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{{Short description|Antibiotic}} |
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{{Unreferenced|date=December 2009}} |
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{{Refimprove|date=August 2013}} |
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{{Drugbox |
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{{Drugbox |
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| verifiedrevid = 458972860 |
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| Verifiedfields = changed |
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| 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 |
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| verifiedrevid = 401811008 |
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| 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 |
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| image = Azlocillin skeletal.svg |
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| image = Azlocillin skeletal.svg |
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<!-- Clinical data --> |
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| tradename = |
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<!--Clinical data--> |
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| tradename = |
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| Drugs.com = {{drugs.com|international|azlocillin}} |
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| Drugs.com = {{drugs.com|international|azlocillin}} |
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<!-- Identifiers --> |
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<!--Identifiers--> |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = 37091-66-0 |
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| CAS_number = 37091-66-0 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = HUM6H389W0 |
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| UNII = HUM6H389W0 |
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| KEGG_Ref = {{keggcite|changed|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = D02339 |
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| KEGG = D02339 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 2956 |
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| ChEBI = 2956 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 1537 |
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| ChEMBL = 1537 |
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<!-- Chemical data --> |
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| C=20 | H=23 | N=5 | O=6 | S=1 |
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<!--Chemical data--> |
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| C=20 | H=23 | N=5 | O=6 | S=1 |
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| molecular_weight = 461.491 g/mol |
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| smiles = O=C(O)3N4C(=O)(NC(=O)(c1ccccc1)NC(=O)N2C(=O)NCC2)4SC3(C)C |
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| smiles = O=C(O)3N4C(=O)(NC(=O)(c1ccccc1)NC(=O)N2C(=O)NCC2)4SC3(C)C |
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| 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 |
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| InChIKey = JTWOMNBEOCYFNV-NFFDBFGFBS |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| 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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| 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 |
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| StdInChIKey = JTWOMNBEOCYFNV-NFFDBFGFSA-N |
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}} |
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'''Azlocillin''' is an ]] ] with an extended spectrum of activity and greater ] potency than the carboxy ]s. |
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'''Azlocillin''' is an ] ] ] with an extended spectrum of activity and greater '']'' potency than the carboxy ]s. |
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Azlocillin is similar to ] and ]. It demonstrates antibacterial activity against a broad spectrum of ], including '']'' and, in contrast to most ]s, exhibits activity against ]. |
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Azlocillin is similar to ] and ]. It demonstrates antibacterial activity against a broad spectrum of ], including '']'' and, in contrast to most ]s, exhibits activity against ]. |
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== Spectrum of bacterial susceptibility == |
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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> |
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* ''Escherichia coli'' 1 μg/mL – 32 μg/mL |
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* ''Haemophilus'' spp. 0.03 μg/mL – 2 μg/mL |
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* ''Pseudomonas aeruginosa'' 4 μg/mL – 6.25 μg/mL |
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== Synthesis == |
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] |
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] |
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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 ]. |
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{{clear}} |
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== See also == |
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* ] |
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== References == |
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{{reflist|30em}} |
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{{PenicillinAntiBiotics}} |
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{{PenicillinAntiBiotics}} |
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] |
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] |
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] |
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] |
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] |
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] |
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{{Antibiotic-stub}} |
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{{Antibiotic-stub}} |
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] |
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] |
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] |
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] |
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