Bekanamycin

Bekanamycin
Clinical data
AHFS/Drugs.com	International Drug Names
ATC code	J01GB13 (WHO) ;
Legal status
Legal status	In general: ℞ (Prescription only);
Identifiers
	IUPAC name (2S,3R,4S,5S,6R)-4-amino-2-{[(2S,3R,4S,6R)-4,6-diamino-3-{[(2R,3R,4R,5S,6R)-3-amino-6-(aminomethyl)-4,5-dihydroxyoxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-6-(hydroxymethyl)oxane-3,5-diol;
CAS Number	4696-76-8 ;
PubChem CID	439318;
ChemSpider	388449 ;
UNII	15JT14C3GI;
ChEBI	CHEBI:28098 ;
ChEMBL	ChEMBL176 ;
NIAID ChemDB	005087;
CompTox Dashboard (EPA)	DTXSID8023185 ;
ECHA InfoCard	100.022.881
Chemical and physical data
Formula	C18H37N5O10
Molar mass	483.519 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1[C@@H]([C@H]([C@@H]([C@H]([C@@H]1N)O[C@@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)N)O)O)O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CN)O)O)N)N;
	InChI 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 ; Key:SKKLOUVUUNMCJE-FQSMHNGLSA-N ;
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Bekanamycin (INN; kanamycin B) is an aminoglycoside antibiotic. It was discovered in 1957, along with Kanamycin A, though it was not identified and named until the next year, when it was studied independently. It was later found to be nearly identically efficacious as Kanamycin A, with the only limitation being lower efficacy towards Mycobacterium agents. Animal studies also showed that Bekanamycin was more toxic than Kanamycin A.

References

↑ Morales MA, Castrillon JL, Hernandez DA (1993). "Effects of bekanamycin and dibekacin on the electrical activity of cardiac pacemaker cells". Archives of Medical Research. 24 (4): 339–345. PMID 8118157.
↑ PubChem. "Bekanamycin". PubChem. Retrieved 2023-07-04.
↑ Umezawa H, Ueda M, Maeda K, Yagishita K, Kondo S, Okami Y, et al. (September 1957). "Production and isolation of a new antibiotic: kanamycin". The Journal of Antibiotics, Series A. 10 (5). Tokyo: 181–188. doi:10.11554/antibioticsa.10.5_181. PMID 13513509.
↑ Cron MJ, Johnson DL, Palermiti FM, Perron Y, Taylor HD, Whitehead DF, et al. (1958-02-01). "Kanamycin. I. Characterization and ACID Hydrolysis Studies". Journal of the American Chemical Society. 80 (3): 752–753. doi:10.1021/ja01536a058. ISSN 0002-7863.
↑ Wakazawa T, Sugano Y, Abe M, Fukatsu S, Shohei K (1961). "Studies on Kanamycin B. I Isolation of Kanamycin B and Its Chemical and Biological Properties". The Journal of Antibiotics, Series A. 14 (4): 180–186. doi:10.11554/antibioticsa.14.4_180.
↑ Finegold SM (July 1959). "Kanamycin". A.M.A. Archives of Internal Medicine. 104 (1): 15–28. doi:10.1001/archinte.1959.00270070017003. PMID 13660522.

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[1] Morales MA, Castrillon JL, Hernandez DA (1993). "Effects of bekanamycin and dibekacin on the electrical activity of cardiac pacemaker cells". Archives of Medical Research. 24 (4): 339–345. PMID 8118157.

[2] PubChem. "Bekanamycin". PubChem. Retrieved 2023-07-04.

[3] Umezawa H, Ueda M, Maeda K, Yagishita K, Kondo S, Okami Y, et al. (September 1957). "Production and isolation of a new antibiotic: kanamycin". The Journal of Antibiotics, Series A. 10 (5). Tokyo: 181–188. doi:10.11554/antibioticsa.10.5_181. PMID 13513509.

[4] Cron MJ, Johnson DL, Palermiti FM, Perron Y, Taylor HD, Whitehead DF, et al. (1958-02-01). "Kanamycin. I. Characterization and ACID Hydrolysis Studies". Journal of the American Chemical Society. 80 (3): 752–753. doi:10.1021/ja01536a058. ISSN 0002-7863.

[5] Wakazawa T, Sugano Y, Abe M, Fukatsu S, Shohei K (1961). "Studies on Kanamycin B. I Isolation of Kanamycin B and Its Chemical and Biological Properties". The Journal of Antibiotics, Series A. 14 (4): 180–186. doi:10.11554/antibioticsa.14.4_180.

[6] Finegold SM (July 1959). "Kanamycin". A.M.A. Archives of Internal Medicine. 104 (1): 15–28. doi:10.1001/archinte.1959.00270070017003. PMID 13660522.