pentasodium N-[(1S)-3-amino-1-{[(1S,2R)-1-{[(1S)-3-amino-1-{[(3S,6S,9R,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-heptaazacyclotricosan-21-yl]carbamoyl}propyl]carbamoyl}-2-hydroxypropyl]carbamoyl}propyl]-6-methyloctanamide pentamethanesulfonate

• ChemBase ID: 133758
• Molecular Formular: C58H115N16Na5O28S5
• Molecular Mass: 1759.89795
• Monoisotopic Mass: 1758.61587353
• SMILES: CCC(C)CCCCC(=O)N[C@@H](CCN)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCN)C(=O)N[C@H]1CCNC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@@H](NC1=O)CCN)CC(C)C)CC(C)C)CCN)CCN)[C@@H](C)O.CS(=O)(=O)[O-].CS(=O)(=O)[O-].CS(=O)(=O)[O-].CS(=O)(=O)[O-].CS(=O)(=O)[O-].[Na+].[Na+].[Na+].[Na+].[Na+]
• Canonical SMILES: [O-]S(=O)(=O)C.[O-]S(=O)(=O)C.[O-]S(=O)(=O)C.[O-]S(=O)(=O)C.[O-]S(=O)(=O)C.NCC[C@@H](C(=O)N[C@H]1CCNC(=O)[C@@H](NC(=O)[C@H](CCN)NC(=O)[C@H](NC(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@@H](NC1=O)CCN)CC(C)C)CC(C)C)CCN)[C@H](O)C)NC(=O)[C@H]([C@H](O)C)NC(=O)[C@@H](NC(=O)CCCCC(CC)C)CCN.[Na+].[Na+].[Na+].[Na+].[Na+]
• InChI: 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
• InChIKey: WSDSONZFNWDYGZ-BKFDUBCBSA-I

NAMES AND DATABASE IDS

Names

• IUPAC name: pentasodium N-[(1S)-3-amino-1-{[(1S,2R)-1-{[(1S)-3-amino-1-{[(3S,6S,9R,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-heptaazacyclotricosan-21-yl]carbamoyl}propyl]carbamoyl}-2-hydroxypropyl]carbamoyl}propyl]-6-methyloctanamide pentamethanesulfonate
• IUPAC Traditional name: pentasodium N-[(1S)-3-amino-1-{[(1S,2R)-1-{[(1S)-3-amino-1-{[(3S,6S,9R,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-heptaazacyclotricosan-21-yl]carbamoyl}propyl]carbamoyl}-2-hydroxypropyl]carbamoyl}propyl]-6-methyloctanamide pentamesylate
• Synonyms: Colimycin sodium methanesulfonate; Methanesulfonic acid derivative of Polymyxin E; Polymyxin E sodium methanesulfonate; Colistin sodium methanesulfonate

Database IDs

• CAS Number: 8068-28-8
• EC Number: 232-516-9
• MDL Number: MFCD00130824
• PubChem SID: 162228035; 24892418
• PubChem CID: 16211791

CALCULATED PROPERTIES

• Acid pKa: 11.570662
• H Acceptors: 18
• H Donor: 18
• LogD (pH = 5.5): -22.614998
• LogD (pH = 7.4): -18.120953
• Log P: -7.6513867
• Molar Refractivity: 302.2701 cm^3
• Polarizability: 120.02434 Å^3
• Polar Surface Area: 490.66 Å^2
• Rotatable Bonds: 29
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• RTECS: GH1650000
• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

DETAILS

Sigma Aldrich - C1511

Biochem/physiol Actions
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.
Cyclopolypeptide antibiotic. Endotoxin-binding capacity3 Colistin′s activity stems from the hydrophobic and hydrophillic regions. They solubilze the cytoplasmic membrane which contributes to the bactericidal effect 4.
Application
Colistin sodium methanesulfate is used to permeabilize bacterial cell membranes and to study mannose-resistant haemagglutination. It is used to study effective treatments of P. aeruginosa infections in cystic fibrosis patients 1 and to study the pharmacokinetics and BAL concentration of colistin in critically ill patients 2.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information