PEXIGANAN ACETATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C122H210N32O22.C2H4O2
Molecular Weight	2537.226
Optical Activity	UNSPECIFIED
Defined Stereocenters	21 / 21
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(O)=O.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=ZYMCXUWEZQKVIO-IJAHCEAPSA-N

InChI=1S/C122H210N32O22.C2H4O2/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;1-2(3)4/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);1H3,(H,3,4)/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

Molecular Formula	C122H210N32O22
Molecular Weight	2477.174
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	21 / 21
E/Z Centers	14
Optical Activity	UNSPECIFIED

Molecular Formula	C2H4O2
Molecular Weight	60.052
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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
What Is the 'Minimum Inhibitory Concentration' (MIC) of Pexiganan Acting on Escherichia coli?-A Cautionary Case Study.	2016	27193536

Sample Use Guides

In Vivo Use Guide

1% cream (frequency of administration not stated)

Route of Administration: Topical

Substance Class	Chemical Created by `admin` on `Sat Dec 16 00:43:55 GMT 2023` Edited by `admin` on `Sat Dec 16 00:43:55 GMT 2023`
Record UNII	63S35FF5KS
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PEXIGANAN ACETATE

Official Name

English

MSI-78

Code

English

LOCILEX

Common Name

English

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-L-LYSINAMIDE ACETATE

Common Name

English

PEXIGANAN ACETATE [MI]

Common Name

English

CYTOLEX

Brand Name

English

PEXIGANAN ACETATE [USAN]

Common Name

English

Code System Code Type Description

PUBCHEM

16137672