Gentamicins

The gentamicins are a group of structurally very closely related aminoglycoside compounds . Under the generic name gentamicin , a type mixture produced by fermentation is used as a medicinal substance against bacterial infections.

history

The first gentamicins were discovered in 1963 by employees of Schering in New Jersey in the products of the bacterial strain Micromonospora purpurea . The spelling with an " i " is derived from the bacterial origin (M i cromonospora) . Aminoglycoside antibiotics derived from Streptom y ces species, on the other hand, are written with “ y ” (for example Tobram y cin or Streptom y cin ).

Structures and properties

The gentamicins are made up of three hexosamines . These are (see figures, from left to right) gentosamine / garosamine , 2-deoxystreptamine and purpurosamine .

Gentamicins
Name (s)	structure	CAS - number	PubChem	Molecular formula	Molar mass
Gentamicin A		13291-74-2	86474	C 18 H 36 N 4 O 10	468.50 g mol −1
Gentamicin A 1
Gentamicin A 2		55715-66-7	86489	C 17 H 33 N 3 O 11	455.46 g mol −1
Gentamicin A 3		55715-67-8	86490	C 18 H 36 N 4 O 10	468.50 g mol −1
Gentamicin A 4
Gentamicin B Betamicin		36889-15-3	37569	C 19 H 38 N 4 O 10	482.53 g mol −1
Gentamicin B 1		36889-16-4	3034288	C 20 H 40 N 4 O 10	496.55 g mol −1
Gentamicin C 1		25876-10-2	441305	C 21 H 43 N 5 O 7	477.59 g mol −1
Gentamicin C 1a		26098-04-4	72396	C 19 H 39 N 5 O 7	449.54 g mol −1
Gentamicin C 2		25876-11-3	72397	C 20 H 41 N 5 O 7	463.57 g mol −1
Gentamicin C 2a		59751-72-3		C 20 H 41 N 5 O 7	463.57 g mol −1
Gentamicin C 2b Micronomicin		52093-21-7	107677	C 20 H 41 N 5 O 7	463.57 g mol −1

The kanamycins and tobramycin also have similar structures . In sisomicin is 4.5 Dehydrogentamicin-C _1a .

Individual evidence

1. ^ Gentamicin . In: Br Med J . 1, No. 5533, January 1967, pp. 158-9. PMID 6015651 . PMC 1840594 (free full text).
2. ↑ Ingo Stock: Bacteria Viruses Active Ingredients . Govi-Verlag, 2009, ISBN 9783774111042 .
3. ↑ Benveniste R, Davies J: Structure-activity relationships among the aminoglycoside antibiotics: role of hydroxyl and amino groups . In: Antimicrob. Agents Chemother. . 4, No. 4, October 1973, pp. 402-9. PMID 4598613 . PMC 444567 (free full text).
4. ↑ Vastola AP Altschaefl J, Harford S: 5-epi-sisomicin and 5-epi-gentamicin B: substrate for aminoglycoside-modifying enzymes did retain activity against aminoglycoside-resistant bacteria . In: Antimicrob. Agents Chemother. . 17, No. 5, May 1980, pp. 798-802. PMID 6967296 . PMC 283878 (free full text).