Temafloxacin

Temafloxacin
Clinical data
Trade names	Omniflox
Routes of; administration	Oral
ATC code	J01MA05 (WHO) ;
Legal status
Legal status	Withdrawn;
Identifiers
	IUPAC name 1-(2,4-Difluorophenyl)-6-fluoro-7-(3-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid;
CAS Number	108319-06-8 ;
PubChem CID	60021;
DrugBank	DB01405 ;
ChemSpider	54143 ;
UNII	1WZ12GTT67;
KEGG	D02469 ;
ChEBI	CHEBI:77788 ;
ChEMBL	ChEMBL277100 ;
CompTox Dashboard (EPA)	DTXSID7044132 ;
Chemical and physical data
Formula	C21H18F3N3O3
Molar mass	417.388 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES Fc1ccc(c(F)c1)N\3c2cc(c(F)cc2C(=O)C(/C(=O)O)=C/3)N4CC(NCC4)C;
	InChI InChI=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) ; Key:QKDHBVNJCZBTMR-UHFFFAOYSA-N ;
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Temafloxacin (marketed by Abbott Laboratories as Omniflox) is a fluoroquinolone antibiotic drug which was withdrawn from sale in the United States shortly after its approval in 1992 because of serious adverse effects resulting in three deaths.^[1]^[2] It is not marketed in Europe.

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 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 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 excretion from the body is primarily due to glomerular filtration in the kidneys.^[7]^[8]^[9]

Clinical uses

The compound was 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]

References

^ "Recalling the Omniflox (Temafloxacin) Tablets" (PDF). Food and Drug Administration. 1992-06-05. Retrieved 2014-10-15.
^ "ABBOTT WITHDRAWS TEMAFLOXACIN - Pharmaceutical industry news". The Pharmaletter. 1992-06-15. Retrieved 2014-10-16.
^ Rubinstein E (2001). "History of quinolones and their side effects". Chemotherapy. 47 Suppl 3 (3): 3–8, discussion 44–8. doi:10.1159/000057838. PMID 11549783. S2CID 21890070.
^ 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. doi:10.1016/0002-9343(91)90312-L. PMID 1662896.
^ 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. S2CID 32791009.
^ ^a ^b ^c Pankey GA (December 1991). "Temafloxacin: an overview". Am. J. Med. 91 (6A): 166S–172S. doi:10.1016/0002-9343(91)90332-r. PMID 1662889.
^ 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.
^ 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.
^ 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.
^ 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. doi:10.1093/jac/28.suppl_C.97. PMID 1787128. Retrieved 2014-10-17.
^ Wise R (December 1991). "Comparative penetration of selected fluoroquinolones into respiratory tract fluids and tissues". Am. J. Med. 91 (6A): 67S–70S. doi:10.1016/0002-9343(91)90313-M. PMID 1662897.
^ Symonds WT, Nix DE (September 1992). "Lomefloxacin and temafloxacin: two new fluoroquinolone antimicrobials". Clin Pharm. 11 (9): 753–66. PMID 1325892.

External links

FDA press release June 5, 1992.

[urlwww.fda.gov-1] "Recalling the Omniflox (Temafloxacin) Tablets" (PDF). Food and Drug Administration. 1992-06-05. Retrieved 2014-10-15.

[ABBOTT_WITHDRAWS_TEMAFLOXACIN-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): 3–8, discussion 44–8. doi:10.1159/000057838. PMID 11549783. S2CID 21890070.

[pmid1662896-4] 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. doi:10.1016/0002-9343(91)90312-L. PMID 1662896.

[pmid1319872-5] 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. S2CID 32791009.

[pmid1662889-6] Pankey GA (December 1991). "Temafloxacin: an overview". Am. J. Med. 91 (6A): 166S–172S. doi:10.1016/0002-9343(91)90332-r. PMID 1662889.

[pmid1318680-7] 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.

[pmid1666497-8] 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.

[pmid1664830-9] 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.

[pmid1787128-10] 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. doi:10.1093/jac/28.suppl_C.97. PMID 1787128. Retrieved 2014-10-17.

[pmid1662897-11] Wise R (December 1991). "Comparative penetration of selected fluoroquinolones into respiratory tract fluids and tissues". Am. J. Med. 91 (6A): 67S–70S. doi:10.1016/0002-9343(91)90313-M. PMID 1662897.

[pmid1325892-12] Symonds WT, Nix DE (September 1992). "Lomefloxacin and temafloxacin: two new fluoroquinolone antimicrobials". Clin Pharm. 11 (9): 753–66. PMID 1325892.

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