Legend: drug field target field enzyme field
| Version | 2.5 | ||||||||||
| Creation Date | 2005-06-13 13:24:05 | ||||||||||
| Update Date | 2009-06-23 18:08:15 | ||||||||||
| Primary Accession Number | DB00781 | ||||||||||
| Secondary Accession Number |
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| Name | Polymyxin B Sulfate | ||||||||||
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| 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. | ||||||||||
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| Chemical 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 | ||||||||||
| Chemical Formula | C56H100N16O17S | ||||||||||
| Chemical Structure | |||||||||||
| CAS Registry Number | 1405-20-5 | ||||||||||
| InChI Identifier | InChI=1/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)/f/h62-72H;1-2H | ||||||||||
| InChI Key | HFMDLUQUEXNBOP-VTFLQOHRCV | ||||||||||
| KEGG Drug | D01066 ![]() |
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| KEGG Compound | C11613 ![]() |
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| PubChem Compound | 5702105 ![]() |
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| PubChem Substance | 8149488 ![]() |
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| ChEBI ID | Not Available | ||||||||||
| PharmGKB ID | PA451028 ![]() |
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| HET ID | Not Available | ||||||||||
| GenBank ID | Not Available | ||||||||||
| Drug ID Number [DIN] | 02242485 ![]() |
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| RxList Link | http://www.rxlist.com/cgi/generic3/polymyxin.htm ![]() |
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| PDRhealth Link | Not Available | ||||||||||
| Wikipedia Link | http://en.wikipedia.org/wiki/Polymyxin_B ![]() |
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| FDA Label | Not Available | ||||||||||
| Material Safety Data Sheet (MSDS) | |||||||||||
| Synthesis Reference | Not Available | ||||||||||
| Average Molecular Weight | 1301.5550 | ||||||||||
| Monoisotopic Molecular Weight | 1300.7173 | ||||||||||
| State | Solid | ||||||||||
| Melting Point | Not Available | ||||||||||
| Experimental Water Solubility | 25 mg/mL Source: PhysProp | ||||||||||
| Predicted Water Solubility | Not Available Calculated using ALOGPS | ||||||||||
| Experimental LogP/Hydrophobicity | -4.861 Source: PhysProp | ||||||||||
| Predicted LogP | Not Available Calculated using ALOGPS | ||||||||||
| Experimental LogS | Not Available | ||||||||||
| Predicted LogS | Not Available Calculated using ALOGPS | ||||||||||
| Experimental Caco2 Permeability | Not Available | ||||||||||
| pKa/Isoelectric Point | Not Available | ||||||||||
| Mass Spectrum | Not Available | ||||||||||
| MOL File | Show | Download ![]() |
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| SDF File | Show | Download ![]() |
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| PDB File | Show | Download ![]() |
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| 2D Structure | |||||||||||
| 3D Structure | |||||||||||
| Experimental PDB ID | Not Available | ||||||||||
| Isomeric SMILES | OS(O)(=O)=O.CC[C@@H](C)CCCCC(=O)N[C@H](CCN)C(=O)N[C@H]([C@@H](C)O)C(=O)N[C@H](CCN)C(=O)N[C@@H]1CCNC(=O)[C@H](NC(=O)[C@@H](CCN)NC(=O)[C@@H](CCN)NC(=O)[C@@H](CC(C)C)NC(=O)[C@@H](CC2=CC=CC=C2)NC(=O)[C@@H](CCN)NC1=O)[C@@H](C)O | ||||||||||
| Canonical SMILES | OS(O)(=O)=O.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(CC2=CC=CC=C2)NC(=O)C(CCN)NC1=O)C(C)O | ||||||||||
| Drug Category |
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| ATC Codes | |||||||||||
| AHFS Codes | Not Available | ||||||||||
| 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. | ||||||||||
| Mechanism of Action | Polymyxin B sulfate has a bactericidal action against almost all gram-negative bacilli except the Proteus group. Polymyxin B sulfate binds to and interferes with the permeability of the bacterial cytoplasmic membrane. | ||||||||||
| Absorption | Not absorbed from the normal alimentary tract. | ||||||||||
| Toxicity | Overdose can cause stomach pains, vomiting, and diarrhea. | ||||||||||
| Protein Binding | Not Available | ||||||||||
| Biotransformation | Not Available | ||||||||||
| Half Life | Not Available | ||||||||||
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| Patient Information | Not Available | ||||||||||
| Contraindications | Show ![]() |
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| Interactions | Show ![]() |
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| Drug Interactions | Not Available | ||||||||||
| Food Interactions | Not Available | ||||||||||
| Pathways | Not Available | ||||||||||
| General References | |||||||||||
| Organisms Affected |
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This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.