Ceftiofur

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Ceftiofur

Systematic (IUPAC) name
(6R,7R)-7-[ [(2Z)-2-(2-Amino-1,3-thiazol-4-yl)- 2-methoxyiminoacetyl]amino]-3-(furan-2- carbonylsulfanylmethyl)-8-oxo-5-thia-1- azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Clinical data
AHFS/Drugs.com	International Drug Names
Legal status	?
Identifiers
CAS number	80370-57-6^Y
ATCvet code	QJ01DD90 QJ51DD90
PubChem	CID 6328657
ChemSpider	4886668^Y
UNII	83JL932I1C^Y
KEGG	D07657^Y
ChEMBL	CHEMBL222913^Y
Chemical data
Formula	C₁₉H₁₇N₅O₇S₃
Mol. mass	523.56 g/mol
SMILES O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)C(=N\OC)/c3nc(sc3)N)CSC(=O)c4occc4)C(=O)O
InChI InChI=1S/C19H17N5O7S3/c1-30-23-11(9-7-34-19(20)21-9)14(25)22-12-15(26)24-13(17(27)28)8(5-32-16(12)24)6-33-18(29)10-3-2-4-31-10/h2-4,7,12,16H,5-6H2,1H3,(H2,20,21)(H,22,25)(H,27,28)/b23-11-/t12-,16-/m1/s1^Y Key:ZBHXIWJRIFEVQY-IHMPYVIRSA-N^Y
Y (what is this?) (verify)

Ceftiofur is an antibiotic of the cephalosporin type (third generation), licensed for use in veterinary medicine. It was first described in 1987.^[1] It is marketed by pharmaceutical company Pfizer as Excenel,^[2] and is the active ingredient in that company's Specramast LC (lactating cow formula) product.

It is resistant to the antibiotic resistance enzyme beta-lactamase, and has activity against Gram-positive and Gram-negative bacteria. E. coli strains resistant to ceftiofur have been reported.^[3]

References

↑ Yancey RJ, Kinney ML, Roberts BJ, Goodenough KR, Hamel JC, Ford CW (1987). "Ceftiofur sodium, a broad-spectrum cephalosporin: evaluation in vitro and in vivo in mice". Am. J. Vet. Res. 48 (7): 1050–3. PMID 3631686.
↑ "Pfizer Animal Health Dairy Information on Products and Solutions". Retrieved 2007-11-20.
↑ Donaldson SC, Straley BA, Hegde NV, Sawant AA, DebRoy C, Jayarao BM (2006). "Molecular epidemiology of ceftiofur-resistant Escherichia coli isolates from dairy calves". Appl. Environ. Microbiol. 72 (6): 3940–8. doi:10.1128/AEM.02770-05. PMC 1489609. PMID 16751500.

External links

Official website

Antibacterials: 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.

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

Cephalosporins/Cephamycins
(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

β-lactamase inh.

Combinations

Other

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

^#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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