Laboratory Synthesis Of Amikacin

Amikacin IUPAC Chemical Name: (S)- O- 3- amino- 3- deoxy- a- D- gluco pyranosyl- (1 ®6)- O- [6- amino- 6- deoxy- a- D- glucopyranosyl- (1 ®4 )]-N 1- (4- amino- 2- hydroxy- 1- oxo butyl)- 2- deoxy- D- strept amine
Amikacin Use: aminoglycoside antibiotic
Amikacin MW: 585.61
MF: C22H43N5O13
Amikacin LD50: 280 mg/kg (M, i.v.); >6 g/kg (M, p.o.)
Reference(s):
DE 2 234 315 (Bristol-Myers; appl. 12.7.1972; USA-prior. 27.1.1972, 13.7.1971).
US 3 781 268 (Bristol-Myers; 25.12.1973; prior. 27.1.1972, 13.7.1971).
Kawaguchi, H. et al.: J. Antibiot. (JANTAJ) 25, 695 (1972). 
Alternative syntheses:

1. NL 7 401 517 (Bristol-Myers; appl. 4.2.1974; USA-prior. 7.2.1973).
2. NL 7 414 668 (Bristol-Myers; appl. 11.11.1974; USA-prior. 14.11.1973, 23.5.1974).
3. US 3 974 137 (Bristol-Myers; 10.8.1976; prior. 23.5.1974).
4. DOS 2 432 644 (Takeda; appl. 8.7.1974; J-prior. 12.7.1973).
5. DOS 2 716 533 (Pfizer; appl. 14.4.1977; GB-prior. 14.4.1976).
6. DOS 2 818 822 (Bristol-Myers; appl. 28.4.1978; USA-prior. 28.4.1977, 20.3.1978).
7. DOS 2 818 992 (Bristol-Myers; appl. 28.4.1978; USA-prior. 28.4.1977; 20.3.1978).

Disulfate pentahydrate:

1. FR 2 308 373 (Bristol-Myers; appl. 22.3.1976; USA-prior. 23.4.1975). 

Amikacin Review:

1. Kawaguchi, H.; Hiroshi: Drug Action Drug Resist. Bact. (DADRBY) 2, 45 (1975).

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