U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of LANCOVUTIDE

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
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.

Approval Year

PubMed

PubMed

TitleDatePubMed
Emerging treatments in cystic fibrosis.
2009 Oct 1

Sample Use Guides

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.
Name Type Language
LANCOVUTIDE
INN   WHO-DD  
INN  
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
Created by admin on Fri Dec 15 15:53:13 GMT 2023 , Edited by admin on Fri Dec 15 15:53:13 GMT 2023
FDA ORPHAN DRUG 107897
Created by admin on Fri Dec 15 15:53:13 GMT 2023 , Edited by admin on Fri Dec 15 15:53:13 GMT 2023
Code System Code Type Description
ChEMBL
CHEMBL2108327
Created by admin on Fri Dec 15 15:53:13 GMT 2023 , Edited by admin on Fri Dec 15 15:53:13 GMT 2023
PRIMARY
PUBCHEM
101611009
Created by admin on Fri Dec 15 15:53:13 GMT 2023 , Edited by admin on Fri Dec 15 15:53:13 GMT 2023
PRIMARY
CHEBI
77834
Created by admin on Fri Dec 15 15:53:13 GMT 2023 , Edited by admin on Fri Dec 15 15:53:13 GMT 2023
PRIMARY
DRUG BANK
DB05029
Created by admin on Fri Dec 15 15:53:13 GMT 2023 , Edited by admin on Fri Dec 15 15:53:13 GMT 2023
PRIMARY
FDA UNII
BPR0F3X56H
Created by admin on Fri Dec 15 15:53:13 GMT 2023 , Edited by admin on Fri Dec 15 15:53:13 GMT 2023
PRIMARY
NCI_THESAURUS
C174642
Created by admin on Fri Dec 15 15:53:13 GMT 2023 , Edited by admin on Fri Dec 15 15:53:13 GMT 2023
PRIMARY
INN
8995
Created by admin on Fri Dec 15 15:53:13 GMT 2023 , Edited by admin on Fri Dec 15 15:53:13 GMT 2023
PRIMARY
CAS
1391-36-2
Created by admin on Fri Dec 15 15:53:13 GMT 2023 , Edited by admin on Fri Dec 15 15:53:13 GMT 2023
PRIMARY