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Colistin Sulfate

CAS# 1264-72-8

Colistin Sulfate

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Chemical structure

Colistin Sulfate

3D structure

Chemical Properties of Colistin Sulfate

Cas No. 1264-72-8 SDF Download SDF
PubChem ID 91885449 Appearance Powder
Formula C52H100N16O17S M.Wt 1253.5
Type of Compound N/A Storage Desiccate at -20°C
Synonyms AOB5071; HY-A0089; Q-200889;
Solubility H2O : ≥ 32 mg/mL (25.53 mM)
*"≥" means soluble, but saturation unknown.
Chemical Name N-[(2S)-4-amino-1-[[(2S,3R)-1-[[(2S)-4-amino-1-oxo-1-[[(3S,6S,9S,12S,15R,18S,21S)-6,9,18-tris(2-aminoethyl)-3-[(1R)-1-hydroxyethyl]-12,15-bis(2-methylpropyl)-2,5,8,11,14,17,20-heptaoxo-1,4,7,10,13,16,19-heptazacyclotricos-21-yl]amino]butan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-1-oxobutan-2-yl]-5-methylheptanamide;sulfuric acid
SMILES CCC(C)CCCC(=O)NC(CCN)C(=O)NC(C(C)O)C(=O)NC(CCN)C(=O)NC1CCNC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC1=O)CCN)CC(C)C)CC(C)C)CCN)CCN)C(C)O.OS(=O)(=O)O
Standard InChIKey VEXVWZFRWNZWJX-NBKAJXASSA-N
Standard InChI InChI=1S/C52H98N16O13.H2O4S/c1-9-29(6)11-10-12-40(71)59-32(13-19-53)47(76)68-42(31(8)70)52(81)64-35(16-22-56)44(73)63-37-18-24-58-51(80)41(30(7)69)67-48(77)36(17-23-57)61-43(72)33(14-20-54)62-49(78)38(25-27(2)3)66-50(79)39(26-28(4)5)65-45(74)34(15-21-55)60-46(37)75;1-5(2,3)4/h27-39,41-42,69-70H,9-26,53-57H2,1-8H3,(H,58,80)(H,59,71)(H,60,75)(H,61,72)(H,62,78)(H,63,73)(H,64,81)(H,65,74)(H,66,79)(H,67,77)(H,68,76);(H2,1,2,3,4)/t29?,30-,31-,32+,33+,34+,35+,36+,37+,38+,39-,41+,42+;/m1./s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Colistin Sulfate

DescriptionColistin, a polypeptide antibiotic, is bactericidal to gram-negative bacteria by interfering with the structure and function of the outer and cytoplasmic membranes of bacteria.In Vitro:Colistins are bactericidal to gram-negative bacteria by a detergent-like mechanism. This mechanism involves interaction with lipopolysaccharides and phospholipids of the outer membrane and electrostatic interference with the outer membrane by competitively displacing divalent cations (calcium and magnesium) from the negatively charged phosphate groups of membrane lipids[1]. Colistin (polymyxin E) owns favorable properties of rapid bacterial killing, a narrow spectrum of activity, and an associated slow development of resistance for the treatment of infections caused by multidrug-resistant gram-negative bacteria. There are two forms of colistin available commercially: colistin (sulfate) mainly for topical use and colistin methanesulfonate (sodium) for parenteral use[2].In Vivo:High concentrations of colistin in rat ELF are achieved as a result of slow and sustained CMS conversion following i.t. instillation[3]. Colistin is often used in piglets but underdosing and overdosing are frequent. Under- or overdoses of colistin do not result in any major disturbance of piglet fecal microbiota and rarely select for chromosomal resistance in the dominant E. coli population[4].

References:
[1]. Hancock RE et al. Peptide antibiotics. Antimicrob Agents Chemother. 1999 Jun;43(6):1317-23. [2]. Li J, et al. In vitro pharmacodynamic properties of colistin and colistin methanesulfonate againstPseudomonas aeruginosa isolates from patients with cystic fibrosis. Antimicrob Agents Chemother. 2001 Mar;45(3):781-5. [3]. W S Yapa S, et al. Population pharmacokinetics of colistin methanesulfonate in rats: achieving sustained lung concentrations of colistin for targeting respiratory infections. Antimicrob Agents Chemother. 2013 Oct;57(10):5087-95. [4]. Fleury MA, et al. Impact of two different colistin dosing strategies on healthy piglet fecal microbiota. Res Vet Sci. 2016 Aug;107:152-60.

Protocol

Animal Administration [3]
Rats: Colistin methanesulfonate (sodium) and colistin (sulfate) dosing solutions are freshly prepared in sterile 0.9% sodium chloride. For the i.v. studies, colistin methanesulfonate (CMS) or sulfate solutions are administered by a bolus injection via the jugular vein cannula. Intratracheal (i.t.) instillation is utilized as the technique for pulmonary administration. Animals are administered i.v. CMS at doses of 14 mg/kg of body weight, 28 mg/kg or 56 mg/kg. In an independent study, rats are administered i.v. colistin at doses of 0.21 mg/kg, 0.41 mg/kg, or 0.62 mg/kg[3].

References:
[1]. Hancock RE et al. Peptide antibiotics. Antimicrob Agents Chemother. 1999 Jun;43(6):1317-23. [2]. Li J, et al. In vitro pharmacodynamic properties of colistin and colistin methanesulfonate againstPseudomonas aeruginosa isolates from patients with cystic fibrosis. Antimicrob Agents Chemother. 2001 Mar;45(3):781-5. [3]. W S Yapa S, et al. Population pharmacokinetics of colistin methanesulfonate in rats: achieving sustained lung concentrations of colistin for targeting respiratory infections. Antimicrob Agents Chemother. 2013 Oct;57(10):5087-95. [4]. Fleury MA, et al. Impact of two different colistin dosing strategies on healthy piglet fecal microbiota. Res Vet Sci. 2016 Aug;107:152-60.

Colistin Sulfate Dilution Calculator

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Colistin Sulfate Molarity Calculator

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Preparing Stock Solutions of Colistin Sulfate

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 0.7978 mL 3.9888 mL 7.9777 mL 15.9553 mL 19.9442 mL
5 mM 0.1596 mL 0.7978 mL 1.5955 mL 3.1911 mL 3.9888 mL
10 mM 0.0798 mL 0.3989 mL 0.7978 mL 1.5955 mL 1.9944 mL
50 mM 0.016 mL 0.0798 mL 0.1596 mL 0.3191 mL 0.3989 mL
100 mM 0.008 mL 0.0399 mL 0.0798 mL 0.1596 mL 0.1994 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Colistin Sulfate

Colistin is a cyclic cationic decapeptide linked to a fatty acid side chain, it belongs to a group of similarly structured bacterial antimicrobial peptides.

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References on Colistin Sulfate

Killing effect of nanoencapsulated colistin sulfate on Pseudomonas aeruginosa from cystic fibrosis patients.[Pubmed:26708265]

J Cyst Fibros. 2016 Sep;15(5):611-8.

Pseudomonas aeruginosa frequently infects the respiratory tract of cystic fibrosis (CF) patients. Multidrug-resistant phenotypes and high capacity to form stable biofilms are common. Recent studies have described the emergence of colistin-resistant isolates in CF patients treated with long-term inhaled colistin. The use of nanoparticles containing antimicrobials can contribute to overcome drug resistance mechanisms. The aim of this study was to explore antimicrobial activity of nanoencapsulated colistin (SLN-NLC) versus free colistin against P. aeruginosa clinical isolates from CF patients and to investigate their efficacy in biofilm eradication. Susceptibility of planktonic bacteria to antimicrobials was examined by using the broth microdilution method and growth curve assay. Minimal biofilm eradication concentration (MBEC) and biofilm prevention concentration (BPC) were determined to assess antimicrobial susceptibility of sessile bacteria. We used atomic force microscopy (AFM) to visualize treated and untreated biofilms and to determine surface roughness and other relevant parameters. Colistin nanoparticles had the same antimicrobial activity as free drug against planktonic bacteria. However, nanoencapsulated colistin was much more efficient in the eradication of biofilms than free colistin. Thus, these formulations have to be considered as a good alternative therapeutic option to treat P. aeruginosa infections.

In vivo therapeutic efficacy and pharmacokinetics of colistin sulfate in an experimental model of enterotoxigenic Escherichia coli infection in weaned pigs.[Pubmed:27234971]

Vet Res. 2016 May 27;47(1):58.

Enterotoxigenic Escherichia coli (ETEC: F4) associated with post-weaning diarrhea (PWD) in pigs has developed resistance against several antimicrobial families, leading to increased use of Colistin Sulfate (CS) for the treatment of this disease. The objective of this study was to determine the efficacy of oral CS treatment in experimental PWD due to ETEC: F4 challenge and determine the effect of this challenge on CS intestinal absorption. In this study, 96 pigs were divided into two trials based on CS dose (100 000 or 50 000 IU/kg). Fecal shedding of ETEC: F4, total E. coli, and CS-resistant E. coli, diarrhea scores, and weight changes were evaluated. Colistin Sulfate plasma concentrations were determined by HPLC-MS/MS. Regardless of the dose, CS treatment resulted in a reduction of fecal ETEC: F4 and total E. coli shedding, and in diarrhea scores but only during the treatment period. However, CS treatment resulted in a slight increase in fecal shedding of CS resistant E. coli and did not prevent weight loss in challenged pigs. In addition, challenge with ETEC: F4 resulted in an increase of CS intestinal absorption. Our study is among the first to demonstrate that under controlled conditions, CS was effective in reducing fecal shedding of ETEC: F4 and total E. coli in experimental PWD. However, CS treatment was associated with a slight selection pressure on E. coli and did not prevent pig weight loss. Further studies are needed in field conditions, to better characterize CS therapeutic regimen efficacy and bacterial resistance dissemination.

The fecal presence of enterotoxin and F4 genes as an indicator of efficacy of treatment with colistin sulfate in pigs.[Pubmed:28056796]

BMC Microbiol. 2017 Jan 5;17(1):6.

BACKGROUND: Enterotoxigenic Escherichia coli (ETEC) strains producing multiple enterotoxins are important causes of post-weaning diarrhea (PWD) in pigs. The aim of the present study was to investigate the fecal presence of ETEC enterotoxin as well as F4 and F18 genes as an indicator of Colistin Sulfate (CS) efficacy for treatment of PWD in pigs. Forty-eight piglets were weaned at the age of 21 days, and were divided into four groups: challenged treated, challenged untreated, unchallenged treated, and unchallenged untreated. Challenge was performed using 10(9) CFU of an ETEC: F4 strain, and treatment was conducted using oral CS at the dose of 50,000 IU/kg. The fecal presence of genes encoding for STa, STb, LT, F4 and F18 was detected using PCR. RESULTS: The PCR amplification of ETEC virulence genes showed that nearly 100% of pigs excreted genes encoding for STa and STb toxins in the feces before the challenge. These genes, in the absence of the gene encoding F4, were considered as a marker for F4-negative ETEC. One day after ETEC: F4 oral challenge pigs in the two challenged groups excreted the genes encoding LT and F4 in the feces. These genes were considered as a marker for F4-positive ETEC. However, the gene encoding F18 was not detected in any fecal samples of the 4 groups throughout the experiment. After only 3 days of successive oral treatment with CS, a significant reduction in both the F4-positive and negative ETEC populations was observed in the challenged treated group compared to the challenged untreated group (p < 0.0001). CONCLUSIONS: Our study is among the first to report that under controlled farming conditions, oral CS treatment had a significant effect on both fecal F4-positive and F4-negative ETEC in pigs. However, CS clinical efficiency was correlated with non-detection of F4-positive ETEC in the feces. Furthermore the fecal presence of F4-negative ETEC was not associated with clinical symptoms of post-weaning diarrhea in pigs.

In vitro and in silico characterization of fibrous scaffolds comprising alternate colistin sulfate-loaded and heat-treated polyvinyl alcohol nanofibrous sheets.[Pubmed:28341150]

Int J Pharm. 2017 May 15;523(1):151-158.

A multilayer mat for dispensing Colistin Sulfate through a body surface was prepared by electrospinning. The fabricated system comprised various polyvinyl alcohol fibrous layers prepared with or without the active ingredient. One of the electrospun layers contained water-soluble Colistin Sulfate and the other was prepared from the same polymer type and composition without the active drug and was finally heat-treated. The heat treatment modified the supramolecular structure and conferred the polymer nanofibre with the rate-controlling function. The microstructure of different layers was tracked by positron annihilation lifetime spectroscopy, and detailed morphological analysis of the fibre mats was performed using a scanning electron microscope. The drug-release profiles of various layer arrangements were studied in relation to their antimicrobial activity. The finite element method was applied to overcome the challenge of diffusion-controlled drug release from multilayer polymer scaffolds. The finite element method was first verified using analytical solutions for a simple arrangement (one drug-loaded swellable fibre and one rate-controlling nonswellable fibre) under perfect sink conditions and in a well-stirred finite volume. The effect of alternate layer arrangements on the drug-release profiles was also investigated to plan for controlled topical drug release from fibrous scaffolds. This design is expected to aid in increasing local effectiveness, thus reducing the systemic loading and the consequent side effects of colistin.

Description

Colistin sulfate is a polypeptide antibiotic which inhibits gram-negative bacteria by binding to lipopolysaccharides and phospholipids in the outer cell membrane of gram-negative bacteria.

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