Etretinate

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Etretinate
Skeletal formula of etretinate
Space-filling model of the etretinate molecule
Clinical data
Trade names Tigason, formerly Tegison
AHFS/Drugs.com Drugs.com archive
MedlinePlus a601010
Pregnancy
category
  • US: X (Contraindicated)
Routes of
administration
Oral
ATC code
Legal status
Legal status
  • US: Withdrawn
Pharmacokinetic data
Protein binding >99%
Metabolites Free acid, Z-form, chain shortening
Elimination half-life 120 days
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
ECHA InfoCard 100.053.727 Edit this at Wikidata
Chemical and physical data
Formula C23H30O3
Molar mass 354.483 g/mol
3D model (JSmol)
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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.[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.

Pharmacology[edit]

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Etretinate has been replaced by acitretin, the free acid (without the ethyl ester).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[edit]

Side effects[edit]

Side effects are those typical of hypervitaminosis A, most commonly[3]

History[edit]

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[edit]

References[edit]

  1. ^ a b c Mutschler, Ernst; Schäfer-Korting, Monika (2001). Arzneimittelwirkungen (in German) (8 ed.). Stuttgart: Wissenschaftliche Verlagsgesellschaft. p. 728f. ISBN 3-8047-1763-2.
  2. ^ Jasek, W, ed. (2007). Austria-Codex (in German) (62nd ed.). Vienna: Österreichischer Apothekerverlag. p. 5669. ISBN 978-3-85200-181-4.
  3. ^ a b c d Drugs.com archive for etretinate
  4. ^ UK Blood Transfusion and Tissue Transplantation Services
  5. ^ a b Drug information sheet: Tigason
  6. ^ 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.
  7. ^ 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.