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.^[1]^[2] It was discovered in 1957, along with Kanamycin A,^[3] though it was not identified and named until the next year, when it was studied independently.^[4] It was later found to be nearly identically efficacious as Kanamycin A, with the only limitation being lower efficacy towards Mycobacterium agents.^[5] Animal studies also showed that Bekanamycin was more toxic than Kanamycin A.^[6]

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.

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