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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| legal_status = Withdrawn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 [[Gram|g]]/[[Mole (unit)|mol]]
| 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 [[Abbott Laboratories]] as '''Omniflox'''), is a [[fluoroquinolone]] [[antibiotic]] 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 [[Abbott Laboratories]] as '''Omniflox''') is a [[fluoroquinolone]] [[antibiotic]] drug which was withdrawn from sale in the [[United States]] shortly after its approval in 1992 because of serious [[adverse effect]]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 |archive-url=https://web.archive.org/web/20110606053652/http://www.fda.gov/ohrms/dockets/ac/98/briefingbook/1998-3454B1_03_WL49.pdf |url-status=dead |archive-date=June 6, 2011 |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 [[Food and Drug Administration]] in January 1992. Severe adverse reactions, including [[allergic reaction]]s and [[hemolytic anemia]],<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 [[Food and Drug Administration]] in January 1992. Severe adverse reactions, including [[allergic reaction]]s and [[hemolytic anemia]],<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 [[gastrointestinal tract]]. The oral [[bioavailability]] is greater than 90%. Temafloxacin has a good tissue penetration in various [[biological fluids]] and [[biological tissues|tissues]], particularly in the respiratory tissues, nasal secretions, [[tonsils]], [[prostate]] and [[Bone marrow|bone]].<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 [[Half-life, biological|half-life]].<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 [[central nervous system]] (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|url-access=subscription }}</ref>

== Clinical uses ==
The compound was indicated for treating lower respiratory tract infections ([[community-acquired pneumonia]], exacerbations of [[Bronchitis#Chronic bronchitis|chronic bronchitis]]), genital and [[urinary tract]] infections ([[prostatitis]], [[Gonococcal urethritis|gonococcal]] and [[non-gonococcal urethritis]], [[cervicitis]]), [[Skin infection|skin]] and [[soft tissue]] 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|url-access=subscription }}</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==
* [[Quinolone antibiotic]]
*[[Fluoroquinolone toxicity]]
*[[Fluoroquinolone]]


==References==
==References==
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==External links==
==External links==
* [http://www.fda.gov/bbs/topics/NEWS/NEW00279.html FDA press release] June 5, 1992.
* [https://web.archive.org/web/20110606053652/http://www.fda.gov/ohrms/dockets/ac/98/briefingbook/1998-3454B1_03_WL49.pdf FDA press release] June 5, 1992.


{{QuinoloneAntiBiotics}}
{{QuinoloneAntiBiotics}}

{{antibiotic-stub}}


[[Category:Fluoroquinolone antibiotics]]
[[Category:Fluoroquinolone antibiotics]]
[[Category:Hepatotoxins]]
[[Category:Withdrawn drugs]]
[[Category:Withdrawn drugs]]
[[Category:Piperazines]]
[[Category:Drugs developed by AbbVie]]
[[Category:1,4-di-hydro-7-(1-piperazinyl)-4-oxo-3-quinolinecarboxylic acids]]

[[it:Temafloxacina]]
[[th:ทีมาฟลอกซาซิน]]