Etretinate

Etretinate

Clinical data
Trade names	Tigason, formerly Tegison
AHFS/Drugs.com	Drugs.com archive
MedlinePlus	a601010
Pregnancy category	US: X (Contraindicated)
Routes of administration	Oral
ATC code	D05BB01 (WHO)
Legal status
Legal status	US: Withdrawn
Pharmacokinetic data
Protein binding	>99%
Metabolites	Free acid, Z-form, chain shortening
Biological half-life	120 days
Identifiers
IUPAC name Ethyl (2E,4E,6E,8E)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoate
CAS Number	54350-48-0 N
PubChem CID	5282375
IUPHAR/BPS	7599
DrugBank	DB00926 Y
ChemSpider	4445538 Y
UNII	65M2UDR9AG
KEGG	D00316 Y
ChEBI	CHEBI:4913 Y
ChEMBL	CHEMBL464 Y
ECHA InfoCard	100.053.727
Chemical and physical data
Formula	C23H30O3
Molar mass	354.483 g/mol
3D model (Jmol)	Interactive image
SMILES O=C(OCC)\C=C(\C=C\C=C(\C=C\c1c(cc(OC)c(c1C)C)C)C)C
InChI 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+ Y Key:HQMNCQVAMBCHCO-DJRRULDNSA-N Y
NY (what is this?)

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 as Tigason.

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, which make dosing difficult.

Etretinate has been replaced by acitretin, the free acid (without the ethyl ester).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, so that it is still a long-acting teratogen and pregnancy is prohibited for two years after therapy.

Side effects are those typical of hypervitaminosis A, most commonly

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.

In Japan, the drug remains on market branded Tigason.