Spectinomycin

Structural formula
General
Surname	Spectinomycin
other names	4a, 7,9-Trihydroxy-2-methyl-6,8- bis (methylamino) decahydro-4 H -pyrano [2,3- b ] [1,4] benzodioxin-4-one; (1 R , 3 S , 5 R , 8 R , 10 R , 11 S , 12 S , 13 R , 14 S ) -8,12,14-trihydroxy-5-methyl-11,13-bis (methylamino) - 2,4,9-trioxatricyclo [8.4.0.0 3,8 ] tetradecan-7-one ( IUPAC ) ;
Molecular formula	C 14 H 24 N 2 O 7
External identifiers / databases
EC number	216-911-3
ECHA InfoCard	100.015.374
PubChem	15541
DrugBank	DB00919
Wikidata	Q416154
Drug information
ATC code	J01 XX04
Drug class	Antibiotic , aminoglycosides
properties
Molar mass	332.35 g · mol -1
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Spectinomycin is an aminoglycoside - antibiotic from Streptomyces ( Streptomyces spectabilis ).

mechanism

The biological activity of spectinomycin is based on the inhibition of protein synthesis on the ribosomes. It binds to the 30S ribosomal subunit and inhibits in bacteria , the protein biosynthesis . Spectinomycin works against gram-positive and gram-negative bacteria and is often used when penicillin-resistant germs are to be combated.

Mutations in the 16S rRNA and the S5 protein of the 30S ribosome subunit can lead to resistance to spectinomycin.

Applications

It is injected to treat gonorrhea , especially in people who are allergic to penicillin . It is also used in selection media in molecular biology.

Side effects

As side effects may itching , chills and rashes occur.

Individual evidence

↑ Template: CL Inventory / not harmonized There is not yet a harmonized classification for this substance . A labeling of spectinomycin in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), which was retrieved on July 12, 2020, is reproduced from a self-classification by the distributor .
↑ Wirmer, J. and Westhof, E. (2006): Molecular contacts between antibiotics and the 30S ribosomal particle . In: Methods Enzymol . 415 ; 180-202; PMID 17116475 ; doi: 10.1016 / S0076-6879 (06) 15012-0
↑ W. Scott Champney: Binding of spectinomycin by ribosomes from Escherichia coli . In: Current Microbiology . tape 21 , no. 4 , 1990, pp. 261-265 , doi : 10.1007 / BF02092166 .
↑ Kehrenberg, C. and Schwarz, S. (2007): Mutations in 16S rRNA and Ribosomal Protein S5 Associated with High-Level Spectinomycin Resistance in Pasteurella multocida . In: Antimicrob Agents Chemother . 51 ; 2244-2246; PMID 17371823 ; doi: 10.1128 / AAC.00229-07

[1] Template: CL Inventory / not harmonized There is not yet a harmonized classification for this substance . A labeling of spectinomycin in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), which was retrieved on July 12, 2020, is reproduced from a self-classification by the distributor .

[Wirmer-2] Wirmer, J. and Westhof, E. (2006): Molecular contacts between antibiotics and the 30S ribosomal particle . In: Methods Enzymol . 415 ; 180-202; PMID 17116475 ; doi: 10.1016 / S0076-6879 (06) 15012-0

[3] W. Scott Champney: Binding of spectinomycin by ribosomes from Escherichia coli . In: Current Microbiology . tape 21 , no. 4 , 1990, pp. 261-265 , doi : 10.1007 / BF02092166 .

[Kehrenberg-4] Kehrenberg, C. and Schwarz, S. (2007): Mutations in 16S rRNA and Ribosomal Protein S5 Associated with High-Level Spectinomycin Resistance in Pasteurella multocida . In: Antimicrob Agents Chemother . 51 ; 2244-2246; PMID 17371823 ; doi: 10.1128 / AAC.00229-07