CAS 1405-20-5|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]carba...

General Information

Structure

Molecular Formula

C₅₆H₉₈N₁₆O₁₃

Molecular Mass

1203.47672

Exact Mass

1202.74992728

Charge

0

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

Canonic 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

Isomeric 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

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

Polarizability

124.05702

Polar Surface Area

490.66

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

Data Source

Academic Data

Data Source

Names and Identifiers

Synonyms

Polymixin B sulfatePolymyxin B SulfatePolymyxin B sulfate saltPolymyxin B sulphate

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

AerosporinPoly-RX

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

Names and Identifiers

Registration numbers

PubChem CID

4868

PubChem SID

46507302160964124

CAS Number

1405-20-5

Registration numbers

Properties

Physical Property

Hydrophobicity(logP)

-4.861

Solubility

25 mg/mL

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule 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]

Molecule Details

References

PubChem Literature

From Data Sources

• 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

References

Bioactivity

PubChem BioAssay

Bioactivity

Molecule

ID:661