Azlocillin: Difference between revisions

Azlocillin
Clinical data
AHFS/Drugs.com	International Drug Names
ATC code	J01CA09 (WHO) ;
Identifiers
	IUPAC name (2S,5R,6R)-3,3-dimethyl-7-oxo-6-{[(2R)-2-{[(2-oxoimidazolidin-1-yl)carbonyl]amino}-2-phenylacetyl]amino}-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid;
CAS Number	37091-66-0 ;
PubChem CID	6479523;
DrugBank	DB01061 ;
ChemSpider	4980416 ;
UNII	HUM6H389W0;
KEGG	D02339 ;
ChEBI	CHEBI:2956 ;
ChEMBL	ChEMBL1537 ;
CompTox Dashboard (EPA)	DTXSID1022639 ;
ECHA InfoCard	100.048.483
Chemical and physical data
Formula	C20H23N5O6S
Molar mass	461.49 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(O)[C@@H]3N4C(=O)[C@@H](NC(=O)[C@@H](c1ccccc1)NC(=O)N2C(=O)NCC2)[C@H]4SC3(C)C;
	InChI InChI=1S/C20H23N5O6S/c1-20(2)13(17(28)29)25-15(27)12(16(25)32-20)22-14(26)11(10-6-4-3-5-7-10)23-19(31)24-9-8-21-18(24)30/h3-7,11-13,16H,8-9H2,1-2H3,(H,21,30)(H,22,26)(H,23,31)(H,28,29)/t11-,12-,13+,16-/m1/s1 ; Key:JTWOMNBEOCYFNV-NFFDBFGFSA-N ;
	(verify)

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Latest revision as of 07:42, 10 September 2024

Azlocillin is an acyl ampicillin antibiotic with an extended spectrum of activity and greater in vitro potency than the carboxy penicillins. Azlocillin is similar to mezlocillin and piperacillin. It demonstrates antibacterial activity against a broad spectrum of bacteria, including Pseudomonas aeruginosa and, in contrast to most cephalosporins, exhibits activity against enterococci.

Spectrum of bacterial susceptibility

Azlocillin is considered a broad spectrum antibiotic and can be used against a number of Gram positive and Gram negative bacteria. The following represents MIC susceptibility data for a few medically significant organisms.^[1]

Escherichia coli 1 μg/mL – 32 μg/mL
Haemophilus spp. 0.03 μg/mL – 2 μg/mL
Pseudomonas aeruginosa 4 μg/mL – 6.25 μg/mL

Synthesis

An interesting alternative synthesis of azlocillin involves activation of the substituted phenylglycine analogue 1 with 1,3-dimethyl-2-chloro-1-imidazolinium chloride (2) and then condensation with 6-APA.

References

^ "Azlocillin sodium salt Susceptibility and Minimum Inhibitory and Concentration (MIC) Data" (PDF). The Antimicrobial Index. toku-e.com.
^ ^a ^b Koenig HB, Metzer KG, Offe HA, Schroeck W (1982). "Azlocillin. Ein Neues Penicillin aus der Acylureidoreihe: Synthese und Chemische Eigenschaften". Eur. J. Med. Chem. - Chim. Ther. (in German). 17 (1): 59–63.
^ Bauer VJ, Safir SR (November 1966). "Octamethylbiguanide perchlorate". Journal of Medicinal Chemistry. 9 (6): 980–1. doi:10.1021/jm00324a056. PMID 4291383.

This systemic antibiotic-related article is a stub. You can help Wikipedia by expanding it.

[1] "Azlocillin sodium salt Susceptibility and Minimum Inhibitory and Concentration (MIC) Data" (PDF). The Antimicrobial Index. toku-e.com.

[Konig-2] Koenig HB, Metzer KG, Offe HA, Schroeck W (1982). "Azlocillin. Ein Neues Penicillin aus der Acylureidoreihe: Synthese und Chemische Eigenschaften". Eur. J. Med. Chem. - Chim. Ther. (in German). 17 (1): 59–63.

[3] Bauer VJ, Safir SR (November 1966). "Octamethylbiguanide perchlorate". Journal of Medicinal Chemistry. 9 (6): 980–1. doi:10.1021/jm00324a056. PMID 4291383.

[1]

[2]

[3]

@@ Line 1: / Line 1: @@
+{{Short description|Antibiotic}}
 {{Refimprove|date=August 2013}}
 {{Drugbox
 | verifiedrevid = 458972860
-| IUPAC_name = (2''S'',5''R'',6''R'')-3,3-dimethyl-7-oxo-6-{[(2''R'')-2-{[(2-oxoimidazolidin-1-yl)carbonyl]amino}-2-phenylacetyl]amino}-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
+| IUPAC_name = (2''S'',5''R'',6''R'')-3,3-dimethyl-7-oxo-6-<nowiki/>{[(2''R'')-2-<nowiki/>{[(2-oxoimidazolidin-1-yl)carbonyl]amino}-2-phenylacetyl]amino}-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
 | image = Azlocillin skeletal.svg
 <!-- Clinical data -->
@@ Line 28: / Line 29: @@
 <!-- Chemical data -->
 | C=20 | H=23 | N=5 | O=6 | S=1
-| molecular_weight = 461.491 g/mol
 | smiles = O=C(O)[C@@H]3N4C(=O)[C@@H](NC(=O)[C@@H](c1ccccc1)NC(=O)N2C(=O)NCC2)[C@H]4SC3(C)C
 | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
@@ Line 36: / Line 36: @@
 }}
-'''Azlocillin''' is an [[acyl]][[ampicillin]] [[antibiotic]] with an extended spectrum of activity and greater ''[[in vitro]]'' potency than the carboxy [[penicillin]]s.
+'''Azlocillin''' is an [[acyl]] [[ampicillin]] [[antibiotic]] with an extended spectrum of activity and greater ''[[in vitro]]'' potency than the carboxy [[penicillin]]s.
 Azlocillin is similar to [[mezlocillin]] and [[piperacillin]]. It demonstrates antibacterial activity against a broad spectrum of [[bacteria]], including ''[[Pseudomonas aeruginosa]]'' and, in contrast to most [[cephalosporin]]s, exhibits activity against [[enterococcus|enterococci]].
 == Spectrum of bacterial susceptibility ==
-Azlocillin is considered a broad spectrum antibiotic and can be used against a number of Gram positive and Gram negative bacteria. The following represents MIC susceptibility data for a few medically significant organisms.<ref>http://www.toku-e.com/Assets/MIC/Azlocillin%20sodium%20salt.pdf</ref>
+Azlocillin is considered a broad spectrum antibiotic and can be used against a number of Gram positive and Gram negative bacteria. The following represents MIC susceptibility data for a few medically significant organisms.<ref>{{cite web | title = Azlocillin sodium salt Susceptibility and Minimum Inhibitory and Concentration (MIC) Data | work = The Antimicrobial Index | publisher = toku-e.com | url = http://www.toku-e.com/Assets/MIC/Azlocillin%20sodium%20salt.pdf}}</ref>
 * ''Escherichia coli'' 1 μg/mL – 32 μg/mL
 * ''Haemophilus'' spp. 0.03 μg/mL – 2 μg/mL
 * ''Pseudomonas aeruginosa'' 4 μg/mL – 6.25 μg/mL
 == Synthesis ==
-[[File:Azlocillin synthesis.svg|thumb|center|700px|Azlocillin synthesis: {{cite patent|FR|2100682}} eidem {{US patent|3933795}} <ref name=Konig>H. B. Konig et al., Eur. J. Med. Chem. - Chim. Ther. 17, 59 (1982).</ref>]]
+[[File:Azlocillin synthesis.svg|thumb|left|600px|Azlocillin synthesis: {{cite patent|country=FR|number=2100682}} eidem {{US patent|3933795}} <ref name=Konig>{{cite journal | vauthors = Koenig HB, Metzer KG, Offe HA, Schroeck W | title = Azlocillin. Ein Neues Penicillin aus der Acylureidoreihe: Synthese und Chemische Eigenschaften | language = German | journal = Eur. J. Med. Chem. - Chim. Ther. | volume = 17 | issue =1 | pages = 59–63 | date = 1982 }}</ref>]]
-[[File:Azlocillin synthesis2.svg|thumb|center|500px|Azlocillin synthesis 2:<ref name=Konig /><ref>{{cite journal|doi=10.1021/jm00324a056|pmid=4291383|title=Octamethylbiguanide Perchlorate|journal=Journal of Medicinal Chemistry|volume=9|issue=6|pages=980|year=1966|last1=Bauer|first1=Victor J.|last2=Safir|first2=S. R.}}</ref>]]
+[[File:Azlocillin synthesis2.svg|thumb|left|450px|Azlocillin synthesis 2:<ref name=Konig /><ref>{{cite journal | vauthors = Bauer VJ, Safir SR | title = Octamethylbiguanide perchlorate | journal = Journal of Medicinal Chemistry | volume = 9 | issue = 6 | pages = 980–1 | date = November 1966 | pmid = 4291383 | doi = 10.1021/jm00324a056 }}</ref>]]
-An interesting alternative synthesis of azlocillin involves activation of the substituted phenylglycine analogue '''1''' with 1,3-dimethyl-2-chloro-1-imidazolinium chloride ('''2''') and then condensation with [[6-APA]].
+An interesting alternative synthesis of azlocillin involves activation of the substituted [[phenylglycine]] analogue '''1''' with 1,3-dimethyl-2-chloro-1-imidazolinium chloride ('''2''') and then condensation with [[6-APA]].
+{{clear}}
 == See also ==
-*[[Methicillin]]
+* [[Methicillin]]
 == References ==
 {{reflist|30em}}
@@ Line 55: / Line 58: @@
 {{PenicillinAntiBiotics}}
-[[Category:Beta-lactam antibiotics]]
+[[Category:Penicillins]]
 [[Category:Enantiopure drugs]]
 [[Category:Imidazolidinones]]
 {{Antibiotic-stub}}