Sisomicin: Difference between revisions

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{{Drugbox
{{Drugbox
| IUPAC_name       = (2''R'',3''R'',4''R'',5''R'')-2-[(1''S'',2''S'',3''R'',4''S'',6''R'')-4,6-Diamino-3-[ [(2''S'',3''R'')-3-amino-6-(aminomethyl)-<br/>3,4-dihydro-2''H''-pyran-2-yl]oxy]-2-<br/>hydroxycyclohexyl]oxy-5-methyl-<br/>4-methylaminooxane-3,5-diol
| Verifiedfields = changed
| image             = Sisomicin.png
| Watchedfields = changed
| CAS_number        =
| verifiedrevid = 443440571
| ATC_prefix        = J01
| IUPAC_name = (2''R'',3''R'',4''R'',5''R'')-2-{[(1''S'',2''S'',3''R'',4''S'',6''R'')-4,6-diamino-3-{[(2''S'',3''R'')-3-amino-6-(aminomethyl)-3,4-dihydro-2''H''-pyran-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-5-methyl-4-(methylamino)oxane-3,5-diol
| ATC_suffix        = GB08
| image = Sisomicin.svg
| PubChem          = 36119
 
| DrugBank          =
<!--Clinical data-->
| C=19|H=37|N=5|O=7
| tradename = bactoCeaze
| molecular_weight  = 447.53 g/mol
| Drugs.com = {{drugs.com|international|sisomicin}}
| bioavailability  =
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| protein_bound    =
| pregnancy_US = <!-- A / B            / C / D / X -->
| metabolism        =
| pregnancy_category =   
| elimination_half-life =
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| excretion        =
| legal_CA = <!--            / Schedule I, II, III, IV, V, VI, VII, VIII -->
| pregnancy_AU     = <!-- A / B1 / B2 / B3 / C / D / X -->
| legal_UK = <!-- GSL        / P      / POM / CD / Class A, B, C -->
| pregnancy_US     = <!-- A / B            / C / D / X -->
| legal_US = <!-- OTC                  / Rx-only  / Schedule I, II, III, IV, V -->
| pregnancy_category=   
| legal_status = Rx Only 
| legal_AU         = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| routes_of_administration = topical
| legal_CA         = <!--            / Schedule I, II, III, IV, V, VI, VII, VIII -->
 
| legal_UK         = <!-- GSL        / P      / POM / CD / Class A, B, C -->
<!--Pharmacokinetic data-->
| legal_US         = <!-- OTC                  / Rx-only  / Schedule I, II, III, IV, V -->
| bioavailability = 
| legal_status     =  
| protein_bound = 
| routes_of_administration =  
| metabolism = 
}}
| elimination_half-life = 
{{SI}}
| excretion = 


<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 
| ATC_prefix = J01
| ATC_suffix = GB08
| PubChem = 36119
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = 
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = X55XSL74YQ
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D02544
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 606051


<!--Chemical data-->
| C=19 | H=37 | N=5 | O=7
| molecular_weight = 447.53 g/mol
}}


'''Sisomicin''' is an [[aminoglycoside]] [[antibiotic]].
'''Sisomicin''' ('''bactoCeaze''' or '''Ensamycin''') is an [[aminoglycoside]] [[antibiotic]], isolated from the
fermentation broth of a new species of the genus ''[[Micromonospora]]''.<ref name="pmid5487129">{{cite journal |author=M. J. Weinstein, J. A. Marquez, R. T. Testa, G. H. Wagman, E. M. Oden, J. A. Waitz |title=Antibiotic 6640, a new Micromonospora-produced aminoglycoside antibiotic. |journal=J. Antibiot. |volume=23 |issue=11 |pages=551–554 |date=Nov 1970 |pmid=5487129 |doi= 10.7164/antibiotics.23.551|pmc= }}</ref> It is a newer broad-spectrum aminoglycoside most structurally related to [[gentamicin]].


Sisomicin is the most predictably active aminoglycoside against gram-positive bacteria.<ref name="pmid6994206">{{cite journal |author=WE Sanders Jr, CC Sanders. |title=Sisomicin: a review of eight years' experience. |journal=Rev Infect Dis. |volume=2 |issue=2 |pages=182–195 |date=Mar–Apr 1980 |pmid=6994206 |doi= 10.1093/clinids/2.2.182|pmc= }}</ref> Like most other aminoglycosides, Sisomicin is bactericidal for sensitive clinical isolates. The minimum bactericidal concentrations (MBC) have been found to be equivalent or very close to the minimum inhibitory concentrations (MIC).<ref name="pmid6994206">{{cite journal |author=ME Levison, D Kaye. |title=In vitro comparison of four aminoglycoside antibiotics: sisomicin, gentamicin, tobramycin, and BB-K8. |journal=Antimicrob Agents Chemother. |volume=5 |issue=6 |pages=667–669 |date=Jun 1974 |pmid=15825423 |doi= 10.1128/aac.5.6.667|pmc=429032 }}</ref> Like other aminoglycosides, most clinical isolates of ''Pseudomonas aeruginosa'' remain susceptible to sisomicin. Resistance to sisomicin may enzymatically or non-enzymatically be mediated. Sisomicin is inactivated by the same enzymes as gentamicin but it is active against many, not all, organisms that resist gentamicin by non-enzymatic mechanisms.<ref name="pmid=649532" >{{cite journal |author=I Phillips, BA King, KP Shannon. |title=The mechanisms of resistance to aminoglycosides in the genus Pseudomonas. |journal=J Antimicrob Chemother. |volume=4 |issue=2 |pages=121–129 |date=Mar 1978 |pmid=649532 |doi= 10.1093/jac/4.2.121|pmc= }}</ref>


Some studies show that sisomicin has been effective in the treatment of infections that either had failed to respond to other drugs or were due to microorganisms resistant ''in vitro'' to other aminoglycosides.<ref name="pmid431401">{{cite journal |author=ME Levison, D Kaye. |title=A randomized comparative trial of three aminoglycosides--comparison of continuous infusions of gentamicin, amikacin and sisomicin combined with carbenicillin in the treatment of infections in neutropenic patients with malignancies. |journal=Medicine (Baltimore). |volume=58 |issue=2 |pages=159–170 |date=Mar 1979 |pmid=431401 |doi= 10.1097/00005792-197903000-00004|pmc= }}</ref><ref name= >{{cite journal |author=DG Maki, WA Craig, WA Agger. |title=A comparative clinical trial of sisomicin and gentamicin in major gram-negative infections. |journal=Infection 7(Suppl. 3) |volume=5 |issue=6 |pages=298–300 |date=Jun 1979 |pmid= |doi= 10.1007/bf01646260|pmc= }}</ref>


== References ==
{{Reflist}}


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Revision as of 12:50, 9 April 2015

Sisomicin
File:Sisomicin.svg
Clinical data
Trade namesbactoCeaze
AHFS/Drugs.comInternational Drug Names
Routes of
administration		topical
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
PubChem CID
UNII
KEGG
ChEMBL
E number{{#property:P628}}
ECHA InfoCard{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
FormulaC19H37N5O7
Molar mass447.53 g/mol
 ☒N☑Y (what is this?)  (verify)

Sisomicin (bactoCeaze or Ensamycin) is an aminoglycoside antibiotic, isolated from the fermentation broth of a new species of the genus Micromonospora.[1] It is a newer broad-spectrum aminoglycoside most structurally related to gentamicin.

Sisomicin is the most predictably active aminoglycoside against gram-positive bacteria.[2] Like most other aminoglycosides, Sisomicin is bactericidal for sensitive clinical isolates. The minimum bactericidal concentrations (MBC) have been found to be equivalent or very close to the minimum inhibitory concentrations (MIC).[2] Like other aminoglycosides, most clinical isolates of Pseudomonas aeruginosa remain susceptible to sisomicin. Resistance to sisomicin may enzymatically or non-enzymatically be mediated. Sisomicin is inactivated by the same enzymes as gentamicin but it is active against many, not all, organisms that resist gentamicin by non-enzymatic mechanisms.[3]

Some studies show that sisomicin has been effective in the treatment of infections that either had failed to respond to other drugs or were due to microorganisms resistant in vitro to other aminoglycosides.[4][5]

References

  1. ↑ M. J. Weinstein, J. A. Marquez, R. T. Testa, G. H. Wagman, E. M. Oden, J. A. Waitz (Nov 1970). "Antibiotic 6640, a new Micromonospora-produced aminoglycoside antibiotic". J. Antibiot. 23 (11): 551–554. doi:10.7164/antibiotics.23.551. PMID 5487129.
  2. ↑ 2.0 2.1 WE Sanders Jr, CC Sanders. (Mar–Apr 1980). "Sisomicin: a review of eight years' experience". Rev Infect Dis. 2 (2): 182–195. doi:10.1093/clinids/2.2.182. PMID 6994206.
  3. ↑ I Phillips, BA King, KP Shannon. (Mar 1978). "The mechanisms of resistance to aminoglycosides in the genus Pseudomonas". J Antimicrob Chemother. 4 (2): 121–129. doi:10.1093/jac/4.2.121. PMID 649532.
  4. ↑ ME Levison, D Kaye. (Mar 1979). "A randomized comparative trial of three aminoglycosides--comparison of continuous infusions of gentamicin, amikacin and sisomicin combined with carbenicillin in the treatment of infections in neutropenic patients with malignancies". Medicine (Baltimore). 58 (2): 159–170. doi:10.1097/00005792-197903000-00004. PMID 431401.
  5. ↑ DG Maki, WA Craig, WA Agger. (Jun 1979). "A comparative clinical trial of sisomicin and gentamicin in major gram-negative infections". Infection 7(Suppl. 3). 5 (6): 298–300. doi:10.1007/bf01646260.

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