Drug/Small Molecule:
etretinate

2D structure

Overview

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. (source: Drug Bank)

Indication

For the treatment of severe psoriasis in adults. (source: Drug Bank)

ATC Therapeutic Category

  • D05BB:Retinoids for treatment of psoriasis

Pharmacology, Interactions, and Contraindications

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. (source: Drug Bank)

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. (source: Drug Bank)

Food Interactions

Avoid alcohol completely up to 2 months after discontinuation.
Increases absorption, take with food. (source: Drug Bank)

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. (source: Drug Bank)

Protein Binding

More than 99% bound to plasma proteins, predominantly lipoproteins, whereas its active metabolite, acetretin (etretin), is predominantly bound to albumin. (source: Drug Bank)

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. (source: Drug Bank)

Toxicity

Symptoms of overdose include headache and vertigo. (source: Drug Bank)

Isomeric SMILES Code:

CCOC(=O)/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C(=C(C=C1C)OC)C)C (source: Drug Bank)

A list of non-curated publications that mention this drug along with other genes is available.

Drug Targets

Gene Description
CRABP1 Uncurated Annotation (source: Drug Bank)
RARA Uncurated Annotation (source: Drug Bank)
RARB Uncurated Annotation (source: Drug Bank)
RARG Uncurated Annotation (source: Drug Bank)
RXRA Uncurated Annotation (source: Drug Bank)
RXRB Uncurated Annotation (source: Drug Bank)
RXRG Uncurated Annotation (source: Drug Bank)

A list of non-curated publications that mention this drug along with other drugs is available.

Drug Interactions

Drug Description
acenocoumarol Uncurated Annotation Retinoids decreases the anticoagulant effect (source: Drug Bank)
dicumarol Uncurated Annotation Retinoids decreases the anticoagulant effect (source: Drug Bank)
doxycycline Uncurated Annotation Increased risk of intracranial hypertension (source: Drug Bank)
methotrexate Uncurated Annotation Acitretin/etretinate increases the effect and toxicity of methotrexate (source: Drug Bank)
minocycline Uncurated Annotation Increased risk of intracranial hypertension (source: Drug Bank)
oxytetracycline Uncurated Annotation Increased risk of intracranial hypertension (source: Drug Bank)
tetracycline Uncurated Annotation Increased risk of intracranial hypertension (source: Drug Bank)
warfarin Uncurated Annotation Retinoids decreases the anticoagulant effect (source: Drug Bank)

Non-Curated Information

A list of non-curated publications that mention this drug along with other diseases is available.

LinkOuts

Web Resource:
Wikipedia
DrugBank:
DB00926
KEGG Drug ID:
D00316
PubChem Compound ID:
3312
PubChem Substance ID:
7847382

Common Searches

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Non-Curated Publications

A list of non-curated publications that mention this drug is available.

PharmGKB integrates drug information from different sources: DrugBank, Open Eye Scientific Software.
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