LANCOVUTIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C89H125N23O25S3
Molecular Weight	2013.279
Optical Activity	UNSPECIFIED
Defined Stereocenters	20 / 20
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)[C@@H]1NC(=O)[C@H](CC2=CC=CC=C2)NC(=O)[C@@H]3NC(=O)[C@H](CC4=CC=CC=C4)NC(=O)[C@@H]5CCCN5C(=O)CNC(=O)[C@H](CC6=CC=CC=C6)NC(=O)[C@@H]7CNCCCC[C@H](NC(=O)[C@@H]8NC(=O)[C@H](CC(N)=O)NC(=O)CNC(=O)[C@@H](NC(=O)[C@H](CSC[C@@H](NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@@H](N)CS[C@H]8C)C(=O)N[C@@H](CS[C@H]3C)C(=O)N7)NC1=O)[C@@H](O)C(O)=O)C(O)=O

InChI

InChIKey=SFWLDKQAUHFCBS-AOEYGKNYSA-N

InChI=1S/C89H125N23O25S3/c1-44(2)67-85(131)107-60-42-138-41-59-80(126)106-61-43-140-46(4)69(87(133)103-56(76(122)108-67)35-49-23-12-7-13-24-49)109-77(123)55(34-48-21-10-6-11-22-48)102-83(129)62-27-18-32-112(62)66(116)39-96-73(119)54(33-47-19-8-5-9-20-47)101-79(125)58(104-81(61)127)37-94-31-17-15-26-53(88(134)135)100-86(132)68(110-78(124)57(36-64(93)114)97-65(115)38-95-84(130)70(111-82(60)128)71(117)89(136)137)45(3)139-40-50(91)72(118)98-51(25-14-16-30-90)74(120)99-52(75(121)105-59)28-29-63(92)113/h5-13,19-24,44-46,50-62,67-71,94,117H,14-18,25-43,90-91H2,1-4H3,(H2,92,113)(H2,93,114)(H,95,130)(H,96,119)(H,97,115)(H,98,118)(H,99,120)(H,100,132)(H,101,125)(H,102,129)(H,103,133)(H,104,127)(H,105,121)(H,106,126)(H,107,131)(H,108,122)(H,109,123)(H,110,124)(H,111,128)(H,134,135)(H,136,137)/t45-,46-,50-,51-,52-,53-,54-,55-,56-,57-,58-,59+,60-,61-,62-,67-,68+,69+,70-,71+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C89H125N23O25S3
Molecular Weight	2013.279
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	20 / 20
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19747007 | https://www.ncbi.nlm.nih.gov/pubmed/21091780

LANCOVUTIDE, also known as duramycin, is a 19-amino-acid tetracyclic peptide antibiotic. It is in clinical development for the treatment of cystic fibrosis (CF). It activates an alternative chloride channel in lung epithelial cells by elevating intracellular calcium levels, and may potentially compensate for CF transmembrane conductance regulator deficiency in the airway epithelium and increase the volume of the airway surface liquid.

Originator

Approval Year

PubMed

Title	Date	PubMed
Emerging treatments in cystic fibrosis.	2009 Oct 1	19747007
Effect of duramycin on chloride transport and intracellular calcium concentration in cystic fibrosis and non-cystic fibrosis epithelia.	2010 Dec	21091780
Airway-rehydrating agents for the treatment of cystic fibrosis: past, present, and future.	2011 Jan	21156814
Therapeutic options for hydrating airway mucus in cystic fibrosis.	2015	25823699

Sample Use Guides

In Vitro Use Guide

Lancovutide stimulates Cl- efflux from cystic fibrosis (CF) bronchial epithelial cells (CFBE) in a narrow concentration range (around 1 uM). However, 100 and 250 uM of lancovutide inhibits Cl⁻ efflux from CFBE cells. An inhibitor of the CF transmembrane conductance regulator, gadolinium chloride, inhibited the lancovutide-induced Cl⁻ efflux. No effect on Cl- efflux was observed in non-CF human bronchial epithelial cells (16HBE), human airway submucosal gland cell line, human pancreatic epithelial cells, CF airway submucosal gland epithelial cells, and CF pancreatic cells. The intracellular Ca2+ was increased by 3 uM lancovutide in 16HBE cells but decreased after 1, and 3 uM of lancovutide in CFBE cells.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:53:13 GMT 2023` Edited by `admin` on `Fri Dec 15 15:53:13 GMT 2023`
Record UNII	BPR0F3X56H
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LANCOVUTIDE

Official Name

English

lancovutide [INN]

Common Name

English

Lancovutide [WHO-DD]

Common Name

English

MOLI1901

Code

English

ANCOVENIN, 2-L-LYSINE-6-(3-AMINOALANINE)-10-L-PHENYLALANINE-12-L-PHENYLALANINE-13-L-VALINE-15-(ERYTHRO-3-HYDROXY-L-ASPARTIC ACID)-, CYCLIC (6->19)-IMINE

Common Name

English

LEUCOPEPTIN

Common Name

English

L-LYSINE, L-CYSTEINYL-L-LYSYL-L-GLUTAMINYL-D-CYSTEINYL-L-CYSTEINYL-3-AMINOALANYL-L-PHENYLALANYLGLYCYL-L-PROLYL-L-PHENYLALANYL-(2S,3S)-2-AMINO-3-MERCAPTOBUTANOYL-L-PHENYLALANYL-L-VALYL-L-CYSTEINYL-(3R)-3-HYDROXY-L-.ALPHA.-ASPARTYLGLYCYL-L-ASPARAGINYL-(2S,

Systematic Name

English

DURAMYCIN

Common Name

English

MOLI-1901

Code

English

Classification Tree Code System Code

EU-Orphan Drug

EU/3/02/120