polymyxin B   Click here for help

GtoPdb Ligand ID: 10338

Synonyms: Aerosporin®
Approved drug
polymyxin B is an approved drug (FDA (1964, no prior history available))
Comment: Polymyxin B is an antimicrobial. It is a mixture of the polypeptides polymyxins B1 and B2, both obtained from Bacillus polymyxa strains. It has bactericidal action against almost all gram-negative bacilli except the Proteus group.
2D Structure
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SMILES / InChI / InChIKey
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Canonical SMILES NCCC(C(=O)NC1CCNC(=O)C(NC(=O)C(CCN)NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC1=O)CCN)Cc1ccccc1)CC(C)C)CCN)C(O)C)NC(=O)C(C(O)C)NC(=O)C(NC(=O)CCCCC(CC)C)CCN
Isomeric SMILES NCCC(C(=O)NC1CCNC(=O)C(NC(=O)C(CCN)NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC1=O)CCN)Cc1ccccc1)CC(C)C)CCN)C(O)C)NC(=O)C(C(O)C)NC(=O)C(NC(=O)CCCCC(CC)C)CCN
InChI InChI=1S/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 Key WQVJHHACXVLGBL-UHFFFAOYSA-N
References
1. Boscutti G, Nardon C, Marchiò L, Crisma M, Biondi B, Dalzoppo D, Dalla Via L, Formaggio F, Casini A, Fregona D. (2018)
Anticancer Gold(III) Peptidomimetics: From Synthesis to in vitro and ex vivo Biological Evaluations.
ChemMedChem, 13 (11): 1131-1145. [PMID:29570944]
2. Döring F, Walter J, Will J, Föcking M, Boll M, Amasheh S, Clauss W, Daniel H. (1998)
Delta-aminolevulinic acid transport by intestinal and renal peptide transporters and its physiological and clinical implications.
J Clin Invest, 101 (12): 2761-7. [PMID:9637710]
3. Ferrari D, Pizzirani C, Adinolfi E, Forchap S, Sitta B, Turchet L, Falzoni S, Minelli M, Baricordi R, Di Virgilio F. (2004)
The antibiotic polymyxin B modulates P2X7 receptor function.
J Immunol, 173 (7): 4652-60. [PMID:15383600]
4. Lu X, Chan T, Xu C, Zhu L, Zhou QT, Roberts KD, Chan HK, Li J, Zhou F. (2016)
Human oligopeptide transporter 2 (PEPT2) mediates cellular uptake of polymyxins.
J Antimicrob Chemother, 71 (2): 403-12. [PMID:26494147]
5. Miyabe J, Ohgaki R, Saito K, Wei L, Quan L, Jin C, Liu X, Okuda S, Nagamori S, Ohki H et al.. (2019)
Boron delivery for boron neutron capture therapy targeting a cancer-upregulated oligopeptide transporter.
J Pharmacol Sci, 139 (3): 215-222. [PMID:30833090]
6. Ocheltree SM, Shen H, Hu Y, Xiang J, Keep RF, Smith DE. (2004)
Mechanisms of cefadroxil uptake in the choroid plexus: studies in wild-type and PEPT2 knockout mice.
J Pharmacol Exp Ther, 308 (2): 462-7. [PMID:14600253]
7. Sawada K, Terada T, Saito H, Hashimoto Y, Inui K. (1999)
Effects of glibenclamide on glycylsarcosine transport by the rat peptide transporters PEPT1 and PEPT2.
Br J Pharmacol, 128 (6): 1159-64. [PMID:10578127]
8. Terada T, Sawada K, Saito H, Hashimoto Y, Inui K. (2000)
Inhibitory effect of novel oral hypoglycemic agent nateglinide (AY4166) on peptide transporters PEPT1 and PEPT2.
Eur J Pharmacol, 392 (1-2): 11-7. [PMID:10748266]
9. Theis S, Hartrodt B, Kottra G, Neubert K, Daniel H. (2002)
Defining minimal structural features in substrates of the H(+)/peptide cotransporter PEPT2 using novel amino acid and dipeptide derivatives.
Mol Pharmacol, 61 (1): 214-21. [PMID:11752223]
10. Xu Q, Wang C, Meng Q, Liu Q, Sun P, Sun H, Guo X, Liu K. (2014)
The oligopeptide transporter 2-mediated reabsorption of entecavir in rat kidney.
Eur J Pharm Sci, 52: 41-7. [PMID:24184752]