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{{Drugbox
| IUPAC_name = 4-[(E,2R,5S)-2-hydroxy-5-methyl-7-[(2R,3S,4Z,6E,10E)-3-methyl-12-oxo-1-oxacyclododeca-4,6,10-trien-2-yl]-4-oxooct-6-enyl]piperidine-2,6-dione
| image = Lactimidomycin.svg
| width = 280

| tradename =
| legal_status =


| bioavailability =
| metabolism =
| elimination_half-life =
| excretion =


| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 134869-15-1
| PubChem = 11669726
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| ChemSpiderID = 9844457
| ChEMBL = 1221911
| KEGG =

| C=26 | H=35 | N=1 | O=6
| molecular_weight = 457.558
| smiles = N2C(=O)CC(CC2=O)CC(O)CC(=O)C(C)\C=C(/C)\C1OC(=O)C=CCCC=CC=CC1C
| StdInChI = 1S/C26H35NO6/c1-17-10-8-6-4-5-7-9-11-25(32)33-26(17)19(3)12-18(2)22(29)16-21(28)13-20-14-23(30)27-24(31)15-20/h4,6,8-12,17-18,20-21,26,28H,5,7,13-16H2,1-3H3,(H,27,30,31)/b6-4+,10-8-,11-9+,19-12+/t17-,18-,21+,26+/m0/s1
| StdInChIKey = OYOKHBHOTQDIPM-BRHOHSSQSA-N
}}

'''Lactimidomycin''' is a [[glutarimide]] antibiotic derived from the bacteria ''[[Streptomyces amphibiosporus]]''.<ref>Sugawara K, Nishiyama Y, Toda S, Komiyama N, Hatori M, Moriyama T, Sawada Y, Kamei H, Konishi M, Oki T. Lactimidomycin, a new glutarimide group antibiotic. Production, isolation, structure and biological activity. ''J Antibiot (Tokyo)''. 1992 Sep;45(9):1433-41. {{PMID|1429229}}</ref><ref>Ju J, Seo JW, Her Y, Lim SK, Shen B. New lactimidomycin congeners shed insight into lactimidomycin biosynthesis in Streptomyces amphibiosporus. ''Org Lett''. 2007 Dec 6;9(25):5183-6. {{PMID|17997563}}</ref> It has [[antifungal]], [[antiviral]] and [[anti-cancer]] properties, acting as a direct inhibitor of [[protein translation]] in [[ribosome]]s.<ref>Schneider-Poetsch T, Ju J, Eyler DE, Dang Y, Bhat S, Merrick WC, Green R, Shen B, Liu JO. Inhibition of eukaryotic translation elongation by cycloheximide and lactimidomycin. ''Nat Chem Biol''. 2010 Mar;6(3):209-217. {{PMID|20118940}}</ref><ref>Micoine K, Persich P, Llaveria J, Lam MH, Maderna A, Loganzo F, Fürstner A. Total syntheses and biological reassessment of lactimidomycin, isomigrastatin and congener glutarimide antibiotics. ''Chemistry''. 2013 Jun 3;19(23):7370-83. doi: 10.1002/chem.201300393. {{PMID|23595541}}</ref><ref>Garreau de Loubresse N, Prokhorova I, Holtkamp W, Rodnina MV, Yusupova G, Yusupov M. Structural basis for the inhibition of the eukaryotic ribosome. ''Nature''. 2014 Sep 25;513(7519):517-22. doi: 10.1038/nature13737. {{PMID|25209664}}</ref> Antiviral activity is seen against a variety of [[RNA virus]]es including [[flavivirus]]es such as [[dengue fever]], [[Kunjin virus]] and [[Modoc virus]], as well as [[vesicular stomatitis virus]] and [[poliovirus]].<ref>Carocci M, Yang PL. Lactimidomycin is a broad-spectrum inhibitor of dengue and other RNA viruses. ''Antiviral Res''. 2016 Apr;128:57-62. doi: 10.1016/j.antiviral.2016.02.005 {{PMID|26872864}}</ref> As lactimidomycin is a [[natural product]] containing an unusual unsaturated 12-membered [[lactone]] ring, it has been the subject of numerous [[total synthesis]] approaches.<ref>Micoine K, Fürstner A. Concise total synthesis of the potent translation and cell migration inhibitor lactimidomycin. ''J Am Chem Soc''. 2010 Oct 13;132(40):14064-6. doi: 10.1021/ja107141p. {{PMID|20831202}}</ref><ref>Larsen BJ, Sun Z, Nagorny P. Synthesis of eukaryotic translation elongation inhibitor lactimidomycin via Zn(II)-mediated Horner-Wadsworth-Emmons macrocyclization. ''Org Lett''. 2013 Jun 21;15(12):2998-3001. doi: 10.1021/ol401186f. {{PMID|23731327}}</ref><ref>Nagasawa T, Kuwahara S. Formal total synthesis of lactimidomycin. ''Org Lett''. 2013 Jun 21;15(12):3002-5. doi: 10.1021/ol401214f. {{PMID|23731346}}</ref><ref>Larsen BJ, Sun Z, Lachacz E, Khomutnyk Y, Soellner MB, Nagorny P. Synthesis and Biological Evaluation of Lactimidomycin and Its Analogues. ''Chemistry''. 2015 Dec 21;21(52):19159-67. doi: 10.1002/chem.201503527. {{PMID|26577990}}</ref>

==References==
{{reflist}}

[[Category:Dengue fever]]
[[Category:Antivirals]]
[[Category:Glutarimides]]
[[Category:Lactones]]

{{Antiinfective-drug-stub}}
{{dictionary-stub1}}

Lactimidomycin - Revision history

Prab at 00:24, 17 March 2025

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