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: 155941
• 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: 24856709; 162250079
• 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

Physical Property

• pH: 6-8 (10 mg/mL in H2O)

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

Product Information

• Ignition Residue: ~20%
• Biological Source: from Bacillus colistinus
• Loss on Drying: ≤1.5% loss on drying
• Empirical Formula (Hill Notation): C58H115N16Na5O28S5

DETAILS

Sigma Aldrich - 27655

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.
Colistin sodium methanesulfate is a cyclopolypeptide antibiotic with 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.
Other Notes
Cyclopolypeptide antibiotic. Endotoxin-binding capacity3
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.