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Revision as of 08:36, 2 March 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{drugbox}} (changes to verified fields - updated 'UNII_Ref', 'ChEMBL_Ref', 'KEGG_Ref') per Chem/Drugbox validation (report errors or [[user t← Previous edit		Latest revision as of 02:37, 11 February 2024 edit undoMaxim Masiutin (talk | contribs)Extended confirmed users, IP block exemptions, Pending changes reviewers31,058 edits Added the cs1 style template to denote Vancouver ("vanc") citation style, because references contain "vauthors" attribute to specify the list of authors. Altered volume. Added issue. | Use this bot. | #UCB_Other
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			{{short description|Chemical compound, antibiotic drug}}
			{{cs1 config|name-list-style=vanc}}
	{{Drugbox		{{Drugbox
	| Verifiedfields = changed		| Verifiedfields = changed
			| Watchedfields = changed
	| verifiedrevid = 401619468		| verifiedrevid = 416705224
	| IUPAC_name = 1-(2,4-Difluorophenyl)-6-fluoro-7-(3-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid		| IUPAC_name = 1-(2,4-Difluorophenyl)-6-fluoro-7-(3-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid
	| image = Temafloxacin.png		| image = Temafloxacin structure.svg
			<!--Clinical data-->
			| tradename = Omniflox
		⚫	| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
		⚫	| pregnancy_US = <!-- A / B / C / D / X -->
		⚫	| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
		⚫	| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->
		⚫	| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
		⚫	| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
		⚫	| legal_status = Withdrawn
		⚫	| routes_of_administration = Oral
			<!--Identifiers-->
			| CAS_number_Ref = {{cascite|correct|CAS}}
		⚫	| CAS_number = 108319-06-8
		⚫	| ATC_prefix = J01
		⚫	| ATC_suffix = MA05
		⚫	| PubChem = 60021
			| DrugBank_Ref = {{drugbankcite|changed|drugbank}}
		⚫	| DrugBank = DB01405
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 54143		| ChemSpiderID = 54143
	| ChEMBL_Ref = {{ebicite|changed|EBI}}		| UNII_Ref = {{fdacite|correct|FDA}}
			| UNII = 1WZ12GTT67
			| KEGG_Ref = {{keggcite|changed|kegg}}
			| KEGG = D02469
			| ChEBI_Ref = {{ebicite|changed|EBI}}
			| ChEBI = 77788
			| ChEMBL_Ref = {{ebicite|correct|EBI}}
	| ChEMBL = 277100		| ChEMBL = 277100
	| InChI = 1/C21H18F3N3O3/c1-11-9-26(5-4-25-11)19-8-18-13(7-16(19)24)20(28)14(21(29)30)10-27(18)17-3-2-12(22)6-15(17)23/h2-3,6-8,10-11,25H,4-5,9H2,1H3,(H,29,30)
			<!--Chemical data-->
	| InChIKey = QKDHBVNJCZBTMR-UHFFFAOYAR
		⚫	| C=21 | H=18 | F=3 | N=3 | O=3
	| smiles = Fc1ccc(c(F)c1)N\3c2cc(c(F)cc2C(=O)C(/C(=O)O)=C/3)N4CC(NCC4)C		| smiles = Fc1ccc(c(F)c1)N\3c2cc(c(F)cc2C(=O)C(/C(=O)O)=C/3)N4CC(NCC4)C
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}		| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
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	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}		| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChIKey = QKDHBVNJCZBTMR-UHFFFAOYSA-N		| StdInChIKey = QKDHBVNJCZBTMR-UHFFFAOYSA-N
⚫	| CAS_number =
⚫	| ATC_prefix = J01
⚫	| ATC_suffix = MA05
⚫	| PubChem = 60021
⚫	| DrugBank =
⚫	| C = 21 |H = 18 |F = 3 |N = 3 |O = 3
	| molecular_weight = 417.381 ]/]
	| bioavailability =
	| protein_bound =
	| metabolism =
	| elimination_half-life =
	| excretion =
⚫	| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
⚫	| pregnancy_US = <!-- A / B / C / D / X -->
	| pregnancy_category=
⚫	| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
⚫	| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->
⚫	| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
⚫	| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
⚫	| legal_status = Withdrawn
⚫	| routes_of_administration = Oral
	}}		}}
	'''Temafloxacin''' (marketed by ] as '''Omniflox'''), is a ] ] drug which was withdrawn from sale in the U.S. shortly after its approval in 1992 because of serious adverse reactions resulting in three deaths.
			'''Temafloxacin''' (marketed by ] as '''Omniflox''') is a ] ] drug which was withdrawn from sale in the ] shortly after its approval in 1992 because of serious ]s resulting in three deaths.<ref name="urlwww.fda.gov">{{cite web |url=https://www.fda.gov/ohrms/dockets/ac/98/briefingbook/1998-3454B1_03_WL49.pdf |title=Recalling the Omniflox (Temafloxacin) Tablets |work= Food and Drug Administration |date= 1992-06-05 |access-date=2014-10-15}}</ref><ref name="ABBOTT WITHDRAWS TEMAFLOXACIN">{{cite web |title=ABBOTT WITHDRAWS TEMAFLOXACIN - Pharmaceutical industry news |work= The Pharmaletter |date= 1992-06-15 |url=http://www.thepharmaletter.com/article/abbott-withdraws-temafloxacin |access-date=2014-10-16}}</ref> It is not marketed in Europe.
⚫	Omniflox was approved to treat lower respiratory tract infections, genital and urinary infections like prostatitis, and skin infections in the U.S. by the ] in January 1992. Severe adverse reactions, including ]s and ],<ref>{{Cite journal | last1 = Rubinstein | first1 = E. | title = History of quinolones and their side effects. | journal = Chemotherapy | volume = 47 Suppl 3 | issue = | pages = 3–8; discussion 44–8 | month = | year = 2001 | doi = | PMID = 11549783 }}</ref> developed in about fifty patients during the first four months of its use, leading to three patient deaths. Abbott withdrew the drug from sale in June 1992.
			== History ==
		⚫	Omniflox was approved to treat lower respiratory tract infections, genital and urinary infections like prostatitis, and skin infections in the United States by the ] in January 1992. Severe adverse reactions, including ]s and ],<ref>{{Cite journal|title=History of quinolones and their side effects.|journal=Chemotherapy|volume=47 Suppl 3|pages=3–8; discussion 44–8|doi=10.1159/000057838|pmid=11549783|last1=Rubinstein|first1=E.|year=2001|issue=3|s2cid=21890070}}</ref> developed in over 100 patients during the first four months of its use, leading to three patient deaths. Abbott withdrew the drug from sale in June 1992.
			== Pharmacokinetics ==
			Following oral administration the compound is well absorbed from the ]. The oral ] is greater than 90%. Temafloxacin has a good tissue penetration in various ] and ], particularly in the respiratory tissues, nasal secretions, ], ] and ].<ref name="pmid1662896">{{cite journal |vauthors=Sorgel F, Naber KG, Kinzig M, Mahr G, Muth P |title=Comparative pharmacokinetics of ciprofloxacin and temafloxacin in humans: a review |journal=Am. J. Med. |volume=91 |issue=6A |pages=51S–66S |date=December 1991 |pmid=1662896 |doi= 10.1016/0002-9343(91)90312-L }}</ref> In these districts the concentrations achieved are equal to or higher than those in serum.<ref name="pmid1319872">{{cite journal |author=Sörgel F |title=Penetration of temafloxacin into body tissues and fluids |journal=Clin Pharmacokinet |volume=22 |pages=57–63 |year=1992 |issue=Suppl 1 |pmid=1319872 |doi= 10.2165/00003088-199200221-00010|s2cid=32791009 }}</ref> The fluoroquinolone has a 7-8 hour ].<ref name="pmid1662889">{{cite journal |author=Pankey GA |title=Temafloxacin: an overview |journal=Am. J. Med. |volume=91 |issue=6A |pages=166S–172S |date=December 1991 |pmid=1662889 |doi= 10.1016/0002-9343(91)90332-r }}</ref>
			The penetration into the ] (CNS)is less pronounced.<ref name="pmid1662889"/> The excretion from the body is primarily due to glomerular filtration in the kidneys.<ref name="pmid1318680">{{cite journal |vauthors=Granneman GR, Carpentier P, Morrison PJ, Pernet AG |title=Pharmacokinetics of temafloxacin in humans after multiple oral doses |journal=Antimicrob. Agents Chemother. |volume=36 |issue=2 |pages=378–86 |date=February 1992 |pmid=1318680 |pmc=188445 |doi= 10.1128/aac.36.2.378|url=}}</ref><ref name="pmid1666497">{{cite journal |vauthors=Granneman GR, Braeckman R, Kraut J, Shupien S, Craft JC |title=Temafloxacin pharmacokinetics in subjects with normal and impaired renal function |journal=Antimicrob. Agents Chemother. |volume=35 |issue=11 |pages=2345–51 |date=November 1991 |pmid=1666497 |pmc=245383 |doi= 10.1128/aac.35.11.2345|url=}}</ref><ref name="pmid1664830">{{cite journal |author=Dudley MN |title=A review of the pharmacokinetic profile of temafloxacin |journal=J. Antimicrob. Chemother. |volume=28 Suppl C |pages=55–64 |date=December 1991 |pmid=1664830 |doi= 10.1093/jac/28.suppl_c.55|url=http://jac.oxfordjournals.org/cgi/pmidlookup?view=long&pmid=1664830 |access-date=2014-10-17}}</ref>
			== Clinical uses ==
			The compound was indicated for treating lower respiratory tract infections (], exacerbations of ]), genital and ] infections (], ] and ], ]), ] and ] infections.<ref name="pmid1662889"/><ref name="pmid1787128">{{cite journal |author=Gentry LO |title=Review of quinolones in the treatment of infections of the skin and skin structure |journal=J. Antimicrob. Chemother. |volume=28 Suppl C |pages=97–110 |date=December 1991 |pmid=1787128 |doi= 10.1093/jac/28.suppl_C.97|url=http://jac.oxfordjournals.org/cgi/pmidlookup?view=long&pmid=1787128 |access-date=2014-10-17}}</ref><ref name="pmid1662897">{{cite journal |author=Wise R |title=Comparative penetration of selected fluoroquinolones into respiratory tract fluids and tissues |journal=Am. J. Med. |volume=91 |issue=6A |pages=67S–70S |date=December 1991 |pmid=1662897 |doi= 10.1016/0002-9343(91)90313-M}}</ref><ref name="pmid1325892">{{cite journal |vauthors=Symonds WT, Nix DE |title=Lomefloxacin and temafloxacin: two new fluoroquinolone antimicrobials |journal=Clin Pharm |volume=11 |issue=9 |pages=753–66 |date=September 1992 |pmid=1325892 }}</ref>
	==See also==		==See also==
			* ]
	*]
	*]
	==References==		==References==
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	==External links==		==External links==
	* June 5, 1992.		* June 5, 1992.
	{{QuinoloneAntiBiotics}}		{{QuinoloneAntiBiotics}}
	{{antibiotic-stub}}
	]		]
			]
	]		]
	]		]
			]
	]
	]