Basic information
- CAS
1405-20-5- Standard SMILES
CCC(C)CCCCC(=O)NC(CCN)C(=O)NC(C(=O)NC(CCN)C(=O)NC1CCNC(=O)C(C(C)O)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- InChIKey
WQVJHHACXVLGBL-UHFFFAOYSA-N- Molecular formula
- C56H98N16O13
- Average molar mass
- 1,203.5 g/mol
- Monoisotopic mass
- 1,202.74992724
Overview
polymyxin B has been reported in Paenibacillus polymyxa with data available.
Names & identifiers
- Preferred name
- Polymyxin B1-d3
- IUPAC
- 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
- English name
- Polymyxin B sulfate
- Molecular formula
- C56H100N16O17S
- Molecular weight
- 1301.56
Names & synonyms
AerosporinPolymyxin B1-d3Spectrum_001117Spectrum2_000490Spectrum3_000549Spectrum4_000481Spectrum5_001331BSPBio_002197KBioGR_000961KBioSS_001597DivK1c_000732SPBio_000359
Show more names
POLYMYXIN BPOLYMYXIN B SULPHATEPOLYMIXIN B SULFATEPOLYMIXIN B SULPHATEpolymyxin B sulfate uspPolymyxin B sulfate for microbiological assayN-[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-heptazacyclotricos-21-yl]carbaMoyl]propyl]carbaMoyl]-2-hydroxy-propyl]carbaMoyl]proPoly-RXAPPLISORB
CHEMBL241797SCHEMBL7799155GTPL10338KBio1_000732KBio2_001597KBio2_004165KBio2_006733KBio3_001697
Database identifiers
Properties
Computed structural properties
- XLogP
- -2.5
- Topological polar surface area
- 491 Ų
- Hydrogen bond donors
- 18
- Hydrogen bond acceptors
- 18
- Rotatable bonds
- 29
- Heavy atoms
- 85
- Formal charge
- 0
- Complexity
- 2,150
Experimental & physicochemical properties
LogP-4.861
Solubility7.44e-02 g/L
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 217 · 217-220°C (dec.)
- storage temp.
- 2 · 2-8°C
- solubility
- 2 O: · H2O: 50 mg/mL
- pka
- 8.9 · pKa 8.9 (Uncertain)
- form
- powder
- color
- colorless or slightly yellow
- PH
- pH (10g/L, 25℃) : 4.5～7.0
- biological source
- Pseudomonas aeruginosa
- optical activity
- 20 · [α]/D 20/D (Rotation: -2.3 +/- 0.2 degrees)
- Water Solubility
- 50 mg/ml/n · Soluble in water at 50mg/ml/n
- Merck
- 14 · 14,7573
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Toxicology
Exposure RoutesEye contact; parenteral (intrathecal, intramuscular injection, intravenous drip). Not absorbed from the normal alimentary tract.
Toxicity Summary
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.
Signs and Symptoms
Facial 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. (L1876)
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Safety data
- F
- 3-8-10
- wgk
- 3
- rtecs
- TR1150000
- ridadr
- 3249
- hs_code
- 2941 90 00
- Toxicity
- dog,LDLo,intracrebral,320ug/kg (0.32mg/kg),BEHAVIORAL: COMA,British Journal of Pharmacology and Chemotherapy. Vol. 23, Pg. 552, 1964.
- risk_code
- 22
- Signal word
- Warning
- Symbol(GHS)
Chemistry & industry
Pharmacology
Metabolism/MetabolitesRoute of Elimination: The drug is excreted slowly by the kidneys.
Uses & manufacturing
Uses
Used in the treatment of infections of the urinary tract, meninges, and bloodstream caused by susceptible strains of <i>Pseudomonas aeruginosa</i>. It may also be used topically and subconjunctivally in the treatment of infections of the eye caused by susceptible strains of Ps. aeruginosa. (L1876)
Applications
UsesBiochemical studies. Polymyxin B is a kind of anti-Gram-negative poly-peptide antibiotics which can alter membrane structure allowing small molecules leakage and inhibit the growth of Gram-negative bacteria. It has bactericidal effect on Escherichia coli through binding to the lipid A portion of bacterial lipopolysaccharide. Mechanism of action: bind and interfere with the permeability o the cellular membrane. Anti-bacteria spectrum: gram negative bacteria.
DescriptionThe polymyxins are cationic peptides originally isolated from B. polymyxa. They bind and kill Gram-negative bacteria. The B series of polymyxins consist of a cyclic heptapeptide and a tripeptide side chain acylated at the amino terminus by a fatty acid. Polymyxin B (sulfate) is a mixture of at least four closely related components, polymyxin B1 to B4, with polymyxin B1 and B2 being the two major components. Polymyxin B (sulfate) has rapid in vitro bactericidal activity against major multidrug-resistant Gram-negative bacteria, such as P. aeruginosa, A. baumannii, and K. pneumoniae.
Usesantibacterial
UsesAntibiotic with bactericidal action on E. coli. Binds to the lipid A portion of bacterial lipopolysaccharides. Induces pore formation in the membranes of cortex cells from excised sorghum roots. Mixtu re of Polymyxin B1 and B2 sulfate. Biological potency (dry basis): >6000U/mg.
UsesPolymyxin B sulfate is used as topical antibiotic agent, often used in combination with neomycin; products include ointments, creams, eye, and ear drops.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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