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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/02/14 19:10:03」(JST)
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Pefloxacin
|
| Systematic (IUPAC) name |
|
1-ethyl-6-fluoro-7-(4-methylpiperazin-1-yl)-4-oxo-quinoline-3-carboxylic acid
|
| Pharmacokinetic data |
| Bioavailability |
100% |
| Protein binding |
20–30% |
| Metabolism |
Hepatic |
| Biological half-life |
8.6 hours |
| Excretion |
Mostly renal, also biliary |
| Identifiers |
| CAS Number |
70458-92-3 Y |
| ATC code |
J01MA03 |
| PubChem |
CID 51081 |
| DrugBank |
DB00487 Y |
| ChemSpider |
46291 Y |
| UNII |
2H52Z9F2Q5 Y |
| KEGG |
D02306 Y |
| ChEBI |
CHEBI:50199 Y |
| ChEMBL |
CHEMBL267648 Y |
| Chemical data |
| Formula |
C17H20FN3O3 |
| Molar mass |
333.358 g/mol |
SMILES
-
O=C(O)\C2=C\N(c1cc(c(F)cc1C2=O)N3CCN(C)CC3)CC
|
InChI
-
InChI=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) Y
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Key:FHFYDNQZQSQIAI-UHFFFAOYSA-N Y
|
| (verify) |
Pefloxacin is a quinolone drug used to treat bacterial infections. Pefloxacin has not been approved for use in the United States.
Contents
- 1 History
- 2 Licensed uses
- 3 Mode of action
- 4 Adverse effects
- 5 References
- 6 External links
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
- ^ http://www.bailii.org/ew/cases/EWHC/Patents/2008/2413.html
- ^ a b c http://www.pefloxacin.com/pefloxacin_usage.htm
- ^ 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.
- ^ http://www.pefloxacin.com/pefloxacin_other.html
- ^ 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.
- ^ 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.
- ^ 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.
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Antibacterials: nucleic acid inhibitors (J01E, J01M)
|
|
Antifolates
(inhibits
purine metabolism,
thereby inhibiting
DNA and RNA synthesis) |
| DHFR inhibitor |
- 2,4-Diaminopyrimidine
- Trimethoprim#
- Brodimoprim
- Tetroxoprim
- Iclaprim†
|
|
Sulfonamides
(DHPS inhibitor) |
Short-
acting |
- Sulfaisodimidine
- Sulfamethizole
- Sulfadimidine
- Sulfapyridine
- Sulfafurazole
- Sulfanilamide
- Sulfathiazole
- Sulfathiourea
|
|
Intermediate-
acting |
- Sulfamethoxazole
- Sulfadiazine#
- Sulfamoxole
|
|
Long-
acting |
- Sulfadimethoxine
- Sulfadoxine
- Sulfalene
- Sulfametomidine
- Sulfametoxydiazine
- Sulfamethoxypyridazine
- Sulfaperin
- Sulfamerazine
- Sulfaphenazole
- Sulfamazone
|
|
| Other/ungrouped |
- Sulfacetamide
- Sulfadicramide
- Sulfametrole
|
|
|
| Combinations |
- Trimethoprim/sulfamethoxazole#
|
|
|
Topoisomerase
inhibitors/
quinolones/
(inhibits
DNA replication) |
| 1st g. |
- Cinoxacin‡
- Flumequine‡
- Nalidixic acid‡
- Oxolinic acid‡
- Pipemidic acid‡
- Piromidic acid‡
- Rosoxacin‡
|
|
Fluoro-
quinolones |
| 2nd g. |
- Ciprofloxacin#
- Ofloxacin
- Enoxacin‡
- Fleroxacin‡
- Lomefloxacin‡
- Nadifloxacin‡
- Norfloxacin‡
- Pefloxacin‡
- Rufloxacin‡
|
|
| 3rd g. |
- Levofloxacin
- Balofloxacin‡
- Grepafloxacin‡
- Pazufloxacin‡
- Sparfloxacin‡
- Temafloxacin‡
- Tosufloxacin‡
|
|
| 4th g. |
- Besifloxacin
- Gatifloxacin
- Finafloxacin
- Gemifloxacin
- Moxifloxacin
- Clinafloxacin†
- Garenoxacin‡
- Prulifloxacin‡
- Sitafloxacin‡
- Trovafloxacin‡/Alatrofloxacin‡
|
|
| Vet. |
- Danofloxacin
- Difloxacin
- Enrofloxacin
- Ibafloxacin
- Marbofloxacin
- Orbifloxacin
- Pradofloxacin
- Sarafloxacin
|
|
|
| Newer non-fluorinated |
|
|
| Related (DG) |
- Aminocoumarins: Novobiocin
|
|
|
Anaerobic DNA
inhibitors |
| Nitro- imidazole derivatives |
- Metronidazole#
- Tinidazole
- Ornidazole
|
|
| Nitrofuran derivatives |
- Nitrofurantoin#
- Furazolidone‡
- Nifurtoinol
|
|
|
| RNA synthesis |
Rifamycins/
RNA polymerase |
- Rifampicin#
- Rifabutin
- Rifapentine
- Rifaximin
- Rifalazil§
|
|
|
- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
|
|
External links
- How Stuff Works - Cipro
- Package insert information
UpToDate Contents
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English Journal
- Molecular Characterization of Intermediate Susceptible Typhoidal Salmonella to Ciprofloxacin, and its Impact.
- Veeraraghavan B1, Anandan S2, Muthuirulandi Sethuvel DP2, Puratchiveeran N2, Walia K3, Devanga Ragupathi NK2.
- Molecular diagnosis & therapy.Mol Diagn Ther.2016 Mar 7. [Epub ahead of print]
- BACKGROUND AND OBJECTIVE: Extensive use of ciprofloxacin to treat Salmonella typhi infections has led to the emergence of resistance, resulting in clinical failure and delayed treatment response. Interpretative breakpoints for ciprofloxacin were revised by the Clinical and Laboratory Standards Insti
- PMID 26951258
- Comprehensive evaluation of formulation factors for ocular penetration of fluoroquinolones in rabbits using cassette dosing technique.
- Sharma C1, Biswas NR2, Ojha S3, Velpandian T2.
- Drug design, development and therapy.Drug Des Devel Ther.2016 Feb 22;10:811-23. doi: 10.2147/DDDT.S95870. eCollection 2016.
- OBJECTIVE: Corneal permeability of drugs is an important factor used to assess the efficacy of topical preparations. Transcorneal penetration of drugs from aqueous formulation is governed by various physiological, physiochemical, and formulation factors. In the present study, we investigated the eff
- PMID 26955263
- Interspecies scaling of excretory amounts using allometry - retrospective analysis with rifapentine, aztreonam, carumonam, pefloxacin, miloxacin, trovafloxacin, doripenem, imipenem, cefozopran, ceftazidime, linezolid for urinary excretion and rifapentine, cabotegravir, and dolutegravir for fecal excretion.
- Srinivas NR1.
- Xenobiotica; the fate of foreign compounds in biological systems.Xenobiotica.2015 Dec 29:1-9. [Epub ahead of print]
- 1. Interspecies allometry scaling for prediction of human excretory amounts in urine or feces was performed for numerous antibacterials. Antibacterials used for urinary scaling were: rifapentine, pefloxacin, trovafloxacin (Gr1/low; <10%); miloxacin, linezolid, PNU-142300 (Gr2/medium; 10-40%);
- PMID 26711252
Japanese Journal
- Oral toxicity of pefloxacin, norfloxacin, ofloxacin and ciprofloxacin : comparison of biomechanical and histopathological effects on Achilles tendon in rats
- Olcay Ercan,Beytemur Ozan,Kaleagasioglu Ferda [他],GULMEZ Turgut,MUTLU Zihni,OLGAC Vakur
- Journal of toxicological sciences 36(3), 339-345, 2011-06-01
- … Four fluoroquinolones (pefloxacin, norfloxacin, ofloxacin and ciprofloxacin) were compared according to their biomechanical and histopathological effects on rat Achilles tendon. … Pefloxacin mesylate dihydrate (40 mg/kg), norfloxacin (40 mg/kg), ofloxacin (20 mg/kg) and ciprofloxacin (50 mg/kg) were administered by gavage twice daily for three consecutive weeks. … The mean elastic modulus of the control group was significantly higher than that of the norfloxacin and pefloxacin groups (p < …
- NAID 10029135941
- Pharmacokinetics of pefloxacin mesylate in human urine using capillary electrophoresis electrochemiluminescence detection
- DENG Biyang,LI Linqiu,SHI Aihong,KANG Yanhui
- Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 877(24), 2585-2588, 2009-08-15
- NAID 10028022336
- Anti-VRE and Anti-MRSA Activities of New Quinolones and Their Synergism with Commercial Antibiotics. Part 2
- SAKAGAMI YOSHIKAZU,KOMEMUSHI SADAO,TSUKAMOTO GORO,KONDO HIROSATO,YOSHIKAWA AKIKO,MURAOKA OSAMU
- Biocontrol science 13(3), 103-109, 2008-09-10
- … Compound A exhibited potent antibacterial activity against VRE and MRSA among the five new quinolone compounds tested, and showed superior activity to pefloxacin, ofloxacin and levofloxacin, which are clinically in use these days. …
- NAID 10022018912
Related Links
- The reference site for pefloxacin including news articles, images, and updated information ... What is Pefloxacin? Pefloxacin is a medication belonging to the antibiotic group known as fluoroquinolones. They work by killing bacteria or ...
- 2. 日本における発売年 1985（昭和60）年 3. 特長 幅広い抗菌スペクトルを有す． 自然耐性菌の出現頻度が低い． 組織移行性が良好で,ほとんどが未変化体のまま腎に排泄される． 4. 承認済有効菌種 本剤に感性のブドウ球菌属
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