Cefacetrile

Cefacetrile: Cefacetrile

Systematic (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

Clinical data

AHFS/Drugs.com International Drug Names

Pregnancy cat. ?

Legal status ?

Routes Intravenous, intramuscular

Pharmacokinetic data

Protein binding 23 to 38%

Half-life 1.2 hours

Excretion Renal (72%)

Identifiers

CAS number 10206-21-0

ATC code J01DB10 QJ51DA34

PubChem CID 91562

DrugBank DB01414

ChemSpider 82675^Y

UNII FDM21QQ344^Y

KEGG D07629^Y

Chemical data

Formula C₁₃H₁₃N₃O₆S

Mol. mass 339.325 g/mol

SMILES eMolecules & PubChem

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

Y(what is this?) (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.

v · d · eAntibacterials: cell envelope antibiotics (J01C-J01D)

Intracellular
inhibit peptidoglycan subunit synthesis and transport: NAM synthesis inhibition (Fosfomycin) • DADAL/AR inhibitors (Cycloserine) • bactoprenol inhibitors (Bacitracin)

Glycopeptide
inhibit PG chain elongation: Vancomycin^# (Oritavancin, Telavancin) • Teicoplanin (Dalbavancin) • Ramoplanin

β-lactams/
(inhibit PBP
cross-links)

Penicillins/
(penams)

Extended sp.

aminopenicillins: Amoxicillin^# • Ampicillin^# (Pivampicillin, Hetacillin, Bacampicillin, Metampicillin, Talampicillin) • Epicillin

carboxypenicillins: Carbenicillin (Carindacillin) • Ticarcillin • Temocillin

ureidopenicillins: Azlocillin • Piperacillin • Mezlocillin
other: Mecillinam (Pivmecillinam) • Sulbenicillin

Narrow sp.

β-lactamase sensitive

Benzylpenicillin (G)^#: Clometocillin • Benzathine benzylpenicillin^# • Procaine benzylpenicillin^# • Azidocillin • Penamecillin
Phenoxymethylpenicillin (V)^#: Propicillin • Benzathine phenoxymethylpenicillin • Pheneticillin

β-lactamase resistant

Cloxacillin^# (Dicloxacillin, Flucloxacillin) • Oxacillin • Meticillin • Nafcillin

Penems

Faropenem

Carbapenems

Biapenem • Ertapenem • antipseudomonal (Doripenem • Imipenem • Meropenem) • Panipenem

Cephalosporins/
(cephems)

1st (P Ec K)

Cefazolin^# • Cefacetrile • Cefadroxil • Cefalexin • Cefaloglycin • Cefalonium • Cefaloridine • Cefalotin • Cefapirin • Cefatrizine • Cefazedone • Cefazaflur • Cefradine • Cefroxadine • Ceftezole

2nd (H E N)

Cefaclor • Cefamandole • Cefminox • Cefonicid • Ceforanide • Cefotiam • Cefprozil • Cefbuperazone • Cefuroxime • Cefuzonam • cephamycin (Cefoxitin, Cefotetan, Cefmetazole) • carbacephem (Loracarbef)

3rd

Cefixime^# • Ceftriaxone^# • antipseudomonal (Ceftazidime^# • Cefoperazone) • Cefcapene • Cefdaloxime • Cefdinir • Cefditoren • Cefetamet • Cefmenoxime • Cefodizime • Cefotaxime • Cefpimizole • Cefpiramide • Cefpodoxime • Cefsulodin • Cefteram • Ceftibuten • Ceftiolene • Ceftizoxime • oxacephem (Flomoxef, Latamoxef ^‡)

4th (antips-)

Cefepime • Cefozopran • Cefpirome • Cefquinome

5th

Ceftobiprole • Ceftaroline fosamil

Veterinary

Ceftiofur • Cefquinome • Cefovecin

Monobactams

Aztreonam • Tigemonam • Carumonam • Tabtoxin

β-lactamase inh.

penam (Sulbactam, Tazobactam) • clavam (Clavulanic acid)

Combinations

Amoxicillin/clavulanic acid^# • Imipenem/cilastatin^# • Ampicillin/flucloxacillin • Ampicillin/sulbactam (Sultamicillin) • Piperacillin/tazobactam

Other
polymyxins/detergent (Colistin, Polymyxin B) • depolarizing (Daptomycin) • hydrolyze NAM-NAG (Lysozyme) • Gramicidin

^#WHO-EM. ^‡Withdrawn from market. Clinical trials: ^†Phase III. ^§Never to phase III

M: BAC

bact (clas)

gr+f/gr+a(t)/gr-p(c)/gr-o

drug(J1p, w, n, m, vacc)

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Systematic (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
Clinical data
AHFS/Drugs.com	International Drug Names
Pregnancy cat.	?
Legal status	?
Routes	Intravenous, intramuscular
Pharmacokinetic data
Protein binding	23 to 38%
Half-life	1.2 hours
Excretion	Renal (72%)
Identifiers
CAS number	10206-21-0
ATC code	J01DB10 QJ51DA34
PubChem	CID 91562
DrugBank	DB01414
ChemSpider	82675^Y
UNII	FDM21QQ344^Y
KEGG	D07629^Y
Chemical data
Formula	C₁₃H₁₃N₃O₆S
Mol. mass	339.325 g/mol
SMILES	eMolecules & PubChem
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
Y(what is this?) (verify)

Academic Dictionaries and Encyclopedias

Wikipedia

Cefacetrile

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