Cloxacillin: Difference between revisions

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{{drugbox
{{Drugbox
| verifiedrevid = 460045783
| IUPAC_name = (2''S'',5''R'',6''R'')-6-{[3-(2-chlorophenyl)-5-methyl-<br>oxazole-4-carbonyl]amino}-3,3-dimethyl-7-oxo-<br>4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
| IUPAC_name = (2''S'',5''R'',6''R'')-6-{[3-(2-chlorophenyl)-5-methyl-<br>oxazole-4-carbonyl]amino}-3,3-dimethyl-7-oxo-<br>4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
| image = Cloxacillin.svg
| image = Clox wiki str.png
| image2 = Clox ball n stick.png
 
<!--Clinical data-->
| tradename = Cloxapen
| Drugs.com = {{drugs.com|CONS|cloxacillin}}
| pregnancy_US = B
| legal_status = 
| routes_of_administration = Oral, [[Intramuscular injection|IM]]
 
<!--Pharmacokinetic data-->
| bioavailability = 37 to 90%
| protein_bound = 95%
| metabolism = 
| elimination_half-life = 30 minutes to 1 hour
| excretion = [[Kidney|Renal]] and biliary
 
<!--Identifiers-->
| CASNo_Ref = {{cascite|correct|CAS}}
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 61-72-3
| CAS_number = 61-72-3
| ATC_prefix = J01
| ATC_prefix = J01
| ATC_suffix = CF02
| ATC_suffix = CF02
| ATC_supplemental =  
| ATC_supplemental =   {{ATCvet|J51|CF02}} {{ATCvet|S01|AA90}}
| PubChem = 6098
| PubChem = 6098
| DrugBank = APRD00882
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| C = 19 | H = 18 | Cl = 1 | N = 3 | O = 5 | S = 1
| DrugBank = DB01147
| molecular_weight = 435.882 g/mol
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| bioavailability = 37 to 90%
| ChemSpiderID = 5873
| protein_bound = 95%
| UNII_Ref = {{fdacite|correct|FDA}}
| metabolism =  
| UNII = O6X5QGC2VB
| elimination_half-life = 30 minutes to 1 hour
| KEGG_Ref = {{keggcite|correct|kegg}}
| excretion = [[Kidney|Renal]] and biliary
| KEGG = D07733
| pregnancy_US = B
| ChEBI_Ref = {{ebicite|correct|EBI}}
| legal_status =  
| ChEBI = 49566
| routes_of_administration = Oral, [[Intramuscular injection|IM]]
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 891
 
<!--Chemical data-->
| C=19 | H=18 | Cl=1 | N=3 | O=5 | S=1  
| molecular_weight = 435.88 g/mol
| smiles = O=C(O)[C@@H]3N4C(=O)[C@@H](NC(=O)c2c(onc2c1ccccc1Cl)C)[C@H]4SC3(C)C
| InChI = 1/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
| InChIKey = LQOLIRLGBULYKD-JKIFEVAIBU
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = LQOLIRLGBULYKD-JKIFEVAISA-N
}}
}}
{{SI}}
'''Cloxacillin''' is an [[antibiotic]] useful for the treatment of a number of [[bacterial]] infections. It is semisynthetic and in the same class as [[penicillin]].
{{EH}}


'''Cloxacillin''' is a semisynthetic [[antibiotic]] in the same class as [[penicillin]]. It is sold under a number of trade names, including '''Cloxapen''' and '''Orbenin'''.
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 is used against [[staphylococci]] that produce [[beta-lactamase]].


This drug has a weaker antibacterial activity than benzylpencillin, and is devoid of serious toxicity except for allergic reactions.
<!-- Society and culture -->
Cloxacillin was discovered and developed by [[Beecham (pharmaceutical company)|Beecham]].<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 [[World Health Organization's List of Essential Medicines]], a list of the most important medication needed in a basic [[health system]].<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>


==See also==
==See also==
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*[[Nafcillin]]
*[[Nafcillin]]
*[[Oxacillin]]
*[[Oxacillin]]
==References==
{{reflist}}


{{PenicillinAntiBiotics}}
{{PenicillinAntiBiotics}}
{{SIB}}
{{antibiotic-stub}}


[[th:คลอกซาซิลลิน]]
[[Category:Beta-lactam antibiotics]]
[[Category:Beta-lactam antibiotics]]
{{WikiDoc Help Menu}}
[[Category:World Health Organization essential medicines]]
{{WS}}
[[Category:Isoxazoles]]
[[Category:Enantiopure drugs]]
[[Category:Organochlorides]]

Latest revision as of 12:56, 7 April 2015

Cloxacillin
Clinical data
Trade namesCloxapen
AHFS/Drugs.comMicromedex Detailed Consumer Information
Pregnancy
category
  • US: B (No risk in non-human studies)
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
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
E number{{#property:P628}}
ECHA InfoCard{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
FormulaC19H18ClN3O5S
Molar mass435.88 g/mol
3D model (JSmol)
  (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.[1] 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.[2]

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.

Template:Antibiotic-stub

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