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convert into a sulfate
a salt or ester of sulphuric acid (同)sulphate

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/06/19 13:41:19」(JST)

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Amikacin is an aminoglycoside antibiotic used to treat different types of bacterial infections. Amikacin works by binding to the bacterial 30S ribosomal subunit, causing misreading of mRNA and leaving the bacterium unable to synthesize proteins vital to its growth.

Medical uses[edit]

Amikacin is most often used for treating severe, hospital-acquired infections with multidrug resistant Gram negative bacteria such as Pseudomonas aeruginosa, Acinetobacter, and Enterobacter. Serratia marcescens and Providencia stuartii are also included in the spectrum. Amikacin can also be used to treat non tubercular mycobacterial infections and tuberculosis (if caused by sensitive strains) when first line drugs fail to control the infection.

Amikacin may be combined with a beta-lactam antibiotic for empiric therapy for people with neutropenia and fever.

Liposomal amikacin for inhalation is currently in late stage clinical trials for the treatment of respiratory diseases, such as cystic fibrosis,^[1] Pseudomonas aeruginosa,^[2] non tubercular mycobacterial infections^[3] and bronchiectasis.^[4]^[5]

Adverse effects[edit]

Side effects of amikacin are similar to other aminoglycosides. Kidney damage and hearing loss are the most important effects. Because of this potential, blood levels of the drug and markers of kidney function (creatinine) may be monitored. Moreover, doses are adjusted specifically based upon serum Creatinine clearance in clinical settings.^{[citation needed]}

Administration[edit]

Amikacin may be administered once or twice a day but must be given by the intravenous, via nebulization, or intramuscular route. There is no oral form available as amikacin is not absorbed orally. In people with kidney failure, dosage must be adjusted according to the creatinine clearance, usually by reducing the dosing frequency.

Resistance[edit]

Amikacin has high resistance against bacterial inactivation. It resists attacks by most bacterial inactivating enzymes, this is accomplished by the L-hydroxyaminobuteroyl amide (L-HABA) moiety attached to N-3 which inhibits acetylation, phosphorylation and adenylation in the distant amino sugar ring (C-2,C-3,C-4). To prevent the development of bacterial resistance to this extremely powerful antibiotic, its use is tightly regulated.

References[edit]

^ "Randomized, open-label, active-controlled, multicenter study to assess the efficacy, safety and tolerability of Arikace™ in Cystic Fibrosis patients with chronic infection due to Pseudomonas aeruginosa" is a European Phase III clinical trial, being conducted across multiple sites in the EU, starting at the Royal Brompton Hospital, Department of Respiratory Medicine, in London. https://www.clinicaltrialsregister.eu/ctr-search/trial/2011-000441-20/GB
^ http://www.clinicaltrials.gov/ct2/show/NCT01315678
^ "A Randomized, Double-Blind, Placebo-Controlled Study of Liposomal Amikacin for Inhalation (Arikace™) in Patients With Recalcitrant Nontuberculous Mycobacterial Lung Disease" is a Phase II clinical trial in collaboration with the US National Institute of Allergy and Infectious Diseases. http://www.clinicaltrials.gov/ct2/show/NCT01315236
^ "A Placebo Controlled, Randomized, Parallel Cohort, Safety And Tolerability Study Of 2 Dose Levels Of Liposomal Amikacin For Inhalation (Arikace™) In Patients With Bronchiectasis Complicated By Chronic Infection Due To Pseudomonas Aeruginosa" Phase II (completed). http://www.clinicaltrials.gov/ct2/show/NCT00775138
^ "A Study to Determine the Safety and Tolerability of Arikace™ Versus Placebo in Patients Who Have Bronchiectasis" is a Phase II clinical trial (as [4]) completed in the UK. http://www.ukctg.nihr.ac.uk/trialdetails/NCT00775138

Edson RS, Terrell CL. The aminoglycosides. Mayo Clin Proc. 1999 May;74(5):519-28. Review. PMID 10319086

UpToDate Contents

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1. アミノグリコシド（非経口）の用量および投与 dosing and administration of parenteral aminoglycosides
2. グラム陰性桿菌性髄膜炎：治療 gram negative bacillary meningitis treatment
3. アミノグリコシド aminoglycosides
4. HIV陰性患者における肺非結核性抗酸菌感染症の治療 treatment of nontuberculous mycobacterial infections of the lung in hiv negative patients
5. Diagnosis and treatment of extensively drug-resistant tuberculosis

English Journal

Spray dried amikacin powder for inhalation in cystic fibrosis patients: A quality by design approach for product construction.

Belotti S1, Rossi A1, Colombo P1, Bettini R1, Rekkas D2, Politis S2, Colombo G3, Balducci AG4, Buttini F5.
International journal of pharmaceutics.Int J Pharm.2014 Aug 25;471(1-2):507-15. doi: 10.1016/j.ijpharm.2014.05.055. Epub 2014 Jun 2.
An amikacin product for convenient and compliant inhalation in cystic fibrosis patients was constructed by spray-drying in order to produce powders of pure drug having high respirability and flowability. An experimental design was applied as a statistical tool for the characterization of amikacin sp
PMID 24886692

Blood Culture Isolates in Neonatal Sepsis and their Sensitivity in Anand District of India.

Patel D1, Nimbalkar A, Sethi A, Kungwani A, Nimbalkar S.
Indian journal of pediatrics.Indian J Pediatr.2014 Aug;81(8):785-90. doi: 10.1007/s12098-013-1314-2. Epub 2014 Jan 11.
OBJECTIVES: To study prevalent organisms in neonatal sepsis, their sensitivity to antibiotics and outcome in neonates with culture proven sepsis.METHODS: This was a retrospective study of hospital records of 4 y. From 276 culture positive reports of 226 newborns, organisms, their sensitivity to diff
PMID 24408399

Pyocyanin Stimulates Quorum Sensing-Mediated Tolerance to Oxidative Stress and Increases Persister Cell Populations in Acinetobacter baumannii.

Bhargava N1, Sharma P2, Capalash N3.
Infection and immunity.Infect Immun.2014 Aug;82(8):3417-25. doi: 10.1128/IAI.01600-14. Epub 2014 Jun 2.
Acinetobacter baumannii and Pseudomonas aeruginosa are nosocomial pathogens with overlapping sites of infection. This work reports that the two can coexist stably in mixed-culture biofilms. In a study intended to improve our understanding of the mechanism of their coexistence, it was found that pyoc
PMID 24891106

Japanese Journal

高齢者におけるアミカシン硫酸塩1日1回400mg投与法の有効性と安全性の検討

医薬品情報学 15(2), 51-56, 2013
NAID 130004551401

黄色ブドウ球菌による感染性心内膜炎と肺梗塞,感染性肺動脈瘤を併発した心室中隔欠損症(VSD)を有するDown症の1症例(東京女子医科大学東医療センター小児科開局40周年記念論文集)

東京女子医科大学雑誌 77(臨時増刊号), E103-E107, 2007-05-31
NAID 110007525363

好中球減少を伴う急性骨髄性白血病に合併した肺非定型抗酸菌症の1手術例

日本呼吸器外科学会雑誌 20(7), 933-937, 2006-11-15
NAID 110004862777

★リンクテーブル★

リンク元	「アミカシン」
関連記事	「sulfate」「sulfated」「sulfa」

「アミカシン」

Amikacin
Systematic (IUPAC) name
	(2S)-4-amino-N-[(2S,3S,4R,5S)-5-amino-2-; [(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-; 6-(hydroxymethyl)oxan-2-yl]oxy-4-[(2R,3R,; 4S,5R,6R)-6-(aminomethyl)-3,4,5-trihydroxy-; oxan-2-yl]oxy-3-hydroxy-cyclohexyl]-2-hydroxy-; butanamide
Clinical data
Trade names	Amikin
AHFS/Drugs.com	monograph
MedlinePlus	a682661
Pregnancy cat.	D (AU) C (US)
Legal status	POM (UK) ℞-only (US)
Routes	Intramuscular, intravenous
Pharmacokinetic data
Protein binding	0-11%
Half-life	2-3 hours
Excretion	Renal
Identifiers
CAS number	37517-28-5
ATC code	D06AX12 J01GB06, S01AA21
PubChem	CID 37768
DrugBank	DB00479
ChemSpider	34635
UNII	84319SGC3C
KEGG	D02543
ChEBI	CHEBI:2637
ChEMBL	CHEMBL177
Chemical data
Formula	C22H43N5O13
Mol. mass	585.603 g/mol
	SMILES O=C(N[C@H]3[C@H](O[C@H]1O[C@@H]([C@@H](O)[C@H](N)[C@H]1O)CO)[C@@H](O)[C@H](O[C@H]2O[C@H](CN)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](N)C3)[C@@H](O)CCN;
	InChI InChI=1S/C22H43N5O13/c23-2-1-8(29)20(36)27-7-3-6(25)18(39-22-16(34)15(33)13(31)9(4-24)37-22)17(35)19(7)40-21-14(32)11(26)12(30)10(5-28)38-21/h6-19,21-22,28-35H,1-5,23-26H2,(H,27,36)/t6-,7+,8-,9+,10+,11-,12+,13+,14+,15-,16+,17-,18+,19-,21+,22+/m0/s1 ; Key:LKCWBDHBTVXHDL-RMDFUYIESA-N ;
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