Florfenicol: Difference between revisions

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Florfenicol
Clinical data
Synonyms	2,2-dichloro-N-((1R,2S)-3-fluoro-1-hydroxy-1-(4-(methylsulfonyl)phenyl)propan-2-yl)ethanamide
AHFS/Drugs.com	International Drug Names
Routes of; administration	intramuscular, subcutaneous
ATCvet code	Template:Infobox drug/formatATCvet; Template:Infobox drug/formatATCvet;
Legal status
Legal status	Veterinary use only;
Identifiers
	IUPAC name 2,2-dichloro-N-[(1R,2S)-3-fluoro-1-hydroxy-1-(4-methanesulfonylphenyl)propan-2-yl]acetamide;
CAS Number	73231-34-2 ;
PubChem CID	114811;
ChemSpider	102776 ;
UNII	9J97307Y1H;
KEGG	D04194 ;
ChEMBL	ChEMBL1241590 ;
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	C12H14Cl2FNO4S
Molar mass	358.21 g/mol
3D model (JSmol)	Interactive image;
	SMILES ClC(Cl)C(=O)N[C@@H]([C@H](O)c1ccc(cc1)S(=O)(=O)C)CF;
	InChI InChI=1S/C12H14Cl2FNO4S/c1-21(19,20)8-4-2-7(3-5-8)10(17)9(6-15)16-12(18)11(13)14/h2-5,9-11,17H,6H2,1H3,(H,16,18)/t9-,10-/m1/s1 ; Key:AYIRNRDRBQJXIF-NXEZZACHSA-N ;
(what is this?) (verify)

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VisualWikitext

Latest revision as of 18:43, 9 April 2015

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

Florfenicol (marketed by Schering-Plough Animal Health under the trade name Nuflor) is a fluorinated synthetic analog of thiamphenicol.^[1]

In the United States, florfenicol is currently indicated for the treatment of bovine respiratory disease (BRD) associated with Mannheimia (Pasteurella) haemolytica, Pasteurella multocida, and Haemophilus somnus, for treatment of bovine interdigital phlegmon (foot rot, acute interdigital necrobacillosis, infectious pododermatitis) associated with Fusobacterium necrophorum and Bacteroides melaninogenicus.

Florfenicol is also used in aquaculture, and is licensed for use in the United States for the control of enteric septicemia in catfish.^[2]

The use of florfenicol in horses, and likely in other equids, typically causes diarrhea. This has been anecdotally reported to progress to lethal cases of acute colitis. Therefore, use of this antimicrobial in the equine patient should be limited to cases in which other, safer, options are not available. ^[3]

Contamination

Florfenicol was among the drug contaminants in a brand of supermarket eggs in Taiwan and Iran.^[4]

External links

Nuflor website

References

↑ Syriopoulou VP, Harding AL, Goldmann DA, Smith AL (February 1981). "In vitro antibacterial activity of fluorinated analogs of chloramphenicol and thiamphenicol". Antimicrob Agents Chemother. 19 (2): 294–7. PMC 181412. PMID 6957162.
↑ Gaunt, P. S.; Langston, C.; Wrzesinski, C.; Gao, D.; Adams, P.; Crouch, L.; Sweeney, D.; Endris, R. "Multidose pharmacokinetics of orally administered florfenicol in the channel catfish ( )". Journal of Veterinary Pharmacology and Therapeutics. 36 (5): 502–506. doi:10.1111/j.1365-2885.2012.01426.x.
↑ Robinson, N.E.; Sprayberry, K.A. (2009). Current therapy in equine medicine. Saunders Elesevier. p. 13. ISBN 978-1-4160-5475-7. Retrieved March 21, 2011.
↑ Lee I-chia (8 January 2013). "Survey suggests certain eggs may be dangerous". Taipei Times. Retrieved 3 November 2014.

Template:Amphenicols

[1] Syriopoulou VP, Harding AL, Goldmann DA, Smith AL (February 1981). "In vitro antibacterial activity of fluorinated analogs of chloramphenicol and thiamphenicol". Antimicrob Agents Chemother. 19 (2): 294–7. PMC 181412. PMID 6957162.

[2] Gaunt, P. S.; Langston, C.; Wrzesinski, C.; Gao, D.; Adams, P.; Crouch, L.; Sweeney, D.; Endris, R. "Multidose pharmacokinetics of orally administered florfenicol in the channel catfish ( )". Journal of Veterinary Pharmacology and Therapeutics. 36 (5): 502–506. doi:10.1111/j.1365-2885.2012.01426.x.

[3] Robinson, N.E.; Sprayberry, K.A. (2009). Current therapy in equine medicine. Saunders Elesevier. p. 13. ISBN 978-1-4160-5475-7. Retrieved March 21, 2011.

[Lee-4] Lee I-chia (8 January 2013). "Survey suggests certain eggs may be dangerous". Taipei Times. Retrieved 3 November 2014.

[1]

[2]

[3]

[4]

@@ Line 1: / Line 1: @@
-{{Drugbox|
+{{Drugbox
-| IUPAC_name = 2,2-dichloro-''N''-((1R,2S)-3-fluoro-1- hydroxy-1-(4-(methylsulfonyl) phenyl) propan-2-yl) ethanamide
+| Verifiedfields = changed
-| image = Florfenicol.png
+| verifiedrevid = 461100919
-| CAS_number=76639-94-6
+| IUPAC_name = 2,2-dichloro-''N''-[(1''R'',2''S'')-3-fluoro-1-hydroxy-1-(4-methanesulfonylphenyl)propan-2-yl]acetamide
-| C=12 | H=14 | Cl=2 | F=1 | N=1 | O=4 | S=1
+| image = Flofenicol Wiki Str.png
+<!--Clinical data-->
+| tradename =
+| Drugs.com = {{drugs.com|international|florfenicol}}
+| pregnancy_category =
+| legal_status = veterinary prescription only
+| routes_of_administration = intramuscular, subcutaneous
+<!--Pharmacokinetic data-->
+| bioavailability =
+| protein_bound =
+| metabolism =
+| elimination_half-life =
+| excretion =
+<!--Identifiers-->
+| CAS_number_Ref = {{cascite|changed|??}}
+| CAS_number = 73231-34-2
+| ATCvet = yes
+| ATC_prefix = J01
+| ATC_suffix = BA90
+| ATC_supplemental =   {{ATCvet|J51|BA90}}
+| PubChem = 114811
+| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
+| ChemSpiderID = 102776
+| UNII_Ref = {{fdacite|correct|FDA}}
+| UNII = 9J97307Y1H
+| KEGG_Ref = {{keggcite|correct|kegg}}
+| KEGG = D04194
+| ChEMBL_Ref = {{ebicite|changed|EBI}}
+| ChEMBL = 1241590
+<!--Chemical data-->
+| C=12 | H=14 | Cl=2 | F=1 | N=1 | O=4 | S=1
 | molecular_weight = 358.21 g/mol
+| smiles = ClC(Cl)C(=O)N[C@@H]([C@H](O)c1ccc(cc1)S(=O)(=O)C)CF
+| InChI = 1/C12H14Cl2FNO4S/c1-21(19,20)8-4-2-7(3-5-8)10(17)9(6-15)16-12(18)11(13)14/h2-5,9-11,17H,6H2,1H3,(H,16,18)/t9-,10-/m1/s1
+| InChIKey = AYIRNRDRBQJXIF-NXEZZACHBQ
+| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
+| StdInChI = 1S/C12H14Cl2FNO4S/c1-21(19,20)8-4-2-7(3-5-8)10(17)9(6-15)16-12(18)11(13)14/h2-5,9-11,17H,6H2,1H3,(H,16,18)/t9-,10-/m1/s1
+| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
+| StdInChIKey = AYIRNRDRBQJXIF-NXEZZACHSA-N
+| synonyms = <small>2,2-dichloro-''N''-((1''R'',2''S'')-3-fluoro-1-hydroxy-1-(4-(methylsulfonyl)phenyl)propan-2-yl)ethanamide</small>
 }}
+__NOTOC__
 {{SI}}
+{{CMG}}
+== Overview ==
+'''Florfenicol''' (marketed by [[Schering-Plough|Schering-Plough Animal Health]] under the trade name Nuflor) is a fluorinated synthetic analog of [[thiamphenicol]].<ref>{{cite journal | author = Syriopoulou VP, Harding AL, Goldmann DA, Smith AL | title = In vitro antibacterial activity of fluorinated analogs of chloramphenicol and thiamphenicol. | journal = Antimicrob Agents Chemother. | volume = 19 | issue = 2 | pages = 294–7 |date=February 1981 | pmid = 6957162 | pmc = 181412}}</ref>
+In the United States, florfenicol is currently indicated for the treatment of [[bovine respiratory disease]] (BRD) associated with ''Mannheimia (Pasteurella) haemolytica'', ''[[Pasteurella multocida]]'', and ''[[Haemophilus somnus]]'', for treatment of bovine interdigital [[phlegmon]] (foot rot, acute interdigital necrobacillosis, infectious pododermatitis) associated with ''[[Fusobacterium necrophorum]]'' and ''[[Bacteroides melaninogenicus]]''.
-'''Florfenicol''' is a fluorinated synthetic analog of [[thiamphenicol]].<ref>{{cite journal | author = Syriopoulou VP, Harding AL, Goldmann DA, Smith AL | title = In vitro antibacterial activity of fluorinated analogs of chloramphenicol and thiamphenicol. | journal = Antimicrob Agents Chemother. | volume = 19 | issue = 2 | pages = 294-7 | year = 1981 | month=Feb | id = PMID 6957162}}</ref>
+Florfenicol is also used in aquaculture, and is licensed for use in the United States for the control of enteric septicemia in catfish.<ref>{{cite journal|last1=Gaunt|first1=P. S.|last2=Langston|first2=C.|last3=Wrzesinski|first3=C.|last4=Gao|first4=D.|last5=Adams|first5=P.|last6=Crouch|first6=L.|last7=Sweeney|first7=D.|last8=Endris|first8=R.|title=Multidose pharmacokinetics of orally administered florfenicol in the channel catfish (                            )|journal=Journal of Veterinary Pharmacology and Therapeutics|volume=36|issue=5|pages=502–506|doi=10.1111/j.1365-2885.2012.01426.x}}</ref>
-==References==
+The use of florfenicol in horses, and likely in other equids, typically causes diarrhea.  This has been anecdotally reported to progress to lethal cases of acute colitis.  Therefore, use of this antimicrobial in the equine patient should be limited to cases in which other, safer, options are not available. <ref>{{cite book |title= Current therapy in equine medicine |last1=Robinson |first1=N.E.|last2=Sprayberry | first2=K.A. |year=2009 |publisher=Saunders Elesevier |isbn=978-1-4160-5475-7 |page=13 |url= http://books.google.com/books?id=q-26Cz4t-P0C&pg=PA13&lpg=PA13&dq=florfenicol+equine&source=bl&ots=lkA2YqACNV&sig=nT1xUaU-axxOe8Hbx_QINeRudzg&hl=en&ei=_F6HTYumApLksQOq6KCDAg&sa=X&oi=book_result&ct=result&resnum=1&sqi=2&ved=0CBQQ6AEwAA#v=onepage&q=florfenicol%20equine&f=false|accessdate=March 21, 2011}}</ref>
-<div class="references-small">
-  <references/>
+==Contamination==
-</div>
+Florfenicol was among the drug contaminants in a brand of supermarket eggs in Taiwan and Iran.<ref name=Lee>{{cite news|last1=Lee I-chia|title=Survey suggests certain eggs may be dangerous|url=http://www.taipeitimes.com/News/taiwan/archives/2013/01/08/2003552041|accessdate=3 November 2014|publisher=Taipei Times|date=8 January 2013}}</ref>
 ==External links==
-* {{PubChem|114811}}
+*[http://www.nuflor.com Nuflor website]
+==References==
+{{reflist|2}}
 {{Amphenicols}}
+[[Category:Drug]]
-[[Category:Antibiotics]]
+[[Category:Amphenicols]]
+[[Category:Sulfones]]
+[[Category:Phenethylamines]]
+[[Category:Alcohols]]
-[[de:Florfenicol]]
+[[Category:Organofluorides]]
+[[Category:Acetamides]]
-{{WH}}
+[[Category:Organochlorides]]
-{{WikiDoc Sources}}