オキサシリン
WordNet
- a form of penicillin resistant to penicillinase and effective against penicillin-resistant staphylococci
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2012/09/01 18:37:53」(JST)
[Wiki en表示]
Oxacillin
|
Systematic (IUPAC) name |
(2S,5R,6R)-3,3-dimethyl-6-[(5-methyl-3-phenyl-
1,2-oxazole-4-carbonyl)amino]-7-oxo-4-thia-1-
azabicyclo[3.2.0]heptane-2-carboxylic acid |
Clinical data |
Trade names |
Bactocill |
AHFS/Drugs.com |
monograph |
MedlinePlus |
a685020 |
Pregnancy cat. |
? |
Legal status |
? |
Identifiers |
CAS number |
66-79-5 Y |
ATC code |
J01CF04 QJ51CF04 |
PubChem |
CID 6098 |
DrugBank |
DB00713 |
ChemSpider |
5873 Y |
UNII |
UH95VD7V76 Y |
KEGG |
D08307 Y |
ChEBI |
CHEBI:49566 N |
ChEMBL |
CHEMBL891 Y |
Chemical data |
Formula |
C19H19N3O5S |
Mol. mass |
401.436 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
|
Physical data |
Density |
1.49 g/cm³ |
Boiling point |
686.8 °C (1268 °F) |
N (what is this?) (verify)
|
Oxacillin sodium (trade name Bactocill) is a narrow spectrum beta-lactam antibiotic of the penicillin class.
It was developed by Beecham.[1]
Uses
Oxacillin is a penicillinase-resistant β-lactam. It is similar to methicillin, and has replaced methicillin in clinical use. Another related compound is nafcillin. Since it is resistant to penicillinase enzymes, such as that produced by Staphylococcus aureus, it is widely used clinically in the US to treat penicillin-resistant Staphylococcus aureus. However, with the introduction and widespread use of both oxacillin and methicillin, antibiotic-resistant strains called oxacillin-resistant Staphylococcus aureus (MRSA/ORSA) have become increasingly prevalent worldwide.
Adverse effects
Further information: Penicillin drug reaction
Side effects include hypersensitivity and local reactions. In high doses, renal, hepatic, or nervous system effects can occur.[2]
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.
- ^ Drugs.com: Bactocill
Antibacterials: cell envelope antibiotics (J01C-J01D)
|
|
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
|
|
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
|
|
β-lactamase resistant
|
- Cloxacillin# (Dicloxacillin
- Flucloxacillin)
- Oxacillin
- Meticillin
- Nafcillin
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|
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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
|
|
2nd (HEN)
|
- 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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|
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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
|
|
|
Other |
- polymyxins/detergent (Colistin
- Polymyxin B)
- depolarizing (Daptomycin)
- hydrolyze NAM-NAG (Lysozyme)
- Gramicidin
|
|
- #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
- The Posttranslocational Chaperone Lipoprotein PrsA Is Involved in both Glycopeptide and Oxacillin Resistance in Staphylococcus aureus.
- Jousselin A, Renzoni A, Andrey DO, Monod A, Lew DP, Kelley WL.SourceService of Infectious Diseases, University Hospital and Medical School of Geneva, Geneva, Switzerland.
- Antimicrobial agents and chemotherapy.Antimicrob Agents Chemother.2012 Jul;56(7):3629-40. Epub 2012 Apr 23.
- Understanding in detail the factors which permit Staphylococcus aureus to counteract cell wall-active antibiotics is a prerequisite to elaborating effective strategies to prolong the usefulness of these drugs and define new targets for pharmacological intervention. Methicillin-resistant S. aureus (M
- PMID 22526301
- Biochemical and Genetic Characterization of Carbapenem-Hydrolyzing β-Lactamase OXA-229 from Acinetobacter bereziniae.
- Bonnin RA, Ocampo-Sosa AA, Poirel L, Guet-Revillet H, Nordmann P.SourceService de Bactériologie-Virologie, INSERM U914 Emerging Resistance to Antibiotics, Hôpital de Bicêtre, Assistance Publique/Hôpitaux de Paris, Faculté de Médecine et Université Paris-Sud, K.-Bicêtre.
- Antimicrobial agents and chemotherapy.Antimicrob Agents Chemother.2012 Jul;56(7):3923-7. Epub 2012 Apr 16.
- Acinetobacter bereziniae (formerly Acinetobacter genomospecies 10) isolate Nec was recovered from a skin sample of a patient hospitalized in Paris, France. It was resistant to penicillins, penicillin-inhibitor combinations, and carbapenems. Cloning and expression in Escherichia coli identified the c
- PMID 22508298
Japanese Journal
- 血液培養における Oxacillin 低感受性MRSAの検索とその症例からの考察
- 仲間 美香,照屋 真利子,中村 梢,儀間 久美子,宮里 博子,大田 茂,山里 香代,大田 英也
- 医学検査 : 日本臨床衛生検査技師会誌 = The Japanese journal of medical technology 59(6), 778-781, 2010-06-25
- NAID 10027748880
- Antibacterial and synergistic effects of Smallanthus sonchifolius leaf extracts against methicillin-resistant Staphylococcus aureus under light intensity
- JOUNG Hee,KWON Dong-Yeul,CHOI Jang-Gi,SHIN Dong-Young,CHUN Soon-Sil,YU Young-Beob,SHIN Dong-Won
- Journal of natural medicines 64(2), 212-215, 2010-05-20
- NAID 10027709622
Related Links
- Oxacillin is a penicillinase-resistant β-lactam. It is similar to methicillin, and has replaced methicillin in clinical use. Another related compound is nafcillin. Since it is resistant to penicillinase enzymes, such as that produced by Staphylococcus ...
Related Pictures
★リンクテーブル★
[★]
- 英
- oxacillin
- ラ
- oxacillinum
- 同
- メチルフェニルイソキサゾリルペニシリン methylphenylisoxazolyl penicillin MPIPC
- 化
- オキサシリンナトリウム oxacillin sodium
- 商
- Prostaphlin
- 関
- 抗菌薬
- 合成ペニシリンであり、ペニシリナーゼに対して安定である。
[★]
クロキサシリンベンザチン
- 関
- cloxacillin、cloxacillin sodium
[★]
- 関
- dicloxacillin