etretinate   Click here for help

GtoPdb Ligand ID: 7599

Synonyms: Ro-109359 | Tegison®
Approved drug
etretinate is an approved drug (FDA (1986))
Compound class: Synthetic organic
Comment: Etretinate is a highly lipophilic second-generation retinoid. Its use has largely been discontinued as it was discovered to be a long-acting teratogen, with detectable levels in plasma up to three years post-therapy.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 2
Hydrogen bond donors 0
Rotatable bonds 8
Topological polar surface area 35.53
Molecular weight 354.22
XLogP 6.53
No. Lipinski's rules broken 1
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Canonical SMILES CCOC(=O)C=C(C=CC=C(C=Cc1c(C)cc(c(c1C)C)OC)C)C
Isomeric SMILES CCOC(=O)/C=C(/C=C/C=C(/C=C/c1c(C)cc(c(c1C)C)OC)\C)\C
InChI InChI=1S/C23H30O3/c1-8-26-23(24)14-17(3)11-9-10-16(2)12-13-21-18(4)15-22(25-7)20(6)19(21)5/h9-15H,8H2,1-7H3/b11-9+,13-12+,16-10+,17-14+
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Summary of Clinical Use Click here for help
Etretinate was used to treat severe psoriasis. The drug was removed from the Canadian and US markets due to the high risk of birth defects associated with its use. Etretinate has been replaced by acitretin, a safer metabolite with a much reduced half-life. The brand name Tigason appears to be in use in Japan.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Psoriasis is characterised by aberrant growth of skin cells. Retinoid-induced activation of RAR modulates the expression of genes essential for regulating cell proliferation and differentiation. These drugs may also possess immunomodulatory and anti-inflammatory activities and may inhibit ornithine decarboxylase, an action likely to decrease polyamine synthesis and keratinization. In this way etretinate helps to normalize the growth cycle of skin cells. The precise MMOA has still to be confirmed.