Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C20H31O3.Na |
| Molecular Weight | 342.4481 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 4 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].CCCCC[C@H](O)\C=C\C=C/C\C=C/C\C=C/CCCC([O-])=O
InChI
InChIKey=RQVLCLFGGVMPGP-OMIIFBLASA-M
InChI=1S/C20H32O3.Na/c1-2-3-13-16-19(21)17-14-11-9-7-5-4-6-8-10-12-15-18-20(22)23;/h4-5,8-11,14,17,19,21H,2-3,6-7,12-13,15-16,18H2,1H3,(H,22,23);/q;+1/p-1/b5-4-,10-8-,11-9-,17-14+;/t19-;/m0./s1
DescriptionCurator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/4451568 | http://adisinsight.springer.com/drugs/800019901 | https://goo.gl/7qS2im | https://www.ncbi.nlm.nih.gov/pubmed/12613928 | https://www.ncbi.nlm.nih.gov/pubmed/12613928
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/4451568 | http://adisinsight.springer.com/drugs/800019901 | https://goo.gl/7qS2im | https://www.ncbi.nlm.nih.gov/pubmed/12613928 | https://www.ncbi.nlm.nih.gov/pubmed/12613928
Icomucret (15(S)-HETE) is an hydroxyeicosatetraenoic acid developed by Alcon Research, Ltd for treatment Ophthalmic Disorders. In vitro Icomucret has been shown to inhibit LTB4 formation, 12-HETE formation and specifically inhibits the neutrophil chemotactic effect of LTB4. The inhibition of LTB4 formation is probably due to modulation of the 5- lipoxygenase (LO) because no changes in PGE2 formation have been determined. In vivo, Icomucret inhibits LTB4-induced erythema and edema, and reduces LTB4 in the synovial fluid of carragheenan-induced experimental arthritis in dogs. Icomucret has also some immunomodulatory effects. It inhibits the mixed lymphocyte reaction, induces generation of murine cytotoxic suppressor T cells, and it decreases interferon production by murine lymphoma cells. Furthermore, IL-4 and IL-13 have recently been shown to be potent activators of the 15-LO in mononuclear cells. Icomucret induces the secretion of membrane-bound mucins from human conjunctival and corneal epithelial cells. Icomucret was evaluated in clinical trials for Dry Eye Syndrome treatment. However from 2007 no future development reported, and Icomucret development sims to be discontinued.
Originator
Approval Year
Sample Use Guides
500 nM in BSS (balanced salt solution) vehicle applied topically to the eye immediately prior to a 2 hour desiccation period.
Route of Administration:
Topical
Segments of human bulbar conjunctival tissue were incubated with Icomucret (1-1000 nM) for 30 minutes at 37 degrees C. Secretion of human ocular mucins MUC1, MUC2, MUC4, and MUC5AC into the incubation media was measured by dot-blot immunoassay using antibodies directed to unique mucin polypeptide epitopes. Sodium dodecyl sulfate-polyacrylamide gel electrophoresis and Western blotting were used to verify the specificity of anti-mucin antibody binding and to investigate the presence of MUC1 mucin in human tears. Icomucret (10^(-8)-10^(-6) M) stimulated secretion of conjunctival mucins in a concentration-dependent manner. Significant increases in total mucin secretion were observed at 10^(-7) M Icomucret with a maximum response (>50% increase above controls) at 10^(-6) M. Results of immunoassays showed that Icomucret differentially stimulates secretion of MUC1 mucin with no detectable effects on MUC2, MUC4, or MUC5AC release.
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85169K4AI9
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23694172
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339046-14-9
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PARENT (SALT/SOLVATE)
SUBSTANCE RECORD
