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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 of LEUKOTRIENE D4

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

Description

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 TargetPharmacologyConditionPotency
0.7 nM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
Unknown
Diagnostic
Unknown

PubMed

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.