同: Nafcil, Unipen

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 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

PrepTutorEJDIC

ソジウム,ナトリウム(金属元素;化学記号はNa)

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2017/05/10 16:10:41」(JST)

wiki en

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]

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 specifically CYP2C9. Several drugs with a narrow theraputic window, such as warfarin and nifedipine, are metabolized by CYP2C9.^[6]

Nafcillin contains salts added as stability media. These added salts could cause 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.

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3. ペニシリン、黄色ブドウ球菌用ペニシリン、広域ペニシリン penicillin antistaphylococcal penicillins and broad spectrum penicillins
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5. 小児における黄色ブドウ球菌菌血症：マネージメントおよび転帰 staphylococcus aureus bacteremia in children management and outcome

English Journal

Effects of vancomycin versus nafcillin in enhancing killing of methicillin-susceptible Staphylococcus aureus causing bacteremia by human cathelicidin LL-37.

Le J1, Dam Q2, Schweizer M3,4, Thienphrapa W2, Nizet V5,2, Sakoulas G2.
European journal of clinical microbiology & infectious diseases : official publication of the European Society of Clinical Microbiology.Eur J Clin Microbiol Infect Dis.2016 May 27. [Epub ahead of print]
Recent studies have demonstrated that anti-staphylococcal beta-lactam antibiotics, like nafcillin, render methicillin-resistant Staphylococcus aureus (MRSA) more susceptible to killing by innate host defense peptides (HDPs), such as cathelicidin LL-37. We compared the effects of growth in 1/4 minimu
PMID 27234592

Cefazolin versus nafcillin for methicillin-sensitive Staphylococcus aureus bloodstream infection: an observational study in a California tertiary medical center.

Pollett S1, Baxi SM2, Rutherford GW3, Doernberg SB4, Bacchetti P3, Chambers HF5.
Antimicrobial agents and chemotherapy.Antimicrob Agents Chemother.2016 May 23. pii: AAC.00243-16. [Epub ahead of print]
Recent observational studies have suggested possible reductions in mortality in those receiving cefazolin versus anti-staphylococcal penicillins. We examined 90-day mortality in patients receiving cefazolin compared to nafcillin for methicillin-susceptible Staphylococcus aureus (MSSA) bloodstream in
PMID 27216053

Adverse Events Lead to Drug Discontinuation More Commonly among Patients Who Receive Nafcillin than among Those Who Receive Oxacillin.

Viehman JA1, Oleksiuk LM2, Sheridan KR1, Byers KE1, He P3, Falcione BA1, Shields RK4.
Antimicrobial agents and chemotherapy.Antimicrob Agents Chemother.2016 Apr 22;60(5):3090-5. doi: 10.1128/AAC.03122-15. Print 2016 May.
Nafcillin and oxacillin are used interchangeably in clinical practice, yet few studies have evaluated the safety of these two agents. Our objective was to compare the differential tolerabilities of nafcillin and oxacillin among hospitalized patients. We conducted a retrospective cohort study of all
PMID 26976858

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,伊藤敞敏
日本畜産學會報 = The Japanese journal of zootechnical science 72(10), 570, 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

Sodium 6-(2-ethoxy-1-naphthamido)penicillanate monohydrate(sodium nafcillin monohydrate)の物性および安定性

矢敷孝司 [他]
武田研究所報 30(1), 138-153, 1971-03
NAID 40018020699

「ナフシリン」

Nafcillin
Clinical data
AHFS/Drugs.com	Monograph
MedlinePlus	a685019
Pregnancy; category	US: B (No risk in non-human studies); ;
Routes of; administration	IM, IV
ATC code	J01CF06 (WHO);
Legal status
Legal status	In general: ℞ (Prescription only);
Pharmacokinetic data
Protein binding	90%
Metabolism	<30% hepatic
Biological half-life	0.5 hours
Excretion	Biliary and renal
Identifiers
	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;
CAS Number	985-16-0 ;
PubChem CID	8982;
DrugBank	DB00607 ;
ChemSpider	8634 ;
UNII	SY07234TTS;
ChEBI	CHEBI:7447 ;
ChEMBL	CHEMBL1443 ;
ECHA InfoCard	100.005.174
Chemical and physical data
Formula	C21H22N2O5S
Molar mass	414.476 g/mol
3D model (Jmol)	Interactive image;
	SMILES O=C(O)[C@@H]3N4C(=O)[C@@H](NC(=O)c2c1ccccc1ccc2OCC)[C@H]4SC3(C)C ;
	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 ; Key:GPXLMGHLHQJAGZ-JTDSTZFVSA-N ;
(verify)

　　[★]

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

日本ではもう販売されていない。

[pmid7887701-1] 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.

[pmid1731755-2] 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.

[POC-IT-3] 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.

[4] 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.

[5] JA Mohr. (1979). Nafcillin-associated hypokalemia. JAMA

[pmid12814453-6] 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.

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案内

nafcillin sodium