ELISIDEPSIN TRIFLUOROACETATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C75H124N14O16.C2HF3O2
Molecular Weight	1591.8946
Optical Activity	UNSPECIFIED
Defined Stereocenters	17 / 17
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure of ELISIDEPSIN TRIFLUOROACETATE

Structure Search

SMILES

OC(=O)C(F)(F)F.[H][C@](NC(=O)[C@H](NC(=O)CC[C@@H](C)CC)C(C)C)([C@@H](C)O)C(=O)N[C@@H](C(C)C)C(=O)N[C@H](C(C)C)C(=O)N1CCC[C@]1([H])C(=O)N[C@@H](CCCN)C(=O)N[C@]([H])([C@@H](C)CC)C(=O)N[C@@H]2[C@@H](C)OC(=O)[C@@H](NC(=O)\C(NC(=O)[C@H](CC3=CC=CC=C3)NC(=O)[C@H](NC(=O)[C@]([H])(NC2=O)[C@@H](C)CC)C(C)C)=C\C)C(C)C

InChI

InChIKey=FUDHRLIJYPGBOX-MWGCIELCSA-N

InChI=1S/C75H124N14O16.C2HF3O2/c1-20-43(15)33-34-53(91)80-54(38(5)6)68(97)87-61(46(18)90)72(101)82-56(40(9)10)69(98)83-57(41(11)12)74(103)89-36-28-32-52(89)66(95)78-50(31-27-35-76)64(93)85-59(44(16)21-2)71(100)88-62-47(19)105-75(104)58(42(13)14)84-63(92)49(23-4)77-65(94)51(37-48-29-25-24-26-30-48)79-67(96)55(39(7)8)81-70(99)60(45(17)22-3)86-73(62)102;3-2(4,5)1(6)7/h23-26,29-30,38-47,50-52,54-62,90H,20-22,27-28,31-37,76H2,1-19H3,(H,77,94)(H,78,95)(H,79,96)(H,80,91)(H,81,99)(H,82,101)(H,83,98)(H,84,92)(H,85,93)(H,86,102)(H,87,97)(H,88,100);(H,6,7)/b49-23-;/t43-,44-,45-,46+,47+,50-,51-,52+,54+,55+,56-,57+,58-,59+,60+,61-,62+;/m0./s1

HIDE SMILES / InChI

Molecular Formula	C75H124N14O16
Molecular Weight	1477.8713
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	17 / 17
E/Z Centers	6
Optical Activity	UNSPECIFIED

Molecular Formula	C2HF3O2
Molecular Weight	114.0233
Charge	0
Count

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

Description
Sources: https://journals.prous.com/journals/servlet/xmlxsl/pk_journals.xml_summary_pr?p_JournalId=2&p_RefId=1497635&p_IsPs=N | https://www.ncbi.nlm.nih.gov/pubmed/21556352 | https://adisinsight.springer.com/drugs/800023321

Elisidepsin (Irvalec®, PM02734) is a depsipeptide produced by chemical synthesis and chosen for development as an antineoplastic agent based on its in vitro activity against human solid tumor cell lines, in vivo activity in hollow fibers and xenografted human tumors, as well as its acceptable preclinical toxicology profile. Elisidepsin causes a typical necrotic cell death and induces profound alterations in tumor cell morphology. Elisidepsin inserts into the plasma membrane causing rapid loss of integrity and necrotic cell death in tumor cells. PharmaMar was developing elisidepsin for the treatment of cancer. However, development of the compound has been suspended.

Originator

Approval Year

PubMed

Title	Date	PubMed
Irvalec inserts into the plasma membrane causing rapid loss of integrity and necrotic cell death in tumor cells.	2011 Apr 27	21556352
Predictive factors of sensitivity to elisidepsin, a novel Kahalalide F-derived marine compound.	2013 Mar 20	23519149

Sample Use Guides

In Vitro Use Guide

Elisidepsin showed potent and broad cytotoxic effects in a cancer cell line panel, being active at concentrations ranging from 0.4 to 2 μM that may be relevant for clinical settings.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 09:58:43 GMT 2023` Edited by `admin` on `Sat Dec 16 09:58:43 GMT 2023`
Record UNII	3I37B5DY4Q
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ELISIDEPSIN TRIFLUOROACETATE

Common Name

English

PM-02734

Common Name

English

IRVALEC

Brand Name

English

ELISIDEPSIN TRIFLUOROACETATE [MI]

Common Name

English

Code System Code Type Description

PUBCHEM

46926348