Cloxacillin: Difference between revisions

Cloxacillin
	File:Cloxacillin.svg
	File:Cloxacillin ball-and-stick.png
Clinical data
Trade names	Cloxapen
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Pregnancy; category	US: B (No risk in non-human studies) ; ;
Routes of; administration	Oral, IM
ATC code	J01CF02 (WHO) Template:ATCvet Template:ATCvet;
Pharmacokinetic data
Bioavailability	37 to 90%
Protein binding	95%
Elimination half-life	30 minutes to 1 hour
Excretion	Renal and biliary
Identifiers
	IUPAC name (2S,5R,6R)-6-{[3-(2-chlorophenyl)-5-methyl-; oxazole-4-carbonyl]amino}-3,3-dimethyl-7-oxo-; 4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid;
CAS Number	61-72-3 ;
PubChem CID	6098;
DrugBank	DB01147 ;
ChemSpider	5873 ;
UNII	O6X5QGC2VB;
KEGG	D07733 ;
ChEBI	CHEBI:49566 ;
ChEMBL	ChEMBL891 ;
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
Formula	C19H18ClN3O5S
Molar mass	435.88 g/mol
3D model (JSmol)	Interactive image;
	SMILES O=C(O)[C@@H]3N4C(=O)[C@@H](NC(=O)c2c(onc2c1ccccc1Cl)C)[C@H]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)

VisualWikitext

Revision as of 12:53, 7 April 2015

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]

References

↑ 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.
↑ "WHO Model List of EssentialMedicines" (PDF). World Health Organization. October 2013. Retrieved 22 April 2014.

Template:Antibiotic-stub

[Greenwood2008-1] 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.

[1]

[2]

@@ Line 1: / Line 1: @@
-{{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
 | image = Cloxacillin.svg
+| image2 = Cloxacillin ball-and-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
 | ATC_prefix = J01
 | ATC_suffix = CF02
-| ATC_supplemental =
+| ATC_supplemental =   {{ATCvet|J51|CF02}} {{ATCvet|S01|AA90}}
 | 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]].
-'''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==
@@ Line 32: / Line 63: @@
 *[[Nafcillin]]
 *[[Oxacillin]]
+==References==
+{{reflist}}
 {{PenicillinAntiBiotics}}
+{{antibiotic-stub}}
-[[th:คลอกซาซิลลิน]]
 [[Category:Beta-lactam antibiotics]]
-{{WikiDoc Help Menu}}
+[[Category:World Health Organization essential medicines]]
-{{WS}}
+[[Category:Isoxazoles]]
+[[Category:Enantiopure drugs]]
+[[Category:Organochlorides]]

v t e Antibacterials for systemic use: beta-lactam antibiotics - penicillins (J01C)
Antibiotics	Amoxicillin • Ampicillin • Azlocillin • Carbenicillin • Cloxacillin • Dicloxacillin • Flucloxacillin • Mezlocillin • Nafcillin • Piperacillin • Pivampicillin • Ticarcillin
Beta-lactamase inhibitors	Sulbactam • Tazobactam • Clavulanic acid
Combinations	Ampicillin/sulbactam (Sultamicillin) • Co-amoxiclav

Cloxacillin: Difference between revisions

Revision as of 12:53, 7 April 2015

See also

References

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