オキサシリンナトリウム
WordNet
- a silvery soft waxy metallic element of the alkali metal group; occurs abundantly in natural compounds (especially in salt water); burns with a yellow flame and reacts violently in water; occurs in sea water and in the mineral halite (rock salt) (同)Na, atomic number 11
- a form of penicillin resistant to penicillinase and effective against penicillin-resistant staphylococci
PrepTutorEJDIC
- ソジウム,ナトリウム(金属元素;化学記号はNa)
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2013/10/19 16:23:55」(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 |
CHEMBL819 N |
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
|
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[edit]
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. MRSA/ORSA is treated using vancomycin.
Adverse effects[edit]
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[edit]
- ^ David Greenwood (2008). Antimicrobial drugs: chronicle of a twentieth century medical triumph. Oxford University Press US. pp. 124–. ISBN 978-0-19-953484-5. 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)
|
|
Glycopeptide |
- inhibit PG chain elongation: Vancomycin# (Oritavancin
- Telavancin)
- Teicoplanin (Dalbavancin)
- Ramoplanin
|
|
β-lactams/
(inhibit PBP
cross-links) |
Penicillins
(penams)
|
Extended sp.
|
- aminopenicillins: Amoxicillin#
- Ampicillin# (Pivampicillin
- Hetacillin
- Bacampicillin
- Metampicillin
- Talampicillin)
- Epicillin
- carboxypenicillins: Carbenicillin (Carindacillin)
- Ticarcillin
- Temocillin
- ureidopenicillins: Azlocillin
- Piperacillin
- Mezlocillin
- other: Mecillinam (Pivmecillinam)
- Sulbenicillin
|
|
Narrow sp.
|
β-lactamase sensitive
|
- Benzylpenicillin (G)#: Clometocillin
- Benzathine benzylpenicillin#
- Procaine benzylpenicillin#
- Azidocillin
- Penamecillin
- Phenoxymethylpenicillin (V)#: Propicillin
- Benzathine phenoxymethylpenicillin
- Pheneticillin
|
|
β-lactamase resistant
|
- Cloxacillin# (Dicloxacillin
- Flucloxacillin)
- Oxacillin
- Meticillin
- Nafcillin
|
|
|
|
Penems
|
|
|
Carbapenems
|
- Biapenem
- Ertapenem
- antipseudomonal (Doripenem
- Imipenem
- Meropenem)
- Panipenem
|
|
Cephalosporins/Cephamycins
(cephems)
|
1st (PEcK)
|
- 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)
|
|
3rd
|
- Cefixime#
- Ceftriaxone#
- antipseudomonal (Ceftazidime#
- Cefoperazone)
- Cefcapene
- Cefdaloxime
- Cefdinir
- Cefditoren
- Cefetamet
- Cefmenoxime
- Cefodizime
- Cefotaxime
- Cefpimizole
- Cefpiramide
- Cefpodoxime
- Cefsulodin
- Cefteram
- Ceftibuten
- Ceftiolene
- Ceftizoxime
- oxacephem (Flomoxef
- Latamoxef ‡)
|
|
4th (antips-)
|
- Cefepime
- Cefozopran
- Cefpirome
- Cefquinome
|
|
5th
|
- Ceftobiprole
- Ceftaroline fosamil
|
|
Veterinary
|
- Ceftiofur
- Cefquinome
- Cefovecin
|
|
|
Monobactams
|
- Aztreonam
- Tigemonam
- Carumonam
- Nocardicin A
|
|
β-lactamase inh.
|
- penam (Sulbactam
- Tazobactam)
- clavam (Clavulanic acid)
|
|
Combinations
|
- 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
- Isoniazid
|
|
- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
|
|
gr+f/gr+a (t)/gr-p (c)/gr-o
|
drug (J1p, w, n, m, vacc)
|
|
|
|
UpToDate Contents
全文を閲覧するには購読必要です。 To read the full text you will need to subscribe.
English Journal
- Heterogeneity of Genetic Pathways toward Daptomycin Nonsusceptibility in Staphylococcus aureus Determined by Adjunctive Antibiotics.
- Berti AD1, Baines SL2, Howden BP3, Sakoulas G4, Nizet V4, Proctor RA5, Rose WE6.
- Antimicrobial agents and chemotherapy.Antimicrob Agents Chemother.2015 May;59(5):2799-806. doi: 10.1128/AAC.04990-14. Epub 2015 Mar 2.
- Daptomycin is increasingly used in combination with other antibiotics to enhance antimicrobial efficacy and/or to mitigate the emergence of daptomycin nonsusceptibility (DNS). This study used a clinical methicillin-resistant Staphylococcus aureus (MRSA) strain in which DNS emerged upon therapy to ex
- PMID 25733508
- Lincosamide resistance is less frequent in Denmark in Staphylococcus pseudintermedius from first-time canine superficial pyoderma compared with skin isolates from clinical samples with unknown clinical background.
- Larsen R1, Boysen L, Berg J, Guardabassi L, Damborg P.
- Veterinary dermatology.Vet Dermatol.2015 Apr 18. doi: 10.1111/vde.12209. [Epub ahead of print]
- BACKGROUND: Antimicrobial resistance may be overestimated in bacterial isolates from clinical samples because veterinarians often submit samples in cases of treatment failure or recurrent cases, which are more frequently associated with resistant strains.HYPOTHESIS/OBJECTIVES: To assess to what exte
- PMID 25891140
- Recycling Antibiotics into GUMBOS: A New Combination Strategy to Combat Multi-Drug-Resistant Bacteria.
- Cole MR1, Hobden JA2, Warner IM3.
- Molecules (Basel, Switzerland).Molecules.2015 Apr 10;20(4):6466-87. doi: 10.3390/molecules20046466.
- The emergence of multi-drug-resistant bacteria, coupled with the lack of new antibiotics in development, is fast evolving into a global crisis. New strategies utilizing existing antibacterial agents are urgently needed. We propose one such strategy in which four outmoded β-lactam antibiotics (ampic
- PMID 25867831
Japanese Journal
- プレカラム蛍光誘導化法による食肉中残留ペニシリン系抗生物質の高速液体クロマトグラフィー分析
- 牛水 徹,佐藤 俊男,齋藤 忠夫 [他],伊藤 敞敏
- 日本畜産學會報 = The Japanese journal of zootechnical science 72(10), J570-J578, 2001-10-25
- … An analytical method was developed for the simultaneous determination of penicillins (benzylpenicillin, oxacillin, cloxacillin, dicloxacillin and nafcillin) remaining in edible tissues (muscle and kidney) of animals (bovine and swine) by pre-column fluorescence derivatization. … Edible animal tissues were extracted with water and deproteinized with sulfuric acid and sodium tangstate, followed by concentration with C18 (solid-phase extraction) cartridge column. …
- NAID 10025835384
- Synergistic Effect of Polyoxotungstates in Combination with β-Lactam Antibiotics on Antibacterial Activity against Methicillin-Resistant Staphylococcus aureus
- YAMASE Toshihiro,FUKUDA Norio,TAJIMA Yutaka
- Biological & pharmaceutical bulletin 19(3), 459-465, 1996-03-15
- … potentiated the antibacterial activity of β-lactam antibiotics such as oxacillin, piperacillin and cefazolin on MRSA with high selectivity. … The depression of bacterial growth with the coexistence of polyoxotungstates and oxacillin was confirmed by the measurement of the bacterial turbidity at 660nm. … Polyoxomolybdates and polyoxovanadates, on the other hand, exhibited hardly any synergisitic effect in combination with oxacillin. …
- NAID 110003641193
- Fast Atom Bombardment Mass Spectrometry of Isoxazolylpenicillins and Their Metabolites in Man
- 村井 靖夫,中川 照眞,宇野 豊三
- Chemical & pharmaceutical bulletin 33(1), 383-387, 1985-01-25
- … All the substances gave positive pseudomolecular ions, as either proton adducts or sodium ion adducts, and some structurally significant fragment ions. …
- NAID 110003625147
Related Links
- Your health care provider probably will give you a several-day supply of oxacillin at a time. If you are receiving oxacillin intravenously (in your vein), you probably will be told to store it in the refrigerator or freezer. Take your ...
- <strong>OXACILLIN</strong> <strong>SODIUM</strong> SALT;<strong>OXACILLIN</strong> <strong>SODIUM</strong>;<strong>OXACILLIN</strong> NA;<strong>OXACILLIN ... Haven't found the right supplier yet ? AliSourcePro ...
★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。
[★]
- 関
- flucloxacillin
[★]
- 関
- dicloxacillin
[★]
クロキサシリンナトリウム