Etretinate

Etretinate

Systematic (IUPAC) name
ethyl 9-(4-methoxy-2,3,6-trimethyl-phenyl)- 3,7-dimethyl-nona- 2,4,6,8-tetraenoate
Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
MedlinePlus	a601010
Pregnancy cat.	?
Legal status	?
Routes	Oral
Pharmacokinetic data
Half-life	120 days
Identifiers
CAS number	54350-48-0 N
ATC code	D05BB01
PubChem	CID 5282375
DrugBank	APRD00966
ChemSpider	4445538 Y
UNII	65M2UDR9AG Y
KEGG	D00316 Y
ChEBI	CHEBI:4913 Y
ChEMBL	CHEMBL464 Y
Chemical data
Formula	C23H30O3
Mol. mass	354.483 g/mol
SMILES	eMolecules & PubChem
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
N(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Etretinate has been replaced by acitretin, a safer metabolite of etretinate.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.^[1]

Side effects

• Hepatitis
• Pseudotumor cerebri
• Diffuse idiopathic skeletal Hyperostosis

References

1. ^ UK Blood Transfusion and Tissue Transplantation Services[1]

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