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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/03/24 21:14:32」(JST)
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| Systematic (IUPAC) name | |
|---|---|
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Ethyl (2E,4E,6E,8E)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoate
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| Clinical data | |
| Trade names | Tigason, formerly Tegison |
| AHFS/Drugs.com | Drugs.com archive |
| MedlinePlus | a601010 |
| Pregnancy category |
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| Routes of administration |
Oral |
| Legal status | |
| Legal status |
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| Pharmacokinetic data | |
| Protein binding | >99% |
| Metabolites | Free acid, Z-form, chain shortening |
| Biological half-life | 120 days |
| Identifiers | |
| CAS Number | 54350-48-0 N |
| ATC code | D05BB01 (WHO) |
| PubChem | CID 5282375 |
| IUPHAR/BPS | 7599 |
| DrugBank | DB00926 Y |
| ChemSpider | 4445538 Y |
| UNII | 65M2UDR9AG Y |
| KEGG | D00316 Y |
| ChEBI | CHEBI:4913 Y |
| ChEMBL | CHEMBL464 Y |
| Chemical data | |
| Formula | C23H30O3 |
| Molar mass | 354.483 g/mol |
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| NY (what is this?) (verify) | |
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.[1] 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 as Tigason.
Contents
- 1 Pharmacology
- 2 Precautions
- 3 Side effects
- 4 History
- 5 See also
- 6 References
Pharmacology
Etretinate is a highly lipophilic, aromatic retinoid. 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 a low therapeutic index and a long elimination half-life (t1/2) of 120 days,[1] which make dosing difficult.
Etretinate has been replaced by acitretin, the free acid (without the ethyl ester). While acitretin is less lipophilic and has a half-life of only 50 hours, it is partly metabolized to etretinate in the body,[1] so that it is still a long-acting teratogen and pregnancy is prohibited for two years after therapy.[2]
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.[3]
- Etretinate should be avoided in children, as it may interfere with bone growth.[3]
- If a patient has ever taken etretinate, he or she is not eligible to donate blood in the United States or the United Kingdom, due to the risk of birth defects.[4] In Japan, people may not donate blood for two years after ceasing to use the medication.[5]
Side effects
Side effects are those typical of hypervitaminosis A, most commonly[3]
- bone or joint pain, stiffness; in long-term treatment diffuse idiopathic skeletal hyperostosis
- muscular or abdominal cramps
- dry, burning, itching eyelids
- unusual bruising
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.[3][6][7]
In Japan, the drug remains on market branded Tigason.[5]
See also
- Isotretinoin
- List of withdrawn drugs
References
- ^ a b c Mutschler, Ernst; Schäfer-Korting, Monika (2001). Arzneimittelwirkungen (in German) (8 ed.). Stuttgart: Wissenschaftliche Verlagsgesellschaft. p. 728f. ISBN 3-8047-1763-2.
- ^ Jasek, W, ed. (2007). Austria-Codex (in German) (62nd ed.). Vienna: Österreichischer Apothekerverlag. p. 5669. ISBN 978-3-85200-181-4.
- ^ a b c d Drugs.com archive for etretinate
- ^ UK Blood Transfusion and Tissue Transplantation Services
- ^ a b Drug information sheet: Tigason
- ^ 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.
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UpToDate Contents
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- 1. 掌蹠膿疱症：治療 palmoplantar pustulosis treatment
- 2. 膿疱性乾癬：マネージメント pustular psoriasis management
- 3. 妊娠時の乾癬のマネージメント management of psoriasis in pregnancy
- 4. 乾癬性関節炎の治療 treatment of psoriatic arthritis
- 5. 汗孔角化症 porokeratosis
English Journal
- Teratogenic risk with etretinate and acitretin treatment.
- Geiger JM1, Baudin M, Saurat JH.
- Dermatology (Basel, Switzerland).Dermatology.1994;189(2):109-16.
- PMID 8075435
- Retinoids in psoriasis and disorders of keratinization.
- Fritsch PO1.
- Journal of the American Academy of Dermatology.J Am Acad Dermatol.1992 Dec;27(6 Pt 2):S8-14.
- PMID 1460124
- Multiple carcinoma in patients with psoriasis caused by psoralen-ultraviolet A therapy, natural killer cell insufficiency, or intensified sun exposure?
- Rubins AY1, Branta DK, Hartmane IV, Rajevska AS, Gutmane RA, Lielbriedis YM.
- Cutis.Cutis.1992 Jun;49(6):430-2.
- PMID 1628511
Related Links
- Tegison Etretinate Dermatology A retinoid for severe psoriasis that is linked to major teratogenicity ... Would be donors who have ever taken the psoriasis drug Tegison (removed from the market because of its risk of causing birth ...
- Tegison - Get up-to-date information on Tegison side effects, uses, dosage, overdose, pregnancy, alcohol and more. Learn more about Tegison ... Message Body (Your Name) thought you would like to see this page from the rxwiki ...
Related Pictures
★リンクテーブル★
| リンク元 | 「エトレチナート」 |
「エトレチナート」
- 英
- etretinate
- 商
- チガソン Tegison