Natamycin |
Last updated: 16/05/2024 |
(Also known as: myprozine; pimaricin; tennectin; pimaricine) |
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A polyene veterinary antifungal treatment | |
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Considered obsolete but may be available in some countries | |
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1955, first isolated | |
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Used topically to control ringworm (dermatophytosis) | |
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Cattle; Horses |
Approval status |
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Not approved | |
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Not approevd |
Chemical structure |
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Natamycin is a chiral molecule | |
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C₃₃H₄₇NO₁₃ | |
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CC1CC=CC=CC=CC=CC(CC2C(C(CC(O2)(CC(CC3C(O3)C=CC(=O)O1)O)O)O)C(=O)O)OC4C(C(C(C(O4)C)O)N)O | |
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C[C@@H]1C/C=C/C=C/C=C/C=C/[C@@H](C[C@H]2[C@@H]([C@H](C[C@](O2)(C[C@H](C[C@@H]3[C@H](O3)/C=C/C(=O)O1)O)O)O)C(=O)O)O[C@H]4[C@H]([C@H]([C@@H]([C@H](O4)C)O)N)O | |
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NCXMLFZGDNKEPB-FFPOYIOWSA-N | |
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InChI=1S/C33H47NO13/c1-18-10-8-6-4-3-5-7-9-11-21(45-32-30(39)28(34)29(38)19(2)44-32)15-25-27(31(40)41)22(36)17-33(42,47-25)16-20(35)14-24-23(46-24)12-13-26(37)43-18/h3-9,11-13,18-25,27-30,32,35-36,38-39,42H,10,14-17,34H2,1-2H3,(H,40,41)/b4-3+,7-5+,8-6+,11-9+,13-12+/t18-,19-,20+,21+,22+,23-,24-,25+,27-,28+,29-,30+,32+,33-/m1/s1 | |
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Yes |
General status |
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Antibacterial, Antifungal, Antimicrobial, Antimycotic | |
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Micro-organism derived substance | |
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>87% (trihydrate) | |
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Natural | |
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The substance binds to ergosterol, a building block in cell walls of yeasts and moulds, which damages the cell wall leading to death. | |
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[Ergosterol, Candida albicans, Binder] | |
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7681-93-8 | |
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231-683-5 | |
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528447 | |
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Alimentary tract & metabolism: Intestinal anti-infectants | |
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A07AA03 | |
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No | |
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Allowed substance (Table 1: Bovine, Equidae) | |
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665.73 | |
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natamycin | |
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- | |
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(1R,3S,5R,7R,8E,12R,14E,16E,18E,20E,22R,24S,25R,26S)-22-[(2R,3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-1,3,26-trihydroxy-12-methyl-10-oxo-6,11,28-trioxatricyclo[22.3.1.05,7]octacosa-8,14,16,18,20-pentaene-25-carboxylic acid | |
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(8E,14E,16E,18E,20E)-(1R,3S,5R,7R,12R,22R,24S,25R,26S)-22-(3-amino-3,6-dideoxy-β-D-mannopyranosyloxy)-1,3,26-trihydroxy-12-methyl-10-oxo-6,11,28-trioxatricyclo[22.3.1.0]octacosa-8,14,16,18,20-pentaene-25-carboxylic acid | |
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White to yellow crystalline powder |
Formulations |
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Mycophyt | Intervet International BV | Not licensed | Not licensed | ||||||
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4100 | Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source |
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97000 | L3 L = Pesticide manuals and hard copy reference books / other sources Ethanol3 = Unverified data of known source |
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850 | L3 L = Pesticide manuals and hard copy reference books / other sources Acetone3 = Unverified data of known source |
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50 | L3 L = Pesticide manuals and hard copy reference books / other sources Benzene3 = Unverified data of known source |
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290 | 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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290 | L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source |
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2.14 X 10-04 | Calculated | - | |||||||
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-3.67 | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) 3 = Unverified data of known source |
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Degradation |
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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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2730 | 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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2730 | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) Rat3 = Unverified data of known source |
Low | ||||||||
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2000 | Q3 Q = Miscellaneous data from online sources Rat3 = Unverified data of known source |
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Intraperitoneal LD₅₀ = 85 mg kg⁻¹ | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) Rat3 = Unverified data of known source |
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Intravenous LD₅₀ = 36 mg kg⁻¹ | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) Rat3 = Unverified data of known source |
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Around 90% is excreted through normal gastrointestinal functions | Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source |
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Health issues |
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No adverse health issues identified |
Handling issues |
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No information available | |||
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III (Slightly hazardous) | |||
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natamycin | ||
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natamycine | ||
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Pimarizin | ||
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natamicina | ||
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natamicina | ||
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natamycine | ||
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Record last updated: | 16/05/2024 |
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 |