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Cefadroxil

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Revision as of 20:35, 10 November 2011 by Beetstra (talk | contribs) (Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'DrugBank', 'ChEMBL').)(diff) ← Previous revision | Latest revision (diff) | Newer revision → (diff) Pharmaceutical compound
Cefadroxil
Clinical data
Trade namesDuricef
AHFS/Drugs.comMonograph
MedlinePlusa682730
Routes of
administration
Oral
ATC code
Pharmacokinetic data
Protein bindingplasma protein
Metabolismunknown
Elimination half-life1.5 hours
Identifiers
IUPAC name
  • (6R,7R)-7-{amino}-3-methyl-8-oxo-5-thia-1-azabicyclooct-2-ene-2-carboxylic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
CompTox Dashboard (EPA)
ECHA InfoCard100.051.397 Edit this at Wikidata
Chemical and physical data
FormulaC16H17N3O5S
Molar mass363.389 g/mol g·mol
3D model (JSmol)
SMILES
  • O=C2N1/C(=C(\CS12NC(=O)(c3ccc(O)cc3)N)C)C(=O)O.O
InChI
  • InChI=1S/C16H17N3O5S.H2O/c1-7-6-25-15-11(14(22)19(15)12(7)16(23)24)18-13(21)10(17)8-2-4-9(20)5-3-8;/h2-5,10-11,15,20H,6,17H2,1H3,(H,18,21)(H,23,24);1H2/t10-,11-,15-;/m1./s1
  • Key:NBFNMSULHIODTC-CYJZLJNKSA-N
  (what is this?)  (verify)

Cefadroxil is a broad-spectrum antibiotic of the cephalosporin type, effective in Gram-positive and Gram-negative bacterial infections. It is a bactericidal antibiotic.

General use

Cefadroxil is a first-generation cephalosporin antibacterial drug that is the para-hydroxy derivative of cefalexin, and is used similarly in the treatment of mild to moderate susceptible infections such as the bacterium Streptococcus pyogenes, causing the disease popularly called strep throat or Streptococcal tonsillitis, urinary tract infection, reproductive tract infection and skin infections.

Pharmacokinetics

Cefadroxil is almost completely absorbed from the gastrointestinal tract. After doses of 500 mg and 1 g by mouth, peak plasma concentrations of about 16 and 30 micrograms/mL respectively are obtained after 1.5 to 2 hours. Although peak concentrations are similar to those of cefalexin, plasma concentrations are more sustained. Dosage with food does not appear to affect the absorption of cefadroxil. About 20% of cefadroxil is reported to be bound to plasma proteins. The plasma half-life of cefadroxil is about 1.5 hours and is prolonged in patients with renal impairment.

Cefadroxil is widely distributed to body tissues and fluids. It crosses the placenta and appears in breast milk.

More than 90% of a dose of cefadroxil may be excreted unchanged in the urine within 24 hours by glomerular filtration and tubular secretion; peak urinary concentrations of 1.8 mg/mL have been reported after a dose of 500 mg. Cefadroxil is removed by haemodialysis.

Dosage

Cefadroxil is given by mouth, and doses are expressed in terms of the anhydrous substance; 1.04 g of cefadroxil monohydrate is equivalent to about 1 g of anhydrous cefadroxil.

Side effects

The most common side effects of Cefadroxil are diarrhoea (which, less commonly, may be bloody), nausea, upset stomach, and vomiting. Other side effects include:

Dental use

Cefadroxil is used as an antibiotic prophylaxis before dental procedures.

(Always consider Amoxicillin plus Metronidazole as first line of treatment for dental procedures. In Case of penicillin allergy consider "Cefadroxil" for prophylaxis.)

Veterinary use

Can be used for treating infected wounds on animals. Usually in powder form mixed with water has a color and smell similar to Tang. Given orally to animals, amount dependent on their weight and severity of infection.

References

  1. "Cefadroxil side effects". Drugs.
Antibacterials active on the cell wall and envelope (J01C-J01D)
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
)
Penicillins (Penams)
Narrow
spectrum
β-lactamase sensitive
(1st generation)
β-lactamase resistant
(2nd generation)
Extended
spectrum
Aminopenicillins (3rd generation)
Carboxypenicillins (4th generation)
Ureidopenicillins (4th generation)
Other
Carbapenems / Penems
Cephems
Cephalosporins
Cephamycins
Carbacephems
1st generation
2nd generation
3rd generation
4th generation
5th generation
Siderophore
Veterinary
Monobactams
β-lactamase inhibitors
Combinations
Polypeptides
Lipopeptides
Other
  • Inhibits PG elongation and crosslinking: Ramoplanin
Intracellular
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