Azidocillin: Difference between revisions

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	{{unreferenced\|date=June 2011}}		{{unreferenced\|date=June 2011}}
	{{~~drugbox~~		{{Drugbox
	\| verifiedrevid = 443223758		\| verifiedrevid = 443223758
		⚫	\| IUPAC_name = 6--3,3-dimethyl-7-oxo-4-thia-1-azabicycloheptane-2-carboxylic acid
		⚫	\| image = Azidocillin.png

			<!--Clinical data-->
			\| tradename =
		⚫	\| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
		⚫	\| pregnancy_US = <!-- A / B / C / D / X -->
		⚫	\| pregnancy_category =
		⚫	\| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
		⚫	\| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII -->
		⚫	\| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C -->
		⚫	\| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
		⚫	\| legal_status =
		⚫	\| routes_of_administration =

			<!--Pharmacokinetic data-->
		⚫	\| bioavailability =
		⚫	\| protein_bound =
		⚫	\| metabolism =
		⚫	\| elimination_half-life =
		⚫	\| excretion =

			<!--Identifiers-->
		⚫	\| CAS_number = 17243-38-8
		⚫	\| ATC_prefix = J01
		⚫	\| ATC_suffix = CE04
		⚫	\| PubChem = 71886
		⚫	\| DrugBank_Ref = {{drugbankcite\|correct\|drugbank}}
		⚫	\| DrugBank = DB08795
		⚫	\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
		⚫	\| ChemSpiderID = 16735689
	\| UNII_Ref = {{fdacite\|correct\|FDA}}		\| UNII_Ref = {{fdacite\|correct\|FDA}}
	\| UNII = R8XDP7L3SL		\| UNII = R8XDP7L3SL
		⚫	\| KEGG_Ref = {{keggcite\|correct\|kegg}}
⚫	\| IUPAC_name = 6--3,3-dimethyl-7-oxo-4-thia-1-azabicycloheptane-2-carboxylic acid
		⚫	\| KEGG = D07235
⚫	\| image = Azidocillin.png
⚫	\| StdInChI_Ref = {{stdinchicite\|correct\|chemspider}}
⚫	\| StdInChI = 1S/C16H17N5O4S/c1-16(2)11(15(24)25)21-13(23)10(14(21)26-16)18-12(22)9(19-20-17)8-6-4-3-5-7-8/h3-7,9-11,14H,1-2H3,(H,18,22)(H,24,25)/t9-,10-,11+,14-/m1/s1
⚫	\| StdInChIKey_Ref = {{stdinchicite\|correct\|chemspider}}
⚫	\| StdInChIKey = ODFHGIPNGIAMDK-NJBDSQKTSA-N
	\| ChEBI_Ref = {{ebicite\|correct\|EBI}}		\| ChEBI_Ref = {{ebicite\|correct\|EBI}}
	\| ChEBI = 51758		\| ChEBI = 51758

⚫	\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
			<!--Chemical data-->
⚫	\| ChemSpiderID = 16735689
		⚫	\| C=16 \| H=17 \| N=5 \| O=4 \| S=1
⚫	\| InChI = 1/C16H17N5O4S/c1-16(2)11(15(24)25)21-13(23)10(14(21)26-16)18-12(22)9(19-20-17)8-6-4-3-5-7-8/h3-7,9-11,14H,1-2H3,(H,18,22)(H,24,25)/t9-,10-,11+,14-/m1/s1
		⚫	\| molecular_weight = 375.40228
	\| smiles = O=C(O)2N3C(=O)(NC(=O)(\N==)c1ccccc1)3SC2(C)C		\| smiles = O=C(O)2N3C(=O)(NC(=O)(\N==)c1ccccc1)3SC2(C)C
		⚫	\| InChI = 1/C16H17N5O4S/c1-16(2)11(15(24)25)21-13(23)10(14(21)26-16)18-12(22)9(19-20-17)8-6-4-3-5-7-8/h3-7,9-11,14H,1-2H3,(H,18,22)(H,24,25)/t9-,10-,11+,14-/m1/s1
	\| InChIKey = ODFHGIPNGIAMDK-NJBDSQKTBL		\| InChIKey = ODFHGIPNGIAMDK-NJBDSQKTBL
		⚫	\| StdInChI_Ref = {{stdinchicite\|correct\|chemspider}}
⚫	\| CAS_number = 17243-38-8
		⚫	\| StdInChI = 1S/C16H17N5O4S/c1-16(2)11(15(24)25)21-13(23)10(14(21)26-16)18-12(22)9(19-20-17)8-6-4-3-5-7-8/h3-7,9-11,14H,1-2H3,(H,18,22)(H,24,25)/t9-,10-,11+,14-/m1/s1
⚫	\| ATC_prefix = J01
		⚫	\| StdInChIKey_Ref = {{stdinchicite\|correct\|chemspider}}
⚫	\| ATC_suffix = CE04
		⚫	\| StdInChIKey = ODFHGIPNGIAMDK-NJBDSQKTSA-N
⚫	\| PubChem = 71886
⚫	\| DrugBank_Ref = {{drugbankcite\|correct\|drugbank}}
⚫	\| DrugBank = DB08795
⚫	\| KEGG_Ref = {{keggcite\|correct\|kegg}}
⚫	\| KEGG = D07235
⚫	\| C=16\|H=17\|N=5\|O=4\|S=1
⚫	\| molecular_weight = 375.40228
⚫	\| bioavailability =
⚫	\| protein_bound =
⚫	\| metabolism =
⚫	\| elimination_half-life =
⚫	\| excretion =
⚫	\| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
⚫	\| pregnancy_US = <!-- A / B / C / D / X -->
⚫	\| pregnancy_category=
⚫	\| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
⚫	\| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII -->
⚫	\| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C -->
⚫	\| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
⚫	\| legal_status =
⚫	\| routes_of_administration =
	}}		}}
	'''Azidocillin''' is a type of ].		'''Azidocillin''' is a type of ].

Revision as of 11:47, 3 September 2011

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Pharmaceutical compound

Azidocillin
Clinical data

ATC code	J01CE04 (WHO)
Identifiers
IUPAC name 6--3,3-dimethyl-7-oxo-4-thia-1-azabicycloheptane-2-carboxylic acid
CAS Number	17243-38-8
PubChem CID	71886
DrugBank	DB08795
ChemSpider	16735689
UNII	R8XDP7L3SL
KEGG	D07235
ChEBI	CHEBI:51758
CompTox Dashboard (EPA)	DTXSID20938154
ECHA InfoCard	100.037.510
Chemical and physical data
Formula	C₁₆H₁₇N₅O₄S
Molar mass	375.40228 g·mol
3D model (JSmol)	Interactive image
SMILES O=C(O)2N3C(=O)(NC(=O)(\N==)c1ccccc1)3SC2(C)C
InChI InChI=1S/C16H17N5O4S/c1-16(2)11(15(24)25)21-13(23)10(14(21)26-16)18-12(22)9(19-20-17)8-6-4-3-5-7-8/h3-7,9-11,14H,1-2H3,(H,18,22)(H,24,25)/t9-,10-,11+,14-/m1/s1 Key:ODFHGIPNGIAMDK-NJBDSQKTSA-N
(verify)

Azidocillin is a type of penicillin.

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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