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Acitretin

Acitretin, sold under the brand name Neotigason among others, is a second-generation retinoid. It is taken orally, and is typically used for psoriasis.[5]

Acitretin
Clinical data
Trade namesSoriatane, Neotigason
AHFS/Drugs.comMonograph
MedlinePlusa601010
Pregnancy
category
  • AU: X (High risk)
Routes of
administration
By mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability60%
Protein binding>99.9%
MetabolismLiver
Elimination half-life49 hours
ExcretionFaeces & urine
Identifiers
  • (2E,4E,6E,8E)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid
CAS Number
  • 55079-83-9 Y
PubChem CID
  • 5284513
IUPHAR/BPS
  • 7598
DrugBank
  • DB00459 Y
ChemSpider
  • 4447573 Y
UNII
  • LCH760E9T7
KEGG
  • D02754 Y
ChEBI
  • CHEBI:50173 Y
ChEMBL
  • ChEMBL1131 Y
CompTox Dashboard (EPA)
  • DTXSID6022553
ECHA InfoCard100.054.050
Chemical and physical data
FormulaC21H26O3
Molar mass326.436 g·mol−1
3D model (JSmol)
  • Interactive image
  • O=C(O)\C=C(\C=C\C=C(\C=C\c1c(cc(OC)c(c1C)C)C)C)C
  • InChI=1S/C21H26O3/c1-14(8-7-9-15(2)12-21(22)23)10-11-19-16(3)13-20(24-6)18(5)17(19)4/h7-13H,1-6H3,(H,22,23)/b9-7+,11-10+,14-8+,15-12+ Y
  • Key:IHUNBGSDBOWDMA-AQFIFDHZSA-N Y
  (verify)

Acitretin is an oral retinoid used in the treatment of severe resistant psoriasis. Because of the potential for problems and severe side effects it is generally used in only very severe cases of psoriasis that have been unresponsive to other treatments. It binds to nuclear receptors that regulates gene transcription. They induce keratinocyte differentiation and reduce epidermal hyperplasia, leading to the slowing of cell reproduction. Acitretin is readily absorbed and widely distributed after oral administration. A therapeutic effect occurs after two to four weeks or longer.

Patients who have received the medication are advised against giving blood for at least three years due to the risk of birth defects.[6]

Adverse effects edit

Acitretin is highly teratogenic and noted for the possibility of severe birth defects. It should not be used by pregnant women or women planning to get pregnant within 3 years following the use of acitretin. Sexually active women of childbearing age who use acitretin should also use at least two forms of birth control concurrently. Men and women who use it should not donate blood for three years after using it, because of the possibility that the blood might be used in a pregnant patient and cause birth defects. In addition, it may cause nausea, headache, itching, dry, red or flaky skin, dry or red eyes, dry or chapped lips, swollen lips, dry mouth, thirst, cystic acne or hair loss.[7][8][9]

Pharmacokinetics edit

It is a metabolite of etretinate, which was used prior to the introduction of acitretin. Etretinate was discontinued because it had a narrow therapeutic index as well as a long elimination half-life (t1/2 = 120 days), making dosing difficult. In contrast, acitretin's half-life is approximately 2 days. However, because acitretin can be reverse metabolised into etretinate which has an extremely long half-life, women must avoid becoming pregnant for at least three years[10] after discontinuing acitretin. Therefore, acitretin is generally not recommended for women of child-bearing age with a risk of becoming pregnant.

Society and culture edit

Brand names edit

It is sold under the brand names Soriatane[4] and Neotigason.[2]

References edit

  1. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
  2. ^ a b NEOTIGASON acitretin 10mg capsule blister pack (52455) Australian Department of Health and Aged Care
  3. ^ Anvisa (31 March 2023). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 4 April 2023). from the original on 3 August 2023. Retrieved 15 August 2023.
  4. ^ a b "Soriatane (acitretin) Capsules". dailymed.nlm.nih.gov. Retrieved 30 December 2023.
  5. ^ Zito PM, Mazzoni T (January 2021). "Acitretin". StatPearls. Treasure Island (FL): StatPearls Publishing. PMID 30137855.
  6. ^ AABB Technical Manual, American Association of Blood Banks
  7. ^ "Soriatane". WebMD. Retrieved 15 August 2015.
  8. ^ "Soriatane Side Effects". Drugs.com. Retrieved 15 August 2015.
  9. ^ . RxList. Archived from the original on 2 December 2013. Retrieved 15 August 2015.
  10. ^ "Important Safety Information for SORIATANE". soriatane.com. Retrieved 31 October 2015.

acitretin, this, article, needs, more, reliable, medical, references, verification, relies, heavily, primary, sources, please, review, contents, article, appropriate, references, unsourced, poorly, sourced, material, challenged, removed, find, sources, news, n. This article needs more reliable medical references for verification or relies too heavily on primary sources Please review the contents of the article and add the appropriate references if you can Unsourced or poorly sourced material may be challenged and removed Find sources Acitretin news newspapers books scholar JSTOR December 2023 Acitretin sold under the brand name Neotigason among others is a second generation retinoid It is taken orally and is typically used for psoriasis 5 AcitretinClinical dataTrade namesSoriatane NeotigasonAHFS Drugs comMonographMedlinePlusa601010PregnancycategoryAU X High risk Routes ofadministrationBy mouthATC codeD05BB02 WHO Legal statusLegal statusAU S4 Prescription only 2 BR Class C2 Retinoids 3 CA only UK POM Prescription only US WARNING 1 Rx only 4 Pharmacokinetic dataBioavailability60 Protein binding gt 99 9 MetabolismLiverElimination half life49 hoursExcretionFaeces amp urineIdentifiersIUPAC name 2E 4E 6E 8E 9 4 methoxy 2 3 6 trimethylphenyl 3 7 dimethylnona 2 4 6 8 tetraenoic acidCAS Number55079 83 9 YPubChem CID5284513IUPHAR BPS7598DrugBankDB00459 YChemSpider4447573 YUNIILCH760E9T7KEGGD02754 YChEBICHEBI 50173 YChEMBLChEMBL1131 YCompTox Dashboard EPA DTXSID6022553ECHA InfoCard100 054 050Chemical and physical dataFormulaC 21H 26O 3Molar mass326 436 g mol 13D model JSmol Interactive imageSMILES O C O C C C C C C C C c1c cc OC c c1C C C C CInChI InChI 1S C21H26O3 c1 14 8 7 9 15 2 12 21 22 23 10 11 19 16 3 13 20 24 6 18 5 17 19 4 h7 13H 1 6H3 H 22 23 b9 7 11 10 14 8 15 12 YKey IHUNBGSDBOWDMA AQFIFDHZSA N Y verify Acitretin is an oral retinoid used in the treatment of severe resistant psoriasis Because of the potential for problems and severe side effects it is generally used in only very severe cases of psoriasis that have been unresponsive to other treatments It binds to nuclear receptors that regulates gene transcription They induce keratinocyte differentiation and reduce epidermal hyperplasia leading to the slowing of cell reproduction Acitretin is readily absorbed and widely distributed after oral administration A therapeutic effect occurs after two to four weeks or longer Patients who have received the medication are advised against giving blood for at least three years due to the risk of birth defects 6 Contents 1 Adverse effects 2 Pharmacokinetics 3 Society and culture 3 1 Brand names 4 ReferencesAdverse effects editAcitretin is highly teratogenic and noted for the possibility of severe birth defects It should not be used by pregnant women or women planning to get pregnant within 3 years following the use of acitretin Sexually active women of childbearing age who use acitretin should also use at least two forms of birth control concurrently Men and women who use it should not donate blood for three years after using it because of the possibility that the blood might be used in a pregnant patient and cause birth defects In addition it may cause nausea headache itching dry red or flaky skin dry or red eyes dry or chapped lips swollen lips dry mouth thirst cystic acne or hair loss 7 8 9 Pharmacokinetics editIt is a metabolite of etretinate which was used prior to the introduction of acitretin Etretinate was discontinued because it had a narrow therapeutic index as well as a long elimination half life t1 2 120 days making dosing difficult In contrast acitretin s half life is approximately 2 days However because acitretin can be reverse metabolised into etretinate which has an extremely long half life women must avoid becoming pregnant for at least three years 10 after discontinuing acitretin Therefore acitretin is generally not recommended for women of child bearing age with a risk of becoming pregnant Society and culture editBrand names edit It is sold under the brand names Soriatane 4 and Neotigason 2 References edit FDA sourced list of all drugs with black box warnings Use Download Full Results and View Query links nctr crs fda gov FDA Retrieved 22 October 2023 a b NEOTIGASON acitretin 10mg capsule blister pack 52455 Australian Department of Health and Aged Care Anvisa 31 March 2023 RDC Nº 784 Listas de Substancias Entorpecentes Psicotropicas Precursoras e Outras sob Controle Especial Collegiate Board Resolution No 784 Lists of Narcotic Psychotropic Precursor and Other Substances under Special Control in Brazilian Portuguese Diario Oficial da Uniao published 4 April 2023 Archived from the original on 3 August 2023 Retrieved 15 August 2023 a b Soriatane acitretin Capsules dailymed nlm nih gov Retrieved 30 December 2023 Zito PM Mazzoni T January 2021 Acitretin StatPearls Treasure Island FL StatPearls Publishing PMID 30137855 AABB Technical Manual American Association of Blood Banks Soriatane WebMD Retrieved 15 August 2015 Soriatane Side Effects Drugs com Retrieved 15 August 2015 Soriatane Acitretin Drug Information Description User Reviews Drug Side Effects Interactions Prescribing Information at RxList RxList Archived from the original on 2 December 2013 Retrieved 15 August 2015 Important Safety Information for SORIATANE soriatane com Retrieved 31 October 2015 Portal nbsp Medicine Retrieved from https en wikipedia org w index php title Acitretin amp oldid 1208056491, wikipedia, wiki, book, books, library,

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