BEKANAMYCIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C18H37N5O10
Molecular Weight	483.5139
Optical Activity	UNSPECIFIED
Defined Stereocenters	15 / 15
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=SKKLOUVUUNMCJE-FQSMHNGLSA-N

InChI=1S/C18H37N5O10/c19-2-6-11(26)12(27)9(23)17(30-6)32-15-4(20)1-5(21)16(14(15)29)33-18-13(28)8(22)10(25)7(3-24)31-18/h4-18,24-29H,1-3,19-23H2/t4-,5+,6+,7+,8-,9+,10+,11+,12+,13+,14-,15+,16-,17+,18+/m0/s1

HIDE SMILES / InChI

Description
Sources: www.drugfuture.com/mt/bekanamycin-sulfate.pdf
Curator's Comment: description was created based on several sources, including: http://www.drugfuture.com/chemdata/Kanamycin.html https://farmaci.agenziafarmaco.gov.it/aifa/servlet/PdfDownloadServlet?pdfFileName=footer_000902_022729_FI.pdf&retry=0&sys=m0b1l3

Bekanamycin is an aminoglycoside and is a congener of kanamycin. It is given topically as the sulfate for the treatment of eye infections. It is reported to be more toxic than kanamycin A. Antibiotic complex produced by Streptomyces kanamyceticus Okami & Umezawa from Japanese soil. There are no known interactions with other drugs.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial 70S ribosome 179 Target ID: CHEMBL2363135 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11459219	Binding Agent 1064		180.0 nM [Kd]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bacterial eye infections 5 Sources: https://farmaci.agenziafarmaco.gov.it/aifa/servlet/PdfDownloadServlet?pdfFileName=footer_000902_022729_FI.pdf&retry=0&sys=m0b1l3	Curative		Approved 8429	Visucloben antibiotico Approved Use It is used in the treatment of eye infections.

PubMed

Title	Date	PubMed
[Comparative studies on the problem of nephrotoxicity of the aminoglycosides: kanamycin, amikacin, butirosin and kanendomycin].	1976	70900
[Experimental study on renal tolerability of aminoglycosides butirosin and bekanamycin (author's transl)].	1980	6155127
In vitro and in vivo susceptibility of atypical mycobacteria to various drugs.	1981 Sep-Oct	7339820
Small molecules that selectively block RNA binding of HIV-1 Rev protein inhibit Rev function and viral production.	1993 Sep 24	8402886
Antimycobacterial activity of phorbol esters from the fruits of Sapium indicum.	2003 Apr	12713411
In vitro and in vivo activities of ruthenium(II) phosphine/diimine/picolinate complexes (SCAR) against Mycobacterium tuberculosis.	2013	23724039

Patents

Sample Use Guides

In Vivo Use Guide

One drop 4 times per day

Route of Administration: Other

In Vitro Use Guide

B. subtilis 168 (strain I) and S. epidermidis ATCC 12228 (strain X) are both susceptible to Bekanamycin (MIC = 4 ug/mL and 0.5 ug/mL, respectively).

Name

Type

Language

BEKANAMYCIN

Official Name

English

Bekanamycin [WHO-DD]

Common Name

English

(1R,2S,3S,4R,6S)-4,6-DIAMINO-3-((3-AMINO-3-DEOXY-.ALPHA.-D-GLUCOPYRANOSYL)OXY)-2-HYDROXYCYCLOHEXYL 2,6-DIAMINO-2,6-DIDEOXY-.ALPHA.-D-GLUCOPYRANOSIDE

Common Name

English

KANAMYCIN B [MI]

Common Name

English

NK-1006

Code

English

KANAMYCIN B

Common Name

English

NK 1006

Code

English

bekanamycin [INN]

Common Name

English

AMINODEOXYKANAMYCIN

Common Name

English

NEBRAMYCIN V

Common Name

English

.ALPHA.-D-GLUCOPYRANOSIDE, (1R,2S,3S,4R,6S)-4,6-DIAMINO-3-((3-AMINO-3-DEOXY-.ALPHA.-D-GLUCOPYRANOSYL)OXY)-2-HYDROXYCYCLOHEXYL 2,6-DIAMINO-2,6-DIDEOXY-

Common Name

English

TOBRAMYCIN IMPURITY A [EP IMPURITY]

Common Name

English

ANTIBIOTIC DERIVED FROM STREPTOMYCES KANAMYCETICUS. KANAMYCIN B

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C2363