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Key Documents

P0972

Sigma-Aldrich

Polymyxin B sulfate

meets USP testing specifications

Synonym(s):

Polymyxin B sulfate salt

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About This Item

Empirical Formula (Hill Notation):
C55H96N16O13 · 2H2SO4
CAS Number:
Molecular Weight:
1385.61
EC Number:
MDL number:
UNSPSC Code:
12352209
NACRES:
NA.21

Agency

USP/NF
meets USP testing specifications

Quality Level

form

powder

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria
fungi

application(s)

pharmaceutical (small molecule)

Mode of action

cell membrane | interferes

storage temp.

2-8°C

SMILES string

O=C(C(NC(C(CCN)NC(CCCCC(C)CC)=O)=O)C(C)O)NC(CCN)C(NC(CCNC(C(NC(C(NC(C(CCN)N1)=O)CCN)=O)C(O)C)=O)C(NC(CCN)C(NC(CC2=CC=CC=C2)C(NC(CC(C)C)C1=O)=O)=O)=O)=O.O=S(O)(O)=O

InChI

1S/C48H82N16O13.H2O4S/c1-27(2)24-37-47(76)59-32(11-19-52)41(70)56-31(10-18-51)43(72)61-35(14-22-65)39(68)54-21-13-34(45(74)57-33(12-20-53)44(73)64-38(48(77)63-37)25-28-6-4-3-5-7-28)60-42(71)30(9-17-50)58-46(75)36(15-23-66)62-40(69)29(8-16-49)55-26-67;1-5(2,3)4/h3-7,26-27,29-38,65-66H,8-25,49-53H2,1-2H3,(H,54,68)(H,55,67)(H,56,70)(H,57,74)(H,58,75)(H,59,76)(H,60,71)(H,61,72)(H,62,69)(H,63,77)(H,64,73);(H2,1,2,3,4)

InChI key

HNDFYNOVSOOGDU-UHFFFAOYSA-N

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General description

Chemical structure: peptide

Application

Polymyxin B sulfate is a strongly cationic cyclic polypeptide antibiotic that is derived from fermentation of Bacilus polymyxa. It is a mixture of B1 and B2 sulfate. The product has been used clinically to treat infections of the urinary tract, meninges and blood stream caused by susceptible strains of Pseudomonas aeruginosa. It also has uses studying multidrug-resistant pathogens, as an immobilized agent for removal of endotoxins, and to induce pore formation in the membranes of cortex cells from excised sorghum roots.

Biochem/physiol Actions

Mode of Action: Polymyxin B Sulfate binds to the lipid A portion of bacterial lipopolysaccharides†, disrupting the cytoplasmic membrane by inducing pores large enough to permit nucleotide leakage in bacterial walls. This disrupts the permeability of the cytoplasmic membrane.

Antimicrobial spectrum: Has bactericidal action on most gram-negative bacilli††, including E. Coli and on most fungi and gram-positive bacteria.

Packaging

This product is packaged in a bottomless glass bottle, with its contents inside an inserted fused cone.

Caution

As supplied, the product should be stored at 2-8°C in the dark. No change was observed in retained samples after three years′ of storage in these conditions. Stock solutions should be sterile filtered and stored at 2-8°C. They are stable at 37°C for 5 days.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Mei-Ling Han et al.
ACS chemical biology, 13(1), 121-130 (2017-11-29)
Polymyxins are last-line antibiotics against life-threatening multidrug-resistant Gram-negative bacteria. Unfortunately, polymyxin resistance is increasingly reported, leaving a total lack of therapies. Using lipidomics and transcriptomics, we discovered that polymyxin B induced lipid A deacylation via pagL in both polymyxin-resistant and
Martti Vaara et al.
Peptides, 91, 8-12 (2017-03-17)
Recent years have brought in an increased interest to develop improved polymyxins. The currently used polymyxins, i.e. polymyxin B and colistin (polymyxin E) are pentacationic lipopeptides that possess a cyclic heptapeptide part with three positive charges, a linear "panhandle" part
Martti Vaara et al.
The Journal of antimicrobial chemotherapy, 73(2), 452-455 (2017-11-18)
Extremely multiresistant strains of Enterobacteriaceae, such as those of Escherichia coli and Klebsiella pneumoniae, are emerging and spreading at a worrisome speed. Polymyxins (polymyxin B, colistin) are used as last-line therapy against such strains, in spite of their notable nephrotoxicity
Sara N Vallerie et al.
PloS one, 3(9), e3151-e3151 (2008-09-06)
It has been established that c-Jun N-terminal kinase 1 (JNK1) is essential to the pathogenesis of insulin resistance and type 2 diabetes. Although JNK influences inflammatory signaling pathways, it remains unclear whether its activity in macrophages contributes to adipose tissue
Amit Kumar et al.
Scientific reports, 7, 39925-39925 (2017-01-05)
To become clinically effective, antimicrobial peptides (AMPs) should be non-cytotoxic to host cells. Piscidins are a group of fish-derived AMPs with potent antimicrobial and antiendotoxin activities but limited by extreme cytotoxicity. We conjectured that introduction of cationic residue(s) at the

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