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Revision as of 20:35, 10 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'DrugBank', 'ChEMBL').← Previous edit Latest revision as of 18:38, 21 October 2024 edit undoJWBE (talk | contribs)Extended confirmed users10,126 edits removed Category:Phenols; added Category:4-Hydroxyphenyl compounds using HotCat 
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{{short description|Antibiotic}}
{{More citations needed|date=September 2024}}
{{Drugbox {{Drugbox
| Verifiedfields = changed | Verifiedfields = changed
| verifiedrevid = 401677554 | verifiedrevid = 460022388
| IUPAC_name = (6''R'',7''R'')-7-{amino}-3-methyl-8-oxo-5-thia-1-azabicyclooct-2-ene-2-carboxylic acid | IUPAC_name = (6''R'',7''R'')-7-{amino}-3-methyl-8-oxo-5-thia-1-azabicyclooct-2-ene-2-carboxylic acid
| image = Cefadroxil.svg | image = Cefadroxil.svg

<!--Clinical data--> <!--Clinical data-->
| tradename = Duricef | tradename = Duricef
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| MedlinePlus = a682730 | MedlinePlus = a682730
| pregnancy_category = | pregnancy_category =
| legal_status = | legal_status = Rx Only
| routes_of_administration = Oral | routes_of_administration = Oral

<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->
| bioavailability = | bioavailability =
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| metabolism = unknown | metabolism = unknown
| elimination_half-life = 1.5 hours | elimination_half-life = 1.5 hours

<!--Identifiers--> <!--Identifiers-->
| CASNo_Ref = {{cascite|correct|CAS}}
| CAS_number_Ref = {{cascite|correct|??}} | CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 66592-87-8 | CAS_number = 66592-87-8
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| UNII_Ref = {{fdacite|correct|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 280111G160 | UNII = 280111G160
| KEGG_Ref = {{keggcite|changed|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D02353 | KEGG = D02353
| ChEBI_Ref = {{ebicite|changed|EBI}} | ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 53667 | ChEBI = 53667
| ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = <!-- blanked - oldvalue: 1644 --> | ChEMBL = 1644
<!--Chemical data-->
| C=16 | H=17 | N=3 | O=5 | S=1 | C=16 | H=17 | N=3 | O=5 | S=1
| molecular_weight = 363.389 g/mol
| smiles = O=C2N1/C(=C(\CS12NC(=O)(c3ccc(O)cc3)N)C)C(=O)O.O | smiles = O=C2N1/C(=C(\CS12NC(=O)(c3ccc(O)cc3)N)C)C(=O)O.O
| InChI = 1/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
| InChIKey = NBFNMSULHIODTC-CYJZLJNKBD
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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 | StdInChI = 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
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| StdInChIKey = NBFNMSULHIODTC-CYJZLJNKSA-N | StdInChIKey = NBFNMSULHIODTC-CYJZLJNKSA-N
}} }}
<!-- Definition and medical uses -->
'''Cefadroxil''' is a ] of the ] type, effective in ] and ] bacterial infections. It is a ] antibiotic. '''Cefadroxil''' (formerly trademarked as '''Duricef''') is a ] of the ] type, effective in ] and ] bacterial infections. It is a ] antibiotic.


<!-- Society and culture -->
== General use ==
It was patented in 1967 and approved for medical use in 1978.<ref name=Fis2006>{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=493 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA493 |language=en}}</ref>
⚫ Cefadroxil is a first-generation cephalosporin antibacterial drug that is the para-hydroxy derivative of ], and is used similarly in the treatment of mild to moderate susceptible infections such as the bacterium ], causing the disease popularly called ] or ], ], ] and ].


== Pharmacokinetics == ==Medical use ==
⚫ Cefadroxil is a first-generation cephalosporin antibacterial drug that is the para-hydroxy derivative of ], and is used similarly in the treatment of mild to moderate susceptible infections such as the bacterium '']'', causing the disease popularly called ] or ], ], ], and ].{{cn|date=March 2023}}
⚫ 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 used as an antibiotic prophylaxis before dental procedures, for patients allergic to penicillins.{{cn|date=March 2023}}
Cefadroxil is widely distributed to body tissues and fluids. It crosses the placenta and appears in breast milk.


===Spectrum of bacterial resistance and susceptibility===
⚫ 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.
Cefadroxil has a broad spectrum of activity and has been effective in treating bacteria responsible for causing tonsillitis, and infections of the skin and urinary tract. Cefadroxil covers similar organisms to Cephalexin given that it is a derivative drug. The following represents MIC susceptibility data for a few medically significant microorganisms.<ref>{{cite web | title = Cefadroxil, Free Acid Susceptibility and Minimum Inhibitory Concentration (MIC) Data | url = http://www.toku-e.com/Assets/MIC/Cefadroxil.pdf }}</ref>
* ''Escherichia coli'': 8 μg/ml
* ''Staphylococcus aureus'': 1 – 2 μg/ml
* ''Streptococcus pneumoniae'': ≤1 – >16 μg/ml


== Dosage == == Side effects ==
⚫ The most common side effects of cefadroxil are ] (which, less commonly, may be bloody), ], ], and ]. Other side effects include<ref name = "Drugs">{{cite web | url = https://www.drugs.com/sfx/cefadroxil-side-effects.html | title = Cefadroxil side effects | publisher = Drugs}}</ref>
], ], and ].


== Pharmacokinetics ==
⚫ 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.
⚫ Cefadroxil is almost completely absorbed from the gastrointestinal tract. After doses of 500&nbsp;mg and 1 g by mouth, peak plasma concentrations of about 16 and 30 micrograms/ml, respectively, are obtained after 1.5 to 2.0 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. Its plasma half-life is about 1.5 hours and is prolonged in patients with renal impairment.{{cn|date=March 2023}}


⚫ 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&nbsp;mg/ml have been reported after a dose of 500&nbsp;mg. Cefadroxil is removed by haemodialysis.
== Side effects ==
⚫ The most common side effects of Cefadroxil are ] (which, less commonly, may be bloody), ], ], and ]. Other side effects include<ref name = "Drugs">{{cite web | url = http://www.drugs.com/sfx/cefadroxil-side-effects.html | title = Cefadroxil side effects | publisher = Drugs}}</ref>:
*]
*]
*]


== Dental use == == Dosage ==
⚫ Cefadroxil is used as an antibiotic prophylaxis before dental procedures.


⚫ 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.<br />
(Always consider Amoxicillin plus Metronidazole as first line of treatment for dental procedures. In Case of penicillin allergy consider "Cefadroxil" for prophylaxis.){{Citation needed|date=November 2009}}
<!-- '''PO''' '''Adults'''. 500&nbsp;mg–1g q12h; '''Peds'''. 15&nbsp;mg/kg q12h; decrease in renal impair. -->


== Veterinary use == == 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 ]. Given orally to animals, amount dependent on their weight and severity of infection. It can be used for treating infected wounds on animals. Usually in powder form mixed with water, it has a color and smell similar to ]. Given orally to animals, the amount is dependent on their weight and severity of infection.


== References == == References ==
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