クロキサシリン
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出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2012/07/17 14:15:52」(JST)
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Cloxacillin
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Systematic (IUPAC) name |
(2S,5R,6R)-6-{[3-(2-chlorophenyl)-5-methyl-
oxazole-4-carbonyl]amino}-3,3-dimethyl-7-oxo-
4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid |
Clinical data |
Trade names |
Cloxapen |
AHFS/Drugs.com |
Micromedex Detailed Consumer Information |
Pregnancy cat. |
B (US) |
Legal status |
? |
Routes |
Oral, IM |
Pharmacokinetic data |
Bioavailability |
37 to 90% |
Protein binding |
95% |
Half-life |
30 minutes to 1 hour |
Excretion |
Renal and biliary |
Identifiers |
CAS number |
61-72-3 Y |
ATC code |
J01CF02 QJ51CF02 QS01AA90 |
PubChem |
CID 6098 |
DrugBank |
DB01147 |
ChemSpider |
5873 Y |
UNII |
O6X5QGC2VB Y |
KEGG |
D07733 Y |
ChEBI |
CHEBI:49566 Y |
ChEMBL |
CHEMBL891 Y |
Chemical data |
Formula |
C19H18ClN3O5S |
Mol. mass |
435.88 g/mol |
SMILES
- O=C(O)[C@@H]3N4C(=O)[C@@H](NC(=O)c2c(onc2c1ccccc1Cl)C)[C@H]4SC3(C)C
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InChI
-
InChI=1S/C19H18ClN3O5S/c1-8-11(12(22-28-8)9-6-4-5-7-10(9)20)15(24)21-13-16(25)23-14(18(26)27)19(2,3)29-17(13)23/h4-7,13-14,17H,1-3H3,(H,21,24)(H,26,27)/t13-,14+,17-/m1/s1 Y
Key:LQOLIRLGBULYKD-JKIFEVAISA-N Y
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Y (what is this?) (verify)
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Cloxacillin is a semisynthetic antibiotic in the same class as penicillin. Cloxacillin was discovered and developed by Beecham.[1] It is sold under a number of trade names, including Cloxapen, Cloxacap, Tegopen and Orbenin.
Cloxacillin is used against staphylococci that produce beta-lactamase, due to its large R chain, which does not allow the beta-lactamases to bind.
This drug has a weaker antibacterial activity than benzylpenicillin, and is devoid of serious toxicity except for allergic reactions.
It has been suggested, in one study, that increased use of cloxacillin may permit reduced use of vancomycin.[2]
See also
- Dicloxacillin
- Flucloxacillin
- Nafcillin
- Oxacillin
References
- ^ David Greenwood (2008). Antimicrobial drugs: chronicle of a twentieth century medical triumph. Oxford University Press US. pp. 124–. ISBN 978-0-19-953484-5. http://books.google.com/books?id=i4_FZHmzjzwC&pg=PA124. Retrieved 18 November 2010.
- ^ Lawrence SL, Roth V, Slinger R, Toye B, Gaboury I, Lemyre B (2005). "Cloxacillin versus vancomycin for presumed late-onset sepsis in the Neonatal Intensive Care Unit and the impact upon outcome of coagulase negative staphylococcal bacteremia: a retrospective cohort study". BMC Pediatr 5: 49. DOI:10.1186/1471-2431-5-49. PMC 1343548. PMID 16375769. http://www.biomedcentral.com/1471-2431/5/49.
Antibacterials: cell envelope antibiotics (J01C-J01D)
|
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Intracellular |
- inhibit peptidoglycan subunit synthesis and transport: NAM synthesis inhibition (Fosfomycin)
- DADAL/AR inhibitors (Cycloserine)
- bactoprenol inhibitors (Bacitracin)
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Glycopeptide |
- inhibit PG chain elongation: Vancomycin# (Oritavancin
- Telavancin)
- Teicoplanin (Dalbavancin)
- Ramoplanin
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β-lactams/
(inhibit PBP
cross-links) |
Penicillins
(penams)
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Extended sp.
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- aminopenicillins: Amoxicillin#
- Ampicillin# (Pivampicillin
- Hetacillin
- Bacampicillin
- Metampicillin
- Talampicillin)
- Epicillin
- carboxypenicillins: Carbenicillin (Carindacillin)
- Ticarcillin
- Temocillin
- ureidopenicillins: Azlocillin
- Piperacillin
- Mezlocillin
- other: Mecillinam (Pivmecillinam)
- Sulbenicillin
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Narrow sp.
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β-lactamase sensitive
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- Benzylpenicillin (G)#: Clometocillin
- Benzathine benzylpenicillin#
- Procaine benzylpenicillin#
- Azidocillin
- Penamecillin
- Phenoxymethylpenicillin (V)#: Propicillin
- Benzathine phenoxymethylpenicillin
- Pheneticillin
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β-lactamase resistant
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- Cloxacillin# (Dicloxacillin
- Flucloxacillin)
- Oxacillin
- Meticillin
- Nafcillin
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Penems
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Carbapenems
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- Biapenem
- Ertapenem
- antipseudomonal (Doripenem
- Imipenem
- Meropenem)
- Panipenem
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Cephalosporins/Cephamycins
(cephems)
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1st (PEcK)
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- Cefazolin#
- Cefacetrile
- Cefadroxil
- Cefalexin
- Cefaloglycin
- Cefalonium
- Cefaloridine
- Cefalotin
- Cefapirin
- Cefatrizine
- Cefazedone
- Cefazaflur
- Cefradine
- Cefroxadine
- Ceftezole
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2nd (HEN)
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- Cefaclor
- Cefamandole
- Cefminox
- Cefonicid
- Ceforanide
- Cefotiam
- Cefprozil
- Cefbuperazone
- Cefuroxime
- Cefuzonam
- cephamycin (Cefoxitin
- Cefotetan
- Cefmetazole)
- carbacephem (Loracarbef)
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3rd
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- Cefixime#
- Ceftriaxone#
- antipseudomonal (Ceftazidime#
- Cefoperazone)
- Cefcapene
- Cefdaloxime
- Cefdinir
- Cefditoren
- Cefetamet
- Cefmenoxime
- Cefodizime
- Cefotaxime
- Cefpimizole
- Cefpiramide
- Cefpodoxime
- Cefsulodin
- Cefteram
- Ceftibuten
- Ceftiolene
- Ceftizoxime
- oxacephem (Flomoxef
- Latamoxef ‡)
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4th (antips-)
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- Cefepime
- Cefozopran
- Cefpirome
- Cefquinome
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5th
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- Ceftobiprole
- Ceftaroline fosamil
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Veterinary
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- Ceftiofur
- Cefquinome
- Cefovecin
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Monobactams
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- Aztreonam
- Tigemonam
- Carumonam
- Nocardicin A
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β-lactamase inh.
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- penam (Sulbactam
- Tazobactam)
- clavam (Clavulanic acid)
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Combinations
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- Amoxicillin/clavulanic acid#
- Imipenem/cilastatin#
- Ampicillin/flucloxacillin
- Ampicillin/sulbactam (Sultamicillin)
- Piperacillin/tazobactam
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Other |
- polymyxins/detergent (Colistin
- Polymyxin B)
- depolarizing (Daptomycin)
- hydrolyze NAM-NAG (Lysozyme)
- Gramicidin
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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gr+f/gr+a(t)/gr-p(c)/gr-o
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UpToDate Contents
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English Journal
- A prospective study of nosocomial urinary tract infection in hip fracture patients.
- Halleberg Nyman M, Johansson JE, Persson K, Gustafsson M.SourceAuthors:?Maria Halleberg Nyman, MSc, RN, PhD Student, Department of Orthopaedics, Orebro University Hospital; Jan-Erik Johansson, MD, Professor, Department of Urology, Orebro University Hospital; Katarina Persson, PhD, Professor, Department of Clinical Medicine, School of Health and Medical Sciences, Orebro University; Margareta Gustafsson, PhD, RN, Senior Lecturer, School of Health and Medical Sciences, Orebro University, Orebro, Sweden.
- Journal of clinical nursing.J Clin Nurs.2011 Sep;20(17-18):2531-9. doi: 10.1111/j.1365-2702.2011.03769.x. Epub 2011 Jul 6.
- Aim.? To investigate risk factors and consequences of nosocomial urinary tract infection in hip fracture patients. Background.? Nosocomial urinary tract infection is a well-known problem in hip fracture patients. There are several risk factors for nosocomial urinary tract infection described in
- PMID 21733026
- Systematic Review on the Etiology and Antibiotic Treatment of Pneumonia in Human Immunodeficiency Virus-infected Children.
- Punpanich W, Groome M, Muhe L, Qazi SA, Madhi SA.SourceFrom the *Department of Science and Technology/National Research Foundation: Vaccine Preventable Diseases, University of the Witwatersrand, Johannesburg, South Africa; †Medical Research Council: Respiratory and Meningeal Pathogens Research Unit, University of the Witwatersrand, Johannesburg, South Africa; ‡Department of Pediatrics, Queen Sirikit National Institute of Child Health, College of Medicine, Rangsit University, Bangkok, Thailand; §Department of Child and Adolescent Health and Development, World Health Organization, Geneva, Switzerland; ¶Department of HIV, World Health Organization, Geneva, Switzerland; and ∥National Institute for Communicable Diseases, National Health Laboratory Services, Sandringham, South Africa.
- The Pediatric infectious disease journal.Pediatr Infect Dis J.2011 Aug 17. [Epub ahead of print]
- BACKGROUND: Community-acquired pneumonia (CAP) is a leading cause of morbidity and mortality in human immunodeficiency virus (HIV)-infected children.OBJECTIVES AND METHODS: A systematic review of studies that were published between January 1990 and February 2009 on the etiology and antimicrobial or
- PMID 21857264
Japanese Journal
- Symmetrical drug-related intertriginous and flexural exanthema (baboon syndrome) with fever induced by oral cloxacillin : Does fever confound the diagnosis?
- CHONG Wei-Sheng,LIM Hua-Liang Joel
- Journal of dermatology 37(9), 830-832, 2010-09-01
- NAID 10027067344
- Case of acute generalized exanthematous pustulosis caused by ampicillin/cloxacillin sodium in a pregnant woman
- MATSUMOTO Yuka,OKUBO Yukari,YAMAMOTO Toshiyuki,ITO Tomonobu,TSUBOI Ryoji
- Journal of dermatology 35(6), 362-364, 2008-06-01
- NAID 10024297115
Related Links
- Cloxacillin is a semisynthetic antibiotic in the same class as penicillin. Cloxacillin was discovered and developed by Beecham. It is sold under a number of trade names, including Cloxapen, Cloxacap, Tegopen and Orbenin. ...
Related Pictures
★リンクテーブル★
[★]
- 英
- cloxacillin
- ラ
- cloxacillinum
- 同
- メチルクロルフェニルイソキサゾリルペニシリン methylchlorophenyl-isoxazolyl penicillin MCIPC
- 化
- クロキサシリンナトリウム cloxacillin sodium、クロキサシリンベンザチン cloxacillin benzathine
- 商
- Tegopen
- 関
- 抗菌薬
参考
[★]
クロキサシリンベンザチン
- 関
- cloxacillin、cloxacillin sodium
[★]
- 関
- flucloxacillin
[★]
- 関
- dicloxacillin