Cefprozil

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Cefprozil

Systematic (IUPAC) name
7-[2-amino-2-(4-hydroxyphenyl)-acetyl]amino-8-oxo-3-prop-1-enyl-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Clinical data
Trade names	Cefzil
AHFS/Drugs.com	monograph
MedlinePlus	a698022
Licence data	US FDA:link
Pregnancy cat.	B (US)
Legal status	℞-only (US)
Routes	Oral
Pharmacokinetic data
Bioavailability	95%
Protein binding	36%
Half-life	1.3 hours
Identifiers
CAS number	92665-29-7^Y
ATC code	J01DC10
PubChem	CID 9887643
DrugBank	DB01150
ChemSpider	8063315^Y
UNII	1M698F4H4E^Y
KEGG	D07651^Y
ChEBI	CHEBI:3506^N
ChEMBL	CHEMBL1742^N
Chemical data
Formula	C₁₈H₁₉N₃O₅S
Mol. mass	389.427 g/mol
SMILES O=C2N1/C(=C(/C=C/C)CS[C@@H]1[C@@H]2NC(=O)[C@@H](c3ccc(O)cc3)N)C(=O)O.O
InChI InChI=1S/C18H19N3O5S.H2O/c1-2-3-10-8-27-17-13(16(24)21(17)14(10)18(25)26)20-15(23)12(19)9-4-6-11(22)7-5-9;/h2-7,12-13,17,22H,8,19H2,1H3,(H,20,23)(H,25,26);1H2/b3-2-;/t12-,13-,17-;/m1./s1^Y Key:ALYUMNAHLSSTOU-HERYOFLYSA-N^Y
N (what is this?) (verify)

Cefprozil, sometimes spelled cefproxil and marketed under the trade name Cefzil, is a second-generation cephalosporin type antibiotic. In Europe it is marketed using the trade names Procef and Cronocef.^{[citation needed]} It can be used to treat bronchitis, ear infections, skin infections, and other bacterial infections.^{[citation needed]} It comes as a tablet and as a liquid suspension.

Although there is a widely quoted cross-allergy risk of 10% between cephalosporins and penicillin, an article in the Journal of Family Practice^[1] has shown no increased risk for cross-allergy for cefprozil and several other second-generation or later cephalosporins.

Spectrum of bacterial susceptibility and resistance

Currently bacteria like Enterobacter aerogenes, Morganella morganii and Pseudomonas aeruginosa are resistant to Cefprozil, while Salmonella Agona and Streptococci are susceptible to Cefprozil. Some of the bacteria like Brucella abortus, Moraxella catarrhalis and Streptococcus pneumonia have developed resistance towards Cefprozil in varying degrees. For detailed minimum inhibition concentration information, please refer to Cefprozil Susceptibility and Resistance Data sheet.^[2]

References

↑ Pichichero, ME (February 2006). "Cephalosporins can be prescribed safely for penicillin-allergic patients". J Fam Pract 55 (2): 106–12. PMID 16451776.
↑ "Cefprozil Susceptibility and Resistance Data". Retrieved 23 July 2013.

External links

Cefprozil MedlinePlus Drug Information

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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