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G1914

Sigma-Aldrich

Gentamicin sulfate

meets USP testing specifications, powder

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Synonym(s):
Gentamicin sulfate salt, Garamycin, Gentiomycin C
CAS Number:
EC Number:
MDL number:
eCl@ss:
42020823
PubChem Substance ID:
NACRES:
NA.76

biological source

Micromonospora purpurea

Quality Level

agency

USP/NF
meets USP testing specifications

form

powder

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria
mycoplasma

application(s)

pharmaceutical (small molecule)

mode of action

protein synthesis | interferes

storage temp.

2-8°C

SMILES string

O=S(O)(O)=O.O[C@]1(C)[C@@H]([C@@H](O)[C@@H](O[C@@H]2[C@@H](O)[C@H](O[C@H]3O[C@@](CC[C@H]3N)([C@@H](C)NC)[H])[C@@H](N)C[C@H]2N)OC1)NC.O[C@]4(C)[C@@H]([C@@H](O)[C@@H](O[C@@H]5[C@@H](O)[C@H](O[C@H]6O[C@@](CC[C@H]6N)([C@@H](C)N)[H])[C@@H](N)C[C@H]5N)OC4)NC.O[

InChI

1S/C21H43N5O7.C20H41N5O7.C19H39N5O7.H2O4S/c1-9(25-3)13-6-5-10(22)19(31-13)32-16-11(23)7-12(24)17(14(16)27)33-20-15(28)18(26-4)21(2,29)8-30-20;1-8(21)12-5-4-9(22)18(30-12)31-15-10(23)6-11(24)16(13(15)26)32-19-14(27)17(25-3)20(2,28)7-29-19;1-19(27)7-28-18(13(26)16(19)24-2)31-15-11(23)5-10(22)14(12(15)25)30-17-9(21)4-3-8(6-20)29-17;1-5(2,3)4/h9-20,25-29H,5-8,22-24H2,1-4H3;8-19,25-28H,4-7,21-24H2,1-3H3;8-18,24-27H,3-7,20-23H2,1-2H3;(H2,1,2,3,4)/t9-,10-,11+,12-,13+,14+,15-,16-,17+,18-,19-,20-,21+;8-,9-,10+,11-,12+,13+,14-,15-,16+,17-,18-,19-,20+;8-,9+,10-,11+,12-,13+,14+,15-,16+,17+,18+,19-;/m110./s1

InChI key

RDEIXVOBVLKYNT-HDZPSJEVSA-N

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General description

Chemical structure: aminoglycoside

Application

Gentamicin sulfate, a broad-spectrum antibiotic, used as a selection agent (gentamicin-resistance gene) in cell culture and molecular biology applications. This product is recommended for use at 50 mg/L.

Biochem/physiol Actions

Mode of action: Gentamicin causes codon misreading by binding to the 30S ribosomal subunit, blocking the translocation of peptidyl-tRNA from the acceptor site to the donor site. The bactericidal effect of gentamicin on Pseudomonas aeruginosa is exerted by the binding of gentamicin to the outer membrane, where it displaces natural cations, destabilizes the membrane, and forms holes in the cell surface.

Antimicrobial spectrum: Includes Gram-negative and Gram-positive bacteria, including strains resistant to tetracycline, chloramphenicol, kanamycin and colistin, particularly strains of Pseudomonas, Proteus, Staphylococcus and Streptococcus.

Components

Gentamicin is an aminoglycoside complex produced by fermentation of Micromonospora purpurea or M. echinospora. It is used as the sulfate salt. There are three components, each consisting of five basic nitrogens and requiresing five equivalents of sulfuric acid per mole of gentamicin base.

Caution

Sterile solutions should be stored at 2-8°C. Solutions have also been shown to be stable at room temperature and in boiling aqueous buffers of pH 2-142.

pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Skin Sens. 1

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves


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