Acitretin

Acitretin
Acitretin
Systematic (IUPAC) name
(2E,4E,6E,8E)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid
Clinical data
Trade names Soriatane
AHFS/Drugs.com monograph
MedlinePlus a601010
Pregnancy cat. X
Legal status  ?
Pharmacokinetic data
Bioavailability 60%
Protein binding 99%
Half-life 49 hours
Identifiers
CAS number 55079-83-9 YesY
ATC code D05BB02
PubChem CID 5284513
DrugBank APRD00778
ChemSpider 4447573 YesY
UNII LCH760E9T7 YesY
KEGG D02754 YesY
ChEBI CHEBI:50173 YesY
ChEMBL CHEMBL1131 YesY
Chemical data
Formula C21H26O3 
Mol. mass 326.429 g/mol
SMILES eMolecules & PubChem
 N(what is this?)  (verify)

Acitretin (trade name Soriatane or Neotigason) is a second generation retinoid. It is taken orally, and is typically used for psoriasis.

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.

Because acitretin can be reverse metabolised into etretinate which has a long half-life, women must avoid becoming pregnant for at least 3 years (http://www.soriatane.com/patient/part.aspx) after discontinuing acitretin. Therefore, acitretin is generally not recommended for women of child bearing age with a risk of becoming pregnant.

Acitretin is the oral retinoid of choice used in the treatment of severe resistant psoriasis. 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 2 to 4 weeks or longer.

If a patient has received the medication, he/she is advised against giving blood for at least 3 years due to the risk of birth defects(AABB Technical Manual).

v · d · eAntipsoriatics (D05)
Topical
Tars
Other
Systemic
Psoralens
Trioxysalen • Methoxsalen • Bergapten
Etretinate • Acitretin

M: INT, SF, LCT

anat/phys/devp

noco(i/b/d/q/u/r/p/m/k/v/f)/cong/tumr(n/e/d), sysi/epon

proc, drug (D2/3/4/5/8/11)


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