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27655

Sigma-Aldrich

Colistin sodium methanesulfonate

from Bacillus colistinus

Synonym(s):

Colimycin sodium methanesulfonate, Methanesulfonic acid derivative of Polymyxin E, Polymyxin E sodium methanesulfonate

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About This Item

Empirical Formula (Hill Notation):
C58H115N16Na5O28S5
CAS Number:
8068-28-8
Molecular Weight:
1759.90
EC Number:
232-516-9
MDL number:
MFCD00130824
UNSPSC Code:
51101500
PubChem Substance ID:
57648263
NACRES:
NA.85

biological source

Bacillus colistinus

Quality Level

200

form

powder or crystals

ign. residue

~20%

loss

≤5.0% loss on drying

color

white to off-white

pH

6.5-8.5

antibiotic activity spectrum

Gram-negative bacteria

mode of action

cell membrane | interferes

storage temp.

2-8°C

SMILES string

[Na+].[Na+].[Na+].[Na+].[Na+].CS([O-])(=O)=O.CS([O-])(=O)=O.CS([O-])(=O)=O.CS([O-])(=O)=O.CS([O-])(=O)=O.CCC(C)CCCCC(=O)N[C@@H](CCN)C(=O)N[C@@H](C(C)O)C(=O)N[C@@H](CCN)C(=O)N[C@H]1CCNC(=O)[C@@H](NC(=O)[C@H](CCN)NC(=O)[C@@H](CCN)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC(=O)[C@H](CCN)NC1=O)C(C)O

InChI

1S/C53H100N16O13.5CH4O3S.5Na/c1-9-30(6)12-10-11-13-41(72)60-33(14-20-54)48(77)69-43(32(8)71)53(82)65-36(17-23-57)45(74)64-38-19-25-59-52(81)42(31(7)70)68-49(78)37(18-24-58)62-44(73)34(15-21-55)63-50(79)39(26-28(2)3)67-51(80)40(27-29(4)5)66-46(75)35(16-22-56)61-47(38)76;5*1-5(2,3)4;;;;;/h28-40,42-43,70-71H,9-27,54-58H2,1-8H3,(H,59,81)(H,60,72)(H,61,76)(H,62,73)(H,63,79)(H,64,74)(H,65,82)(H,66,75)(H,67,80)(H,68,78)(H,69,77);5*1H3,(H,2,3,4);;;;;/q;;;;;;5*+1/p-5/t30?,31-,32-,33+,34-,35+,36+,37+,38+,39+,40-,42+,43+;;;;;;;;;;/m1........../s1

InChI key

WSDSONZFNWDYGZ-BKFDUBCBSA-I

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Related Categories

General description

Chemical structure: peptide

Application

Colistin sodium methanesulfate is used to permeabilize bacterial cell membranes and to study mannose-resistant haemagglutination.

Biochem/physiol Actions

Colistin sodium methanesulfate is a cyclopolypeptide antibiotic with endotoxin-binding capacity Colistin′s activity stems from the hydrophobic and hydrophillic regions. They solubilze the cytoplasmic membrane which contributes to the bactericidal effect .
Mode of Action: Binds to lipids on the cell cytoplasmic membrane of Gram-negative bacteria and disrupts the cell wall integrity.
Antimicrobial spectrum: Gram-negative bacteria.

Packaging

1g, 5g

Other Notes

Keep container tightly closed in a dry and well-ventilated place. Keep in a dry place. Keep in a dry place.

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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M.J. Rogers et al.
Infection (Munich), 14, 79-79 (1986)
Matthew E Falagas et al.
Expert review of anti-infective therapy, 6(5), 593-600 (2008-10-14)
Despite the constantly increasing need for new antimicrobial agents, antibiotic drug discovery and development seem to have greatly decelerated in recent years. Presented with the significant problem of advancing antimicrobial resistance, the global scientific community has attempted to find alternative
Roberto Imberti et al.
Chest, 138(6), 1333-1339 (2010-06-19)
Infections caused by multidrug-resistant gram-negative bacteria have caused a resurgence of interest in colistin. To date, information about pharmacokinetics of colistin is very limited in critically ill patients, and no attempts have been made to evaluate its concentration in BAL.
Kavi J Littlewood et al.
Journal of cystic fibrosis : official journal of the European Cystic Fibrosis Society, 11(5), 419-426 (2012-06-22)
Various inhaled antibiotics are currently used for treating chronic Pseudomonas aeruginosa lung infection in cystic fibrosis (CF) patients, however their relative efficacies are unclear. We compared the efficacy of the inhaled antibiotics tobramycin (TIP, TIS-T, TIS-B), colistimethate sodium (colistin) and
Roberto Imberti et al.
Antimicrobial agents and chemotherapy, 56(8), 4416-4421 (2012-06-13)
Intraventricular colistin, administered as colistin methanesulfonate (CMS), is the last resource for the treatment of central nervous system infections caused by panresistant Gram-negative bacteria. The doses and daily regimens vary considerably and are empirically chosen; the cerebrospinal fluid (CSF) pharmacokinetics
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