Jump to content

Etretinate

From Wikipedia, the free encyclopedia

This is an old revision of this page, as edited by Vanished user 0x8cSXE0x6 (talk | contribs) at 21:50, 22 August 2015. The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

Etretinate
Skeletal formula of etretinate
Space-filling model of the etretinate molecule
Clinical data
AHFS/Drugs.comMicromedex Detailed Consumer Information
MedlinePlusa601010
Routes of
administration
Oral
ATC code
Pharmacokinetic data
Elimination half-life120 days
Identifiers
  • ethyl 9-(4-methoxy-2,3,6-trimethyl-phenyl)- 3,7-dimethyl-nona- 2,4,6,8-tetraenoate
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.053.727 Edit this at Wikidata
Chemical and physical data
FormulaC23H30O3
Molar mass354.483 g/mol g·mol−1
3D model (JSmol)
  • O=C(OCC)\C=C(\C=C\C=C(\C=C\c1c(cc(OC)c(c1C)C)C)C)C
  • InChI=1S/C23H30O3/c1-8-26-23(24)14-17(3)11-9-10-16(2)12-13-21-18(4)15-22(25-7)20(6)19(21)5/h9-15H,8H2,1-7H3/b11-9+,13-12+,16-10+,17-14+ checkY
  • Key:HQMNCQVAMBCHCO-DJRRULDNSA-N checkY
 ☒NcheckY (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. 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Etretinate has been replaced by acitretin, a safer metabolite of etretinate.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 in the United States or the United Kingdom, due to the risk of birth defects.[1]

Side effects

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

  1. ^ UK Blood Transfusion and Tissue Transplantation Services
  2. ^ 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.
  3. ^ 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. ^ a b Tigason