N-[(1S)-3-amino-1-{[(1S,2R)-1-{[(1S)-3-amino-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-heptaazacyclotricosan-21-yl]carbamoyl}propyl]carbamoyl}-2-hydroxypropyl]carbamoyl}propyl]-5-methylheptanamide

• ChemBase ID: 682
• Molecular Formular: C52H98N16O13
• Molecular Mass: 1155.43392
• Monoisotopic Mass: 1154.74992728
• SMILES: O=C1N[C@@H](CC(C)C)C(=O)N[C@@H](CCN)C(=O)N[C@@H](CCN)C(=O)N[C@@H]([C@H](O)C)C(=O)NCC[C@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)CCCC(CC)C)CCN)[C@H](O)C)CCN)C(=O)N[C@H](C(=O)N[C@@H]1CC(C)C)CCN
• Canonical SMILES: 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)CCCC(CC)C)CCN
• InChI: InChI=1S/C52H98N16O13/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/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)/t29?,30-,31-,32+,33+,34+,35+,36+,37+,38+,39-,41+,42+/m1/s1
• InChIKey: YKQOSKADJPQZHB-QNPLFGSASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(1S)-3-amino-1-{[(1S,2R)-1-{[(1S)-3-amino-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-heptaazacyclotricosan-21-yl]carbamoyl}propyl]carbamoyl}-2-hydroxypropyl]carbamoyl}propyl]-5-methylheptanamide
• IUPAC Traditional name: colistin
• Brand Name: Colistin sulfate; Colistin sulfate, nonsterile; Colistin sulphate; Polymyxin E sulfate; Polymyxin E. Sulfate
• Synonyms: Colistin

Database IDs

• CAS Number: 1264-72-8
• PubChem SID: 46505467; 160964145
• PubChem CID: 5311054

CALCULATED PROPERTIES

JChem

• Acid pKa: 11.595611
• H Acceptors: 18
• H Donor: 18
• LogD (pH = 5.5): -23.059572
• LogD (pH = 7.4): -18.565655
• Log P: -8.095956
• Molar Refractivity: 297.6691 cm^3
• Polarizability: 118.19399 Å^3
• Polar Surface Area: 490.66 Å^2
• Rotatable Bonds: 28
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -1.29
• LOG S: -3.69
• Solubility (Water): 2.38e-01 g/l

PROPERTIES

Physical Property

• Solubility: 5.64E+005 mg/L
• Hydrophobicity(logP): -2.4

DETAILS

DrugBank - DB00803

• Drug Groups: approved
• Description: Cyclic polypeptide antibiotic from Bacillus colistinus. It is composed of Polymyxins E1 and E2 (or Colistins A, B, and C) which act as detergents on cell membranes. Colistin is less toxic than Polymyxin B, but otherwise similar; the methanesulfonate is used orally. [PubChem]
• Indication: For the treatment of acute or chronic infections due to sensitive strains of certain gram-negative bacilli, particularly Pseudomonas aeruginosa.
• Pharmacology: Colistin is a polymyxin antibiotic agent. Polymyxins are cationic polypeptides that disrupt the bacterial cell membrane through a detergentlike mechanism. With the development of less toxic agents, such as extended-spectrum penicillins and cephalosporins, parenteral polymyxin use was largely abandoned, except for the treatment of multidrug-resistant pulmonary infections in patients with cystic fibrosis. More recently, however, the emergence of multidrug-resistant gram-negative bacteria, such as Pseudomonas aeruginosa and Acinetobacter baumannii, and the lack of new antimicrobial agents have led to the revived use of the polymyxins.
• Toxicity: Oral LD₅₀ in rats is 5450 mg/kg. Overdosage with colistimethate can cause neuromuscular blockade characterized by paresthesia, lethargy, confusion, dizziness, ataxia, nystagmus, disorders of speech and apnea. Respiratory muscle paralysis may lead to apnea, respiratory arrest and death.
• Affected Organisms: Gram-negative bacilli
• Biotransformation: As 80% of the dose can be recovered unchanged in the urine, and there is no biliary excretion, it can be assumed that the remaining drug is inactivated in the tissues, however the mechanism is unknown.
• Absorption: Very poor absorption from gastrointestinal tract.
• Half Life: 5 hours
• External Links: Wikipedia