ETALOCIB

Details

Stereochemistry	ACHIRAL
Molecular Formula	C33H33FO6
Molecular Weight	544.6099
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCC1=C(OC2=C(C=CC=C2)C(O)=O)C=CC=C1OCCCOC3=C(CC)C=C(C(O)=C3)C4=CC=C(F)C=C4

InChI

InChIKey=YFIZRWPXUYFCSN-UHFFFAOYSA-N

InChI=1S/C33H33FO6/c1-3-9-25-29(12-7-13-30(25)40-31-11-6-5-10-26(31)33(36)37)38-18-8-19-39-32-21-28(35)27(20-22(32)4-2)23-14-16-24(34)17-15-23/h5-7,10-17,20-21,35H,3-4,8-9,18-19H2,1-2H3,(H,36,37)

HIDE SMILES / InChI

Molecular Formula	C33H33FO6
Molecular Weight	544.6099
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/9547580 | https://www.ncbi.nlm.nih.gov/pubmed/7786309 | https://www.ncbi.nlm.nih.gov/pubmed/8613940 | https://www.ncbi.nlm.nih.gov/pubmed/9862783 | https://www.ncbi.nlm.nih.gov/pubmed/15846111 | https://www.ncbi.nlm.nih.gov/pubmed/15172119 | https://www.ncbi.nlm.nih.gov/pubmed/17414622 | https://adisinsight.springer.com/drugs/800003262

Etalocib (LY-293111 or VML 295) is a potent and orally active leukotriene B4 receptor antagonist of the biphenylphenol class. It efficiently blocks neutrophil activation and subsequent inflammation. Additionally, it exerts antineoplastic properties through induction of cell cycle arrest and apoptosis in tumor cells. Etalocib was being developed for the treatment of inflammatory diseases and solid tumors.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Leukotriene B4 receptor 3 Target ID: CHEMBL2095160 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7473568	Antagonist 2778	3.3 nM [IC50]
Leukotriene B4 receptor 1 4 Target ID: CHEMBL3911 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8709092\|https://www.ncbi.nlm.nih.gov/pubmed/9862783	Antagonist 2778	25.0 nM [Ki]
Peroxisome proliferator-activated receptor gamma 111 Target ID: CHEMBL235 Sources: https://www.hindawi.com/journals/ppar/2008/827096/\|https://www.ncbi.nlm.nih.gov/pubmed/19190780	Agonist 2678

PubMed

Title	Date	PubMed
Pharmacologic actions of the second-generation leukotriene B4 receptor antagonist LY293111: in vitro studies.	1999 Jan	9862783
Preclinical characterization of 2-[3-[3-[(5-ethyl-4'-fluoro-2-hydroxy[1,1'-biphenyl]-4-yl)oxy]propoxy]-2-propylphenoxy]benzoic acid metabolism: in vitro species comparison and in vivo disposition in rats.	2003 Nov	14570771
The Role of PPARgamma Receptors and Leukotriene B(4) Receptors in Mediating the Effects of LY293111 in Pancreatic Cancer.	2008	19190780
5-lipoxygenase: underappreciated role of a pro-inflammatory enzyme in tumorigenesis.	2010	21833182

Patents

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:03:57 UTC 2023` Edited by `admin` on `Fri Dec 15 16:03:57 UTC 2023`
Record UNII	THY6RIW44R
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ETALOCIB

Official Name

English

2-(3-(3-((5-ETHYL-4'-FLUORO-2-HYDROXYBIPHENYL-4-YL)OXY)PROPOXY)-2-PROPYLPHENOXY)BENZOIC ACID

Systematic Name

English

BENZOIC ACID, 2-(3-(3-((5-ETHYL-4'-FLUORO-2-HYDROXY(1,1'-BIPHENYL)-4-YL)OXY)PROPOXY)-2-PROPYLPHENOXY)-

Common Name

English

etalocib [INN]

Common Name

English

Etalocib [WHO-DD]

Common Name

English

LY-293111

Code

English

LY-193111

Code

English

LY293111

Code

English

ETALOCIB [USAN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C308