Advanced search
Publication Cover
Expert Opinion on Therapeutic Patents Volume 13, 2003 - Issue 6
Submit an article Journal homepage
52
Views
35
CrossRef citations to date
0
Altmetric
Review

Recent progress in the field of macrolide antibiotics

Todd C Henninger Johnson & Johnson Pharmaceutical Research & Development, LLC, 1000 Route 202, PO Box 300, Raritan, NJ 08869, USA. [email protected]
Pages 787-805 | Published online: 02 Mar 2005

Bibliography

  • MA Z, NEMOTO PA: Discovery and development of ketolides as a new generation of macrolide antimicrobial agents. Curc Med. Chem. -fect. Agents (2002) 1(1):15–34.
  • WU YJ, SU WG: Recent developments on ketolides and macrolides. Curr: Med. Chem. (2001) 8(14):1727–1758.
  • ••Good combination review of the chemistryand microbiology of the most important recent macrolides.
  • RESEK JE, WANG XC, BHATIA AV: Highlights of recent research on the synthesis of ketolide antibiotics. Can: Opin. Drug Discov. Dev. (2000) 3(6):807–817.
  • WU YJ: Highlights of semi-synthetic developments from erythromycin A. Curc Pharm. Design (2000) 6(2):181–223.
  • CHU DTW: Progress in macrolide and ketolide antibacterials. In: Annual Reports in Medicinal Chemistry Doherty AM (Ed.), Academic Press, San Diego, USA (2000) 35:145–155.
  • OMURA S: Macrolide Antibiotics: Chemistry, Biology, and Practice (2nd Edition). Omura S (Ed.), Academic Press, San Diego, USA (2002).
  • SCHONFELD W, KIRST HA: Macrolide Antibiotics. Schonfeld W, Kirst HA (Eds), Birkhauser Verlag, Basel, Switzerland (2002).
  • ZHANEL GG, WALTERS M, NOREDDIN A et al: The ketolides: a critical review. Drugs(2002) 62(12):1771–1804.
  • ••A thorough compilation of data onketolides.
  • ZHONG P, SHORTRIDGE V: The emerging new generation of antibiotic: ketolides. Carr. Drug Targets - Infect. Disord. (2001) 1(2):125–131.
  • BRYSKIER A: Ketolides - telithromycin, an example of a new class of antibacterial agents. Clin. Microbial. Infect. (2000) 6(12):661–669.
  • BLONDEAU JM, DECAROLIS E, METZLER, KL, HANSEN GT: The macrolides. Expert Opin. Investig. Drugs (2002) 11(2):189–215.
  • KANEKO T, MCARTHUR H, SUTCLIFFE J: Recent developments in the area of macrolide antibiotics. Expert Opin. Ther: Pat. (2000) 10(4):403–425.
  • ••Excellent review of the prior art.
  • KIRST HA: Recent developments with macrolide antibiotics. Expert Opin. Thec Pat. (1998) 8(2):111–120.
  • FAGHIH R, NELLANS HN, PLATTNER JJ: Motilides and motilactides: design and development of motilin receptor agonists as a new class of gastrointestinal prokinetic drugs. Drugs Future (1998) 23(8):861–872.
  • CULIC O, ERAKOVIC V, PARNHAM MJ: Anti-inflammatory effects of macrolides. Ear: Pharmacol. (2001) 429(1-3):209–229.
  • ZALEWSKA-KASZUBSKA J, GORSKA D: Anti-inflammatory capabilities of macrolides. Pharmacol. Res. (2001) 44(6):451–454.
  • WOO PCY, LAU SKP, YUEN KY: Macrolides as immunomodulatory agents. Carr: Med. Chem.: Anti -In/Jam. Anti-Allergy Agents (2002) 1(2):131–141.
  • YATSUNAMI J, HAYASHI SI: Fourteen-membered macrolides as anti-angiogenic compounds. Anti-Cancer Res. (2001) 21(6B):4253–4258.
  • ZHANEL GG, DUECK M, HOBAN DJ et al.: Review of macrolides and ketolides: focus on respiratory tract infections. Drugs (2001) 61(4):443–498.
  • ••Excellent comparison of the variousmacrolide derivatives including detailed in vitro data.
  • POEHLSGAARD J, DOUTHWAITE S: The macrolide binding site on the bacterial ribosome. Carr: Drug Targets - Infect. Disord. (2002) 2(1):67–78.
  • •Incorporates the latest information from X-ray crystallographic studies of the ribosome.
  • LECLERCQ R: Mechanisms of resistance to macrolides and lincosamides: nature of the resistance elements and their clinical implications. Clin. Infect. Dir. (2002) 34(4):482.
  • ••Thorough but concise review of macrolideresistance.
  • CHAMPNEY WS: Bacterial ribosomal subunit synthesis: a novel antibiotic target. Cum Drug Targets - Infect. Disord (2001) 1(1):19–36.
  • WEISBLUM B: Erythromycin resistance by ribosome modification. Antimicrob. Agents Chemother. (1995) 39(3):577–585.
  • LIU M, DOUTHWAITE S: Activity of the ketolide telithromycin is refractory to Erm monomethylation of bacterial rRNA. Antimicrob. Agents Chemother. (2002) 46(6):1629–1633.
  • SHAIN CS, AMSDEN GW: Telithromycin: the first of the ketolides. Ann. Pharmacother. (2002) 36(3):452–464.
  • BARMAN BALFOUR JA, FIGGITT DP: Telithromycin. Drugs (2001) 61(6):815–829.
  • XIONG YQ, LE TP: Telithromycin (HMR 3647): the first ketolide antibiotic. Drugs Today (2001) 37(9):617–628.
  • YASSIN HM, DEVER LL: Telithromycin: a new ketolide antimicrobial for treatment of respiratory tract infections. Expert Opin. Investig. Drugs (2001) 10(2):353–367.
  • JOHNSON AP: Telithromycin Aventis Pharma. Carr: Opin. Investig. Drugs (2001) 2(12):1691–1701.
  • FELMINGHAM D: Microbiological profile of telithromycin, the first ketolide antimicrobial. Clin. Microbiol Infect. (2001) 7\(Supp1.3):2–10.
  • DOUGHERTY TJ, BARRETT JF: ABT-773: a new ketolide antibiotic. Expert Opin. Investig. Drugs (2001) 10(2):343–351.
  • SORBERA LA, RABASSEDA J, CASTANER J: ABT-773. Drugs Future (2000) 25(5):445–453.
  • DOUTHWAITE S: Structure-activity relationships of ketolides versus macrolides. Cl/n. Microbiol. Infect. (2001) 7\(Supp1.3) :11–17.
  • HANSEN LH, MAUVAIS P, DOUTHWAITE S: The macrolide-ketolide antibiotic binding site is formed by structures in domains II and V of 23S ribosomal RNA. Mol. Microbiol. (1999) 31(2):623–631.
  • SCHLUNZEN F, ZARIVACH R, HARMS J et al.: Structural basis for the interaction of antibiotics with the peptidyl transferase center in eubacteria. Nature (London) (2001) 413:814–821.
  • BERTHO G, GHARBI-BENAROUS J, DELAFORGE M, LANG C, PARENT A, GIRAULT JP: Conformational analysis of ketolide, conformations of RU O04 in solution and bound to bacterial ribosomes. J. Med. Chem. (1998) 41(18):3373–3386.
  • MA Z, CLARK RF, BRAZZALE A et al Novel erythromycin derivatives with aryl groups tethered to the C-6 position are potent protein synthesis inhibitors and active against mukidrug-resistant respiratory pathogens. Med. Chem. (2001) 44(24):4137–4156.
  • ••Detailed account of the discovery of and SAR around ABT-773 (cethromycin).
  • OR YS, CLARK RF, WANG Set al: Design, synthesis, and antimicrobial activity of 6-0-substituted ketolides active against resistant respiratory tract pathogens. Med. Chem. (2000) 43(6):1045–1049.
  • PHAN LT, CLARK RE RUPP M, OR YS, CHU DTW, MA Z: Synthesis of 2-fluoro-6-0-propargy1-11,12-carbamate ketolides. A novel class of antibiotics. Org. Lett. (2000) 2(19):2951–2954.
  • DENIS A, BRETINF, FROMENTIN C et al.: P-Keto-ester chemistry and ketolides. Synthesis and antibacterial activity of 2-halo, 2-methyl and 2,3 enol-ether ketolides. Bioorg. Med. Chem. Lett. (2000) 10(17):2019–2022.
  • DENIS A, BONNEFOY A: Novel fluoroketolides: synthesis and antibacterial activity. Drugs Future (2001) 26(10):975–984.
  • MA Z, FLORJANCIC AS: HMR-3562 Aventis Pharma. Carr: Opin. Investig. Drugs (2001) 2(12):1702–1705.
  • HENNINGER T, ABBANAT D, BAUM E et al.: Synthesis and antibacterial activity of C6-carbamate ketolides. 42nd ICAAC. San Diego, USA (2002) Abstract F–1661.
  • SU W, SMYTH K, RAIN VILLE Jet al.: The in vitroand in vivo activity of CP-642959 and its related diastereomers. 41st ICAAC Chicago, USA (2001) Abstract F–1168.
  • GIRARD D, CIMOCHOWSKI CR, FINEGAN SM, SU WG: In vivo antibacterial activity of CP-642,959, a new C-9 oxime ketolide against resistant pneumococci and Haemophilus influenzae. 41st ICAAC Chicago, USA (2001) Abstract F–1169.
  • GIRARD D, FINEGAN SM, SU WG, ZHANG D, RAUNIG DL: Pharmacokinetics and pharmacodynamics of CP-642,959 in murine lung infection models. 41st ICAAC Chicago, USA (2001) Abstract F–1170.
  • KANEKO T, MCMILLEN W SUTCLIFFE J, DUIGNAN J, PETITPAS J: Synthesis and in vitro activity of C2-substituted C9-oidme ketolides. 40th ICAAC Toronto, Canada (2000) Abstract F–1815.
  • GIRARD D, MATHIEU HVV, FINEGAN SM, CIMOCHOWSKI CR, KANEKO TK, MCMILLEN W: In vivo antibacterial activity of CP-654,743, a new C2-fluoro ketolide, against macrolide resistant pneumococci and Haemophilus influenzae. 40th ICAAC Toronto, Canada (2000) Abstract F–1816.
  • GIRARD D, MATHIEU HVV, SHEPARD RM, YEE S, KANEKO TK, MCMILLEN W: Pharmacokinetics of CP-654,743, a new C2-fluoro ketolide active against macrolide resistant respiratory pathogens, in preclinical species. 40th ICAAC Toronto, Canada (2000) Abstract F–1817.
  • BUSH K, ABBANAT D, ASHLEY G et al.: In vitro and in vivo SAR of ketolides derived from R13-modified erythromycin A and picromycin core structures. 40th ICAAC Toronto, Canada (2000) Abstract F–1821.
  • ABBANAT DR, ASHLEY G, CARNEY J et al.: In vitro and in vivo activities of 15-methyl ketolide derivatives of erythromycin A. 41st ICAAC Chicago, USA (2001) Abstract F–1173.
  • MACIELAG M, ABBANAT D, ASHLEY G et al.: Structure-antibacterial activity relationships of ketolides derived from 15-methylerythromycin A. 41st ICAAC Chicago, USA (2001) Abstract F–1174.
  • MACIELAG M, ABBANAT D, ASHLEY G et al.: Structure-activity studies of 15-methyl ketolides: optimization of the heterocyclic substituent. 42nd ICAAC. San Diego, USA (2002) Abstract F–1662.
  • ABBANAT D, WEBB G, ASHLEY G et a]:In vitro antibacterial activities of naphthyridine-containing ketolides. 42nd ICAAC. San Diego, USA (2002) Abstract F–1663.
  • DENTS A, RENOU C: Novel N-demethylation of ketolide: application to the solution phase parallel synthesis of N-desosaminyl-substituted ketolides using ion exchange resins. Tetrahedron Lett. (2002) 43(23):4171–4174.
  • ALIHODZIC S, KOBREHEL G, LAZAREVSKI G et al: Synthesis and antibacterial activity of isomeric 15-membered azalides. 41st ICAAC Chicago, USA (2001) Abstract F–1177.
  • TAKAHASHI Y, YOSHIZUMI S, OKEZAKI E et al: Anti-Mycobacterium a vium-complex activity of GI-448, a novel macrolide. 41st ICAAC Chicago, USA (2001) Abstract F–1175.
  • YOSHIDA T, NISHIMOTO A, TAKAHASHI Y et al.: Discovery and SAR of macrolide agents with potent activities against Mycobacterium avium-complex. 41st ICAAC Chicago, USA (2001) Abstract F–1176.
  • PAVLOVIC D, NARANDJA A: Synthesis and structure-activity relationships of novel desmycosin ketolides. 222nd ACS Meeting Chicago, USA (2001) MEDI–240.
  • CREEMER LC, TOTH JE, KIRST HA: Synthesis and M vitro antimicrobial activity of 3-keto 16-membered macrolides derived from tylosin.J. Antibiot. (2002) 55(0427–436.
  • LAZAROVA TI, BINET SM, VO NH, CHEN JS, PHAN LT, OR YS: Synthesis of new 14-membered macrolide antibiotics via a novel ring contraction metathesis. Org. Lett. (2003) 5(4):443–445.
  • •Novel chemistry that converts 16-membered macrolides to 14-membered macrolides.
  • VO NH, WANG J, HALEY T, NAPPER A, PHAN LT, OR Y: 9-Amino derivatives of novel 14-membered ring macrolide antibiotics derived from leucomycins: chemistry and M vitro biological activities. 42nd ICAAC San Diego, USA (2002) Abstract F–1664.
  • LAZAROVA TI, BINET SM, EVANS J et al.: Synthesis and biological evaluation of a new class of 14-membered ring macrolide antibiotics. 42nd ICAAC. San Diego, USA (2002) Abstract F–1665.
  • CHAMPNEY WS, TOBER CL: Preferentialinhibition of protein synthesis by ketolide antibiotics in Haemophilus influenzae cells. Carr. Microbiol (2003) 46(2):103–108.
  • ZHANEL GG, HOBAN DJ: Ketolides in the treatment of respiratory infections. Expert Opin. Pharmacother. (2002) 3(3):277–297.
  • DOUCET-POPULAIRE F, BURIANKOVA K, WEISER J, PERNODET JL: Natural and acquired macrolide resistance in mycobacteria. Carr: Drug Targets - Infect. Disord. (2002) 2(0355–370.

Website

  • http://www.iddb3.com Telithromycin. IDDB3 database report (18 February 2003).
  • http://www.iddb3.com Cethromycin. IDDB3 database report (4 December 2002).

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Order Reprints Request Corporate Permissions

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

Request Academic Permissions

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.

Related research

People also read lists articles that other readers of this article have read.

Recommended articles lists articles that we recommend and is powered by our AI driven recommendation engine.

Cited by lists all citing articles based on Crossref citations.
Articles with the Crossref icon will open in a new tab.