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Chapter 17 : Spectinomycin

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Spectinomycin, Page 1 of 2

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Abstract:

The spectinomycin is a disaccharide antibiotic with a neutral sugar fused to actinamine (N,N'dimethyl-2-epi-streptamine) by a β-glycoside bond and a hemiacetal type of bond (1,4-dioxane), producing a tricyclic structure. The 3'-(R)-isomer has good antibacterial activity, in contrast to the 3'-(S)-aminospectinomycin isomer. The difference in activity between the isomers is probably due to the poor binding of the molecule at the ribosomal receptor sites, which occurs through hydrogen bonds. The attachment of an α-hydroxyl group to this molecule reintroduces antibacterial activity weaker than that of spectinomycin, showing clearly the importance of the hydroxyl groups and their spatial positions. Spectinomycin and trospectomycin are inactive or weakly active against methicillin-susceptible and -resistant strains of and coagulase-negative staphylococci. Trospectomycin exhibits good activity against penicillin G-susceptible and -resistant strains of , whereas spectinomycin is inactive. Against gram-positive bacilli, trospectomycin is more active than spectinomycin. Spectinomycin is inactive against anaerobic bacteria, while trospectomycin possesses activity weaker than that of clindamycin. Trospectomycin and spectinomycin possess good activity against . Trospectomycin is much more active than spectinomycin against spectinomycin-susceptible strains of , including strains resistant to ampicillin through a plasmid-mediated (PPNG) or chromosomal (CMRNG) mechanism, with or without resistance to tetracyclines.

Citation: Bryskier A. 2005. Spectinomycin, p 470-474. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch17

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Citation: Bryskier A. 2005. Spectinomycin, p 470-474. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch17
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Citation: Bryskier A. 2005. Spectinomycin, p 470-474. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch17
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Citation: Bryskier A. 2005. Spectinomycin, p 470-474. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch17
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Citation: Bryskier A. 2005. Spectinomycin, p 470-474. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch17
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References

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8. Jacobus NV,, Tally FP, 1988, Activity of trospectomycin against Bacteroides fragilis and other Bacteroides species, Antimicrob Agents Chemother, 32, 584586.
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12. Loria GR,, Sammartino C,, Nicholas RA,, Ayling RD, 2003, In vitro susceptibilities of field isolates of Mycoplasma agalactiae to oxytetracycline, tylosin, enrofloxacin, spiramycin and lincomycinspectinomycin, Res Vet Sci, 75, 37.
13. Novak E,, Griffith DL,, Paxton LM,, Metzler CM,, Francom SF, 1988, Human safety and pharmacokinetics of multiple intramuscular doses of trospectomycin sulfate (U-63366F)—a novel spectinomycin analogue, 28th Intersci Conf Antimicrob Agents Chemother, abstract 97.
14. Novak E,, Zurenko GE,, Paxton LM,, Francom SF,, Oliver LK, 1987, Trospectomycin sulfate [6′-N-propylspecinomycin (U-63366F)]: safety and pharmacokinetics in man after single-dose iv administration, 27th Intersci Conf Antimicrob Agents Chemother, abstract 271.
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16. Rettig JP,, Nelson JD,, Kusmies H, 1980, Spectinomycin therapy for gonorrhoea in prepubertal children, Am J Dis Child, 134, 359.
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18. Rice RJ,, Thompson SE,, Arko RJ,, Hunter EF,, Burleigh PM,, Craig BT,, Larsen AF, 1988, Tissue fluid penetration and antitreponemal activity of trospectomycin (a new spectinomycin analog) in the rabbit syphilis model, Sex Transm Dis, 15, 152155.
19. Sanson-Lepors MJ,, Casin IM,, Thebault M-C, Arlet G,, Perol Y, 1986, In vitro activities of U-63366, a spectinomycin analog; roxithromycin (RU 28965), a new macrolide antibiotic; and five quinolone derivatives against Haemophilus ducreyi, Antimicrob Agents Chemother, 30, 512513.
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24. Zurenko GE,, Ford CW,, Novak E, 1988, Trospectomycin, a novel spectinomycin analogue: antibacterial activity and preliminary human pharmacokinetics, Drugs Exp Clin Res, 14, 403409.
25. Zurenko GE,, Yagi BH,, Vavra JJ,, Wentworth BB, 1988, In vitro antibacterial activity of trospectomycin (U-63366F), a novel spectinomycin analog, Antimicrob Agents Chemother, 32, 216223.

Tables

Generic image for table
Table 1

Citation: Bryskier A. 2005. Spectinomycin, p 470-474. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch17
Generic image for table
Table 2

Citation: Bryskier A. 2005. Spectinomycin, p 470-474. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch17
Generic image for table
Table 3

Citation: Bryskier A. 2005. Spectinomycin, p 470-474. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch17
Generic image for table
Table 4

Citation: Bryskier A. 2005. Spectinomycin, p 470-474. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch17
Generic image for table
Table 5

Citation: Bryskier A. 2005. Spectinomycin, p 470-474. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch17
Generic image for table
Table 6

Citation: Bryskier A. 2005. Spectinomycin, p 470-474. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch17
Generic image for table
Table 7

Citation: Bryskier A. 2005. Spectinomycin, p 470-474. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch17
Generic image for table
Table 8

Citation: Bryskier A. 2005. Spectinomycin, p 470-474. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch17
Generic image for table
Table 9

Citation: Bryskier A. 2005. Spectinomycin, p 470-474. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch17
Generic image for table
Table 10

Citation: Bryskier A. 2005. Spectinomycin, p 470-474. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch17

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