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

NC[C@@H]1CC[C@@H](N)[C@@H](O[C@@H]2[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)O1

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

HIDE SMILES / InChI

Molecular Formula	C18H37N5O8
Molecular Weight	451.5151
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	13 / 13
E/Z Centers	0
Optical Activity	UNSPECIFIED

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 8583	DIBEKACIN MEIJI Approved Use Unknown

PubMed

Title	Date	PubMed
Perioperative antimicrobials in chest surgery patients positive for methicillin-resistant Staphylococcus aureus.	2010-12	21170640
[Evaluation of once a day of arbekacin administration to neonates as a new object of peak concentration].	2010-11	21226325
Cytotoxicity of five fluoroquinolone and two nonsteroidal anti-inflammatory benzalkonium chloride-free ophthalmic solutions in four corneoconjunctival cell lines.	2010-09-20	20922036
Mycobacterium abscessus corneal ulcer following sutured clear corneal cataract incision.	2010-09	21052916
Side effects of aminoglycosides on the kidney, ear and balance in cystic fibrosis.	2010-07	20627927
Biological activities of pargamicin A, a novel cyclic peptide antibiotic from Amycolatopsis sp.	2010-06	20339400
Pharmacokinetics and pharmacodynamics of once-daily arbekacin during continuous venovenous hemodiafiltration in critically ill patients.	2009-12	20012736
Characterization of beta-lactam antibiotic-induced vancomycin-resistant MRSA (BIVR) in a patient with septicemia during long-term vancomycin administration.	2009-10	19856063
Characterization of the enzyme aac(3)-Id in a clinical isolate of Salmonella enterica serovar Haifa causing traveler's diarrhea.	2009-10	19403206
Effect of PEGylation of N-WASP181-200 on the inhibitory potency for renal aminoglycoside accumulation.	2009-08-19	19572636
MRSA-pyomyositis in a patient with acute myelogenous leukemia after intensive chemotherapy.	2009-08	19661356
[Case with large abdominal abscess associated with a ventriculoperitoneal shunt].	2009-04	19364027
[Analysis of factors affecting long-term administration of anti-methicillin resistant Staphylococcus aureus (MRSA) drugs].	2009-03	19252392
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.	2008-10	18834367
[Appropriate use of anti-methicillin-resistant Staphylococcus aureus agents in a retrospective study].	2008-07	18591876
Evaluation of the clinical application of cystatin C, a new marker of the glomerular filtration rate, for the initial dose-setting of arbekacin.	2008-06	18452409
Population pharmacokinetics of arbekacin in burn patients.	2008-06	18320181
Influences of dosage regimen and co-administration of low-molecular weight proteins and basic peptides on renal accumulation of arbekacin in mice.	2008-03	18192282
[Analysis of factors in selecting anti-methicillin-resistant Staphylococcus aureus drugs by doctors].	2008-01	18176058
Prediction of aminoglycoside response against methicillin-resistant Staphylococcus aureus infection in burn patients by artificial neural network modeling.	2008-01	18083323
Microbiological and clinical study of methicillin-resistant Staphylococcus aureus (MRSA) carrying VraS mutation: changes in susceptibility to glycopeptides and clinical significance.	2008-01	18029148
Recovery of corneal thickness promoted by glucocorticoid administration after phacoemulsification in eyes affected by Fuchs' dystrophy.	2007-11-20	18773276
Effect of varying the 4''-position of arbekacin derivatives on antibacterial activity against MRSA and Pseudomonas aeruginosa.	2007-11-15	17889537
[In vitro activity of arbekacin against clinical isolates of Staphylococcus species and gram-negative bacilli].	2007-08	18094591
Synthesis and antibacterial activity of 5-deoxy-5-episubstituted arbekacin derivatives.	2007-07-01	17502146
[Appropriate usage of antibiotics by therapeutic drug monitoring].	2007-06	17541241
Experimental study of calcium phosphate cement impregnated with dideoxy-kanamycin B.	2007-05	17530381
16S rRNA methylase-producing, gram-negative pathogens, Japan.	2007-04	17553289
Trends in the gentamicin and arbekacin susceptibility of methicillin-resistant Staphylococcus aureus and the genes encoding aminoglycoside-modifying enzymes.	2007-04	17458673
[Appropriate use of anti-MRSA drugs (discussion)].	2007-02	17436859
Effect of ophthalmic solution components on acrylic intraocular lenses.	2007-01	17189806
Comparative evaluation of the in vitro antimycobacterial activities of six aminoglycoside antibiotics using an agar dilution method.	2006-12	17267338
[Comparative studies on activities of antimicrobial agents against causative organisms isolated from patients with urinary tract infections (2004). I. Susceptibility distribution].	2006-06	16913404
Development of immunoassays for the detection of kanamycin in veterinary fields.	2006-06	16645333
Trends of arbekacin-resistant MRSA strains in Japanese hospitals (1979 to 2000).	2006-04	16830890
Synergy of arbekacin-based combinations against vancomycin hetero-intermediate Staphylococcus aureus.	2006-04	16614499
Synergistic effect of [10]-gingerol and aminoglycosides against vancomycin-resistant enterococci (VRE).	2006-03	16508142
Surfactant induced glistenings: surface active ingredients in ophthalmic solutions may enhance water entry into the voids of implanted acrylic intraocular lenses.	2006	17956212
Factors influencing neonatal therapeutic effect of anti-MRSA drugs.	2005-07	16035373
Global spread of multiple aminoglycoside resistance genes.	2005-06	15963295
[Combination effect of pazufloxacin and anti-mrsa drugs against beta-lactam antibiotic induced vancomycin-resistant MRSA (BIVR)].	2005-02	15847221
Synergistic effect of fosfomycin and arbekacin on a methicillin-resistant Staphylococcus aureus-induced biofilm in a rat model.	2005-01	15620825
Detection of a novel aph(2") allele (aph[2"]-Ie) conferring high-level gentamicin resistance and a spectinomycin resistance gene ant(9)-Ia (aad 9) in clinical isolates of enterococci.	2005	16201926
Dosage regimen of arbekacin for methicillin-resistant Staphylococcus aureus infection in newborns and infants.	2004-12	15660861
Effect of arbekacin on a methicillin-resistant Staphylococcus aureus-induced biofilm in a rat model.	2004-10	16163460
Characterization of a bifunctional aminoglycoside-modifying enzyme with novel substrate specificity and its gene from a clinical isolate of methicillin-resistant Staphylococcus aureus with high arbekacin resistance.	2004-10	15638329
[Resistance of bacteria and antibiotic prescription in Fann University Teaching Hospital, Dakar].	2003	15776629
[An early and specific indicator of aminoglycoside nephrotoxicity: isoenzyme B of urinary N-acetyl-beta-D-glucosaminidase (NAG)].	1986-05	3534703
In vitro and in vivo susceptibility of atypical mycobacteria to various drugs.	1981-09-01	7339820
Combined effect of 3', 4'-dideoxykanamycin B and potent diuretics on the cochlea. (A scanning and transmission electron microscopic evaluation).	1977-09	895312

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).

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:18:28 GMT 2025` Edited by `admin` on `Mon Mar 31 18:18:28 GMT 2025`
Record UNII	45ZFO9E525
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DIBEKACIN [MI]

Preferred Name

English

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

Classification Tree Code System Code

WHO-ATC

J01GB09