Compound ID | 691

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Iseganan

Synonym(s): IB-367  |  Iseganan HCl

Class: Antimicrobial peptide

Agent Type: Semisynthetic; Direct acting;
Spectrum of activity: Gram-positive
Mechanism of action: Membrane-active agent
Target Pathogen: Active against Staphylococcus aureus
Description: An analogue of the natural product protegrin-1; also shows anti-fungal activity; currently being developed in different formulations: rinse for mucositis, aerosolized liquid for respiratory infection, and gel for pneumoniae; Loury DJ, Embree J, So W, et al. Topical administration of IB-367, a novel antimicrobial peptide, reduced the severity of oral mucositis, in 5-FU-treated hamsters. 38th-Intersci-Conf-Antimicrobial-Agents-Chemother 1998; 277.
Institute where first reported: Intrabiotics (Ardea Biosciences, USA)
Year first mentioned: 1997
Highest development stage: Phase 3 (NCT00118781)
Development status: Inactive
Chemical structure(s):
Click here for structure editor
Molecular weight: 1900.29
Iso. SMILES: CC(C)C[C@@H](C(=O)N[C@H]1CSSC[C@H](NC(=O)[C@@H](NC(=O)[C@@H]2CSSC[C@@H](C(=O)N[C@H](C(=O)NCC(=O)N[C@H](C(=O)N[C@H](C(=O)N2)CC3=CC=CC=C3)CCCNC(=N)N)CCCNC(=N)N)NC(=O)[C@@H](NC1=O)CC4=CC=C(C=C4)O)C(C)C)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)N[C@@H](CCCNC(=N)N)C(=O)N)NC(=O)CNC(=O)CNC(=O)[C@H](CCCNC(=N)N)N
InChI Key: GUCYBPFJNGVFEB-XELKFLSISA-N
Can. SMILES: CC(C)C[C@@H](C(=O)N[C@H]1CSSC[C@@H](C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)N[C@@H](CCCNC(=N)N)C(=O)N)NC(=O)[C@H](C(C)C)NC(=O)[C@@H]2CSSC[C@@H](C(=O)N[C@@H](CCCNC(=N)N)C(=O)NCC(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CC3=CC=CC=C3)C(=O)N2)NC(=O)[C@H](CC4=CC=C(C=C4)O)NC1=O)NC(=O)CNC(=O)CNC(=O)[C@H](CCCNC(=N)N)N
InChI: InChI=1S/C78H126N30O18S4/c1-39(2)28-49(99-57(111)32-93-56(110)31-94-63(115)45(79)16-10-24-89-75(81)82)66(118)103-53-36-128-130-38-55(72(124)107-60(40(3)4)73(125)96-34-58(112)97-46(62(80)114)17-11-25-90-76(83)84)106-74(126)61(41(5)6)108-71(123)54-37-129-127-35-52(104-68(120)51(102-70(53)122)30-43-20-22-44(109)23-21-43)69(121)100-47(18-12-26-91-77(85)86)64(116)95-33-59(113)98-48(19-13-27-92-78(87)88)65(117)101-50(67(119)105-54)29-42-14-8-7-9-15-42/h7-9,14-15,20-23,39-41,45-55,60-61,109H,10-13,16-19,24-38,79H2,1-6H3,(H2,80,114)(H,93,110)(H,94,115)(H,95,116)(H,96,125)(H,97,112)(H,98,113)(H,99,111)(H,100,121)(H,101,117)(H,102,122)(H,103,118)(H,104,120)(H,105,119)(H,106,126)(H,107,124)(H,108,123)(H4,81,82,89)(H4,83,84,90)(H4,85,86,91)(H4,87,88,92)/t45-,46-,47-,48-,49-,50-,51-,52-,53-,54-,55-,60-,61-/m0/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/16131103
Guide to Pharmacology: iseganan
Citations:
  • https://doi.org/10.1164/rccm.200504-656oc
  • https://doi.org/10.1016/S1079-2104(99)70131-9
  • https://doi.org/10.1517/13543784.11.8.1161

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