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{{SI}}
{{Drugbox
| Verifiedfields = changed
| verifiedrevid = 416705224
| IUPAC_name = 1-(2,4-Difluorophenyl)-6-fluoro-7-(3-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid
| image = Temafloxacin.png


<!--Clinical data-->
| tradename = 
| 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| legal_status = Withdrawn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


'''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(marketed by [[Abbott Laboratories]] as '''Omniflox'''), is a [[fluoroquinolone]] [[antibiotic]] drug which was withdrawn from sale in the U.S. shortly after its approval in 1992 because of serious adverse reactions resulting in three deaths. 
<!--Identifiers-->
| ATC_prefix = J01
| ATC_suffix = MA05
| PubChem = 60021
| DrugBank_Ref = {{drugbankcite|changed|drugbank}}
| DrugBank = DB01405
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 54143
| UNII_Ref = {{fdacite|changed|FDA}}
| UNII = 1WZ12GTT67
| KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG = D02469
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 77788
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 277100


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]], 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.   
<!--Chemical data-->
| C=21 | H=18 | F=3 | N=3 | O=3
| molecular_weight = 417.381 [[Gram|g]]/[[Mole (unit)|mol]]
| smiles = Fc1ccc(c(F)c1)N\3c2cc(c(F)cc2C(=O)C(/C(=O)O)=C/3)N4CC(NCC4)C
| 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)
| InChIKey = QKDHBVNJCZBTMR-UHFFFAOYAR
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/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)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = QKDHBVNJCZBTMR-UHFFFAOYSA-N
}}
 
'''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=http://www.fda.gov/ohrms/dockets/ac/98/briefingbook/1998-3454B1_03_WL49.pdf |title=Recalling the Omniflox (Temafloxacin) Tablets |format= pdf |work= Food and Drug Administration |date= 1992-06-05 |accessdate=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  |accessdate=2014-10-16}}</ref>
 
== 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 | 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 | year = 2001 | doi =  10.1159/000057838| 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.
 
== Pharmacokinetic ==
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 |author=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= |url= |accessdate=2014-10-17}}</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 Suppl 1 |issue= |pages=57–63 |year=1992 |pmid=1319872 |doi= 10.2165/00003088-199200221-00010|url= |accessdate=2014-10-17}}</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= |url= |accessdate=2014-10-17}}</ref>
The penetration into the [[central nervous system]] (CNS)is less pronounced.<ref name="pmid1662889"/>The escretion from the body is primarily due to the glomerular filtration.<ref name="pmid1318680">{{cite journal |author=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=http://aac.asm.org/cgi/pmidlookup?view=long&pmid=1318680 |accessdate=2014-10-17}}</ref><ref name="pmid1666497">{{cite journal |author=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=http://aac.asm.org/cgi/pmidlookup?view=long&pmid=1666497 |accessdate=2014-10-17}}</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 |issue= |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 |accessdate=2014-10-17}}</ref>
 
== Clinical uses ==
The compound is indicated for treating lower respiratory tract infections ([[community-acquired pneumonia]], exacerbations of [[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">{{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= |url= |accessdate=2014-10-17}}</ref><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 |issue= |pages=97–110 |date=December 1991  |pmid=1787128 |doi= |url=http://jac.oxfordjournals.org/cgi/pmidlookup?view=long&pmid=1787128 |accessdate=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= |url= |accessdate=2014-10-17}}</ref><ref name="pmid1325892">{{cite journal |author=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 |doi= |url= |accessdate=2014-10-17}}</ref>
 
==See also==
* [[Quinolones]]
 
==References==
{{reflist}}


==External links==
==External links==
* [http://www.fda.gov/bbs/topics/NEWS/NEW00279.html FDA press release] June 5, 1992.
* [http://www.fda.gov/bbs/topics/NEWS/NEW00279.html FDA press release] June 5, 1992.{{Dead link|date=April 2011}}


{{QuinoloneAntiBiotics}}
{{QuinoloneAntiBiotics}}


[[Category:Fluoroquinolone antibiotics]]
[[Category:Fluoroquinolone antibiotics]]
[[Category:Withdrawn drugs]]
[[Category:Piperazines]]




{{WH}}
{{antibiotic-stub}}
{{WikiDoc Sources}}

Revision as of 14:55, 9 April 2015

Temafloxacin
Clinical data
Routes of
administration		Oral
ATC code
Legal status
Legal status
  • Withdrawn
Identifiers
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
FormulaC21H18F3N3O3
Molar mass417.381 g/mol
3D model (JSmol)
 ☒N☑Y (what is this?)  (verify)

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 effects resulting in three deaths.[1][2]

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 reactions and hemolytic anemia,[3] 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.

Pharmacokinetic

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 tissues, particularly in the respiratory tissues, nasal secretions, tonsils, prostate and bone.[4] In these districts the concentrations achieved are equal to or higher than those in serum.[5] The fluoroquinolone has a 7-8 hour half-life.[6] The penetration into the central nervous system (CNS)is less pronounced.[6]The escretion from the body is primarily due to the glomerular filtration.[7][8][9]

Clinical uses

The compound is indicated for treating lower respiratory tract infections (community-acquired pneumonia, exacerbations of chronic bronchitis), genital and urinary tract infections (prostatitis, gonococcal and non-gonococcal urethritis, cervicitis), skin and soft tissue infections.[6][10][11][12]

See also

References

  1. ↑ "Recalling the Omniflox (Temafloxacin) Tablets" (pdf). Food and Drug Administration. 1992-06-05. Retrieved 2014-10-15.
  2. ↑ "ABBOTT WITHDRAWS TEMAFLOXACIN - Pharmaceutical industry news". The Pharmaletter. 1992-06-15. Retrieved 2014-10-16.
  3. ↑ Rubinstein, E. (2001). "History of quinolones and their side effects". Chemotherapy. 47 Suppl 3: 3–8, discussion 44–8. doi:10.1159/000057838. PMID 11549783.
  4. ↑ Sorgel F, Naber KG, Kinzig M, Mahr G, Muth P (December 1991). "Comparative pharmacokinetics of ciprofloxacin and temafloxacin in humans: a review". Am. J. Med. 91 (6A): 51S–66S. PMID 1662896. |access-date= requires |url= (help)
  5. ↑ Sörgel F (1992). "Penetration of temafloxacin into body tissues and fluids". Clin Pharmacokinet. 22 Suppl 1: 57–63. doi:10.2165/00003088-199200221-00010. PMID 1319872. |access-date= requires |url= (help)
  6. ↑ 6.0 6.1 6.2 Pankey GA (December 1991). "Temafloxacin: an overview". Am. J. Med. 91 (6A): 166S–172S. PMID 1662889. |access-date= requires |url= (help)
  7. ↑ Granneman GR, Carpentier P, Morrison PJ, Pernet AG (February 1992). "Pharmacokinetics of temafloxacin in humans after multiple oral doses". Antimicrob. Agents Chemother. 36 (2): 378–86. doi:10.1128/aac.36.2.378. PMC 188445. PMID 1318680. Retrieved 2014-10-17.
  8. ↑ Granneman GR, Braeckman R, Kraut J, Shupien S, Craft JC (November 1991). "Temafloxacin pharmacokinetics in subjects with normal and impaired renal function". Antimicrob. Agents Chemother. 35 (11): 2345–51. doi:10.1128/aac.35.11.2345. PMC 245383. PMID 1666497. Retrieved 2014-10-17.
  9. ↑ Dudley MN (December 1991). "A review of the pharmacokinetic profile of temafloxacin". J. Antimicrob. Chemother. 28 Suppl C: 55–64. doi:10.1093/jac/28.suppl_c.55. PMID 1664830. Retrieved 2014-10-17.
  10. ↑ Gentry LO (December 1991). "Review of quinolones in the treatment of infections of the skin and skin structure". J. Antimicrob. Chemother. 28 Suppl C: 97–110. PMID 1787128. Retrieved 2014-10-17.
  11. ↑ Wise R (December 1991). "Comparative penetration of selected fluoroquinolones into respiratory tract fluids and tissues". Am. J. Med. 91 (6A): 67S–70S. PMID 1662897. |access-date= requires |url= (help)
  12. ↑ Symonds WT, Nix DE (September 1992). "Lomefloxacin and temafloxacin: two new fluoroquinolone antimicrobials". Clin Pharm. 11 (9): 753–66. PMID 1325892. |access-date= requires |url= (help)

External links

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