DIBEKACIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C18H37N5O8
Molecular Weight	451.5151
Optical Activity	UNSPECIFIED
Defined Stereocenters	13 / 13
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]2(O[C@H]1O[C@H](CN)CC[C@H]1N)[C@@H](N)C[C@@H](N)[C@]([H])(O[C@H]3O[C@H](CO)[C@@H](O)[C@H](N)[C@H]3O)[C@H]2O

InChI

InChIKey=JJCQSGDBDPYCEO-XVZSLQNASA-N

InChI=1S/C18H37N5O8/c19-4-6-1-2-7(20)17(28-6)30-15-8(21)3-9(22)16(14(15)27)31-18-13(26)11(23)12(25)10(5-24)29-18/h6-18,24-27H,1-5,19-23H2/t6-,7+,8-,9+,10+,11-,12+,13+,14-,15+,16-,17+,18+/m0/s1

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Description
Sources: http://www.ncbi.nlm.nih.gov/pubmed/6376062

Dibekacin is a semisynthetic aminoglycoside antibiotic useful in the treatment of severe gram-negative bacterial infections. The drug is marketed in Japan.

Originator

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Infections 6 Sources: http://www.ncbi.nlm.nih.gov/pubmed/7289045	Curative		Approved 8429	DIBEKACIN MEIJI Approved Use Unknown

PubMed

Title	Date	PubMed
Neuromuscular blocking effects of the aminoglycoside antibiotics arbekacin, astromicin, isepamicin and netilmicin on the diaphragm and limb muscles in the rabbit.	2001	11598419
[Combination effect of arbekacin and cefepime on mixed culture of MRSA and P. aeruginosa].	2001 Feb	11338680
[Effect of arbekacin on the production of toxic shock syndrome toxin 1 by methicillin-resistant Staphylococcus aureus].	2001 Jul	11560056
In vitro antimicrobial activity of the aminoglycoside arbekacin tested against oxacillin-resistant Staphylococcus aureus isolated in Brazilian hospitals.	2001 Jun	11506776
[MRSA].	2001 Nov	11808124
Integration analysis of pSK41 in the chromosome of a methicillin-resistant Staphylococcus aureus K-1.	2002	12111746
Mechanical properties of the femur after injection of calcium phosphate cement containing arbekacin sulfate and polylactic acid in a rat model of experimental osteoporosis.	2002	12077664
[Survey of susceptibility of methicillin-resistant Staphylococcus aureus to antimicrobial agents in Hokusetsu General Hospital].	2002 Dec	12621730
[Arbekacin resistant gene, aacA/aphD, in Staphylococcus aureus is lost during in vitro passage].	2002 Jan	11871141
[Antibacterial activities and PK/PD parameters of aminoglycosides against recent clinical isolates of gram-negative rods].	2002 Oct	12532635
Methicillin-resistant Staphylococcus aureus and methicillin-resistant Staphylococcus epidermidis infections in the cornea.	2002 Oct	12484707
Contact dermatitis from arbekacin sulfate: report of a case.	2002 Oct	12433003
Treatment outcome of two-stage revision total hip arthroplasty for infected hip arthroplasty using antibiotic-impregnated cement spacer.	2003	12560882
Pharmacokinetics and dosing of arbekacin in preterm and term newborn infants.	2003 Apr	12709144
[Relationship between arbekacin-susceptibility and aminoglycoside-resistant gene of methicillin-resistant Staphylococcus aureus (MRSA)].	2003 Feb	12723397
[Pulsed-field gel electrophoresis type and antimicrobial susceptibility of arbekacin mupirocin and teicoplanin resistant methicillin-resistant Staphylococcus aureus].	2003 Feb	12661081
Efficacy and safety of arbekacin for staphylococcal infection in the NICU.	2003 Jun	12828585
Arbekacin is actively secreted in the rat intestine via a different efflux system from P-glycoprotein.	2003 Jun	12791416
[Epidemiological study of Arbekacin-resistant, methicillin resistant Staphylococcus aureus in Saitama Medical School Hospital].	2004 Apr	15176234
Dosage regimen of arbekacin for methicillin-resistant Staphylococcus aureus infection in newborns and infants.	2004 Dec	15660861
Artificial neural network modeling to predict the plasma concentration of aminoglycosides in burn patients.	2004 May	15183849
Clinical glycopeptide-intermediate staphylococci tested against arbekacin, daptomycin, and tigecycline.	2004 Oct	15474322
[Combination effect of pazufloxacin and anti-mrsa drugs against beta-lactam antibiotic induced vancomycin-resistant MRSA (BIVR)].	2005 Feb	15847221
Synergistic effect of fosfomycin and arbekacin on a methicillin-resistant Staphylococcus aureus-induced biofilm in a rat model.	2005 Jan	15620825
Comparative evaluation of the in vitro antimycobacterial activities of six aminoglycoside antibiotics using an agar dilution method.	2006 Dec	17267338
16S rRNA methylase-producing, gram-negative pathogens, Japan.	2007 Apr	17553289
Trends in the gentamicin and arbekacin susceptibility of methicillin-resistant Staphylococcus aureus and the genes encoding aminoglycoside-modifying enzymes.	2007 Apr	17458673
[In vitro activity of arbekacin against clinical isolates of Staphylococcus species and gram-negative bacilli].	2007 Aug	18094591
[Appropriate use of anti-MRSA drugs (discussion)].	2007 Feb	17436859
Effect of ophthalmic solution components on acrylic intraocular lenses.	2007 Jan	17189806
[Appropriate usage of antibiotics by therapeutic drug monitoring].	2007 Jun	17541241
Experimental study of calcium phosphate cement impregnated with dideoxy-kanamycin B.	2007 May	17530381
Prediction of aminoglycoside response against methicillin-resistant Staphylococcus aureus infection in burn patients by artificial neural network modeling.	2008 Jan	18083323
Influences of dosage regimen and co-administration of low-molecular weight proteins and basic peptides on renal accumulation of arbekacin in mice.	2008 Mar	18192282
Recommended dose of arbekacin, an aminoglycoside against methicillin-resistant Staphylococcus aureus, does not achieve desired serum concentration in critically ill patients with lowered creatinine clearance.	2008 Oct	18834367
MRSA-pyomyositis in a patient with acute myelogenous leukemia after intensive chemotherapy.	2009 Aug	19661356
Effect of PEGylation of N-WASP181-200 on the inhibitory potency for renal aminoglycoside accumulation.	2009 Aug 19	19572636
Pharmacokinetics and pharmacodynamics of once-daily arbekacin during continuous venovenous hemodiafiltration in critically ill patients.	2009 Dec	20012736
[Analysis of factors affecting long-term administration of anti-methicillin resistant Staphylococcus aureus (MRSA) drugs].	2009 Mar	19252392
Characterization of the enzyme aac(3)-Id in a clinical isolate of Salmonella enterica serovar Haifa causing traveler's diarrhea.	2009 Oct	19403206
Biological activities of pargamicin A, a novel cyclic peptide antibiotic from Amycolatopsis sp.	2010 Jun	20339400

Patents

Sample Use Guides

In Vivo Use Guide

3 mg/kg/day in two intramuscular doses for ten days or 100 mg administered by intravenous drip infusion for 2 hours, twice in a day for 3 - 10 days.

Route of Administration: Other

In Vitro Use Guide

Minimum inhibitory concentrations of Dibekacin were tested against such strains as: S. aureus (max 0.78 mcg/ml), S. epidermidis (0.78 mcg/ml), Micrococcus flavus and Micrococcus luteus (6.25 mcg/ml), Bacillus anthracis (0.39 mcg/ml), B. subtilis (< 0.2 mcg/ml), B. cereus (1.56 mcg/ml), E. coli (0.2 - 100 mcg/ml), Pseudomonas aeruginosa (< 0.2 mcg/ml), P. aeruginosa (1.56 - 100 mcg/ml), Serratia sp. 4 (0.78 mcg/ml), Klebsiella pneumoniae PCI602 (0.39 mcg/ml).

Name

Type

Language

DIBEKACIN

Official Name

English

O-3-AMINO-3-DEOXY-.ALPHA.-D-GLUCOPYRANOSYL-(1->4)-O-(2,6-DIAMINO-2,3,4,6-TETRADEOXY-.ALPHA.-D-ERYTHRO-HEXOPYRANOSYL-(1->6))-2-DEOXY-L-STREPTAMINE

Common Name

English

DIBEKACIN [JAN]

Common Name

English

dibekacin [INN]

Common Name

English

Dibekacin [WHO-DD]

Common Name

English

DIBEKACIN [MI]

Common Name

English

Classification Tree Code System Code

WHO-ATC

J01GB09