PEXIGANAN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C122H210N32O22
Molecular Weight	2477.174
Optical Activity	UNSPECIFIED
Defined Stereocenters	21 / 21
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC[C@H](C)[C@H](NC(=O)CN)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC2=CC=CC=C2)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C)C(=O)N[C@@H](CC3=CC=CC=C3)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(N)=O

InChI

InChIKey=KGZGFSNZWHMDGZ-KAYYGGFYSA-N

InChI=1S/C122H210N32O22/c1-13-77(9)102(152-98(155)71-132)120(174)135-73-100(157)139-86(50-26-35-59-125)110(164)150-96(69-82-44-20-16-21-45-82)118(172)148-93(66-74(3)4)116(170)145-90(54-30-39-63-129)113(167)142-87(51-27-36-60-126)109(163)137-79(11)105(159)141-88(52-28-37-61-127)112(166)143-91(55-31-40-64-130)114(168)149-95(68-81-42-18-15-19-43-81)107(161)134-72-99(156)138-85(49-25-34-58-124)108(162)136-80(12)106(160)147-97(70-83-46-22-17-23-47-83)119(173)153-101(76(7)8)121(175)146-92(56-32-41-65-131)115(169)154-103(78(10)14-2)122(176)151-94(67-75(5)6)117(171)144-89(53-29-38-62-128)111(165)140-84(104(133)158)48-24-33-57-123/h15-23,42-47,74-80,84-97,101-103H,13-14,24-41,48-73,123-132H2,1-12H3,(H2,133,158)(H,134,161)(H,135,174)(H,136,162)(H,137,163)(H,138,156)(H,139,157)(H,140,165)(H,141,159)(H,142,167)(H,143,166)(H,144,171)(H,145,170)(H,146,175)(H,147,160)(H,148,172)(H,149,168)(H,150,164)(H,151,176)(H,152,155)(H,153,173)(H,154,169)/t77-,78-,79-,80-,84-,85-,86-,87-,88-,89-,90-,91-,92-,93-,94-,95-,96-,97-,101-,102-,103-/m0/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9878992 | https://www.ncbi.nlm.nih.gov/pubmed/25583717 | https://www.ncbi.nlm.nih.gov/pubmed/10103181 | https://adisinsight.springer.com/drugs/800002904 | https://www.ncbi.nlm.nih.gov/pubmed/30569865

Pexiganan is a 22-amino-acid synthetic cationic peptide. It is an analog of magainin 2, which is a host defense peptide isolated from frog skin. The drug is thought to act by disturbing the permeability of the cell membrane or cell wall. Pexiganan exhibited in vitro broad-spectrum antibacterial activity when it was tested against 3,109 clinical isolates of gram-positive and gram-negative, anaerobic and aerobic bacteria. It is currently in phase 3 clinical trials as a topical antimicrobial agent for the treatment of mild infections associated with diabetic foot ulcers. In vitro data for pexiganan acetate suggest that the drug does have hemolytic activity at concentrations relevant for antibacterial activity. In association with tigecycline, pexiganan administration could overcome antibiotic resistance and increase the effectiveness of treatment against P. aeruginosa sepsis.

Originator

Approval Year

PubMed

Title	Date	PubMed
Pexiganan acetate.	1998 Dec	9878992
In vitro antibacterial properties of pexiganan, an analog of magainin.	1999 Apr	10103181
In vitro spectrum of pexiganan activity when tested against pathogens from diabetic foot infections and with selected resistance mechanisms.	2015 Mar	25583717
What Is the 'Minimum Inhibitory Concentration' (MIC) of Pexiganan Acting on Escherichia coli?-A Cautionary Case Study.	2016	27193536
In vitro spectrum of pexiganan activity; bactericidal action and resistance selection tested against pathogens with elevated MIC values to topical agents.	2016 Sep	27352729
In Vitro Activities of Pexiganan and 10 Comparator Antimicrobials against 502 Anaerobic Isolates Recovered from Skin and Skin Structure Infections.	2017 Dec	28993327
In Vitro Activity of Pexiganan and 10 Comparator Antimicrobials against 234 Isolates, Including 93 Pasteurella Species and 50 Anaerobic Bacterial Isolates Recovered from Animal Bite Wounds.	2017 Jun	28373186
Efficacy of Pexiganan Combination with Tigecycline in a Mouse Model of Pseudomonas aeruginosa Sepsis.	2018	30569865
Cost-effective downstream processing of recombinantly produced pexiganan peptide and its antimicrobial activity.	2018 Jan 24	29368022

Sample Use Guides

In Vivo Use Guide

1% cream (frequency of administration not stated)

Route of Administration: Topical

Name

Type

Language

PEXIGANAN

Official Name

English

7-L-LYSINE-8-L-LYSINE-10-L-LYSINE-18-L-LYSINE-19-DE-L-GLUTAMIC ACID-21-L-LEUCINE-23-L-LYSINAMIDE MAGAININ I

Common Name

English

L-LYSINAMIDE, GLYCYL-L-ISOLEUCYLGLYCYL-L-LYSYL-L-PHENYLALANYL-L-LEUCYL-L-LYSYL-L-LYSYL-L-ALANYL-L-LYSYL-L-LYSYL-L-PHENYLALANYLGLYCYL-L-LYSYL-L-ALANYL-L-PHENYLALANYL-L-VALYL-L-LYSYL-L-ISOLEUCYL-L-LEUCYL-L-LYSYL-

Systematic Name

English

PEXIGANAN [MI]

Common Name

English

GLY-ILE-GLY-LYS-PHE-LEU-LYS-LYS-ALA-LYS-LYS-PHE-GLY-LYS-ALA-PHE-VAL-LYS-ILE-LEU-LYS-LYS-NH2

Common Name

English

pexiganan [INN]

Common Name

English

Code System Code Type Description

PUBCHEM

16132253