Bacitracin zinc |
![]() Last updated: 14/09/2025 |
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(Not known by any other names) |
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A broad spectrum antibiotic used primarily against gram-positive infections often in combination with other antibacterial compounds such as tetracyclin or prednisolone | |
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Used to treart mastitis in lactating cows. Sometimes used as a growth promotor but now banned in many countries. | |
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Meat poultry; Pigs; Sheep; Cattle; Rabbits |
Approval status |
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Not approved | |
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Not approved |
Chemical structure |
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Bacitracin zinc exhibits structural and stereoisomerism due to its nature as a mixture of closely related cyclic polypeptides, primarily bacitracins A, B1, B2, and B3. These components differ slightly in their amino acid sequences and side chains, leading to positional isomers and sequence isomers within the mixture. Additionally, bacitracin contains both L- and D-amino acids, which introduces stereoisomerism at multiple chiral centres throughout the peptide backbone. One notable isomeric feature involves the N-terminal thiazoline ring, which is stereochemically fragile and prone to epimerization during synthesis or storage. This can lead to the formation of undesired epimers that may alter the biological activity or stability of the compound. | |
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C₆₆H₁₀₁N₁₇O₁₆SZn | |
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CCC(C)C1C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NCCCCC(C(=O)NC(C(=O)N1)CCCN)NC(=O)C(C(C)CC)NC(=O)C(CCC(=O)[O-])NC(=O)C(CC(C)C)NC(=O)C2CSC(=N2)C(C(C)CC)N)CC(=O)N)CC(=O)[O-])CC3=CN=CN3)CC4=CC=CC=C4.[Zn+2] | |
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CC[C@H](C)[C@H]1C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)NCCCC[C@@H](C(=O)N[C@@H](C(=O)N1)CCCN)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@@H](CCC(=O)[O-])NC(=O)[C@H](CC(C)C)NC(=O)C2CSC(=N2)C(C(C)CC)N)CC(=O)N)CC(=O)[O-])CC3=CN=CN3)CC4=CC=CC=C4.[Zn+2] | |
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UCRLQOPRDMGYOA-FCHFGNCGSA-L | |
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InChI=1S/C66H103N17O16S.Zn/c1-9-35(6)52(69)66-81-48(32-100-66)63(97)76-43(26-34(4)5)59(93)74-42(22-23-50(85)86)58(92)83-53(36(7)10-2)64(98)75-40-20-15-16-25-71-55(89)46(29-49(68)84)78-62(96)47(30-51(87)88)79-61(95)45(28-39-31-70-33-72-39)77-60(94)44(27-38-18-13-12-14-19-38)80-65(99)54(37(8)11-3)82-57(91)41(21-17-24-67)73-56(40)90;/h12-14,18-19,31,33-37,40-48,52-54H,9-11,15-17,20-30,32,67,69H2,1-8H3,(H2,68,84)(H,70,72)(H,71,89)(H,73,90)(H,74,93)(H,75,98)(H,76,97)(H,77,94)(H,78,96)(H,79,95)(H,80,99)(H,82,91)(H,83,92)(H,85,86)(H,87,88);/q;+2/p-2/t35?,36-,37-,40-,41+,42+,43-,44+,45-,46-,47+,48?,52?,53-,54-;/m0./s1 | |
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Yes |
General status |
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Medicinal drug, Antibiotic, Antibacterial, Antimicrobial, Medicated feed additive, Growth promotor | |
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Polypeptide complex | |
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Natural | |
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Inhibits the biosynthesis of bacterium cell wall | |
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[C55-isoprenyl pyrophosphate, Antagonist], [Insulin-degrading enzyme, Antagonist]; [Alpha-2-macroglobulin, Antagonist] | |
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1405-89-6 | |
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215-787-8 · | |
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16219032 | |
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Alimentary tract & metabolism: Intestinal anti-infective | |
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QA07AA93 | |
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No | |
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Allowed substance (Table 1: Bovine, Rabbit) | |
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1486.1 | |
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zinc;(4R)-4-[[(2S)-2-[[2-(1-amino-2-methylbutyl)-4,5-dihydro-1,3-thiazole-4-carbonyl]amino]-4-methylpentanoyl]amino]-5-[[(2S,3S)-1-[[(3S,6R,9S,12R,15S,18R,21S)-3-(2-amino-2-oxoethyl)-18-(3-aminopropyl)-12-benzyl-15-[(2S)-butan-2-yl]-6-(carboxylatomethyl)-9-(1H-imidazol-5-ylmethyl)-2,5,8,11,14,17,20-heptaoxo-1,4,7,10,13,16,19-heptazacyclopentacos-21-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-5-oxopentanoate | |
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Banned in EU as growth promotor; Not approved as feed additive in EU | |
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Commercial |
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Considered obsolete but may be available in some countries | |||
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1945, isolated | |||
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Usually formulated as a medicated feed additive or feed grade antibiotic | |||
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Bacitracin zinc is produced through a two-phase process involving microbial fermentation followed by chemical salification. First, Bacillus licheniformis is cultured under optimised conditions, typically in a submerged fermentation system using nutrient-rich media derived from agricultural waste like soybean meal or cucumber peel. After 48 hours of fermentation at around 37 DegC and pH 7, the bacitracin-rich broth is filtered to isolate the crude antibiotic. In the second phase, a zinc salt solution (such as zinc sulphate) is added to the filtrate under acidic conditions (pH 2.5–6.0), followed by gradual pH adjustment to 6.5–8.5 using sodium hydroxide. | |||
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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 Bacitracin zinc will push emissions higher. |
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Bacitracin has been identified in poultry manure and litter and so may be transferred to soils if spread. However, data suggests it rapidly degrades. |
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4.5 | F3 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 ) USEPA data - DT₅₀ in chicken litter 2-7 days; Degradation in pig faeces DT₅₀ <2.0 days3 = Unverified data of known source |
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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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desamidobasitracin | - | Chickens; Pigs | - |
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Terrestrial ecotoxicology |
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> 3751 | 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 ) Mouse4 = Verified data |
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Aquatic ecotoxicology |
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74.0 | R4 R = Peer reviewed scientific publications Salmo gairdneri4 = Verified data |
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34.0 | R4 R = Peer reviewed scientific publications Daphnia magna4 = Verified data |
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> 1.0 | R4 R = Peer reviewed scientific publications Chlorella ellipsoidea4 = Verified data |
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General |
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High (class III) | - | - | ||||||||
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> 3751 | 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 ) Mouse4 = Verified data |
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Poisonous by intraperitoneal and intravenous routes | ||||||||||
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Some slight metabolism. Almost all of dose given orally is excreted in the urine within 24 hr. | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) 3 = Unverified data of known source |
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Health issues |
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May cause contact dermititis or skin sensitisation May cause gastrointestinal problems May cause delayed hypersensitivity |
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No information available | |||
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Health: H315, H317, H319, H335 Environment: H412 |
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Not listed (Not listed) | |||
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bacitracin zinc | ||
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Record last updated: | 14/09/2025 |
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 |