Maduramicin

Maduramicin is a polyether ionophore antibiotic that has been found in Nocardia. It selectively binds to potassium, rubidium, sodium, lithium, and cesium ions over divalent cations. Maduramicin is active against Gram-positive bacteria (MICs = 0.9-125 µg/ml) but not Gram-negative bacteria (MICs = >1,000 µg/ml) or fungi (MICs = 250->1,000 µg/ml). It reduces the viability of asexual and gametocyte P. falciparum parasites (EC50s = 1.3 and 14.8 nM, respectively) and reduces P. berghei transmission in a mouse model of malaria when administered at doses of 4 and 8 mg/kg. Maduramicin (5-10 ppm in the diet) reduces the severity of lesions and completely protects chicks against mortality in a model of coccidiosis induced by E. tenella. Formulations containing maduramicin have been used in the treatment of coccidiosis in chickens.Formal Name: (2R,3S,4S,5R,6S)-6-[(1R)-1-[(2S,5R,7S,8R,9S)-2-[(2S,2'R,3'S,5R,5'R)-3'-[(2,6-dideoxy-3,4-di-O-methyl-beta-L-arabino-hexopyranosyl)oxy]octahydro-2-methyl-5'-[(2S,3S,5R,6S)-tetrahydro-6-hydroxy-3,5,6-trimethyl-2H-pyran-2-yl][2,2'-bifuran]-5-yl]-9-hydroxy-2,8-dimethyl-1,6-dioxaspiro[4.5]dec-7-yl]ethyl]tetrahydro-2-hydroxy-4,5-dimethoxy-3-methyl-2H-pyran-2-acetic acid. CAS Number: 79356-08-4. Synonyms: Antibiotic X 14868A, Maduramycin. Molecular Formula: C47H80O17. Formula Weight: 917.1. Purity: >85%. Formulation: (Request formulation change), A solid. Solubility: DMF: soluble, DMSO: soluble, Ethanol: soluble, Methanol: soluble. SMILES: CO[C@@H]1[C@@H](OC)[C@H](C)O[C@@](O[C@@H]2[C@@]([C@]3(C)CC[C@@]([C@@]4(C)O[C@@]5(C[C@H](O)[C@@H](C)[C@]([C@@H](C)[C@]6([H])O[C@@](CC(O)=O)(O)[C@@H](C)[C@H](OC)[C@H]6OC)([H])O5)CC4)([H])O3)([H])O[C@]([C@]7([H])[C@@H](C)C[C@@H](C)[C@@](C)(O)O7)([H])C2). InChi Code: InChI=1S/C47H80O17/c1-23-18-24(2)45(9,51)61-36(23)31-19-32(58-35-20-30(53-10)40(55-12)28(6)57-35)42(59-31)44(8)15-14-33(60-44)43(7)16-17-46(64-43)21-29(48)25(3)37(62-46)26(4)38-41(56-13)39(54-11)27(5)47(52,63-38)22-34(49)50/h23-33,35-42,48,51-52H,14-. InChi Key: RWVUEZAROXKXRT-VQLSFVLHSA-N. Origin: Bacterium/Actinomadura yunnaense.