Cefprozil
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| 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 |
APRD00461 |
| ChemSpider |
8063315 Y |
| UNII |
1M698F4H4E Y |
| KEGG |
D07651 Y |
| ChEMBL |
CHEMBL1742  N |
| Chemical data |
| Formula |
C18H19N3O5S |
| Mol. mass |
389.427 g/mol |
| SMILES |
eMolecules & PubChem |
InChI
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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
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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 Practice1 has shown no increased risk for cross-allergy for cefprozil and several other second-generation or later cephalosporins.
References
- ^ Pichichero, ME (February 2006). "Cephalosporins can be prescribed safely for penicillin-allergic patients". J Fam Pract 55 (2): 106–12. PMID 16451776. http://www.jfponline.com/pdf%2F5502%2F5502JFP%5FAppliedEvidence1%2Epdf.
External links
- Cefprozil MedlinePlus Drug Information
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Antibacterials: cell envelope antibiotics (J01C-J01D)
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| Intracellular |
inhibit peptidoglycan subunit synthesis and transport: NAM synthesis inhibition (Fosfomycin) • DADAL/AR inhibitors (Cycloserine) • bactoprenol inhibitors (Bacitracin)
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| Glycopeptide |
inhibit PG chain elongation: Vancomycin# (Oritavancin, Telavancin) • Teicoplanin (Dalbavancin) • Ramoplanin
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β-lactams/
(inhibit PBP
cross-links) |
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Penicillins
(penams)
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Extended sp.
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aminopenicillins: Amoxicillin# • Ampicillin# (Pivampicillin, Hetacillin, Bacampicillin, Metampicillin, Talampicillin) • Epicillin
carboxypenicillins: Carbenicillin (Carindacillin) • Ticarcillin • Temocillin
ureidopenicillins: Azlocillin • Piperacillin • Mezlocillin
other: Mecillinam (Pivmecillinam) • Sulbenicillin
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Narrow sp.
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β-lactamase sensitive
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Benzylpenicillin (G)#: Clometocillin • Benzathine benzylpenicillin# • Procaine benzylpenicillin# • Azidocillin • Penamecillin
Phenoxymethylpenicillin (V) #: Propicillin • Benzathine phenoxymethylpenicillin • Pheneticillin
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β-lactamase resistant
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Cloxacillin# (Dicloxacillin, Flucloxacillin) • Oxacillin • Meticillin • Nafcillin
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Penems
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Faropenem
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Carbapenems
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Biapenem • Ertapenem • antipseudomonal (Doripenem • Imipenem • Meropenem) • Panipenem
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Cephalosporins/Cephamycins
(cephems)
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1st (PEcK)
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Cefazolin# • Cefacetrile • Cefadroxil • Cefalexin • Cefaloglycin • Cefalonium • Cefaloridine • Cefalotin • Cefapirin • Cefatrizine • Cefazedone • Cefazaflur • Cefradine • Cefroxadine • Ceftezole
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2nd (HEN)
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Cefaclor • Cefamandole • Cefminox • Cefonicid • Ceforanide • Cefotiam • Cefprozil • Cefbuperazone • Cefuroxime • Cefuzonam • cephamycin (Cefoxitin, Cefotetan, Cefmetazole) • carbacephem (Loracarbef)
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3rd
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Cefixime# • Ceftriaxone# • antipseudomonal (Ceftazidime# • Cefoperazone) • Cefcapene • Cefdaloxime • Cefdinir • Cefditoren • Cefetamet • Cefmenoxime • Cefodizime • Cefotaxime • Cefpimizole • Cefpiramide • Cefpodoxime • Cefsulodin • Cefteram • Ceftibuten • Ceftiolene • Ceftizoxime • oxacephem (Flomoxef, Latamoxef ‡)
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4th (antips-)
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Cefepime • Cefozopran • Cefpirome • Cefquinome
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5th
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Ceftobiprole • Ceftaroline fosamil
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Veterinary
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Ceftiofur • Cefquinome • Cefovecin
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Monobactams
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Aztreonam • Tigemonam • Carumonam • Nocardicin A
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β-lactamase inh.
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penam (Sulbactam, Tazobactam) • clavam (Clavulanic acid)
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Combinations
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Amoxicillin/clavulanic acid# • Imipenem/cilastatin# • Ampicillin/flucloxacillin • Ampicillin/sulbactam (Sultamicillin) • Piperacillin/tazobactam
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| Other |
polymyxins/detergent (Colistin, Polymyxin B) • depolarizing (Daptomycin) • hydrolyze NAM-NAG (Lysozyme) • Gramicidin
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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gr+f/gr+a(t)/gr-p(c)/gr-o
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