Polymyxin B Sulfate (T3D3529)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationXML
Record Information
Version2.0
Creation Date2009-07-30 17:59:06 UTC
Update Date2014-12-24 20:26:07 UTC
Accession NumberT3D3529
Identification
Common NamePolymyxin B Sulfate
ClassSmall Molecule
DescriptionPolymyxin 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.
Compound Type
  • Amide
  • Amine
  • Anti-Bacterial Agent
  • Drug
  • Metabolite
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
Aerosporin
Metamyxin
Polimixina B
Polomyxin B
Poly-Rx
Polyfax
Polymixin B sulfate
Polymixin B sulphate
Polymyxin b
Polymyxin b sulfate
Polymyxin B sulfate
Polymyxin B sulfate salt
Polymyxin b sulfic acid
Polymyxin b sulphate
Polymyxin B sulphate
Polymyxin B sulphate salt
Polymyxin b sulphic acid
Polymyxin-B-Sulfat
Polymyxine b
Polymyxine B (sulfate de)
Polymyxini B sulfas
Polymyxinum B
Polyxx
Chemical FormulaC56H98N16O13
Average Molecular Mass1203.477 g/mol
Monoisotopic Mass1202.750 g/mol
CAS Registry Number1405-20-5
IUPAC NameN-[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
Traditional Namepolymyxin B sulfate
SMILESCCC(C)CCCCC(O)=NC(CCN)C(O)=NC(C(C)O)C(O)=NC(CCN)C(O)=NC1CCN=C(O)C(N=C(O)C(CCN)N=C(O)C(CCN)N=C(O)C(CC(C)C)N=C(O)C(CC2=CC=CC=C2)N=C(O)C(CCN)N=C1O)C(C)O
InChI IdentifierInChI=1/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)
InChI KeyInChIKey=WQVJHHACXVLGBL-UHFFFAOYNA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as polypeptides. These are peptides containing ten or more amino acid residues.
KingdomOrganic compounds
Super ClassOrganic Polymers
ClassPolypeptides
Sub ClassNot Available
Direct ParentPolypeptides
Alternative Parents
Substituents
  • Polypeptide
  • Cyclic alpha peptide
  • Macrolactam
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • N-substituted-alpha-amino acid
  • Alpha-amino acid or derivatives
  • Monocyclic benzene moiety
  • Fatty amide
  • N-acyl-amine
  • Fatty acyl
  • Benzenoid
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Amino acid or derivatives
  • Carboxamide group
  • Lactam
  • Organoheterocyclic compound
  • Azacycle
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Carbonyl group
  • Alcohol
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary aliphatic amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
Solubility25 mg/mL
LogP-4.861
Predicted Properties
PropertyValueSource
Water Solubility0.074 g/LALOGPS
logP-0.89ALOGPS
logP-7.2ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)11.57ChemAxon
pKa (Strongest Basic)10.23ChemAxon
Physiological Charge5ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count18ChemAxon
Polar Surface Area490.66 ŲChemAxon
Rotatable Bond Count29ChemAxon
Refractivity313.22 m³·mol⁻¹ChemAxon
Polarizability129.71 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-0900000000-2fc106a88490958609482017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-4910000111-09aa17c0c5e9e1d3a2512017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9420000000-50618abf83d40012137d2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-1159-0941000000-9241d7871d46b3a90d912017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bu9-1910000111-2dc8c378fec3170a9d1c2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-08fu-5921000300-2f55ebc350da3657d7e32017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udr-2590000000-5b17104b7709c34658942021-10-11View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fri-1920000010-5f45af1d0f0e081ca1ce2021-10-11View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9420000000-67757bce91a0fadb30442021-10-11View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-47b6f40976ca4be0e87c2021-10-11View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fdo-6931100016-e4ef6ce119c6e64a028a2021-10-11View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0007-9510000120-71306b33c0302f309ff92021-10-11View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-09-25View Spectrum
Toxicity Profile
Route of ExposureEye contact; parenteral (intrathecal, intramuscular injection, intravenous drip). Not absorbed from the normal alimentary tract.
Mechanism of ToxicityPolymyxin 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.
Metabolism Route of Elimination: The drug is excreted slowly by the kidneys.
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesUsed in the treatment of infections of the urinary tract, meninges, and bloodstream caused by susceptible strains of Pseudomonas aeruginosa. It may also be used topically and subconjunctivally in the treatment of infections of the eye caused by susceptible strains of Ps. aeruginosa. (3)
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsFacial flushing, dizziness progressing to ataxia, drowsiness, peripheral paresthesias (circumoral and stocking glove), apnea due to concurrent use of curariform muscle relaxants, other neurotoxic drugs or inadvertent overdosage, and signs of meningeal irritation with intrathecal administration, e.g., fever, headache, stiff neck and increased cell count and protein cerebrospinal fluid. Other reactions occasionally reported: Drug fever, urticarial rash, pain (severe) at intramuscular injection sites, and thrombophlebitis at intravenous injection sites. (3)
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDDB00781
HMDB IDHMDB14919
PubChem Compound ID4868
ChEMBL IDCHEMBL1200626
ChemSpider ID4702
KEGG IDC11613
UniProt IDNot Available
OMIM ID
ChEBI ID506404
BioCyc IDNot Available
CTD IDNot Available
Stitch IDPolymyxin
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkPolymyxin_B
References
Synthesis ReferenceNot Available
MSDSLink
General References
  1. 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. doi: 10.1517/13543784.17.5.661 . [18447592 ]
  2. 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. [17878146 ]
  3. Rxlist. Polymyxin-B [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available