ナフシリン
WordNet
- a penicillinase-resistant form of penicillin (trade name Nafcil) used (usually in the form of its sodium salt) to treat infections caused by penicillin-resistant strains of staphylococci (同)Nafcil
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2014/12/22 17:06:53」(JST)
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Nafcillin
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Systematic (IUPAC) name |
(2S,5R,6R)-6-[(2-ethoxy-1-naphthoyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid |
Clinical data |
AHFS/Drugs.com |
monograph |
MedlinePlus |
a685019 |
Pregnancy cat. |
|
Legal status |
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Routes |
IM, IV |
Pharmacokinetic data |
Protein binding |
90% |
Metabolism |
<30% hepatic |
Half-life |
0.5 hours |
Excretion |
Biliary and renal |
Identifiers |
CAS number |
985-16-0 Y |
ATC code |
J01CF06 |
PubChem |
CID 8982 |
DrugBank |
DB00607 |
ChemSpider |
8634 Y |
UNII |
SY07234TTS Y |
ChEBI |
CHEBI:7447 Y |
ChEMBL |
CHEMBL1443 Y |
Chemical data |
Formula |
C21H22N2O5S |
Mol. mass |
414.476 g/mol |
SMILES
- O=C(O)[C@@H]3N4C(=O)[C@@H](NC(=O)c2c1ccccc1ccc2OCC)[C@H]4SC3(C)C
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InChI
-
InChI=1S/C21H22N2O5S/c1-4-28-13-10-9-11-7-5-6-8-12(11)14(13)17(24)22-15-18(25)23-16(20(26)27)21(2,3)29-19(15)23/h5-10,15-16,19H,4H2,1-3H3,(H,22,24)(H,26,27)/t15-,16+,19-/m1/s1 Y
Key:GPXLMGHLHQJAGZ-JTDSTZFVSA-N Y
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Y (what is this?) (verify) |
Nafcillin sodium is a narrow-spectrum[1] beta-lactam antibiotic[2] of the penicillin class. As a beta-lactamase-resistant penicillin, it is used to treat infections caused by Gram-positive bacteria, in particular, species of staphylococci that are resistant to other penicillins.
Nafcillin is considered therapeutically equivalent to oxacillin, although its safety profile is somewhat different.[3]
Contents
- 1 Indications
- 2 Side-effects
- 3 Interactions
- 4 References
Indications
Nafcillin is indicated in the treatment of staphylococcal infections, except those caused by MRSA.[3]
U.S. clinical practice guidelines recommend either nafcillin or oxacillin as the first-line treatment of choice for staphylococcal endocarditis in patients without artificial heart valves.[4]
Side-effects
As with all penicillins, serious life-threatening allergic reactions can occur.
Milder side-effects include:
- Hypokalemia[5]
- Nausea and vomiting
- Diarrhea, often due to suppression of normal gastrointestinal bacteria, which, on occasion, leads to a more serious super-infection with an organism like Clostridium difficile
- Abdominal pain
- Yeast infections (thrush) affecting the mouth and tongue or vagina
- Agranulocytosis, neutropenia
Interactions
There is evidence that it induces cytochrome P-450 enzymes.[6]
The other aspect of this medication is that this medication contains lots of salts as media. So it could cause some edema or fluid accumulation. It would be prudent to avoid this medication if there were a concern for a congestive heart failure or kidney disease.
References
- ^ Palmer DL, Pett SB, Akl BF (March 1995). "Bacterial wound colonization after broad-spectrum versus narrow-spectrum antibiotics". Ann. Thorac. Surg. 59 (3): 626–31. doi:10.1016/0003-4975(94)00992-9. PMID 7887701.
- ^ Tan AK, Fink AL (January 1992). "Identification of the site of covalent attachment of nafcillin, a reversible suicide inhibitor of beta-lactamase". Biochem. J. 281 (1): 191–6. PMC 1130660. PMID 1731755.
- ^ a b Pham P, Bartlett JG (January 2, 2009). "Nafcillin". Point-of-Care Information Technology ABX Guide. Johns Hopkins University. Retrieved on July 10, 2009. Freely available with registration.
- ^ Bonow RO, Carabello BA, Kanu C, et al. (August 2006). "ACC/AHA 2006 guidelines for the management of patients with valvular heart disease: a report of the American College of Cardiology/American Heart Association Task Force on Practice Guidelines (writing committee to revise the 1998 Guidelines for the Management of Patients With Valvular Heart Disease): developed in collaboration with the Society of Cardiovascular Anesthesiologists: endorsed by the Society for Cardiovascular Angiography and Interventions and the Society of Thoracic Surgeons". Circulation 114 (5): e84–231. doi:10.1161/CIRCULATIONAHA.106.176857. PMID 16880336.
- ^ JA Mohr. (1979). Nafcillin-associated hypokalemia. JAMA
- ^ Lang CC, Jamal SK, Mohamed Z, Mustafa MR, Mustafa AM, Lee TC (June 2003). "Evidence of an interaction between nifedipine and nafcillin in humans". Br J Clin Pharmacol 55 (6): 588–90. doi:10.1046/j.1365-2125.2003.01789.x. PMC 1884262. PMID 12814453.
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.
|
- 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 (antipseudomonal)
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- Cefepime
- Cefozopran
- Cefpirome
- Cefquinome
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5th
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- Ceftobiprole
- Ceftaroline fosamil
- Ceftolozane
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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
- Isoniazid
|
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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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drug (J1p, w, n, m, vacc)
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UpToDate Contents
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English Journal
- Vascular graft infections and role of PET/CT in patients with persistent bacteraemia.
- Shahani L1.
- BMJ case reports.BMJ Case Rep.2015 Mar 16;2015. pii: bcr2014207678. doi: 10.1136/bcr-2014-207678.
- Prosthetic vascular graft infection although a rare complication of vascular reconstruction surgery; has been associated with significant morbidity and mortality. The author presents two patients with prosthetic aortic graft presenting as fever and methicillin sensitive Staphylococcus aureus bactera
- PMID 25777486
- Novel quorum-quenching agents promote methicillin-resistant Staphylococcus aureus (MRSA) wound healing and sensitize MRSA to β-lactam antibiotics.
- Kuo D1, Yu G1, Hoch W1, Gabay D1, Long L2, Ghannoum M2, Nagy N3, Harding CV3, Viswanathan R4, Shoham M5.
- Antimicrobial agents and chemotherapy.Antimicrob Agents Chemother.2015 Mar;59(3):1512-8. doi: 10.1128/AAC.04767-14. Epub 2014 Dec 22.
- The dwindling repertoire of antibiotics to treat methicillin-resistant Staphylococcus aureus (MRSA) calls for novel treatment options. Quorum-quenching agents offer an alternative or an adjuvant to antibiotic therapy. Three biaryl hydroxyketone compounds discovered previously (F1, F12, and F19; G. Y
- PMID 25534736
Japanese Journal
- Assessment of molecularly imprinted sol-gel materials for selective room temperature phosphorescence recognition of nafcillin
- FERNANDEZ-GONZALEZ A.,BADIA LAINO R.,DIAZ-CARCIA M. E.,GUARDIA L.,VIALE A.
- Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 804(1), 247-254, 2004-05-05
- NAID 10016549814
- <Abstract of Published Report>Application of Ion-exchange Cartridge Clean-up in Food Analysis IV. : Confirmatory Asay of Benzylpenicillin, Phenoxymethylpenicillin, Oxacillin, Cloxacillin, Nafcillin and Dicloxacillin in Bovine Tissues by Liquid Chromatography-Electrospray Ionization Tandem Mass Spectmetry.
- ITO Yuko,IKAI Yoshitomo,OKA Hisao,MATSUMOTO Hiroshi,MIYAZAKI Yutaka,TAKEBA Kazue,NAGASE Hisamitsu
- 岐阜藥科大學紀要 51, 67, 2002-06-30
- NAID 110000054632
Related Links
- Nafcillinとは?goo Wikipedia (ウィキペディア) 。出典:Wikipedia(ウィキペディア)フリー百科事典。 Nafcillinとは - goo Wikipedia (ウィキペディア) gooトップ サイトマップ スタートページに設定 RSS ヘルプ メニューへスキップ 本文へ メール ...
- Nafcillin official prescribing information for healthcare professionals. Includes: indications, dosage, adverse reactions, pharmacology and more. ... CLINICAL PHARMACOLOGY In a study of five healthy adults administered a single ...
Related Pictures
★リンクテーブル★
[★]
- 英
- nafcillin, NFPC
- 化
- ナフシリンナトリウム nafcillin sodium
- 関
- 抗菌薬、βラクタム系抗菌薬、ペニシリン系抗菌薬
[★]
ナフシリン nafcillin