Glycylcycline: Difference between revisions
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{{Short description|Class of antiobiotics}} |
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| ⚫ | '''Glycylcyclines''' are a |
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| ⚫ | '''Glycylcyclines''' are a class of antibiotics derived from [[tetracycline]]. These tetracycline analogues are specifically designed to overcome two common mechanisms of [[Tetracycline#Mechanism and resistance|tetracycline resistance]], namely resistance mediated by acquired [[Efflux (microbiology)|efflux pumps]] and/or ribosomal protection. Presently, [[tigecycline]] is the only glycylcycline approved for antibiotic use. |
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== History == |
== History == |
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The development of these agents was spurred by the increasing prevalence of bacteria resistant to tetracyclines. These agents were first synthesized in the early 1990s by making modifications to the tetracyclines. By adding a bulky N,N-dimethylglycylamido [[side chain]] to position 9 of [[minocycline]], the compound became less susceptible to tetracycline resistance mediated by acquired efflux pumps and/or ribosomal protection. Further development of this initial work led to the creation of [[tigecycline]], the first glycylcycline available for clinical use. |
The development of these agents was spurred by the increasing prevalence of bacteria resistant to tetracyclines. These agents were first synthesized in the early 1990s by making modifications to the tetracyclines. By adding a bulky N,N-dimethylglycylamido [[side chain]] to position 9 of [[minocycline]], the compound became less susceptible to tetracycline resistance mediated by acquired efflux pumps and/or ribosomal protection. Further development of this initial work led to the creation of [[tigecycline]], the first glycylcycline available for clinical use.{{cn|date=March 2023}} |
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===Approvals=== |
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*[[Tigecycline]] (FDA approved May 27, 2005)<ref>{{cite web |title=Drugs@FDA: FDA Approved Drug Products – Tigecycline |url=https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&ApplNo=091620 |website=fda.gov |publisher=United States Food and Drug Administration |access-date=15 March 2019}}</ref> |
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== Mechanism of action == |
== Mechanism of action == |
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Glycylcycline antibiotics have a similar [[mechanism of action]] as tetracycline antibiotics. Both classes of antibiotics bind to the 30S [[Ribosome|ribosomal]] subunit to prevent the amino-acyl tRNA from binding to the A site of the ribosome. However, the glycylcyclines appear to bind more effectively than the tetracyclines |
Glycylcycline antibiotics have a similar [[mechanism of action]] as tetracycline antibiotics. They block protein synthesis hence preventing bacterial reproduction. Both classes of antibiotics bind to the 30S [[Ribosome|ribosomal]] subunit to prevent the amino-acyl tRNA from binding to the A site of the ribosome. However, the glycylcyclines appear to bind more effectively than the tetracyclines.<ref>{{cite journal |vauthors=Bergeron J, Ammirati M, Danley D, etal |title=Glycylcyclines bind to the high-affinity tetracycline ribosomal binding site and evade Tet(M)- and Tet(O)-mediated ribosomal protection |journal=Antimicrob. Agents Chemother. |volume=40 |issue=9 |pages=2226–8 |date=September 1996 |doi=10.1128/AAC.40.9.2226 |pmid=8878615 |pmc=163507 |url=}}</ref> |
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== Mechanisms of resistance == |
== Mechanisms of resistance == |
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While glycylcyclines have greater efficacy against organisms with tetracycline resistance mediated by acquired efflux pumps and/or ribosomal protection, |
While glycylcyclines have greater efficacy against organisms with tetracycline resistance mediated by acquired efflux pumps and/or ribosomal protection, glycylcyclines are not effective against organisms with [[chromosomal efflux pump]]s, such as ''[[Pseudomonas]]'' and Proteae.<ref>{{cite journal |author=Livermore DM |title=Tigecycline: what is it, and where should it be used? |journal=J. Antimicrob. Chemother. |volume=56 |issue=4 |pages=611–4 |date=October 2005 |pmid=16120626 |doi=10.1093/jac/dki291 |doi-access=free }}</ref> |
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== Side effects and contraindications == |
== Side effects and contraindications == |
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| ⚫ | Since glycylcyclines are similar to tetracyclines, they share many of the same side effects and contraindications as tetracyclines. These side effects may include nausea/vomiting, headache, [[photosensitivity]], [[tooth discoloration|discoloration of growing teeth]], and fetal damage.<ref>{{cite web|title=List of adverse events for Tigecycline|url=http://www.rxlist.com/tygacil-side-effects-drug-center.htm|website=Tygacil Side Effects Center|publisher=RxList.com|access-date=18 December 2016}}</ref> |
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| ⚫ | These antibiotics should not be given to pregnant women due to risk of fetal harm. Additionally, these drugs should not be administered during periods of tooth development because of the risk of tooth discoloration. Due to glycylcyclines' similarities with tetracyclines, hypersensitivity reactions to tetracycline antibiotics may predispose one to hypersensitivity reactions with glycylcycline antibiotics; hence, glycylcyclines should be used with caution in these patients. |
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| ⚫ | These antibiotics should not be given to pregnant women due to risk of fetal harm. Additionally, these drugs should not be administered during periods of tooth development because of the risk of tooth discoloration. Due to glycylcyclines' similarities with tetracyclines, hypersensitivity reactions to tetracycline antibiotics may predispose one to hypersensitivity reactions with glycylcycline antibiotics; hence, glycylcyclines should be used with caution in these patients.{{cn|date=March 2023}} |
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== References == |
== References == |
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{{reflist}} |
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* [http://www.formularyjournal.com/formulary/article/articleDetail.jsp?id=177008 Tigecycline: A novel glycylcycline antiobiotic]. Aug 1, 2005. By: Kara L. Smith, BSc, Sarah M. McCabe, BSc, Jeffrey R. Aeschlimann, PharmD. ''Formulary''. |
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*{{cite journal |vauthors=Smith KL, McCabe SM, Aeschlimann JR |title=Tigecycline: A novel glycylcycline antiobiotic |journal=Formulary |date=August 1, 2005 |url=http://www.formularyjournal.com/formulary/article/articleDetail.jsp?id=177008 |access-date=November 26, 2005 |archive-url=https://web.archive.org/web/20070928204927/http://www.formularyjournal.com/formulary/article/articleDetail.jsp?id=177008 |archive-date=September 28, 2007 |url-status=dead }} |
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== External links == |
== External links == |
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* [http://www.tygacil.com/ Tygacil (tigecycline IV) manufacturer website.] |
* [https://web.archive.org/web/20080706124941/http://www.tygacil.com/ Tygacil (tigecycline IV) manufacturer website.] |
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* {{cite journal | |
* {{cite journal |vauthors=Zhanel GG, Homenuik K, Nichol K, etal |title=The glycylcyclines: a comparative review with the tetracyclines |journal=Drugs |volume=64 |issue=1 |pages=63–88 |year=2004 |pmid=14723559 |doi=10.2165/00003495-200464010-00005|s2cid=46964579 }} |
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* [http://www.rxlist.com/tygacil-side-effects-drug-center.htm RxList.com list of adverse reactions to Tigecycline] |
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{{TetracyclineAntiBiotics}} |
{{TetracyclineAntiBiotics}} |
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[[Category:Glycylcycline antibiotics| |
[[Category:Glycylcycline antibiotics| ]] |
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[[Category:Tetracyclic compounds]] |
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{{antibiotic-stub}} |
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Latest revision as of 18:42, 26 January 2024
Glycylcyclines are a class of antibiotics derived from tetracycline. These tetracycline analogues are specifically designed to overcome two common mechanisms of tetracycline resistance, namely resistance mediated by acquired efflux pumps and/or ribosomal protection. Presently, tigecycline is the only glycylcycline approved for antibiotic use.
History
[edit]The development of these agents was spurred by the increasing prevalence of bacteria resistant to tetracyclines. These agents were first synthesized in the early 1990s by making modifications to the tetracyclines. By adding a bulky N,N-dimethylglycylamido side chain to position 9 of minocycline, the compound became less susceptible to tetracycline resistance mediated by acquired efflux pumps and/or ribosomal protection. Further development of this initial work led to the creation of tigecycline, the first glycylcycline available for clinical use.[citation needed]
Approvals
[edit]- Tigecycline (FDA approved May 27, 2005)[1]
Mechanism of action
[edit]Glycylcycline antibiotics have a similar mechanism of action as tetracycline antibiotics. They block protein synthesis hence preventing bacterial reproduction. Both classes of antibiotics bind to the 30S ribosomal subunit to prevent the amino-acyl tRNA from binding to the A site of the ribosome. However, the glycylcyclines appear to bind more effectively than the tetracyclines.[2]
Mechanisms of resistance
[edit]While glycylcyclines have greater efficacy against organisms with tetracycline resistance mediated by acquired efflux pumps and/or ribosomal protection, glycylcyclines are not effective against organisms with chromosomal efflux pumps, such as Pseudomonas and Proteae.[3]
Side effects and contraindications
[edit]Since glycylcyclines are similar to tetracyclines, they share many of the same side effects and contraindications as tetracyclines. These side effects may include nausea/vomiting, headache, photosensitivity, discoloration of growing teeth, and fetal damage.[4]
These antibiotics should not be given to pregnant women due to risk of fetal harm. Additionally, these drugs should not be administered during periods of tooth development because of the risk of tooth discoloration. Due to glycylcyclines' similarities with tetracyclines, hypersensitivity reactions to tetracycline antibiotics may predispose one to hypersensitivity reactions with glycylcycline antibiotics; hence, glycylcyclines should be used with caution in these patients.[citation needed]
References
[edit]- ^ "Drugs@FDA: FDA Approved Drug Products – Tigecycline". fda.gov. United States Food and Drug Administration. Retrieved 15 March 2019.
- ^ Bergeron J, Ammirati M, Danley D, et al. (September 1996). "Glycylcyclines bind to the high-affinity tetracycline ribosomal binding site and evade Tet(M)- and Tet(O)-mediated ribosomal protection". Antimicrob. Agents Chemother. 40 (9): 2226–8. doi:10.1128/AAC.40.9.2226. PMC 163507. PMID 8878615.
- ^ Livermore DM (October 2005). "Tigecycline: what is it, and where should it be used?". J. Antimicrob. Chemother. 56 (4): 611–4. doi:10.1093/jac/dki291. PMID 16120626.
- ^ "List of adverse events for Tigecycline". Tygacil Side Effects Center. RxList.com. Retrieved 18 December 2016.
- Smith KL, McCabe SM, Aeschlimann JR (August 1, 2005). "Tigecycline: A novel glycylcycline antiobiotic". Formulary. Archived from the original on September 28, 2007. Retrieved November 26, 2005.
External links
[edit]- Tygacil (tigecycline IV) manufacturer website.
- Zhanel GG, Homenuik K, Nichol K, et al. (2004). "The glycylcyclines: a comparative review with the tetracyclines". Drugs. 64 (1): 63–88. doi:10.2165/00003495-200464010-00005. PMID 14723559. S2CID 46964579.
- RxList.com list of adverse reactions to Tigecycline