Cefacetrile: Difference between revisions

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	{{Unreferenced stub\|auto=yes\|date=December 2009}}		{{Unreferenced stub\|auto=yes\|date=December 2009}}
	{{Drugbox \| verifiedrevid = 443507673		{{Drugbox
			\| verifiedrevid = 443507673
	\|
	\| IUPAC_name = (6''R'',7''R'')-3-(acetyloxymethyl)-7--<br>8-oxo-5-thia-1-azabicyclooct-2-ene-2-<br>carboxylic acid		\| IUPAC_name = (6''R'',7''R'')-3-(acetyloxymethyl)-7--<br>8-oxo-5-thia-1-azabicyclooct-2-ene-2-<br>carboxylic acid
	\| image = Cefacetrile.svg		\| image = Cefacetrile.svg

⚫	\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
			<!--Clinical data-->
⚫	\| ChemSpiderID = 82675
			\| tradename =
⚫	\| UNII_Ref = {{fdacite\|correct\|FDA}}
			\| Drugs.com = {{drugs.com\|international\|cefacetrile}}
⚫	\| UNII = FDM21QQ344
		⚫	\| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
⚫	\| InChI = 1/C13H13N3O6S/c1-6(17)22-4-7-5-23-12-9(15-8(18)2-3-14)11(19)16(12)10(7)13(20)21/h9,12H,2,4-5H2,1H3,(H,15,18)(H,20,21)/t9-,12-/m1/s1
		⚫	\| pregnancy_US = <!-- A / B / C / D / X -->
⚫	\| smiles = O=C2N1/C(=C(\CS12NC(=O)CC#N)COC(=O)C)C(=O)O
		⚫	\| pregnancy_category =
⚫	\| InChIKey = RRYMAQUWDLIUPV-BXKDBHETBM
		⚫	\| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S8 -->
		⚫	\| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII -->
		⚫	\| legal_UK = <!-- GSL / P / POM / CD / 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 = 23 to 38%
		⚫	\| metabolism =
		⚫	\| elimination_half-life = 1.2 hours
		⚫	\| excretion = ] (72%)

			<!--Identifiers-->
	\| CASNo_Ref = {{cascite\|correct\|CAS}}		\| CASNo_Ref = {{cascite\|correct\|CAS}}
⚫	\| StdInChI_Ref = {{stdinchicite\|correct\|chemspider}}
⚫	\| StdInChI = 1S/C13H13N3O6S/c1-6(17)22-4-7-5-23-12-9(15-8(18)2-3-14)11(19)16(12)10(7)13(20)21/h9,12H,2,4-5H2,1H3,(H,15,18)(H,20,21)/t9-,12-/m1/s1
⚫	\| StdInChIKey_Ref = {{stdinchicite\|correct\|chemspider}}
⚫	\| StdInChIKey = RRYMAQUWDLIUPV-BXKDBHETSA-N
	\| CAS_number = 10206-21-0		\| CAS_number = 10206-21-0
	\| ATC_prefix = J01		\| ATC_prefix = J01
	\| ATC_suffix = DB10		\| ATC_suffix = DB10
	\| ATC_supplemental = {{ATCvet\|J51\|DA34}}		\| ATC_supplemental = {{ATCvet\|J51\|DA34}}
	\| PubChem = 91562		\| PubChem = 91562
	\| DrugBank_Ref = {{drugbankcite\|correct\|drugbank}}		\| DrugBank_Ref = {{drugbankcite\|correct\|drugbank}}
	\| DrugBank = DB01414		\| DrugBank = DB01414
		⚫	\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
		⚫	\| ChemSpiderID = 82675
		⚫	\| UNII_Ref = {{fdacite\|correct\|FDA}}
		⚫	\| UNII = FDM21QQ344
	\| KEGG_Ref = {{keggcite\|correct\|kegg}}		\| KEGG_Ref = {{keggcite\|correct\|kegg}}
	\| KEGG = D07629		\| KEGG = D07629

⚫	\| C = 13 \| H = 13 \| N = 3 \| O = 6 \| S = 1
			<!--Chemical data-->
		⚫	\| C=13 \| H=13 \| N=3 \| O=6 \| S=1
	\| molecular_weight = 339.325 g/mol		\| molecular_weight = 339.325 g/mol
		⚫	\| smiles = O=C2N1/C(=C(\CS12NC(=O)CC#N)COC(=O)C)C(=O)O
⚫	\| bioavailability =
		⚫	\| InChI = 1/C13H13N3O6S/c1-6(17)22-4-7-5-23-12-9(15-8(18)2-3-14)11(19)16(12)10(7)13(20)21/h9,12H,2,4-5H2,1H3,(H,15,18)(H,20,21)/t9-,12-/m1/s1
⚫	\| protein_bound = 23 to 38%
		⚫	\| InChIKey = RRYMAQUWDLIUPV-BXKDBHETBM
⚫	\| metabolism =
		⚫	\| StdInChI_Ref = {{stdinchicite\|correct\|chemspider}}
⚫	\| elimination_half-life = 1.2 hours
		⚫	\| StdInChI = 1S/C13H13N3O6S/c1-6(17)22-4-7-5-23-12-9(15-8(18)2-3-14)11(19)16(12)10(7)13(20)21/h9,12H,2,4-5H2,1H3,(H,15,18)(H,20,21)/t9-,12-/m1/s1
⚫	\| excretion = ] (72%)
		⚫	\| StdInChIKey_Ref = {{stdinchicite\|correct\|chemspider}}
⚫	\| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
		⚫	\| StdInChIKey = RRYMAQUWDLIUPV-BXKDBHETSA-N
⚫	\| pregnancy_US = <!-- A / B / C / D / X -->
⚫	\| pregnancy_category =
⚫	\| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S8 -->
⚫	\| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII -->
⚫	\| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
⚫	\| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
⚫	\| legal_status =
⚫	\| routes_of_administration = ], ]
	}}		}}
	'''Cefacetrile''' (], also spelled cephacetrile) is a ] first generation ] ] effective in ] and ] bacterial infections. It is a ] antibiotic. Cefacetrile is marketed under the trade names '''Celospor''', '''Celtol''', and '''Cristacef'''.		'''Cefacetrile''' (], also spelled cephacetrile) is a ] first generation ] ] effective in ] and ] bacterial infections. It is a ] antibiotic. Cefacetrile is marketed under the trade names '''Celospor''', '''Celtol''', and '''Cristacef'''.

Revision as of 05:23, 30 August 2011

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Pharmaceutical compound

Cefacetrile
Clinical data

AHFS/Drugs.com	International Drug Names
Routes of administration	Intravenous, intramuscular
ATC code	J01DB10 (WHO) QJ51DA34 (WHO)
Pharmacokinetic data
Protein binding	23 to 38%
Elimination half-life	1.2 hours
Excretion	Renal (72%)
Identifiers
IUPAC name (6R,7R)-3-(acetyloxymethyl)-7-- 8-oxo-5-thia-1-azabicyclooct-2-ene-2- carboxylic acid
CAS Number	10206-21-0
PubChem CID	91562
DrugBank	DB01414
ChemSpider	82675
UNII	FDM21QQ344
KEGG	D07629
CompTox Dashboard (EPA)	DTXSID0022779
ECHA InfoCard	100.030.449
Chemical and physical data
Formula	C₁₃H₁₃N₃O₆S
Molar mass	339.325 g/mol g·mol
3D model (JSmol)	Interactive image
SMILES O=C2N1/C(=C(\CS12NC(=O)CC#N)COC(=O)C)C(=O)O
InChI InChI=1S/C13H13N3O6S/c1-6(17)22-4-7-5-23-12-9(15-8(18)2-3-14)11(19)16(12)10(7)13(20)21/h9,12H,2,4-5H2,1H3,(H,15,18)(H,20,21)/t9-,12-/m1/s1 Key:RRYMAQUWDLIUPV-BXKDBHETSA-N
(verify)

Cefacetrile (INN, also spelled cephacetrile) is a broad-spectrum first generation cephalosporin antibiotic effective in Gram-positive and Gram-negative bacterial infections. It is a bacteriostatic antibiotic. Cefacetrile is marketed under the trade names Celospor, Celtol, and Cristacef.

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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