Iseganan
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Iseganan

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Iseganan is an antimicrobial peptide, potentially used to prevent oral mucositis.

Category
Peptide APIs
Catalog number
BAT-009064
CAS number
257277-05-7
Molecular Formula
C78H126N30O18S4
Molecular Weight
1900.29
IUPAC Name
(1R,4S,7R,12R,15S,18R,21S,24S,30S)-N-[(2S)-1-[[2-[[(2S)-1-amino-5-carbamimidamido-1-oxopentan-2-yl]amino]-2-oxoethyl]amino]-3-methyl-1-oxobutan-2-yl]-7-[[(2S)-2-[[2-[[2-[[(2S)-2-amino-5-carbamimidamidopentanoyl]amino]acetyl]amino]acetyl]amino]-4-methylpentanoyl]amino]-21-benzyl-24,30-bis(3-carbamimidamidopropyl)-4-[(4-hydroxyphenyl)methyl]-3,6,14,17,20,23,26,29,32-nonaoxo-15-propan-2-yl-9,10,34,35-tetrathia-2,5,13,16,19,22,25,28,31-nonazabicyclo[16.14.4]hexatriacontane-12-carboxamide
Synonyms
Antimicrobial peptide IB-367; Iseganan [INN]
Appearance
White or Off-white Lyophilized Powder
Density
1.5±0.1 g/cm3
Sequence
RGGLCYCRGRFCVCVGR
Storage
Store at -20°C
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
InChI Key
GUCYBPFJNGVFEB-XELKFLSISA-N
Canonical SMILES
CC(C)CC(C(=O)NC1CSSCC(NC(=O)C(NC(=O)C2CSSCC(C(=O)NC(C(=O)NCC(=O)NC(C(=O)NC(C(=O)N2)CC3=CC=CC=C3)CCCNC(=N)N)CCCNC(=N)N)NC(=O)C(NC1=O)CC4=CC=C(C=C4)O)C(C)C)C(=O)NC(C(C)C)C(=O)NCC(=O)NC(CCCNC(=N)N)C(=O)N)NC(=O)CNC(=O)CNC(=O)C(CCCNC(=N)N)N
1. Iseganan HCl: a novel antimicrobial agent
Francis J Giles, Rebecca Redman, Salim Yazji, Lisa Bellm Expert Opin Investig Drugs. 2002 Aug;11(8):1161-70. doi: 10.1517/13543784.11.8.1161.
Iseganan HCl is an antimicrobial peptide under development for the prevention of oral mucositis, a severe consequence of some chemotherapy and radiation therapy regimens. Several attributes of iseganan make it an optimal candidate for study in this clinical situation where both local and systemic host defenses may be impaired. These include broad spectrum and rapid bactericidal activity, a lack of observed resistance and cross-resistance and stability in biological fluids. Clinical trials of patients receiving stomatotoxic chemotherapy followed by a haematopoietic stem cell transplant show iseganan reduces the occurrence of oral mucositis and ameliorates sequelae such as mouth pain, throat pain and difficulty swallowing. Iseganan is well-tolerated, which is partly attributable to a lack of systemic absorption following topical oral administration. Other promising areas of investigation include topical oral application for the prevention of ventilator-associated pneumonia and nebulisation for treatment of chronic lung infection in patients with cystic fibrosis. Future studies will expand on the role of iseganan as a novel antimicrobial.
3. Iseganan (IntraBiotics pharmaceuticals)
Jeffrey H Toney Curr Opin Investig Drugs. 2002 Feb;3(2):225-8.
Iseganan (IB-367) is a protegrin under development by IntraBiotics, as part of a larger protegrin program, for the potential treatment of oral mucositis, a frequent side effect of anticancer therapies. The company is developing three formulations of the drug: A rinse for the potential treatment of mucositis, an aerosolized liquid for the potential treatment of respiratory infection and a gel formulation for the potential treatment of pneumonia [376325]. Iseganan kills a broad-spectrum of bacteria and fungi, including those resistant to conventional antimicrobial drugs, by attaching to and destroying the integrity of the lipid cell membrane [241594]. Until August 1999, Pharmacia & Upjohn was a codeveloper of iseganan. IntraBiotics re-acquired the global rights to iseganan in December 1999, and both companies agreed to terminate the collaboration [335766]. In May 2000, analysts at SG Cowen predicted the drug's potential market at US $100 to US $200 million [376325].
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