Temafloxacin: Difference between revisions
Appearance
Content deleted Content added
Updating {{drugbox}} (changes to verified fields - updated 'UNII_Ref', 'ChEMBL_Ref', 'KEGG_Ref') per Chem/Drugbox validation (report errors or [[user t |
GreenC bot (talk | contribs) Rescued 2 archive links. Wayback Medic 2.5 per WP:URLREQ#fda.gov |
||
(81 intermediate revisions by 41 users not shown) | |||
Line 1: | Line 1: | ||
{{short description|Chemical compound, antibiotic drug}} |
|||
{{cs1 config|name-list-style=vanc}} |
|||
{{Drugbox |
{{Drugbox |
||
| Verifiedfields = changed |
| Verifiedfields = changed |
||
| Watchedfields = changed |
|||
| verifiedrevid = |
| verifiedrevid = 416705224 |
||
| IUPAC_name |
| IUPAC_name = 1-(2,4-Difluorophenyl)-6-fluoro-7-(3-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid |
||
| image |
| image = Temafloxacin structure.svg |
||
<!--Clinical data--> |
|||
| tradename = Omniflox |
|||
⚫ | |||
⚫ | |||
⚫ | |||
⚫ | |||
⚫ | |||
⚫ | |||
⚫ | |||
⚫ | |||
<!--Identifiers--> |
|||
| CAS_number_Ref = {{cascite|correct|CAS}} |
|||
⚫ | |||
⚫ | |||
⚫ | |||
⚫ | |||
| DrugBank_Ref = {{drugbankcite|changed|drugbank}} |
|||
⚫ | |||
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
||
| ChemSpiderID = 54143 |
| ChemSpiderID = 54143 |
||
| |
| 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 |
|||
⚫ | |||
| 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}} |
||
Line 15: | Line 45: | ||
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
||
| StdInChIKey = QKDHBVNJCZBTMR-UHFFFAOYSA-N |
| StdInChIKey = QKDHBVNJCZBTMR-UHFFFAOYSA-N |
||
⚫ | |||
⚫ | |||
⚫ | |||
⚫ | |||
⚫ | |||
⚫ | |||
| molecular_weight = 417.381 [[Gram|g]]/[[Mole (unit)|mol]] |
|||
| bioavailability = |
|||
| protein_bound = |
|||
| metabolism = |
|||
| elimination_half-life = |
|||
| excretion = |
|||
⚫ | |||
⚫ | |||
| pregnancy_category= |
|||
⚫ | |||
⚫ | |||
⚫ | |||
⚫ | |||
⚫ | |||
⚫ | |||
}} |
}} |
||
'''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 |
||
== 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== |
||
Line 49: | Line 66: | ||
==External links== |
==External links== |
||
* [http://www.fda.gov/ |
* [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: |
[[Category:Drugs developed by AbbVie]] |
||
[[Category:1,4-di-hydro-7-(1-piperazinyl)-4-oxo-3-quinolinecarboxylic acids]] |
|||
[[it:Temafloxacina]] |
|||
[[th:ทีมาฟลอกซาซิน]] |