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Cloxacillin was discovered and developed by ].<ref name="Greenwood2008">{{cite book|author=David Greenwood|title=Antimicrobial drugs: chronicle of a twentieth century medical triumph|url=http://books.google.com/books?id=i4_FZHmzjzwC&pg=PA124|accessdate=18 November 2010|year=2008|publisher=Oxford University Press US|isbn=978-0-19-953484-5|pages=124–}}</ref> It is sold under a number of trade names, including '''Cloxapen''', '''Cloxacap''', '''Tegopen''' and '''Orbenin'''. It is on the ], a list of the most important medication needed in a basic ].<ref>{{cite web|title=WHO Model List of EssentialMedicines|url=http://apps.who.int/iris/bitstream/10665/93142/1/EML_18_eng.pdf?ua=1|work=World Health Organization|accessdate=22 April 2014|date=October 2013}}</ref> Cloxacillin was discovered and developed by ].<ref name="Greenwood2008">{{cite book|author=David Greenwood|title=Antimicrobial drugs: chronicle of a twentieth century medical triumph|url=http://books.google.com/books?id=i4_FZHmzjzwC&pg=PA124|accessdate=18 November 2010|year=2008|publisher=Oxford University Press US|isbn=978-0-19-953484-5|pages=124–}}</ref> It is sold under a number of trade names, including '''Cloxapen''', '''Cloxacap''', '''Tegopen''' and '''Orbenin'''. It is on the ], a list of the most important medication needed in a basic ].<ref>{{cite web|title=WHO Model List of EssentialMedicines|url=http://apps.who.int/iris/bitstream/10665/93142/1/EML_18_eng.pdf?ua=1|work=World Health Organization|accessdate=22 April 2014|date=October 2013}}</ref>
==Synthesis==

]
==See also== ==See also==
*] *]

Revision as of 07:45, 4 March 2015

Pharmaceutical compound
Cloxacillin
Clinical data
Trade namesCloxapen
AHFS/Drugs.comMicromedex Detailed Consumer Information
Routes of
administration
Oral, IM
ATC code
Pharmacokinetic data
Bioavailability37 to 90%
Protein binding95%
Elimination half-life30 minutes to 1 hour
ExcretionRenal and biliary
Identifiers
IUPAC name
  • (2S,5R,6R)-6-{amino}-3,3-dimethyl-7-oxo-
    4-thia-1-azabicycloheptane-2-carboxylic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.468 Edit this at Wikidata
Chemical and physical data
FormulaC19H18ClN3O5S
Molar mass435.88 g/mol g·mol
3D model (JSmol)
SMILES
  • O=C(O)3N4C(=O)(NC(=O)c2c(onc2c1ccccc1Cl)C)4SC3(C)C
InChI
  • InChI=1S/C19H18ClN3O5S/c1-8-11(12(22-28-8)9-6-4-5-7-10(9)20)15(24)21-13-16(25)23-14(18(26)27)19(2,3)29-17(13)23/h4-7,13-14,17H,1-3H3,(H,21,24)(H,26,27)/t13-,14+,17-/m1/s1
  • Key:LQOLIRLGBULYKD-JKIFEVAISA-N
  (verify)

Cloxacillin is an antibiotic useful for the treatment of a number of bacterial infections. It is semisynthetic and in the same class as penicillin.

Cloxacillin is used against staphylococci that produce beta-lactamase, due to its large R chain, which does not allow the beta-lactamases to bind. This drug has a weaker antibacterial activity than benzylpenicillin, and is devoid of serious toxicity except for allergic reactions.

Cloxacillin was discovered and developed by Beecham. It is sold under a number of trade names, including Cloxapen, Cloxacap, Tegopen and Orbenin. It is on the World Health Organization's List of Essential Medicines, a list of the most important medication needed in a basic health system.

Synthesis

Cloxacillin synthesis:

See also

References

  1. David Greenwood (2008). Antimicrobial drugs: chronicle of a twentieth century medical triumph. Oxford University Press US. pp. 124–. ISBN 978-0-19-953484-5. Retrieved 18 November 2010.
  2. "WHO Model List of EssentialMedicines" (PDF). World Health Organization. October 2013. Retrieved 22 April 2014.
  3. Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.1039/JR9630005838, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with |doi=10.1039/JR9630005838 instead.
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
Other
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