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编号: 682
• 分子式: C52H98N16O13
• 平均质量: 1155.43392
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 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传统名: colistin
• 商标名: Colistin sulfate; Colistin sulfate, nonsterile; Colistin sulphate; Polymyxin E sulfate; Polymyxin E. Sulfate
• 别名: Colistin

登记号

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

理论计算性质

JChem

• Acid pKa: 11.595611
• 质子受体: 18
• 质子供体: 18
• LogD (pH = 5.5): -23.059572
• LogD (pH = 7.4): -18.565655
• Log P: -8.095956
• 摩尔折射率: 297.6691 cm^3
• 极化性: 118.19399 Å^3
• 极化表面积: 490.66 Å^2
• 可自由旋转的化学键: 28
• 里宾斯基五规则: false

ALOGPS 2.1

• Log P: -1.29
• LOG S: -3.69
• 溶解度: 2.38e-01 g/l

分子性质

理化性质

• 溶解度: 5.64E+005 mg/L
• 疏水性(logP): -2.4

详细说明

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