Etretinate

Etretinate

Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
MedlinePlus	a601010
Routes of administration	Oral
ATC code	D05BB01 (WHO)
Pharmacokinetic data
Elimination half-life	120 days
Identifiers
IUPAC name ethyl 9-(4-methoxy-2,3,6-trimethyl-phenyl)- 3,7-dimethyl-nona- 2,4,6,8-tetraenoate
CAS Number	54350-48-0 N
PubChem CID	5282375
DrugBank	DB00926 Y
ChemSpider	4445538 Y
UNII	65M2UDR9AG
KEGG	D00316 Y
ChEBI	CHEBI:4913 Y
ChEMBL	ChEMBL464 Y
CompTox Dashboard (EPA)	DTXSID0023036
ECHA InfoCard	100.053.727
Chemical and physical data
Formula	C23H30O3
Molar mass	354.483 g/mol g·mol−1
3D model (JSmol)	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?)  (verify)

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 was subsequently removed from the United States market in 1998 and the Canadian market in 1996, due to the high risk of birth defects.

Properties

Etretinate has a low therapeutic index and a long elimination half-life (t_1/2) of 120 days, which make dosing difficult.

Etretinate is an aromatic retinoid, and therefore highly lipophilic. 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Etretinate has been replaced by acitretin, a safer metabolite of etretinate.

Precautions

• Etretinate is a teratogen, and may cause birth defects long after use. Therefore, birth control is advised during therapy, and for at least three years after therapy has stopped.
• Etretinate should be avoided in children, as it may interfere with bone growth.

• If a patient has ever taken etretinate, he or she is not eligible to donate blood, due to the risk of birth defects.

Side effects

• Hepatitis
• Pseudotumor cerebri
• Diffuse idiopathic skeletal Hyperostosis