Colistin sodium methanesulfonate
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| Category | Antibiotics |
| Catalog number | BBF-03840 |
| CAS | 8068-28-8 |
| Molecular Weight | 1749.8 |
| Molecular Formula | C58H105N16Na5O28S5 |
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Description
A unique sparingly soluble cyclic polypeptide antibiotic known as a polymyxin. It has a bactericidal effect on bacteria by targeting the cell membrane and modifying its permeability.
Specification
| Storage | Store at 2-8°C |
| IUPAC Name | pentasodium;[2-[(2S,5R,8S,11S,14S,17S,22S)-17-[(1R)-1-hydroxyethyl]-22-[[(2S)-2-[[(2S,3R)-3-hydroxy-2-[[(2S)-2-[[(6R)-6-methyloctanoyl]amino]-4-(sulfonatomethylamino)butanoyl]amino]butanoyl]amino]-4-(sulfonatomethylamino)butanoyl]amino]-5,8-bis(2-methylpropyl)-3,6,9,12,15,18,23-heptaoxo-11,14-bis[2-(sulfonatomethylamino)ethyl]-1,4,7,10,13,16,19-heptazacyclotricos-2-yl]ethylamino]methanesulfonate |
| Canonical SMILES | CCC(C)CCCCC(=O)NC(CCNCS(=O)(=O)[O-])C(=O)NC(C(C)O)C(=O)NC(CCNCS(=O)(=O)[O-])C(=O)NC1CCNC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC1=O)CCNCS(=O)(=O)[O-])CC(C)C)CC(C)C)CCNCS(=O)(=O)[O-])CCNCS(=O)(=O)[O-])C(C)O.[Na+].[Na+].[Na+].[Na+].[Na+] |
| InChI | InChI=1S/C58H110N16O28S5.5Na/c1-9-35(6)12-10-11-13-46(77)65-38(14-20-59-28-103(88,89)90)53(82)74-48(37(8)76)58(87)70-41(17-23-62-31-106(97,98)99)50(79)68-43-19-25-64-57(86)47(36(7)75)73-54(83)42(18-24-63-32-107(100,101)102)67-49(78)39(15-21-60-29-104(91,92)93)69-55(84)44(26-33(2)3)72-56(85)45(27-34(4)5)71-52(81)40(66-51(43)80)16-22-61-30-105(94,95)96;;;;;/h33-45,47-48,59-63,75-76H,9-32H2,1-8H3,(H,64,86)(H,65,77)(H,66,80)(H,67,78)(H,68,79)(H,69,84)(H,70,87)(H,71,81)(H,72,85)(H,73,83)(H,74,82)(H,88,89,90)(H,91,92,93)(H,94,95,96)(H,97,98,99)(H,100,101,102);;;;;/q;5*+1/p-5/t35-,36-,37-,38+,39+,40+,41+,42+,43+,44+,45-,47+,48+;;;;;/m1../s1 |
| InChI Key | IQWHCHZFYPIVRV-VLLYEMIKSA-I |
| Source | Bacillus polymyxa |
Properties
| Appearance | White to Light Yellow Powder |
| Antibiotic Activity Spectrum | Gram-negative bacteria |
Reference Reading
1.Inhaled colistimethate sodium in ventilator-associated tracheobronchitis due to multidrug-resistant Gram-negative bacteria.
Maskin LP1, Setten M2, Rodríguez PO3, Bonelli I4, Attie S4, Stryjewski ME5, Valentini R4. Int J Antimicrob Agents. 2015 Feb;45(2):199-200. doi: 10.1016/j.ijantimicag.2014.09.010. Epub 2014 Oct 16.
2.Characterization of urinary metabolites as biomarkers of colistin-induced nephrotoxicity in rats by a liquid chromatography/mass spectrometry-based metabolomics approach.
Jeong ES1, Kim G1, Moon KS2, Kim YB2, Oh JH2, Kim HS1, Jeong J3, Shin JG1, Kim DH4. Toxicol Lett. 2016 Apr 25;248:52-60. doi: 10.1016/j.toxlet.2016.02.018. Epub 2016 Mar 3.
Colistin is a polypeptide antibiotic that effectively treats infections caused by multidrug-resistant Gram-negative bacteria, but its clinical use is limited due to nephrotoxicity. The purpose of the present study was to identify biomarkers of colistin-induced nephrotoxicity and to further characterize the mechanisms underlying this process by analyzing urinary metabolites using untargeted metabolomic approach. Rats receiving intraperitoneal administration of colistin sodium methanesulfonate (CMS) (25 or 50mg/kg) exhibited histopathological changes in the kidney and increased blood urea nitrogen levels. Additionally, the levels of phenylalanine, tryptophan, and tyrosine in the urine of the CMS-treated group were significantly higher than those of the control group, suggesting that colistin caused proximal tubular damage. Urinary acetylcarnitine and butyrylcarnitine levels also increased after CMS treatment, but the levels of purine metabolites and metabolites related to the tricarboxylic acid cycle were reduced.
3.The antimicrobial effect of colistin methanesulfonate on Mycobacterium tuberculosis in vitro.
van Breda SV1, Buys A2, Apostolides Z3, Nardell EA4, Stoltz AC5. Tuberculosis (Edinb). 2015 Jul;95(4):440-6. doi: 10.1016/j.tube.2015.05.005. Epub 2015 May 21.
Polymyxins have previously been described to have activity against Mycobacterium tuberculosis (MTB), but further research was abandoned due to systemic toxicity concerns to achieve the required MIC. Colistin methanesulfonate (CMS), a polymyxin, is well tolerated when inhaled directly into the lungs, resulting in high local concentrations. We report here for the first time, MIC and MBC data for CMS determined by the microtiter Alamar Blue assay (MABA). We also determined how the MIC would be affected by the presence of pulmonary surfactant (PS) and if any synergy with isoniazid (INH) and rifampicin (RIF) exists. The effect of CMS on the ultrastructure of MTB was also determined. The MIC for CMS was 16 mg/L, while the MBC was 256 mg/L. MIC for CMS in PS was antagonised by eight fold. For synergy, indifference was determined while time-kill assays revealed a greater killing effect when CMS was used together with INH. Ultrastructure analysis suggests that the disruption of the outer polysaccharide layer of MTB by CMS may lead to enhanced uptake of INH.
4.Association between the introduction of a new cystic fibrosis inhaled antibiotic class and change in prevalence of patients receiving multiple inhaled antibiotic classes.
Dasenbrook EC1, Konstan MW2, VanDevanter DR3. J Cyst Fibros. 2015 May;14(3):370-5. doi: 10.1016/j.jcf.2014.11.005. Epub 2014 Dec 11.
BACKGROUND: In 2010, aztreonam for inhalation solution joined aminoglycosides and colistimethate as a new cystic fibrosis (CF) chronic inhaled antimicrobial therapy. We studied how the introduction of this new inhaled antibiotic class changed the management of US CF patients.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
