Azlocillin: Difference between revisions

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			{{Short description\|Antibiotic}}
	{{Unreferenced\|date=December 2009}}
			{{Refimprove\|date=August 2013}}

	{{Drugbox		{{Drugbox
		⚫	\| verifiedrevid = 458972860
	\| Verifiedfields = changed
		⚫	\| IUPAC_name = (2''S'',5''R'',6''R'')-3,3-dimethyl-7-oxo-6-<nowiki/>{amino}-2-phenylacetyl]amino}-4-thia-1-azabicycloheptane-2-carboxylic acid
⚫	\| verifiedrevid = ~~401811008~~
⚫	\| IUPAC_name = (2''S'',5''R'',6''R'')-3,3-dimethyl-7-oxo-6-{amino}-2-phenylacetyl]amino}-4-thia-1-azabicycloheptane-2-carboxylic acid
	\| image = Azlocillin skeletal.svg		\| image = Azlocillin skeletal.svg
		⚫	<!-- Clinical data -->

		⚫	\| tradename =
⚫	<!--Clinical data-->
⚫	\| tradename =
	\| Drugs.com = {{drugs.com\|international\|azlocillin}}		\| Drugs.com = {{drugs.com\|international\|azlocillin}}
		⚫	<!-- Identifiers -->

⚫	<!--Identifiers-->
	\| CASNo_Ref = {{cascite\|correct\|CAS}}
	\| CAS_number_Ref = {{cascite\|correct\|??}}		\| CAS_number_Ref = {{cascite\|correct\|??}}
	\| CAS_number = 37091-66-0		\| CAS_number = 37091-66-0
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	\| UNII_Ref = {{fdacite\|correct\|FDA}}		\| UNII_Ref = {{fdacite\|correct\|FDA}}
	\| UNII = HUM6H389W0		\| UNII = HUM6H389W0
	\| KEGG_Ref = {{keggcite\|~~changed~~\|kegg}}		\| KEGG_Ref = {{keggcite\|correct\|kegg}}
	\| KEGG = D02339		\| KEGG = D02339
	\| ChEBI_Ref = {{ebicite\|~~changed~~\|EBI}}		\| ChEBI_Ref = {{ebicite\|correct\|EBI}}
	\| ChEBI = 2956		\| ChEBI = 2956
	\| ChEMBL_Ref = {{ebicite\|~~changed~~\|EBI}}		\| ChEMBL_Ref = {{ebicite\|correct\|EBI}}
	\| ChEMBL = 1537		\| ChEMBL = 1537
		⚫	<!-- Chemical data -->

		⚫	\| C=20 \| H=23 \| N=5 \| O=6 \| S=1
⚫	<!--Chemical data-->
⚫	\| C=20 \| H=23 \| N=5 \| O=6 \| S=1
	\| molecular_weight = 461.491 g/mol
	\| smiles = O=C(O)3N4C(=O)(NC(=O)(c1ccccc1)NC(=O)N2C(=O)NCC2)4SC3(C)C		\| smiles = O=C(O)3N4C(=O)(NC(=O)(c1ccccc1)NC(=O)N2C(=O)NCC2)4SC3(C)C
	\| InChI = 1/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
	\| InChIKey = JTWOMNBEOCYFNV-NFFDBFGFBS
	\| StdInChI_Ref = {{stdinchicite\|correct\|chemspider}}		\| StdInChI_Ref = {{stdinchicite\|correct\|chemspider}}
	\| StdInChI = 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		\| StdInChI = 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
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	\| StdInChIKey = JTWOMNBEOCYFNV-NFFDBFGFSA-N		\| StdInChIKey = JTWOMNBEOCYFNV-NFFDBFGFSA-N
	}}		}}

	'''Azlocillin''' is an ]] ] with an extended spectrum of activity and greater ] potency than the carboxy ]s.		'''Azlocillin''' is an ] ] ] with an extended spectrum of activity and greater '']'' potency than the carboxy ]s.
	Azlocillin is similar to ] and ]. It demonstrates antibacterial activity against a broad spectrum of ], including '']'' and, in contrast to most ]s, exhibits activity against ].		Azlocillin is similar to ] and ]. It demonstrates antibacterial activity against a broad spectrum of ], including '']'' and, in contrast to most ]s, exhibits activity against ].

			== 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>{{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 ==
			]
			]
			An interesting alternative synthesis of azlocillin involves activation of the substituted ] analogue '''1''' with 1,3-dimethyl-2-chloro-1-imidazolinium chloride ('''2''') and then condensation with ].
			{{clear}}
			== See also ==
			* ]

			== References ==
			{{reflist\|30em}}

	{{PenicillinAntiBiotics}}		{{PenicillinAntiBiotics}}

	]		]
	]		]
	]		]


	{{Antibiotic-stub}}		{{Antibiotic-stub}}

	]
	]
	]
	]

Latest revision as of 07:42, 10 September 2024

Antibiotic

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Pharmaceutical compound

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-{amino}-2-phenylacetyl]amino}-4-thia-1-azabicycloheptane-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
3D model (JSmol)	Interactive image
SMILES O=C(O)3N4C(=O)(NC(=O)(c1ccccc1)NC(=O)N2C(=O)NCC2)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)

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.

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.
^ 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.

Antibacterials active on the cell wall and envelope (J01C-J01D)

β-lactams
(inhibit synthesis
of peptidoglycan
layer of bacterial
cell wall by binding
to and inhibiting
PBPs, a group of
D-alanyl-D-alanine
transpeptidases)

Penicillins (Penams)

Narrow
spectrum

β-lactamase sensitive (1st generation)	Benzylpenicillin (G) Benzathine benzylpenicillin Procaine benzylpenicillin Phenoxymethylpenicillin (V) Propicillin Pheneticillin Azidocillin Clometocillin Penamecillin
β-lactamase resistant (2nd generation)	Cloxacillin (Dicloxacillin Flucloxacillin) Oxacillin Nafcillin Methicillin

Extended
spectrum

Aminopenicillins (3rd generation)	Amoxicillin Ampicillin (Pivampicillin Hetacillin Bacampicillin Lenampicillin Metampicillin Talampicillin) Epicillin
Carboxypenicillins (4th generation)	Ticarcillin Carbenicillin / Carindacillin Temocillin
Ureidopenicillins (4th generation)	Piperacillin Azlocillin Mezlocillin
Other	Mecillinam (Pivmecillinam) Sulbenicillin

Carbapenems / Penems

Cephems
Cephalosporins
Cephamycins
Carbacephems

1st generation	Cefazolin Cefalexin Cefadroxil Cefapirin Cefazedone Cefazaflur Cefradine Cefroxadine Ceftezole Cefaloglycin Cefacetrile Cefalonium Cefaloridine Cefalotin Cefatrizine
2nd generation	Cefaclor Cefprozil Cefuroxime Cefuroxime axetil Cefamandole Cefonicid Ceforanide Cefuzonam Cephamycin (Cefoxitin Cefotetan Cefminox Cefbuperazone Cefmetazole) Carbacephem (Loracarbef)
3rd generation	Cefixime Ceftriaxone Cefotaxime Antipseudomonal (Ceftazidime Cefoperazone) Cefdinir Cefcapene Cefdaloxime Ceftizoxime Cefmenoxime Cefpiramide Cefpodoxime Ceftibuten Cefditoren Cefotiam Cefetamet Cefodizime Cefpimizole Cefsulodin Cefteram Ceftiolene Oxacephem (Flomoxef Latamoxef)
4th generation	Cefepime Cefozopran Cefpirome Cefquinome
5th generation	Ceftaroline fosamil Ceftolozane Ceftobiprole
Siderophore	Cefiderocol
Veterinary	Ceftiofur Cefquinome Cefovecin

Monobactams

β-lactamase inhibitors

Combinations

Polypeptides

Lipopeptides	Insert into bacterial cell wall causing perforation and depolarization: Daptomycin Surfactin
Other	Inhibits PG elongation and crosslinking: Ramoplanin

Intracellular

Inhibit PG subunit synthesis and transport: NAM synthesis inhibition (Fosfomycin)
DADAL/AR inhibitors (Cycloserine)
bactoprenol inhibitors (Bacitracin)

Other

WHO-EM
Withdrawn from market
Clinical trials:
- Phase III
- Never to phase III

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Categories:

Latest revision as of 07:42, 10 September 2024

Spectrum of bacterial susceptibility

Synthesis

See also

References