OMIGANAN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C90H127N27O12
Molecular Weight	1779.1451
Optical Activity	UNSPECIFIED
Defined Stereocenters	13 / 13
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC[C@H](C)[C@H](N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC1=CNC2=C1C=CC=C2)C(=O)N3CCC[C@H]3C(=O)N[C@@H](CC4=CNC5=C4C=CC=C5)C(=O)N[C@@H](CC6=CNC7=C6C=CC=C7)C(=O)N8CCC[C@H]8C(=O)N[C@@H](CC9=CNC%10=C9C=CC=C%10)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCCN)C(N)=O

InChI

InChIKey=MVPAMLBUDIFYGK-BHDRXCTLSA-N

InChI=1S/C90H127N27O12/c1-5-51(4)75(92)85(127)113-68(41-50(2)3)80(122)109-67(32-18-38-102-90(98)99)79(121)114-71(44-54-48-105-62-27-12-8-23-58(54)62)86(128)116-39-19-34-74(116)84(126)112-70(43-53-47-104-61-26-11-7-22-57(53)61)82(124)115-72(45-55-49-106-63-28-13-9-24-59(55)63)87(129)117-40-20-33-73(117)83(125)111-69(42-52-46-103-60-25-10-6-21-56(52)60)81(123)110-66(31-17-37-101-89(96)97)78(120)108-65(30-16-36-100-88(94)95)77(119)107-64(76(93)118)29-14-15-35-91/h6-13,21-28,46-51,64-75,103-106H,5,14-20,29-45,91-92H2,1-4H3,(H2,93,118)(H,107,119)(H,108,120)(H,109,122)(H,110,123)(H,111,125)(H,112,126)(H,113,127)(H,114,121)(H,115,124)(H4,94,95,100)(H4,96,97,101)(H4,98,99,102)/t51-,64-,65-,66-,67-,68-,69-,70-,71-,72-,73-,74-,75-/m0/s1

HIDE SMILES / InChI

Description
Sources: https://clinicaltrials.gov/ct2/show/NCT03688971 | https://clinicaltrials.gov/ct2/show/NCT02576847 | https://clinicaltrials.gov/ct2/show/NCT00211497 | https://www.ncbi.nlm.nih.gov/pubmed/14508884

Omiganan (previously known as MBI-226), is a synthetic, linear, 12 amino acid, cationic peptide analog of indolicidin, being developed as a topical gel for prevention of catheter-associated infections. In September 2000, a phase III trial of omiganan for the potential prevention of catheter-related bloodstream infections was initiated. In July 2018 was completed phase III clinical trial where was evaluated the long-term safety of once-daily application of omiganan topical gel in subjects with severe papulopustular rosacea. In addition, omiganan successfully completed phase II clinical trials where was determined its safety/tolerability in patients with mild to moderate atopic dermatitis and in human subjects with facial acne vulgaris. Besides, omiganan is ongoing phase II to explore the efficacy and pharmacodynamic effects of its topical gel in facial seborrheic dermatitis.

Approval Year

PubMed

Title	Date	PubMed
Quality control guidelines for MIC susceptibility testing of omiganan pentahydrochloride (MBI 226), a novel antimicrobial peptide.	2004 Mar	15004130
Omiganan interaction with bacterial membranes and cell wall models. Assigning a biological role to saturation.	2007 May	17383609
Antimicrobial activity of omiganan pentahydrochloride against contemporary fungal pathogens responsible for catheter-associated infections.	2008 Mar	18180345

Sample Use Guides

In Vivo Use Guide

Omiganan gel applied once daily

Route of Administration: Transdermal

In Vitro Use Guide

Omiganan, a bactericidal and fungicidal cationic peptide being developed as a topical gel for prevention of catheter-associated infections, inhibited commonly occurring fungal pathogens including Candida spp. (106 isolates) at

Name

Type

Language

OMIGANAN

Official Name

English

L-LYSINAMIDE, L-ISOLEUCYL-L-LEUCYL-L-ARGINYL-L-TRYPTOPHYL-L-PROLYL-L-TRYPTOPHYL-L-TRYPTOPHYL-L-PROLYL-L-TRYPTOPHYL-L-ARGINYL-L-ARGINYL-

Common Name

English

OMIGANAN [MI]

Common Name

English

omiganan [INN]

Common Name

English

Code System Code Type Description

DRUG BANK

DB06610