Gentamicin
Title: Gentamicin
CAS Registry Number: 1403-66-3
CAS Name: Gentamycin
Literature References: Antibiotic complex produced by fermentation of Micromonospora purpurea or M. echinospora and variants thereof: M. J. Weinstein et al., Antimicrob. Agents Chemother. 1963, 1. Isoln, purification and characterization: J. P. Rosselet et al., ibid. 14. Industrial pats.: G. M. Luedemann, M. J. Weinstein; Charney, US 3091572; US 3136704 (1963, 1964, both to Schering). Consists of three closely related components, gentamicins C1, C2, C1a, and also gentamicin A which differs from the other members of the complex but is similar to kanamycin C, q.v. Separation of gentamicin C components: H. Maehr, C. P. Schaffner, J. Chromatogr. 30, 572 (1967); Wagman et al., ibid. 34, 210 (1968). Structures contain 2-deoxystreptamine, q.v., linked to two saccharide units, these being garosamine and a purpurosamine in the C series gentamicins. Structure studies: D. J. Cooper et al., J. Chem. Soc. C 1971, 960, 2876, 3126. Structure of gentamicin A: H. Maehr, C. P. Schaffner, J. Am. Chem. Soc. 89, 6787 (1967); 92 1697 (1969). Sepn and structures of gentamicins A1 to A4: Nagabhushan et al., J. Org. Chem. 40, 2830, 2835 (1975). Synthetic studies: W. Meyer zu Reckendorf, Bischof, Ber. 105, 2546 (1972); M. Chmielewski et al., Carbohydr. Res. 70, 275 (1979). Review of activity, toxicity and clinical pharmacology: J. Black et al., Antimicrob. Agents Chemother. 1963, 138-147. Comprehensive description: B. E. Rosenkrantz et al., Anal. Profiles Drug Subs. 9, 295-340 (1980). Determn in serum by immunoassay: H. A. Holt et al., J. Antimicrob. Chemother. 34, 747 (1994). Review of clinical use: S. B. Shrimpton et al., ibid. 31, 599-606 (1993). Clinical effect on chloride transport in cystic fibrosis: M. Wilschanski et al., Am. J. Respir. Crit. Care Med. 161, 860 (2000).
Properties: White amorphous powder, mp 102-108°. [a]D25 +146°. Freely sol in water; sol in pyridine, DMF, in acidic media with salt formation; moderately sol in methanol, ethanol, acetone. Practically insol in benzene, halogenated hydrocarbons.
Melting point: mp 102-108°
Optical Rotation: [a]D25 +146°
 
Derivative Type: Gentamicin C1
CAS Registry Number: 25876-10-2
Molecular Formula: C21H43N5O7
Molecular Weight: 477.60
Percent Composition: C 52.81%, H 9.07%, N 14.66%, O 23.45%
Properties: mp 94-100°. [a]D25 +158°.
Melting point: mp 94-100°
Optical Rotation: [a]D25 +158°
 
Derivative Type: Gentamicin C2
CAS Registry Number: 25876-11-3
Molecular Formula: C20H41N5O7
Molecular Weight: 463.57
Percent Composition: C 51.82%, H 8.91%, N 15.11%, O 24.16%
Properties: mp 107-124°. [a]D25 +160°.
Melting point: mp 107-124°
Optical Rotation: [a]D25 +160°
 
Derivative Type: Gentamicin C1a
CAS Registry Number: 26098-04-4
CAS Name: O-3-Deoxy-4-C-methyl-3-(methylamino)-b-L-arabinopyranosyl-(1®6)-O-[2,6-diamino-2,3,4,6-tetradeoxy-a-D-erythro-hexopyranosyl-(1®4)]-2-deoxy-D-streptamine
Additional Names: gentamicin D
Molecular Formula: C19H39N5O7
Molecular Weight: 449.54
Percent Composition: C 50.76%, H 8.74%, N 15.58%, O 24.91%
 
Derivative Type: Gentamicin A
CAS Registry Number: 13291-74-2
CAS Name: O-2-Amino-2-deoxy-a-D-glucopyranosyl-(1®4)-O-[3-deoxy-3-(methylamino)-a-D-xylopyranosyl-(1®6)]-2-deoxy-D-streptamine
Molecular Formula: C18H36N4O10
Molecular Weight: 468.50
Percent Composition: C 46.15%, H 7.75%, N 11.96%, O 34.15%
 
Derivative Type: Hydrochloride
Properties: mp 194-209°. [a]D25 +113°. Freely sol in water, methanol; slightly in ether. Practically insol in other organic solvents.
Melting point: mp 194-209°
Optical Rotation: [a]D25 +113°
 
Derivative Type: C complex sulfate
CAS Registry Number: 1405-41-0
Trademarks: Alcomicin (Alcon); Cidomycin (Aventis); Duragentam (Merck KGaA); Garamycin (Schering-Plough); Garasol (Schering-Plough); Genoptic (Allergan); Gentacin (Schering-Plough); Gent-Ak (Akorn); Gentalline (Schering-Plough); Gentalyn (Essex); Gentibioptal (Farmila); Genticin (Roche); Gentocin (Schering-Plough); Gentogram (Merck-Sante); Gent-Ophtal (Winzer); Lugacin (Sandoz); Ophtagram (Chauvin); Pangram (Virbac); Refobacin (Merck KGaA); Septopal (Merck KGaA); Sulmycin (Essex)
Properties: White, hygroscopic powder, mp 218-237°. [a]D25 +102°. Sol in ethylene glycol, formamide. LD50 in mice (mg base/kg): 430 i.p.; 485 s.c.; 75 i.v.; >9050 orally (Black).
Melting point: mp 218-237°
Optical Rotation: [a]D25 +102°
Toxicity data: LD50 in mice (mg base/kg): 430 i.p.; 485 s.c.; 75 i.v.; >9050 orally (Black)
 
Therap-Cat: Antibacterial.
Therap-Cat-Vet: Antibacterial.
Keywords: Antibacterial (Antibiotics); Aminoglycosides.

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