Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Etretinate: Difference between pages

{{short description|Chemical compound}}

| Watchedfields = changed

| verifiedrevid = 461098208

| IUPAC_name = Ethyl (2''E'',4''E'',6''E'',8''E'')-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoate

| width = 300

| alt = Skeletal formula of etretinate

| image2 = Etretinate 3D spacefill.png

| alt2 = Space-filling model of the etretinate molecule

| width2 = 280

| tradename = Tigason, formerly Tegison

| Drugs.com = {{drugs.com|MMX|etretinate}}

| pregnancy_US = X

| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled -->

| legal_BR = F4

| legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-07-24 |title=RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |url-status=live |archive-url=https://web.archive.org/web/20230827163149/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |archive-date=2023-08-27 |access-date=2023-08-27 |publisher=[[Diário Oficial da União]] |language=pt-BR |publication-date=2023-07-25}}</ref>

| legal_CA = <!-- OTC, Rx-only, Schedule I, II, III, IV, V, VI, VII, VIII -->

| legal_DE = <!-- Anlage I, II, III or Unscheduled -->

| legal_NZ = <!-- Class A, B, C -->

| legal_UK = <!-- GSL, P, POM, CD, CD Lic, CD POM, CD No Reg POM, CD (Benz) POM, CD (Anab) POM or CD Inv POM / Class A, B, C -->

| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->

| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV -->

| legal_EU =

| legal_US_comment = Withdrawn

| protein_bound = >99%

| metabolism =

| metabolites = Free acid, ''Z''-form, chain shortening

| IUPHAR_ligand = 7599

| CAS_number_Ref = {{cascite|changed|??}}

| CAS_number = 54350-48-0

| UNII_Ref = {{fdacite|correct|FDA}}

| KEGG_Ref = {{keggcite|correct|kegg}}

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEMBL_Ref = {{ebicite|correct|EBI}}

'''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]].<ref name="Mutschler">{{cite book | vauthors = Mutschler E, Schäfer-Korting M |title=Arzneimittelwirkungen |language=German |location=Stuttgart|publisher=Wissenschaftliche Verlagsgesellschaft|year=2001|edition=8|page=728f|isbn=3-8047-1763-2}}</ref> It was subsequently removed from the [[Canada|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==

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]] (''t''_1/2) of 120 days,<ref name="Mutschler" /> which make dosing difficult.

Etretinate has been replaced by [[acitretin]], the free acid (without the [[ethyl group|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,<ref name="Mutschler" /> so that it is still a long-acting [[teratogen]] and pregnancy is prohibited for two years after therapy.<ref name="Austria-Codex">{{cite book|title=Austria-Codex| veditors = Jasek W |publisher= Österreichischer Apothekerverlag |location=Vienna |year=2007 |edition=62nd |isbn=978-3-85200-181-4 |page=5669 |language=German}}</ref>

==Precautions==

*Etretinate is a [[teratogen]], and may cause [[birth defect]]s long after use. Therefore, birth control is advised during therapy, and for at least three years after therapy has stopped.<ref name="MMX" />

*Etretinate should be avoided in [[children]], as it may interfere with [[bone growth]].<ref name="MMX" />

*If a patient has ever taken etretinate, they are not eligible to [[blood donation|donate blood]] in the United States, the United Kingdom, Ireland or Québec, due to the risk of birth defects.<ref>{{cite web | title = Donor Selection Guidelines: Etretinate | url = http://www.transfusionguidelines.org.uk/index.aspx?Publication=WB&Section=5&PageID=3630&AZLetter=E | work = UK Blood Transfusion and Tissue Transplantation Services }}</ref><ref>{{cite web | title = Medications taken on a regular basis that exclude you from donating blood | url = https://www.hema-quebec.qc.ca/sang/donneur-sang/puis-je-donner/medicaments/medicaments-s-t-u.en.html | work = Héma-Québec }}</ref><ref>{{Cite web |title=Health FAQs |url=https://www.giveblood.ie/can-i-give-blood/faqs/health-faqs/health-questions/0-information-about-this-page.html |access-date=2023-10-21 |website=www.giveblood.ie |language=en-ie}}</ref> In Japan, people may not donate blood for two years after ceasing to use the medication.<ref name=JapaneseDrugs/>

==Side effects==

Side effects are those typical of [[hypervitaminosis A]], most commonly<ref name="MMX" />

* 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 FDA in 1986 to treat severe [[psoriasis]]. It was subsequently removed from the [[Canada|Canadian]] market in 1996 and the [[United States]] market in 1998 due to the high risk of birth defects.<ref name="MMX">{{drugs.com|MMX|etretinate}} for etretinate</ref><ref name="Qureshi-2011">{{cite journal | vauthors = Qureshi ZP, Seoane-Vazquez E, Rodriguez-Monguio R, Stevenson KB, Szeinbach SL | title = Market withdrawal of new molecular entities approved in the United States from 1980 to 2009 | journal = Pharmacoepidemiology and Drug Safety | volume = 20 | issue = 7 | pages = 772–7 | date = July 2011 | pmid = 21574210 | doi = 10.1002/pds.2155 | s2cid = 23821961 }}</ref><ref name=Fung-2001>{{cite journal| vauthors = Fung M, Thornton A, Mybeck K, Wu JH, Hornbuckle K, Muniz E |title=Evaluation of the Characteristics of Safety Withdrawal of Prescription Drugs from Worldwide Pharmaceutical Markets-1960 to 1999|journal=Therapeutic Innovation & Regulatory Science |date=1 January 2001 |volume=35 |issue=1 |pages=293–317 |doi=10.1177/009286150103500134 |s2cid=73036562}}</ref>

In Japan, the drug remains on market branded ''Tigason''.<ref name=JapaneseDrugs>{{cite web | title = Tigason Drug information sheet | work = RAD-AR Council Japan | url = http://rad-ar.or.jp/siori/english/kekka.cgi?n=1052 | archive-url = https://web.archive.org/web/20130127000838/http://rad-ar.or.jp/siori/english/kekka.cgi?n=1052 | archive-date = 27 January 2013 }}</ref>

== See also ==

* [[Isotretinoin]]

* [[List of withdrawn drugs]]

== References ==

{{Reflist|2}}

{{Antipsoriatics}}

{{Retinoid receptor modulators}}

[[Category:Retinoids]]

[[Category:Withdrawn drugs]]

[[Category:Ethyl esters]]

[[Category:Phenol ethers]]

[[Category:Polyenes]]