Overview
| IUPAC Name: | ethyl 9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoate |
|---|---|
| Trade Names: | Tegison; Tigason |
| PharmGKB Accession Id: | PA449554 |
Description
Etretinate is a medication used to treat severe psoriasis. It is a synthetic aromatic retinoid. The mechanism of action of etretinate is still incompletely understood although, like retinoic acid, it is thought to interfere with the terminal differentiation of keratinocytes. It is thought to bind to the retinoic acid receptors. Etretinate is also believed to enhance the binding of cAMP to the regulatory RI subunit of cAMP dependent protein kinases. It was removed from the United States market in 1998 and the Canadian market in 1996 as a psoriasis medication, due to the high risk of birth defects. Etretinate is now used to treat T-cell lymphomas. It also appears to inhibit NADH oxidase activity.
Indication
For the treatment of severe psoriasis in adults.
ATC Therapeutic Category
- D05BB:Retinoids for treatment of psoriasis
Pharmacology and Interactions
Mechanism Of Action
The mechanism of action of the active metabolite, acitretin, is unknown, however it is believed to work by targeting specific receptors (retinoid receptors) in the skin which help normalize the growth cycle of skin cells.
Pharmacology
The active metabolite responsible for etretinate's effects, acitretin, is a retinoid. Retinoids have a structure similar to vitamin A and are involved in the normal growth of skin cells. Acitretin works by inhibiting the excessive cell growth and keratinisation (process by which skin cells become thickened due to the deposition of a protein within them) seen in psoriasis. It therefore reduces the thickening of the skin, plaque formation and scaling.
Food Interactions
Avoid alcohol completely up to 2 months after discontinuation. Increases absorption, take with food.
Absorption, Distribution, Metabolism, Elimination & Toxicity
Biotransformation
Extensively metabolized, with significant first-pass metabolism to the pharmacologically active acid form. Subsequent metabolism results in the inactive 13-cis acid form, chain-shortened breakdown products, and conjugates that are ultimately excreted.
Protein Binding
More than 99% bound to plasma proteins, predominantly lipoproteins, whereas its active metabolite, acetretin (etretin), is predominantly bound to albumin.
Absorption
Absorbed in the small intestine. Studies in normal volunteers indicate that the absorption of etretinate is greater in patients consuming whole milk or a high-fat diet than in patients in a fasting state.
Half Life
In one study, the apparent terminal half-life of etretinate after 6 months of therapy was approximately 120 days. In another study of 47 patients who had undergone chronic therapy with etretinate, 5 patients had detectable serum drug concentrations (0.5 to 12 ng/mL) 2.1 to 2.9 years after therapy was completed.
Toxicity
Symptoms of overdose include headache and vertigo.
Chemical Properties
Chemical Formula:
C23H30O3
SMILES Code:
CCOC(=O)/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C(=C(C=C1C)OC)C)C
(Format: OpenEye Isomeric)
Molecular Weight ( average / monoisotopic )
354.4825 / 354.2195
Non-Curated Information
A list of non-curated publications that mention this drug along with other genes is available.
Drug Targets
Non-Curated Information
A list of non-curated publications that mention this drug along with other drugs is available.
Drug Interactions
| acenocoumarol | Retinoids decreases the anticoagulant effect |
| anisindione | Retinoids decreases the anticoagulant effect |
| demeclocycline | Increased risk of intracranial hypertension |
| dicumarol | Retinoids decreases the anticoagulant effect |
| doxycycline | Increased risk of intracranial hypertension |
| methacycline | Increased risk of intracranial hypertension |
| methotrexate | Acitretin/etretinate increases the effect and toxicity of methotrexate |
| minocycline | Increased risk of intracranial hypertension |
| oxytetracycline | Increased risk of intracranial hypertension |
| rolitetracycline | Increased risk of intracranial hypertension |
| tetracycline | Increased risk of intracranial hypertension |
| warfarin | Retinoids decreases the anticoagulant effect |
Non-Curated Information
A list of non-curated publications that mention this drug along with other diseases is available.
LinkOuts
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Non-Curated Publications
A list of non-curated publications that mention this drug is available.