Bacitracin methylenedisalicylic acid |
Last updated: 08/02/2024 |
(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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Considered obsolete but may be available in some countries | |
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1945, isolated | |
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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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Isomeric | |
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C₈₁H₁₁₇N₁₇O₂₃S | |
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CCC(C)C(C1=NC(CS1)C(=O)NC(CC(C)C)C(=O)NC(CCC(=O)O)C(=O)NC(C(C)CC)C(=O)NC(CCCCN)C(=O)NC(CCCN)C(=O)NC(C(C)CC)C(=O)NC(CC2=CC=CC=C2)C(=O)NC(CC3=CN=CN3)C(=O)NC(CC(=O)O)C(=O)NC(CC(=O)N)C(=O)O)N.C1=CC=C(C(=C1)C(=O)OCOC(=O)C2=CC=CC=C2O)O | |
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CC[C@H](C)[C@@H](C(=O)N[C@@H](CCCCN)C(=O)N[C@H](CCCN)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@H](CC1=CC=CC=C1)C(=O)N[C@@H](CC2=CN=CN2)C(=O)N[C@H](CC(=O)O)C(=O)N[C@@H](CC(=O)N)C(=O)O)NC(=O)[C@@H](CCC(=O)O)NC(=O)[C@H](CC(C)C)NC(=O)C3CSC(=N3)C(C(C)CC)N.C1=CC=C(C(=C1)C(=O)OCOC(=O)C2=CC=CC=C2O)O | |
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POMORUSPLDFVEK-PHXAWWDYSA-N | |
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InChI=1S/C66H105N17O17S.C15H12O6/c1-9-35(6)52(70)65-81-48(32-101-65)62(96)76-43(26-34(4)5)58(92)74-42(22-23-50(85)86)57(91)83-53(36(7)10-2)63(97)75-40(20-15-16-24-67)55(89)73-41(21-17-25-68)56(90)82-54(37(8)11-3)64(98)79-44(27-38-18-13-12-14-19-38)59(93)77-45(28-39-31-71-33-72-39)60(94)78-46(30-51(87)88)61(95)80-47(66(99)100)29-49(69)84;16-12-7-3-1-5-10(12)14(18)20-9-21-15(19)11-6-2-4-8-13(11)17/h12-14,18-19,31,33-37,40-48,52-54H,9-11,15-17,20-30,32,67-68,70H2,1-8H3,(H2,69,84)(H,71,72)(H,73,89)(H,74,92)(H,75,97)(H,76,96)(H,77,93)(H,78,94)(H,79,98)(H,80,95)(H,82,90)(H,83,91)(H,85,86)(H,87,88)(H,99,100);1-8,16-17H,9H2/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 | |
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Polypeptide | |
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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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55852-84-1 | |
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259-862-3 | |
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11980094 | |
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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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1729.0 | |
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(4R)-5-[[(2S,3S)-1-[[(2S)-6-amino-1-[[(2R)-5-amino-1-[[(2S,3S)-1-[[(2R)-1-[[(2S)-1-[[(2R)-1-[[(1S)-3-amino-1-carboxy-3-oxopropyl]amino]-3-carboxy-1-oxopropan-2-yl]amino]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-1-oxopentan-2-yl]amino]-1-oxohexan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-4-[[(2S)-2-[[2-(1-amino-2-methylbutyl)-4,5-dihydro-1,3-thiazole-4-carbonyl]amino]-4-methylpentanoyl]amino]-5-oxopentanoic acid;(2-hydroxybenzoyl)oxymethyl 2-hydroxybenzoate | |
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Banned in EU as growth promotor; Not approved as feed additive in EU | |
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Formulations |
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Usually formulated as a medicated feed premix |
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Released into the environment via the excretion of treated animals |
Degradation |
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22.5 | R4 R = Peer reviewed scientific publications Soil & chicken manure at 20 °C for bacitracin4 = Verified data |
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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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Soil adsorption and mobility |
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Fate indices |
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Known soil and groundwater metabolites |
None
Other known metabolites |
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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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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 metabolism, excreted in the urine and faeces 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 |
Handling issues |
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No information available | |||
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Not listed (Not listed) | |||
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bacitracin methylenedisalicylic acid | ||
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Record last updated: | 08/02/2024 |
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 |