benzylpenicillin involves combining two key components: benzylpenicillin and procaine. First, benzylpenicillin is produced through fermentation of Penicillium chrysogenum in a nutrient-rich medium under aerobic conditions. After fermentation, the penicillin is extracted using solvent partitioning, typically with amyl acetate or butyl acetate, and then purified through crystallization. Separately, procaine base is synthesised via chemical methods involving p-aminobenzoic acid and diethylaminoethanol. The two compounds are then reacted in equimolar amounts to form the procaine salt of benzylpenicillin. | |||
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As microbial-based products tend to use fermentation-based production processes rather than chemical synthesis, they typically have a lower fossil fuel input in formulation and active ingredient creation, and also have reduced downstream emissions due to biodegradability and minimal soil disruption, their life-cycle GHG emissions are expected to be low. Whilst hard and precise data is not available, broad estimates suggest that typically emissions are likely to be below 5 kg CO₂e/kg. However, the semi-synthetic production process of procaine benzylpenicillin will push emissions higher. |
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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 metabolites |
None
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Terrestrial ecotoxicology |
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200 | Q3 Q = Miscellaneous data from online sources Rat3 = Unverified data of known source |
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General |
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High (class III) | - | - | ||||||||
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200 | Q3 Q = Miscellaneous data from online sources Rat3 = Unverified data of known source |
Moderate | ||||||||
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Majority is metabolised and the metabolised are rapidly (in minutes) excreted mostly 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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May cause cardiac and vasodilation effects May cause serious allergic reactions Harmful if swallowed |
Handling issues |
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When heated to decomposition it emits toxic fumes of nitroxides IMDG Transport Hazard Class 6.1 Hygroscopic in air |
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Not listed (Not listed) | |||
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UN2811 | |||
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Packaging Group III (minor danger) | |||
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procaine benzylpenicillin | ||
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Record last updated: | 16/09/2025 |
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 |