LEUKOTRIENE D4

Possibly Marketed Outside US

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C25H40N2O6S
Molecular Weight	496.66
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	4
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCCC\C=C/C\C=C/C=C/C=C/[C@@H](SC[C@H](N)C(=O)NCC(O)=O)[C@@H](O)CCCC(O)=O

InChI

InChIKey=YEESKJGWJFYOOK-IJHYULJSSA-N

InChI=1S/C25H40N2O6S/c1-2-3-4-5-6-7-8-9-10-11-12-13-16-22(21(28)15-14-17-23(29)30)34-19-20(26)25(33)27-18-24(31)32/h6-7,9-13,16,20-22,28H,2-5,8,14-15,17-19,26H2,1H3,(H,27,33)(H,29,30)(H,31,32)/b7-6-,10-9-,12-11+,16-13+/t20-,21-,22+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C25H40N2O6S
Molecular Weight	496.66
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	4
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23859232
Curator's Comment: The description was created based on several sources, including https://www.drugbank.ca/drugs/DB11858 | https://clinicaltrials.gov/ct2/show/NCT01963741 | https://clinicaltrials.gov/ct2/show/NCT02574975 | https://www.ncbi.nlm.nih.gov/pubmed/16149443 | https://www.ncbi.nlm.nih.gov/pubmed/23403082 | https://www.ncbi.nlm.nih.gov/pubmed/17623009 | https://www.ncbi.nlm.nih.gov/pubmed/16042577 | https://www.ncbi.nlm.nih.gov/pubmed/28165820

Leukotriene D4 (LTD4, 5(S)-hydroxy-6(R)-S-cysteinylglycyl-7,9,11,14-(E, E, Z, Z)-eicosatetraenoic acid) is a pro-inflammatory mediator produced by eosinophils and mast cells, that is known to mediate its effects through specific cell-surface receptors belonging to the G-protein-coupled receptor family, namely the high-affinity CysLT (cysteinyl leukotriene) receptor. LTD4 is associated with the pathogenesis of several inflammatory disorders, such as asthma and inflammatory bowel disease. LTD4 is triggering many processes central to asthma – mucus secretion, bronchoconstriction and increased vascular permeability. Potent LTD4 antagonists protect (by about 50%) against exercise- and allergen-induced bronchoconstriction, suggesting that leukotrienes contribute to bronchoconstrictor responses. Leukotriene D4 has been used in trials studying the diagnostic of Asthma and Allergic Rhinitis.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cysteinyl leukotriene receptor 1 20 Target ID: CHEMBL1798 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23403082	Agonist 2678		0.7 nM [IC50]
Cysteinyl leukotriene receptor 2 3 Target ID: CHEMBL4330 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23859232	Agonist 2678

Conditions

Condition	Modality	Targets	Highest Phase	Product
Asthma 241 Sources: https://clinicaltrials.gov/ct2/show/NCT02574975	Diagnostic		Phase IV 63	Unknown Approved Use Unknown
Allergic rhinitis 100 Sources: https://clinicaltrials.gov/ct2/show/NCT01963741	Diagnostic		Not Provided 504	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
[Leukotriene (B4, C4, D4, E4)].	2005 Aug	16149443

Patents

Sample Use Guides

In Vivo Use Guide

Nasal provocation test was induced by leukotriene D4 with a stepwisely concentration method (4 mcg/ml, 8 mcg/ml, 16 mcg/ml).

Route of Administration: Nasal

In Vitro Use Guide

Mouse microglial cell line BV2, transfected with hCysLT1R or hCysLT2R were used for activity evaluation. Cells were seeded on 35-mm Petri dishes at a density of 1.5×10^5 cells/dish. LTD4 (0.01–100 nmol/L) was added to the culture for 3 h in the presence or absence of CysLT receptor antagonists. One hour before cell harvest, fluorescent microspheres (red, diameter 1 μm, Invitrogen) were added at a density of 6×10^7 particles/dish. The cells were then washed thoroughly with PBS containing 1% bovine serum albumin and detached by trypsinization. Then, the cells were quenched with 1% FBS and subjected to FACScan analysis using a FC500MCL flow cytometer (Beckman Coulter Inc, USA). Fluorescence intensity was detected in the FL-2 channel (564–606 nm) and reflected the phagocytic activity of the cells.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:06:39 UTC 2023` Edited by `admin` on `Fri Dec 15 15:06:39 UTC 2023`
Record UNII	5FNY4416UE
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LEUKOTRIENE D4

Common Name

English

S-((1R,2E,4E,6Z,9Z)-1-((1S)-4-CARBOXY-1-HYDROXYBUTYL)-2,4,6,9-PENTADECATETRAENYL)-L-CYSTEINYLGLYCINE

Systematic Name

English

GLYCINE, S-((1R,2E,4E,6Z,9Z)-1-((1S)-4-CARBOXY-1-HYDROXYBUTYL)-2,4,6,9-PENTADECATETRAEN-1-YL)-L-CYSTEINYL-

Systematic Name

English

LEUKOTRIENE D

Common Name

English

LTD4

Common Name

English

LEUKOTRIENE D4 [MI]

Common Name

English

Code System Code Type Description

CHEBI

28666