Cefacetrile: Difference between revisions

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			{{Short description\|Chemical compound}}
	{{Unreferenced stub\|auto=yes\|date=December 2009}}
	{{Drugbox		{{Drugbox
			\| Watchedfields = changed
	\| verifiedrevid = ~~443508901~~		\| verifiedrevid = 447440132
	\| 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

	<!--Clinical data-->		<!--Clinical data-->
	\| tradename =		\| tradename = Celospor, Celtol, Cristacef
	\| Drugs.com = {{drugs.com\|international\|cefacetrile}}		\| Drugs.com = {{drugs.com\|international\|cefacetrile}}
	\| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->		\| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
	\| pregnancy_US = <!-- A / B / C / D / X -->		\| pregnancy_US = <!-- A / B / C / D / X -->
	\| pregnancy_category =		\| pregnancy_category =
	\| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S8 -->		\| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S8 -->
	\| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII -->		\| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII -->
	\| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->		\| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
	\| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->		\| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
	\| legal_status =		\| legal_status = Rx-only
	\| routes_of_administration = ], ]		\| routes_of_administration = ], ], intra]

	<!--Pharmacokinetic data-->		<!--Pharmacokinetic data-->
	\| bioavailability =		\| bioavailability =
	\| protein_bound = 23 to 38%		\| protein_bound = 23 to 38%
	\| metabolism =		\| metabolism =
	\| elimination_half-life = 1.2 hours		\| elimination_half-life = 1.2 hours
	\| excretion = ] (72%)		\| excretion = ] (72%)

	<!--Identifiers-->		<!--Identifiers-->
	\| ~~CASNo_Ref~~ = {{cascite\|correct\|~~CAS~~}}		\| CAS_number_Ref = {{cascite\|correct\|??}}
	\| 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\|DB10}}
	\| PubChem = 91562		\| PubChem = 91562
			\| ChEMBL = 2104099
	\| DrugBank_Ref = {{drugbankcite\|correct\|drugbank}}		\| DrugBank_Ref = {{drugbankcite\|correct\|drugbank}}
	\| DrugBank = DB01414		\| DrugBank = DB01414
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	\| KEGG_Ref = {{keggcite\|correct\|kegg}}		\| KEGG_Ref = {{keggcite\|correct\|kegg}}
	\| KEGG = D07629		\| KEGG = D07629

	<!--Chemical data-->		<!--Chemical data-->
	\| C=13 \| H=13 \| N=3 \| O=6 \| S=1		\| C=13 \| H=13 \| N=3 \| O=6 \| S=1
	\| molecular_weight = 339.325 g/mol
	\| smiles = O=C2N1/C(=C(\CS12NC(=O)CC#N)COC(=O)C)C(=O)O		\| smiles = O=C2N1/C(=C(\CS12NC(=O)CC#N)COC(=O)C)C(=O)O
	\| 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
	\| InChIKey = RRYMAQUWDLIUPV-BXKDBHETBM
	\| StdInChI_Ref = {{stdinchicite\|correct\|chemspider}}		\| 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		\| 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
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	\| StdInChIKey = RRYMAQUWDLIUPV-BXKDBHETSA-N		\| StdInChIKey = RRYMAQUWDLIUPV-BXKDBHETSA-N
	}}		}}
	'''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.<ref>{{cite web\|url=http://www.emea.europa.eu/docs/en_GB/document_library/Maximum_Residue_Limits_-_Report/2009/11/WC500011465.pdf\|publisher=], Committee for Veterinary Medicinal Products\|title=Cefacetrile Summary Report\|year=1998\|access-date=2012-01-25\|archive-date=2020-05-26\|archive-url=https://web.archive.org/web/20200526024746/https://www.ema.europa.eu/en/documents/mrl-report/cefacetrile-summary-report-1-committee-veterinary-medicinal-products_en.pdf\|url-status=dead}}</ref><ref name="AC">{{cite book \|title= Austria-Codex \| veditors = Haberfeld H \|publisher=Österreichischer Apothekerverlag \|location=Vienna \|year=2007 \|edition=2007/2008 \|isbn=978-3-85200-183-8 \|language=German}}</ref> Cefacetrile is marketed under the trade names '''Celospor''', '''Celtol''', and '''Cristacef''',<ref>{{cite journal \| vauthors = Horiuchi N, Oyakawa Y, Oka R, Fujiwara T \| title = \| journal = The Japanese Journal of Antibiotics \| volume = 33 \| issue = 10 \| pages = 1145–55 \| date = October 1980 \| pmid = 7206219 }}</ref> and as '''Vetimast''' for the treatment of ] infections in lactating cows.<ref name="AC" />
			==Synthesis==
			]).]]
			It was made by reacting ] (7-aminocephalosporanic acid) with cyanoacetyl chloride in the presence of ].{{cn\|date=March 2023}}

			== References ==
			{{Reflist}}

	{{CephalosporinAntiBiotics}}		{{CephalosporinAntiBiotics}}
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	]		]
	]		]
			]

			]
			]

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

	]

Latest revision as of 16:13, 21 November 2023

Chemical compound Pharmaceutical compound

Cefacetrile
Clinical data

Trade names	Celospor, Celtol, Cristacef
AHFS/Drugs.com	International Drug Names
Routes of administration	Intravenous, intramuscular, intramammary
ATC code	J01DB10 (WHO) QJ51DB10 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
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
ChEMBL	ChEMBL2104099
CompTox Dashboard (EPA)	DTXSID0022779
ECHA InfoCard	100.030.449
Chemical and physical data
Formula	C₁₃H₁₃N₃O₆S
Molar mass	339.32 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, and as Vetimast for the treatment of mammary infections in lactating cows.

Synthesis

It was made by reacting 7-ACA (7-aminocephalosporanic acid) with cyanoacetyl chloride in the presence of tributylamine.

References

"Cefacetrile Summary Report" (PDF). European Medicines Agency, Committee for Veterinary Medicinal Products. 1998. Archived from the original (PDF) on 2020-05-26. Retrieved 2012-01-25.
^ Haberfeld H, ed. (2007). Austria-Codex (in German) (2007/2008 ed.). Vienna: Österreichischer Apothekerverlag. ISBN 978-3-85200-183-8.
Horiuchi N, Oyakawa Y, Oka R, Fujiwara T (October 1980). "". The Japanese Journal of Antibiotics. 33 (10): 1145–55. PMID 7206219.

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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