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 Y
ATC code	D05BB02
PubChem	CID 5284513
DrugBank	APRD00778
ChemSpider	4447573 Y
UNII	LCH760E9T7 Y
KEGG	D02754 Y
ChEBI	CHEBI:50173 Y
ChEMBL	CHEMBL1131 Y
Chemical data
Formula	C21H26O3
Mol. mass	326.429 g/mol
SMILES	eMolecules & PubChem
InChI 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
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 (t_1/2=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).