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Cefacetrile

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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%
Eliminationhalf-life	1.2 hours
Excretion	Renal (72%)
Identifiers
IUPAC name (6R,7R)-3-(acetyloxymethyl)-7-[(2-cyanoacetyl)amino]- 8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2- carboxylic acid
CAS Number	10206-21-0^Y
PubChemCID	91562
DrugBank	DB01414^Y
ChemSpider	82675^Y
UNII	FDM21QQ344
KEGG	D07629^Y
ChEMBL	ChEMBL2104099
CompTox Dashboard(EPA)	DTXSID0022779
ECHA InfoCard	100.030.449
Chemical and physical data
Formula	C₁₃H₁₃N₃O₆S
Molar mass	339.32 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=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^Y Key:RRYMAQUWDLIUPV-BXKDBHETSA-N^Y
(verify)

Cefacetrile (INN, also spelled cephacetrile) is abroad-spectrum first generationcephalosporin antibiotic effective ingram-positive andgram-negative bacterial infections. It is abacteriostatic antibiotic.^[1]^[2] Cefacetrile is marketed under the trade namesCelospor,Celtol, andCristacef,^[3] and asVetimast for the treatment ofmammary infections in lactating cows.^[2]

It was made by reacting7-ACA (7-aminocephalosporanic acid) with cyanoacetyl chloride in the presence oftributylamine.^{[citation needed]}

^"Cefacetrile Summary Report"(PDF).European Medicines Agency, Committee for Veterinary Medicinal Products. 1998. Archived fromthe original(PDF) on 2020-05-26. Retrieved2012-01-25.
^^a ^bHaberfeld 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). "[Clinical evaluation of cephacetrile (Celtol) for respiratory infections (author's transl)]".The Japanese Journal of Antibiotics.33 (10):1145–55.PMID 7206219.

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)

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^‡

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^‡

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

Combinations

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

Intracellular

Other

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