Polymyxin B sulphate

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Polymyxin B sulphate
Category Antibiotics
Catalog number BBF-03827
CAS 1405-20-5
Molecular Weight 1301.56
Molecular Formula C56H100N16O17S

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BBF-03827 25 g $439 In stock

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Description

Polymyxin B is an antibiotic produced by Bacillus polymyxia strains. It is effective against gram-negative infections.

Specification

Related CAS 4135-11-9
Synonyms Aerosporin; PMB; Poly-RX
Storage RT
IUPAC Name N-[4-amino-1-[[1-[[4-amino-1-oxo-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-heptazacyclotricos-21-yl]amino]butan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-1-oxobutan-2-yl]-6-methyloctanamide;sulfuric acid
Canonical 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(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC1=O)CCN)CC2=CC=CC=C2)CC(C)C)CCN)CCN)C(C)O.OS(=O)(=O)O
InChI InChI=1S/C56H98N16O13.H2O4S/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;1-5(2,3)4/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);(H2,1,2,3,4)
InChI Key HFMDLUQUEXNBOP-UHFFFAOYSA-N

Properties

Appearance powder
Antibiotic Activity Spectrum Gram-negative bacteria
Boiling Point 1651°C at 760 mmHg
Melting Point 18°C
Solubility Soluble in DMSO
LogP -4.861

Toxicity

Carcinogenicity No indication of carcinogenicity to humans (not listed by IARC).
Mechanism Of Toxicity Polymyxin B sulfate has a bactericidal action against almost all gram-negative bacilli except the Proteus group. Polymyxin B sulfate interacts with the lipopolysaccharide of the cytoplasmic outer membrane of Gram-negative bacteria, altering membrane permeability and causing cell death. It does not need to enter the cell.

Reference Reading

1.Accuracy of Turbidimetric Limulus Amebocyte Lysate Assay for the Recovery of Endotoxin Interacted with Commonly Used Antimicrobial Agents of Endodontic Therapy.
Marinho AC1, Polay AR2, Gomes BP3. J Endod. 2015 Oct;41(10):1653-9. doi: 10.1016/j.joen.2015.05.020. Epub 2015 Aug 5.
INTRODUCTION: This study was conducted to investigate whether the interaction between the turbidimetric limulus amebocyte lysate (LAL) substrate for endotoxin measurement and the substances/antimicrobial agents used in endodontic therapy can lead to the inhibition/enhancement of endotoxin recovery.
2.Determination of ototoxicity of common otic drops using isolated cochlear outer hair cells.
Jinn TH1, Kim PD, Russell PT, Church CA, John EO, Jung TT. Laryngoscope. 2001 Dec;111(12):2105-8.
OBJECTIVES: Otic drops are commonly used not only for otitis externa, but also for otorrhea in the presence of tympanostomy tubes or tympanic membrane perforations. Many studies have demonstrated the ototoxicity of common otic preparations such as Cortisporin otic drops (Monarch Pharmaceuticals, Bristol, TN). The purpose of this study was to assess the relative ototoxicity of common otic preparations by direct exposure to isolated cochlear outer hair cells (OHCs).
3.Identification and quantitation of polymyxin B, framycetin, and dexamethasone in an ointment by using thin-layer chromatography with densitometry.
Krzek J1, Maślanka A, Lipner P. J AOAC Int. 2005 Sep-Oct;88(5):1549-54.
A new thin-layer chromatographic-densitometric method has been developed for rapid identification and quantitative determination of polymyxin B, framycetin, and dexamethasone in a dental ointment. Silica gel 60 and F254 silica gel 60 plates were used for separating antibiotics and dexamethasone acetate, respectively. When determining framycetin and polymyxin B, chromatograms were developed by using 2 mobile phases, namely methanol and methanol-n-butanol-ammonia (25%)-chloroform (14 + 4 + 9 + 12, v/v/v/v/). The densitometric measurements were made at 550 nm after detection with 0.3% ninhydrin solution. Dexamethasone was determined by using the mobile phase cyclohexane-ethyl acetate (2 + 3, v/v) and ultraviolet densitometric recording at 245 nm. The results obtained for individual constituents with the chromatographic-densitometric method demonstrate similar accuracy, relative standard deviation values from 1.49 to 2.47%, and relative error values from 0.
4.Acute otitis externa: efficacy and tolerability of N-chlorotaurine, a novel endogenous antiseptic agent.
Neher A1, Nagl M, Appenroth E, Gstöttner M, Wischatta M, Reisigl F, Schindler M, Ulmer H, Stephan K. Laryngoscope. 2004 May;114(5):850-4.
OBJECTIVE: The study's objective was to test the tolerability and efficacy of the endogenous antiseptic N-chlorotaurine (NCT) in comparison with a standard clinical treatment according to a phase IIb clinical trial protocol.

Spectrum

Predicted LC-MS/MS Spectrum - 10V, Positive

Experimental Conditions

Ionization Mode: Positive
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da

13C NMR Spectrum

Experimental Conditions

Solvent: D2O
Nucleus: 13C
Frequency: 100

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