Etretinate
 | |
| Systematic (IUPAC) name | |
|---|---|
| ethyl 9-(4-methoxy-2,3,6-trimethyl-phenyl)- 3,7-dimethyl-nona- 2,4,6,8-tetraenoate | |
| Clinical data | |
| AHFS/Drugs.com | Micromedex Detailed Consumer Information |
| MedlinePlus | a601010 |
| Oral | |
| Pharmacokinetic data | |
| Half-life | 120 days |
| Identifiers | |
54350-48-0  | |
| D05BB01 | |
| PubChem | CID 5282375 |
| DrugBank |
DB00926  |
| ChemSpider |
4445538 |
| UNII |
65M2UDR9AG |
| KEGG |
D00316 |
| ChEBI |
CHEBI:4913 |
| ChEMBL |
CHEMBL464 |
| Chemical data | |
| Formula | C23H30O3 |
| 354.483 g/mol | |
|
SMILES
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Etretinate (trade name Tegison) is a medication developed by Hoffmann–La Roche that was approved by the FDA in 1986 to treat severe psoriasis. It is a second-generation retinoid. It was subsequently removed from the Canadian market in 1996 and the United States market in 1998 due to the high risk of birth defects. It remains on the market in Japan.
Properties
Etretinate has a low therapeutic index and a long elimination half-life (t1/2) of 120 days, which make dosing difficult.
Etretinate is an aromatic retinoid, and therefore highly lipophilic. It is stored and released from adipose tissue, so its effects can continue long after dosage stops. It is detectable in the plasma for up to three years following therapy.
Etretinate has been replaced by acitretin, a safer metabolite of etretinate.
Precautions
- Etretinate is a teratogen, and may cause birth defects long after use. Therefore, birth control is advised during therapy, and for at least three years after therapy has stopped.
- Etretinate should be avoided in children, as it may interfere with bone growth.
- If a patient has ever taken etretinate, he or she is not eligible to donate blood, due to the risk of birth defects.[1]
Side effects
- Hepatitis
- Pseudotumor cerebri
- Diffuse idiopathic skeletal Hyperostosis
History
The drug was approved by the FDA in 1986 to treat severe psoriasis. It was subsequently removed from the Canadian market in 1996 and the United States market in 1998 due to the high risk of birth defects.[2][3]
In Japan, the drug remains on market branded Tigason.[4] People may not donate blood for two years after ceasing to use the medication.[4]
See also
References
- ↑ UK Blood Transfusion and Tissue Transplantation Services
- ↑ Qureshi, ZP; Seoane-Vazquez, E; Rodriguez-Monguio, R; Stevenson, KB; Szeinbach, SL (July 2011). "Market withdrawal of new molecular entities approved in the United States from 1980 to 2009.". Pharmacoepidemiology and drug safety 20 (7): 772–7. doi:10.1002/pds.2155. PMID 21574210.
- ↑ Fung, M.; Thornton, A.; Mybeck, K.; Wu, J. H.-h.; Hornbuckle, K.; Muniz, E. (1 January 2001). "Evaluation of the Characteristics of Safety Withdrawal of Prescription Drugs from Worldwide Pharmaceutical Markets-1960 to 1999". Therapeutic Innovation & Regulatory Science 35 (1): 293–317. doi:10.1177/009286150103500134.
- ↑ 4.0 4.1 Tigason
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