Kitasamycin |
![]() Last updated: 15/09/2025 |
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(Also known as: selectomycin; leucomycin; antibiotic A 6599; stereomycine; turimycin) |
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A macrolide antibiotic drug produced by streptomyces kitasatoensis and which has antimicrobial activity against a wide spectrum of gram-positive pathogens | |
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Used against several arthropod parasites, including grubs, lice, mites and screw worms | |
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Pigs; Poultry |
Approval status |
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Not approved | |
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Not approved |
Chemical structure |
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Kitasamycin exhibits isomerism primarily through stereoisomerism, due to its multiple chiral centres that create distinct three-dimensional arrangements of atoms. These stereoisomers, including enantiomers and diastereomers, significantly influence the antibiotic’s biological activity. It also shows geometric (E/Z) isomerism around certain double bonds in its macrocyclic lactone ring, affecting its molecular conformation and interaction with bacterial targets. Additionally, its flexible ring structure allows for conformational isomerism, where different spatial arrangements can exist without altering the chemical formula. | |
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C₃₅H₅₉NO₁₃ | |
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CC1CC=CC=CC(C(CC(C(C(C(CC(=O)O1)O)OC)OC2C(C(C(C(O2)C)OC3CC(C(C(O3)C)O)(C)O)N(C)C)O)CC=O)C)O | |
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C[C@@H]1C/C=C/C=C/[C@@H]([C@@H](C[C@@H]([C@@H]([C@H]([C@@H](CC(=O)O1)O)OC)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)C)O[C@H]3C[C@@]([C@H]([C@@H](O3)C)O)(C)O)N(C)C)O)CC=O)C)O | |
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XYJOGTQLTFNMQG-KJHBSLKPSA-N | |
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InChI=1S/C35H59NO13/c1-19-16-23(14-15-37)31(32(44-8)25(39)17-26(40)45-20(2)12-10-9-11-13-24(19)38)49-34-29(41)28(36(6)7)30(21(3)47-34)48-27-18-35(5,43)33(42)22(4)46-27/h9-11,13,15,19-25,27-34,38-39,41-43H,12,14,16-18H2,1-8H3/b10-9+,13-11+/t19-,20-,21-,22+,23+,24+,25-,27+,28-,29-,30-,31+,32+,33+,34+,35-/m1/s1 | |
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Yes |
General status |
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Antibiotic, Antibacterial, Antimicrobial, Medicinal drug, Growth promotor, Feed additive | |
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Macrolide | |
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Natural | |
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Inhibits the protein synthesis process | |
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[50S rRNA, Antagonist] | |
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39405-35-1 | |
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Antiinfectants for systemic use: Antibacterials for system use | |
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QJ01FA93 | |
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No | |
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701.84 | |
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2-[(4R,5S,6S,7R,9R,10R,11E,13E,16R)-6-[(2S,3R,4R,5S,6R)-5-[(2S,4R,5S,6S)-4,5-Dihydroxy-4,6-dimethyloxan- 2-yl]oxy-4-dimethylamino-3-hydroxy-6-methyloxan-2-yl]oxy-4,10-dihydroxy- 5-methoxy-9,16-dimethyl-2-oxo-1-oxacyclohexadeca-11,13-dien-7-yl]acetaldehyde | |
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Evidence of use in third world countries | |
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White crystalline solid |
Commercial |
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1960, developed | |||
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Usually supplied as a premix feed | |||
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Kitasamycin is produced through a fermentation process using Streptomyces kitasatoensis, a soil-dwelling bacterium. The production begins with the preparation of a high-yielding industrial strain, cultivated from single colonies and slant spores under controlled conditions. These spores are then used to inoculate seed cultures, which are scaled up in fermentation tanks. During fermentation, specific nutrients and surfactants are added to optimize antibiotic yield. After fermentation, the broth is filtered to separate the biomass, and kitasamycin is extracted using organic solvents. The crude product undergoes purification to isolate the active compound. | |||
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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. |
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Substance may enter the environment via the faeces of treated animals or by leaching from spilt medicated feed. |
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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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4965 | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) Rat3 = Unverified data of known source |
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Aquatic ecotoxicology |
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General |
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High (class III) | - | - | ||||||||
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4965 | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) Rat3 = Unverified data of known source |
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Intraperitoneal LD₅₀ = 711 mg kg⁻¹ | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) Rat3 = Unverified data of known source |
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Intravenous LD₅₀ = 320 mg kg⁻¹ | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) Mouse3 = Unverified data of known source |
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Mainly excreted through hepatobiliary system, mostly in bile and faeces with lesser amounts lost in 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 gastrointestinal problems |
Handling issues |
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No information available | |||
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Not listed (Not listed) | |||
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kitasamycin | ||
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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 |