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{{drugbox
{{drugbox
| IUPAC_name = 1-ethyl-6-fluoro-7- (4-methylpiperazin-1-yl)- 4-oxo-quinoline-3-carboxylic acid
| Watchedfields = changed
| image = Pefloxacin.svg
| verifiedrevid = 464197549
| IUPAC_name = 1-ethyl-6-fluoro-7-(4-methylpiperazin-1-yl)-4-oxo-quinoline-3-carboxylic acid
| image = Pefloxacin.png
| width = 220
| CASNo_Ref = {{cascite|correct|CAS}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 46291
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 2H52Z9F2Q5
| InChI = 1/C17H20FN3O3/c1-3-20-10-12(17(23)24)16(22)11-8-13(18)15(9-14(11)20)21-6-4-19(2)5-7-21/h8-10H,3-7H2,1-2H3,(H,23,24)
| InChIKey = FHFYDNQZQSQIAI-UHFFFAOYAD
| smiles = O=C(O)\C2=C\N(c1cc(c(F)cc1C2=O)N3CCN(C)CC3)CC
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 267648
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C17H20FN3O3/c1-3-20-10-12(17(23)24)16(22)11-8-13(18)15(9-14(11)20)21-6-4-19(2)5-7-21/h8-10H,3-7H2,1-2H3,(H,23,24)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = FHFYDNQZQSQIAI-UHFFFAOYSA-N
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 70458-92-3
| CAS_number = 70458-92-3
| ATC_prefix = J01
| ATC_prefix = J01
| ATC_suffix = MA03
| ATC_suffix = MA03
| ATC_supplemental =  
| ATC_supplemental =  
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 50199
| PubChem = 51081
| PubChem = 51081
| DrugBank = APRD00108
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00487
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D02306
| C=17 | H=20 | F=1 | N=3 | O=3
| C=17 | H=20 | F=1 | N=3 | O=3
| molecular_weight = 333.358 g/mol
| molecular_weight = 333.358 g/mol
Line 24: Line 47:
| routes_of_administration =  
| routes_of_administration =  
}}
}}
__NOTOC__
{{SI}}
{{SI}}
{{EH}}
{{CMG}}
==Overview==
'''Pefloxacin''' is a [[quinolone]] drug used to treat bacterial infections. It is an analog of [[norfloxacin]], belonging to the 3rd generation of quinolones.  Pefloxacin has not been approved for use in the United States.


'''Pefloxacin''' is an [[antimicrobial]] agent.  It is a synthetic [[fluoroquinolone]], belonging to the 3rd generation of [[quinolone]]s.
==History==


==Mode of Action==
Pefloxacin was developed in 1979 and approved in France for human use in 1985.<ref> http://www.bailii.org/ew/cases/EWHC/Patents/2008/2413.html</ref>


*Chromosomal DNA in bacterial cells occurs mainly in the form of a double stand ring.
==Licensed uses==
*One of a group of bacterial enzymes- DNA gyrase is responsible for the supercoiling process.
*Pefloxacin bactericidal affect is due to its ability to inhibit the activity of this vital enzyme.
*Uncomplicated gonococcal urethritis in males.<ref name=p_usage>http://www.pefloxacin.com/pefloxacin_usage.htm</ref>
*The result of this inhibitions is the prevention of bacterial DNA replication.
*Although inhibition of DNA replication is undoubtedly the chief means by which Abaktal exerts its antibacterial effect, two other actions are also observed:
**Pefloxacin reduces the ability of E-coli and staphylococcus to adhere to the walls of uroephithelial cells.
**Pefloxacin has effects on the immune system, stimulating the phagocytic activity of white blood.


*Bacterial infections in the gastrointestinal system.<ref name=p_usage/>


==Spectrum of antibacterial activity==
*Genitourinary tract infections.<ref name=p_usage/>


*Extensive in vitro & in vivo testing has established that Abaktal has a broad antibacterial spectrum.
*Gonorrhoeae. however this indication is no longer effective due to bacterial resistance.<ref>{{cite journal |author= |title=Update to CDC's sexually transmitted diseases treatment guidelines, 2006: fluoroquinolones no longer recommended for treatment of gonococcal infections |journal=MMWR Morb. Mortal. Wkly. Rep. |volume=56 |issue=14 |pages=332–6 |date=April 2007 |pmid=17431378 |url=http://www.cdc.gov/mmwr/preview/mmwrhtml/mm5614a3.htm |author1= Centers for Disease Control and Prevention (CDC)}}</ref>
*The [[MIC]]s of Pefloxacin even against bacteria resistant to beta-lactams and aminoglycosides are very low
*Initial plasma level of 4.0 mcg/ml, well above M.I.C. for sensitive pathogens, are ready and rapidly attained after a single 400mg dose (oral or i.v.)
*Excellent tissue penetration level is achieved with Pefloxacin in human and animals studies
*Species usually sensitive (MIC < 1pg/ml)are ''[[Escherichia coli]]'', ''[[Klebsiella]]'', ''[[Enterobacter]]'', ''[[Serratia]]'', ''[[Proteus mirabilis]]'', ''[[Protues vulgaris]]'', ''[[Citrobacter]]'', ''[[Salmonella]]'', ''[[Shigella]]'', ''[[Haemophilus influenzae]]'', ''[[Staphalococcus aureus]]'', and ''[[Neisseria gonorrhoea]]''.
*Species variably sensitive include ''[[Streptococcus]]'' and ''[[Pneumococcus]]'', ''[[Pseudomonas aeruginosa]]'', ''[[Acinetobacter]]'', ''[[Clostridium perfringens]]'', ''[[Mycoplasma]]'', and ''[[Chlamydia]]''.


Pefloxacin has been increasingly used as a veterinary medicine to treat microbial infections.<ref> http://www.pefloxacin.com/pefloxacin_other.html</ref>


==Pharmacokinetics==
==Mode of action==


*After oral administration, Abaktal is well absorbed; the bio availability is 100%.
Pefloxacin is a [[broad-spectrum antibiotic]] that is active against both [[Gram-positive]] and [[Gram-negative]] bacteria. It functions by inhibiting [[DNA gyrase]], a type II [[topoisomerase]], and topoisomerase IV,<ref>{{cite journal |author=Drlica K, Zhao X |title=DNA gyrase, topoisomerase IV, and the 4-quinolones |journal=Microbiol Mol Biol Rev. |volume=61 |issue=3 |pages=377–92 |date=1 September 1997|pmid=9293187 |pmc=232616 |url=http://mmbr.asm.org/cgi/pmidlookup?view=long&pmid=9293187 }}</ref> which is an enzyme necessary to separate, replicated DNA, thereby inhibiting cell division.
*Peak plasma levels is reached in 1-1.5 hours
*Peak serum levels of 3.8-6.6mcg/ml is attained after single dose of 400mg
*Peak serum levels after multiple dose of 400mg, 12 hourly is 8-10 mcg/ml
*Steady state concentration  is achieved
*Dose depended increase in plasma level over the dose of 200- 800mg
*Food slows the absorption but does not effects bio availability
*Oral & injectable forms are bio-equivalent
*Elimination half life is 11-12 hours mainly through metabolites
*Pefloxacin is metabolized in liver (85%-90%)
*Plasma protein binding is 20-30%
*Major route of elimination is renal – 9-16% of the drugs is eliminated unchanged
*Major metabolites constitute up to 84% of drugs recovered in urine 
*Limited excretion via bile
*N-dismethyl pefloxacin (norfloxacin) activity unknown
*Pefloxacin N-oxide active
*Oxodimethyl activity unknown
*Oxo pefloxacin activity unknown
*Pefloxacin achieves high tissue concentration


Tissue Concentration
==Adverse effects==
Bronchial tissues         5 mcg/ml
Tendinitis and rupture, usually of the Achilles tendon, are a class-effects of the fluoroquinolones, most frequently reported with pefloxacin.<ref>{{cite journal |author=Khaliq Y, Zhanel GG |title=Musculoskeletal injury associated with fluoroquinolone antibiotics |journal=Clin Plast Surg |volume=32 |issue=4 |pages=495–502, vi |date=October 2005 |pmid=16139623 |doi=10.1016/j.cps.2005.05.004 |url=http://journals.elsevierhealth.com/retrieve/pii/S0094-1298(05)00043-X}}
Oropharyngeal concentration 6 mcg/ml
</ref>  The estimated risk of tendon damage during pefloxacin therapy has been estimated by the French authorities in 2000 to be 1 case per 23,130 treatment days as compared to ciprofloxacin where it has been estimated to be 1 case per 779,600.<ref>{{cite journal |author=Casparian JM, Luchi M, Moffat RE, Hinthorn D |title=Quinolones and tendon ruptures |journal=South. Med. J. |volume=93 |issue=5 |pages=488–91 |date=May 2000 |pmid=10832946 |url=http://meta.wkhealth.com/pt/pt-core/template-journal/lwwgateway/media/landingpage.htm?issn=0038-4348&volume=93&issue=5&spage=488 |doi=10.1097/00007611-200093050-00008}}</ref>
Tonsils                         9 mcg/ml
Maxillary sinus cavity sinus    2.82 mcg/ml, 4.1 mcg/ml, 2-8mcg/ml
aspirate sinus cystic fluid
nasal secretions
Muscles                         5.6 mcg /ml
Gall bladder                 80 mcg /ml
Bile                         78 mcg /ml
Kidney                         90 mcg /ml
Prostate                 10 mcg /ml
Gynecological tissue         38 mcg/ml 4-6 higher than serum conc.,  
Myometrium-                    38.6 mcg /ml,
Fallopian tube                  31.9 mcg /ml,
Ovaries                        44.8mcg/ml
Pancreatic tissue         4.6mcg/ml
Peritonium                 3.5mcg/ml


 
==References==
*There are no major change in plasma pharmacokinetics as a function of renal impairment
{{Reflist|2}}
*Elimination half life increase slightly to approx.15 hours
*There is a fall in urinary excretion of Abaktal & its metabolites
*There is no major change in Abaktal plasma levels whatever the degrees of renal impairment
*Pefloxacin is not readily dialyzed
*There are marked changes in pharmacokinetics in patients with hepatic impairment
*Marked increase in :
**Elimination half life 3-5 times
**Area under curve 3-6 times
**Urinary excretion of unchanged Abaktal 3-4 times
*Careful monitoring of plasma levels together with appropriate dosage adjustment will be necessary
 
 
 
==Indications==
 
===Indicated for the following conditions:===
*Respiratory infections
*Ear, nose and throat infections
*Renal and urinary infections
*Gynaecological infection
*Abdominal and hepato-biliary infections
*Bone and joint infections 
*Skin and soft tissue infection
*Septicaemia and endocarditis
 
 
===Contraindications===
*Children or adolescents
*Pregnant women
*Nursing mothers
*History of hypersensitivity to quinolones
*Patients with a history of tendon lesion tendinitis or tendon rupture
 
==Precaution & side effects==
 
===Precautions===
*Hepatic dysfunction
*Avoid exposure to sunlight during treatment
 
===Side effects===
*Nausea
*Skin rash
*Photo sensitivity reaction
*Insomnia
*Headache
*Myalgia
*Thrombo-cytopenia
 
==Drug comparisons==
===Pefloxacin vs. Ciprofloxacin===
{| class="wikitable"
! ||Pefloxacin 400mg oral || Ciprofloxacin 500mg oral
|-
| Bioavailability || 100% || 50-70%
|-
| Peak plasma conc.(mcg/ml) || 8-10 || 2.3-2.7
|-
| Trough || 4-5 || 0.3-0.4
|-
| Plasma half life (hours) || 11-12 || 4-5
|}
 
===Pefloxacin vs. Norfloxacin===
{| class="wikitable"
! || Pefloxacin 400mg oral || Norfloxacin 400mg oral
|-
| Absorption || 100% || 30-40%
|-
| Peak plasma conc.(mcg/ml) || 4-5 || 1.4-1.6
|-
| Plasma protein binding || 30% || 15%
|-
| Plasma half life (hours) || 11-12 || 3-4
|-
| Urinary Excretion || 60% || 30-50%
|}
 
==Dosage & Presentation==
 
Oral Tablets: 400mg Twice daily
 
Injection: Administer by slow I.V. at a dosage of 400mg diluted in 100 or 250 ml of 5% isotonic solution (Over a period of 1 hr)
Twice daily


{{QuinoloneAntiBiotics}}
{{QuinoloneAntiBiotics}}
{{SIB}}


[[th:พีฟลอกซาซิน]]
[[Category:Fluoroquinolone antibiotics]]
[[Category:Fluoroquinolone antibiotics]]
{{WH}}
[[Category:Piperazines]]
{{WikiDoc Sources}}
[[Category:Drug]]

Latest revision as of 16:53, 20 August 2015

Pefloxacin
Clinical data
ATC code
Pharmacokinetic data
Bioavailability100%
Protein binding20–30%
MetabolismHepatic
Elimination half-life8.6 hours
ExcretionMostly renal, also biliary
Identifiers
CAS Number
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
FormulaC17H20FN3O3
Molar mass333.358 g/mol
3D model (JSmol)
  (verify)

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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

Pefloxacin is a quinolone drug used to treat bacterial infections. It is an analog of norfloxacin, belonging to the 3rd generation of quinolones. Pefloxacin has not been approved for use in the United States.

History

Pefloxacin was developed in 1979 and approved in France for human use in 1985.[1]

Licensed uses

  • Uncomplicated gonococcal urethritis in males.[2]
  • Bacterial infections in the gastrointestinal system.[2]
  • Genitourinary tract infections.[2]
  • Gonorrhoeae. however this indication is no longer effective due to bacterial resistance.[3]

Pefloxacin has been increasingly used as a veterinary medicine to treat microbial infections.[4]

Mode of action

Pefloxacin is a broad-spectrum antibiotic that is active against both Gram-positive and Gram-negative bacteria. It functions by inhibiting DNA gyrase, a type II topoisomerase, and topoisomerase IV,[5] which is an enzyme necessary to separate, replicated DNA, thereby inhibiting cell division.

Adverse effects

Tendinitis and rupture, usually of the Achilles tendon, are a class-effects of the fluoroquinolones, most frequently reported with pefloxacin.[6] The estimated risk of tendon damage during pefloxacin therapy has been estimated by the French authorities in 2000 to be 1 case per 23,130 treatment days as compared to ciprofloxacin where it has been estimated to be 1 case per 779,600.[7]

References

  1. ↑ http://www.bailii.org/ew/cases/EWHC/Patents/2008/2413.html
  2. ↑ 2.0 2.1 2.2 http://www.pefloxacin.com/pefloxacin_usage.htm
  3. ↑ Centers for Disease Control and Prevention (CDC) (April 2007). "Update to CDC's sexually transmitted diseases treatment guidelines, 2006: fluoroquinolones no longer recommended for treatment of gonococcal infections". MMWR Morb. Mortal. Wkly. Rep. 56 (14): 332–6. PMID 17431378.
  4. ↑ http://www.pefloxacin.com/pefloxacin_other.html
  5. ↑ Drlica K, Zhao X (1 September 1997). "DNA gyrase, topoisomerase IV, and the 4-quinolones". Microbiol Mol Biol Rev. 61 (3): 377–92. PMC 232616. PMID 9293187.
  6. ↑ Khaliq Y, Zhanel GG (October 2005). "Musculoskeletal injury associated with fluoroquinolone antibiotics". Clin Plast Surg. 32 (4): 495–502, vi. doi:10.1016/j.cps.2005.05.004. PMID 16139623.
  7. ↑ Casparian JM, Luchi M, Moffat RE, Hinthorn D (May 2000). "Quinolones and tendon ruptures". South. Med. J. 93 (5): 488–91. doi:10.1097/00007611-200093050-00008. PMID 10832946.

Template:QuinoloneAntiBiotics

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