N-[3-amino-1-({1-[(3-amino-1-{[6,9,18-tris(2-aminoethyl)-15-benzyl-3-(1-hydroxyethyl)-12-(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

• ChemBase ID: 661
• Molecular Formular: C56H98N16O13
• Molecular Mass: 1203.47672
• Monoisotopic Mass: 1202.74992728
• SMILES: CCC(C)CCCCC(=O)NC(CCN)C(=O)NC(C(C)O)C(=O)NC(CCN)C(=O)NC1CCNC(=O)C(NC(=O)C(CCN)NC(=O)C(CCN)NC(=O)C(CC(C)C)NC(=O)C(Cc2ccccc2)NC(=O)C(CCN)NC1=O)C(C)O
• Canonical SMILES: NCCC(C(=O)NC1CCNC(=O)C(NC(=O)C(CCN)NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC1=O)CCN)Cc1ccccc1)CC(C)C)CCN)C(O)C)NC(=O)C(C(O)C)NC(=O)C(NC(=O)CCCCC(CC)C)CCN
• InChI: InChI=1S/C56H98N16O13/c1-7-32(4)13-11-12-16-44(75)63-36(17-23-57)51(80)72-46(34(6)74)56(85)68-39(20-26-60)48(77)67-41-22-28-62-55(84)45(33(5)73)71-52(81)40(21-27-61)65-47(76)37(18-24-58)66-53(82)42(29-31(2)3)69-54(83)43(30-35-14-9-8-10-15-35)70-49(78)38(19-25-59)64-50(41)79/h8-10,14-15,31-34,36-43,45-46,73-74H,7,11-13,16-30,57-61H2,1-6H3,(H,62,84)(H,63,75)(H,64,79)(H,65,76)(H,66,82)(H,67,77)(H,68,85)(H,69,83)(H,70,78)(H,71,81)(H,72,80)
• InChIKey: WQVJHHACXVLGBL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[3-amino-1-({1-[(3-amino-1-{[6,9,18-tris(2-aminoethyl)-15-benzyl-3-(1-hydroxyethyl)-12-(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
• IUPAC Traditional name: N-[3-amino-1-({1-[(3-amino-1-{[6,9,18-tris(2-aminoethyl)-15-benzyl-3-(1-hydroxyethyl)-12-(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
• Brand Name: Aerosporin; Poly-RX
• Synonyms: Polymixin B sulfate; Polymyxin B sulfate salt; Polymyxin B sulphate; Polymyxin B Sulfate

Database IDs

• CAS Number: 1405-20-5
• PubChem SID: 46507302; 160964124
• PubChem CID: 4868

CALCULATED PROPERTIES

JChem

• Acid pKa: 11.573131
• H Acceptors: 18
• H Donor: 18
• LogD (pH = 5.5): -22.212782
• LogD (pH = 7.4): -17.71875
• Log P: -7.249171
• Molar Refractivity: 313.2155 cm^3
• Polarizability: 124.05702 Å^3
• Polar Surface Area: 490.66 Å^2
• Rotatable Bonds: 29
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -0.89
• LOG S: -4.21
• Solubility (Water): 7.44e-02 g/l

PROPERTIES

Physical Property

• Solubility: 25 mg/mL
• Hydrophobicity(logP): -4.861

DETAILS

DrugBank - DB00781

• Drug Groups: approved
• Description: Polymyxin B sulfate is a mixture of polymyxins B1 and B2, obtained from Bacillus polymyxa strains. They are basic polypeptides of about eight amino acids and have cationic detergent action on cell membranes. Polymyxin B is used for infections with gram-negative organisms, but may be neurotoxic and nephrotoxic. All gram-positive bacteria, fungi, and the gram-negative cocci, N. gonorrhea and N. menigitidis, are resistant. It is appropriate for treatment of infections of the urinary tract, meninges, and blood stream, caused by susceptible strains of Pseudomonas aeruginosa.
• Indication: For treatment of infections of the urinary tract, meninges, and blood stream, caused by susceptible strains of Pseudomonas aeruginosa.
• Pharmacology: Polymyxin B sulfate is a mixture of polymyxins B1 and B2, obtained from Bacillus polymyxa strains. They are basic polypeptides of about eight amino acids and have cationic detergent action on cell membranes. Polymyxin B is used for infections with gram-negative organisms, but may be neurotoxic and nephrotoxic. All gram-positive bacteria, fungi, and the gram-negative cocci, N. gonorrhea and N. menigitidis, are resistant.
• Toxicity: Overdose can cause stomach pains, vomiting, and diarrhea.
• Affected Organisms: Enteric bacteria and other eubacteria
• Absorption: Not absorbed from the normal alimentary tract.
• Elimination: The drug is excreted slowly by the kidneys.
• References: Yuan Z, Tam VH: Polymyxin B: a new strategy for multidrug-resistant Gram-negative organisms. Expert Opin Investig Drugs. 2008 May;17(5):661-8. [Pubmed] ; Zavascki AP, Goldani LZ, Li J, Nation RL: Polymyxin B for the treatment of multidrug-resistant pathogens: a critical review. J Antimicrob Chemother. 2007 Dec;60(6):1206-15. Epub 2007 Sep 17. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

REFERENCES

• Yuan Z, Tam VH: Polymyxin B: a new strategy for multidrug-resistant Gram-negative organisms. Expert Opin Investig Drugs. 2008 May;17(5):661-8. Pubmed
• Zavascki AP, Goldani LZ, Li J, Nation RL: Polymyxin B for the treatment of multidrug-resistant pathogens: a critical review. J Antimicrob Chemother. 2007 Dec;60(6):1206-15. Epub 2007 Sep 17. Pubmed