Grepafloxacin: Difference between revisions

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{{drugbox
 
| IUPAC_name = 1-cyclopropyl-6-fluoro-5-methyl-7-(3-methylpiperazin-1-yl)- 4-oxo-quinoline- 3-carboxylic acid
{{Drugbox
| verifiedrevid = 461123703
| IUPAC_name = (''RS'')-1-cyclopropyl-6-fluoro-5-methyl-7-(3-methylpiperazin-1-yl)- 4-oxo-quinoline- 3-carboxylic acid
| image = Grepafloxacin.svg
| image = Grepafloxacin.svg
| imagename = 1 : 1 mixture (racemate)
| drug_name = Grepafloxacin
<!--Clinical data-->
| tradename = 
| Drugs.com = {{drugs.com|MTM|grepafloxacin}}
| pregnancy_category = 
| legal_status = 
| routes_of_administration =
<!--Pharmacokinetic data-->
| bioavailability = 
| protein_bound = 50%
| metabolism = 
| elimination_half-life =
<!--Identifiers-->
| CASNo_Ref = {{cascite|correct|CAS}}
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 119914-60-2
| CAS_number = 119914-60-2
| ATC_prefix = J01
| ATC_prefix = J01
| ATC_suffix = MA11
| ATC_suffix = MA11
| ATC_supplemental =  
| ATC_supplemental =
| PubChem = 72474
| PubChem = 72474
| DrugBank = APRD01003
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| C = 19 | H = 22 | F = 1 | N = 3 | O = 3
| DrugBank = DB00365
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 65391
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = L1M1U2HC31
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C11368
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 583
 
<!--Chemical data-->
| C=19 | H=22 | F=1 | N=3 | O=3  
| molecular_weight = 359.395 g/mol
| molecular_weight = 359.395 g/mol
| bioavailability =  
| smiles = O=C(O)\C2=C\N(c1cc(c(F)c(c1C2=O)C)N3CC(NCC3)C)C4CC4
| protein_bound = 50%
| InChI = 1/C19H22FN3O3/c1-10-8-22(6-5-21-10)15-7-14-16(11(2)17(15)20)18(24)13(19(25)26)9-23(14)12-3-4-12/h7,9-10,12,21H,3-6,8H2,1-2H3,(H,25,26)
| metabolism =  
| InChIKey = AIJTTZAVMXIJGM-UHFFFAOYAY
| elimination_half-life =  
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| pregnancy_category =  
| StdInChI = 1S/C19H22FN3O3/c1-10-8-22(6-5-21-10)15-7-14-16(11(2)17(15)20)18(24)13(19(25)26)9-23(14)12-3-4-12/h7,9-10,12,21H,3-6,8H2,1-2H3,(H,25,26)
| legal_status =  
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| routes_of_administration =  
| StdInChIKey = AIJTTZAVMXIJGM-UHFFFAOYSA-N
}}
}}
{{SI}}
'''Grepafloxacin hydrochloride''' (trade name '''Raxar''', [[Glaxo Wellcome]]) was an oral broad-spectrum [[fluoroquinolone]] [[antibacterial]] agent used to treat [[bacteria]]l [[infection]]s.  Grepafloxacin was withdrawn world wide from markets in 1999,<ref name="urlwww.fda.gov">{{cite web |url=http://www.fda.gov/ohrms/dockets/ac/00/backgrd/3634b1a_tab5a.pdf |title= Glaxo Wellcome voluntary withdrawn Raxar (Grepafloxacin) |format= |work= |accessdate=2014-10-12}}</ref><ref name="urlLetter -Raxar">{{cite web |url=http://www.fda.gov/ohrms/dockets/ac/00/backgrd/3634b1a_tab5b.htm |title=Withdrawal of Product: RAXAR (grepafloxacin HCl) 600 mg Tablets, 400 mg Tablets, and 200 mg Tablets |work= U.S. Food and Drug Administation |accessdate=2014-10-12}}</ref> owing to its side effect of lengthening the [[QT interval]] on the [[electrocardiogram]], leading to cardiac events and [[Sudden cardiac death|sudden death]].<ref>{{Cite journal  | last1 = Sprandel | first1 = KA. | last2 = Rodvold | first2 = KA. | title = Safety and tolerability of fluoroquinolones. | journal = Clin Cornerstone | volume = Suppl 3 | issue =  | pages = S29-36 | year = 2003 | doi =  | PMID = 14992418 }}</ref>


== Clinical uses ==
Grepafloxacin was used  for treating exacerbations of chronic bronchitis caused by susceptible bacteria (e.g. [[Haemophilus influenzae]], [[Streptococcus pneumoniae]], [[Moraxella catarrhalis]]),<ref name="pmid9449270">{{cite journal |author=Chodosh S, Lakshminarayan S, Swarz H, Breisch S |title=Efficacy and safety of a 10-day course of 400 or 600 milligrams of grepafloxacin once daily for treatment of acute bacterial exacerbations of chronic bronchitis: comparison with a 10-day course of 500 milligrams of ciprofloxacin twice daily |journal=Antimicrob. Agents Chemother. |volume=42 |issue=1 |pages=114–20 |date=January 1998  |pmid=9449270 |pmc=105465 |doi= |url=http://aac.asm.org/cgi/pmidlookup?view=long&pmid=9449270 |accessdate=2014-10-12}}</ref><ref name="pmid9484875">{{cite journal |author=Langan CE, Cranfield R, Breisch S, Pettit R |title=Randomized, double-blind study of grepafloxacin versus amoxycillin in patients with acute bacterial exacerbations of chronic bronchitis |journal=J. Antimicrob. Chemother. |volume=40 Suppl A |issue= |pages=63–72 |date=December 1997  |pmid=9484875 |doi= 10.1093/jac/40.suppl_1.63|url=http://jac.oxfordjournals.org/cgi/pmidlookup?view=long&pmid=9484875 |accessdate=2014-10-12}}</ref><ref name="pmid10588313">{{cite journal |author=Langan CE, Zuck P, Vogel F, McIvor A, Peirzchala W, Smakal M, Staley H, Marr C |title=Randomized, double-blind study of short-course (5 day) grepafloxacin versus 10 day clarithromycin in patients with acute bacterial exacerbations of chronic bronchitis |journal=J. Antimicrob. Chemother. |volume=44 |issue=4 |pages=515–23 |date=October 1999  |pmid=10588313 |doi= 10.1093/jac/44.4.515|url=http://jac.oxfordjournals.org/cgi/pmidlookup?view=long&pmid=10588313 |accessdate=2014-10-12}}</ref> community-acquired pneumonia (including those, in addition to the above germs, caused by [[Mycoplasma pneumoniae]])<ref name="pmid9484876">{{cite journal |author=O'Doherty B, Dutchman DA, Pettit R, Maroli A |title=Randomized, double-blind, comparative study of grepafloxacin and amoxycillin in the treatment of patients with community-acquired pneumonia |journal=J. Antimicrob. Chemother. |volume=40 Suppl A |issue= |pages=73–81 |date=December 1997  |pmid=9484876 |doi= 10.1093/jac/40.suppl_1.73|url=http://jac.oxfordjournals.org/cgi/pmidlookup?view=long&pmid=9484876 |accessdate=2014-10-12}}</ref><ref name="pmid10719006">{{cite journal |author=Felmingham D |title=Respiratory pathogens: assessing resistance patterns in Europe and the potential role of grepafloxacin as treatment of patients with infections caused by these organisms |journal=J. Antimicrob. Chemother. |volume=45 |issue= |pages=1–8 |date=March 2000  |pmid=10719006 |doi= 10.1093/jac/45.suppl_2.1|url=http://jac.oxfordjournals.org/cgi/pmidlookup?view=long&pmid=10719006 |accessdate=2014-10-12}}</ref> [[gonorrhea]] and [[non-gonococcal urethritis]] and [[cervicitis]] (for example caused by [[Chlamydia trachomatis]] or [[Ureaplasma urealyticum]]).<ref name="pmid9484871">{{cite journal |author=Ridgway GL, Salman H, Robbins MJ, Dencer C, Felmingham D |title=The in-vitro activity of grepafloxacin against Chlamydia spp., Mycoplasma spp., Ureaplasma urealyticum and Legionella spp |journal=J. Antimicrob. Chemother. |volume=40 Suppl A |issue= |pages=31–4 |date=December 1997  |pmid=9484871 |doi= 10.1093/jac/40.suppl_1.31|url=http://jac.oxfordjournals.org/cgi/pmidlookup?view=long&pmid=9484871 |accessdate=2014-10-12}}</ref><ref name="pmid9785106">{{cite journal |author=McCormack WM, Martin DH, Hook EW, Jones RB |title=Daily oral grepafloxacin vs. twice daily oral doxycycline in the treatment of Chlamydia trachomatis endocervical infection |journal=Infect Dis Obstet Gynecol |volume=6 |issue=3 |pages=109–15 |year=1998 |pmid=9785106 |pmc=1784789 |doi=10.1155/S1064744998000210 |url= |accessdate=2014-10-12}}</ref>


'''Grepafloxacin hydrochloride''' (Raxar®, [[Glaxo Wellcome]]) is an oral broad-spectrum [[quinoline]] [[antibacterial]] agent used to treat [[bacteria]]l [[infection]]s.  Grepafloxacin was withdrawn in the [[United States]] due to its side effect of lengthening the [[QT interval]] on the [[electrocardiogram]], leading to cardiac events and [[sudden death]].
==See also==
*[[Quinolones]]
 
==References==
{{Reflist}}


{{QuinoloneAntiBiotics}}
{{QuinoloneAntiBiotics}}
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[[Category:Fluoroquinolone antibiotics]]
[[Category:Fluoroquinolone antibiotics]]
[[Category:Withdrawn drugs]]
[[Category:Withdrawn drugs]]
 
[[Category:Piperazines]]
 
[[Category:Cyclopropanes]]
 
 
[[th:เกรพพาฟลอกซาซิน]]
{{WH}}
{{WikiDoc Sources}}

Revision as of 12:59, 10 April 2015

Grepafloxacin
File:Grepafloxacin.svg
Clinical data
AHFS/Drugs.comMultum Consumer Information
ATC code
Pharmacokinetic data
Protein binding50%
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
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
FormulaC19H22FN3O3
Molar mass359.395 g/mol
3D model (JSmol)
  (verify)

Grepafloxacin hydrochloride (trade name Raxar, Glaxo Wellcome) was an oral broad-spectrum fluoroquinolone antibacterial agent used to treat bacterial infections. Grepafloxacin was withdrawn world wide from markets in 1999,[1][2] owing to its side effect of lengthening the QT interval on the electrocardiogram, leading to cardiac events and sudden death.[3]

Clinical uses

Grepafloxacin was used for treating exacerbations of chronic bronchitis caused by susceptible bacteria (e.g. Haemophilus influenzae, Streptococcus pneumoniae, Moraxella catarrhalis),[4][5][6] community-acquired pneumonia (including those, in addition to the above germs, caused by Mycoplasma pneumoniae)[7][8] gonorrhea and non-gonococcal urethritis and cervicitis (for example caused by Chlamydia trachomatis or Ureaplasma urealyticum).[9][10]

See also

References

  1. ↑ "Glaxo Wellcome voluntary withdrawn Raxar (Grepafloxacin)" (PDF). Retrieved 2014-10-12.
  2. ↑ "Withdrawal of Product: RAXAR (grepafloxacin HCl) 600 mg Tablets, 400 mg Tablets, and 200 mg Tablets". U.S. Food and Drug Administation. Retrieved 2014-10-12.
  3. ↑ Sprandel, KA.; Rodvold, KA. (2003). "Safety and tolerability of fluoroquinolones". Clin Cornerstone. Suppl 3: S29–36. PMID 14992418.
  4. ↑ Chodosh S, Lakshminarayan S, Swarz H, Breisch S (January 1998). "Efficacy and safety of a 10-day course of 400 or 600 milligrams of grepafloxacin once daily for treatment of acute bacterial exacerbations of chronic bronchitis: comparison with a 10-day course of 500 milligrams of ciprofloxacin twice daily". Antimicrob. Agents Chemother. 42 (1): 114–20. PMC 105465. PMID 9449270. Retrieved 2014-10-12.
  5. ↑ Langan CE, Cranfield R, Breisch S, Pettit R (December 1997). "Randomized, double-blind study of grepafloxacin versus amoxycillin in patients with acute bacterial exacerbations of chronic bronchitis". J. Antimicrob. Chemother. 40 Suppl A: 63–72. doi:10.1093/jac/40.suppl_1.63. PMID 9484875. Retrieved 2014-10-12.
  6. ↑ Langan CE, Zuck P, Vogel F, McIvor A, Peirzchala W, Smakal M, Staley H, Marr C (October 1999). "Randomized, double-blind study of short-course (5 day) grepafloxacin versus 10 day clarithromycin in patients with acute bacterial exacerbations of chronic bronchitis". J. Antimicrob. Chemother. 44 (4): 515–23. doi:10.1093/jac/44.4.515. PMID 10588313. Retrieved 2014-10-12.
  7. ↑ O'Doherty B, Dutchman DA, Pettit R, Maroli A (December 1997). "Randomized, double-blind, comparative study of grepafloxacin and amoxycillin in the treatment of patients with community-acquired pneumonia". J. Antimicrob. Chemother. 40 Suppl A: 73–81. doi:10.1093/jac/40.suppl_1.73. PMID 9484876. Retrieved 2014-10-12.
  8. ↑ Felmingham D (March 2000). "Respiratory pathogens: assessing resistance patterns in Europe and the potential role of grepafloxacin as treatment of patients with infections caused by these organisms". J. Antimicrob. Chemother. 45: 1–8. doi:10.1093/jac/45.suppl_2.1. PMID 10719006. Retrieved 2014-10-12.
  9. ↑ Ridgway GL, Salman H, Robbins MJ, Dencer C, Felmingham D (December 1997). "The in-vitro activity of grepafloxacin against Chlamydia spp., Mycoplasma spp., Ureaplasma urealyticum and Legionella spp". J. Antimicrob. Chemother. 40 Suppl A: 31–4. doi:10.1093/jac/40.suppl_1.31. PMID 9484871. Retrieved 2014-10-12.
  10. ↑ McCormack WM, Martin DH, Hook EW, Jones RB (1998). "Daily oral grepafloxacin vs. twice daily oral doxycycline in the treatment of Chlamydia trachomatis endocervical infection". Infect Dis Obstet Gynecol. 6 (3): 109–15. doi:10.1155/S1064744998000210. PMC 1784789. PMID 9785106. |access-date= requires |url= (help)

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