Etretinate

Title: Etretinate
CAS Registry Number: 54350-48-0
CAS Name: (all-E)-9-(4-Methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoic acid ethyl ester
Manufacturers' Codes: Ro-10-9359
Trademarks: Tegison (Roche); Tigason (Roche)
Molecular Formula: C23H30O3
Molecular Weight: 354.48
Percent Composition: C 77.93%, H 8.53%, O 13.54%
Literature References: Aromatic analog of retinoic acid, q.v. Prepn: W. Bollag et al., DE 2414619; eidem, US 4105681 and US 4215215 (1974, 1978, 1980 all to Hoffmann-La Roche). Effects on skin metabolism: W. P. Raab, B. M. Gmeiner, Arch. Dermatol. Res. 256, 247 (1976). Toxicity study in organ culture: D. R. Bard, I. Lasnitzki, Br. J. Cancer 35, 110 (1977). Pharmacokinetics: R. Haenni, Dermatologica 157, Suppl, 5 (1978). Mutation study: H. J. Juhl et al., Mutat. Res. 58, 317 (1978). HPLC determn in plasma: R. Haenni et al., J. Chromatogr. 162, 615 (1979). Toxicology, carcinogenicity and teratogenicity study: J. J. Kamm, J. Am. Acad. Dermatol. 6, 652 (1982). Clinical evaluation in psoriatic arthritis: M. L. Ciompi et al., Int. J. Tissue React. 10, 25 (1988). Review: H. Mayer et al., Experientia 34, 1105-1119 (1978). Review of pharmacology and therapeutic efficacy: A. Ward et al., Drugs 26, 9-43 (1983); of clinical pharmacology: A. Vahlquist, O. Rollman, Dermatologica 175, Suppl. 1, 20-27 (1987). Book: The Retinoids Vol. 1-2, M. B. Sporn et al., Eds. (Academic Press, New York, 1984).
Properties: Crystals, mp 104-105°. LD50 in mice (1 day): >4000 mg/kg i.p. (Bollag). LD50 (20 day) in mice, rats (mg/kg): 1176, >2000 i.p.; >2000, >4000 orally (Kamm).
Melting point: mp 104-105°
Toxicity data: LD50 in mice (1 day): >4000 mg/kg i.p. (Bollag); LD50 (20 day) in mice, rats (mg/kg): 1176, >2000 i.p.; >2000, >4000 orally (Kamm)
Derivative Type: Free acid see Acitretin
Therap-Cat: Antipsoriatic.
Keywords: Antipsoriatic.
Etrimfos Etryptamine Etymemazine Eucalyptol Eucatropine

Etretinate
Etretinate.svg
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
Legal status  ?
Routes Oral
Pharmacokinetic data
Half-life 120 days
Identifiers
CAS number 54350-48-0 N
ATC code D05BB01
PubChem CID 5282375
DrugBank DB00926
ChemSpider 4445538 YesY
UNII 65M2UDR9AG YesY
KEGG D00316 YesY
ChEBI CHEBI:4913 YesY
ChEMBL CHEMBL464 YesY
Chemical data
Formula C23H30O3 
Mol. mass 354.483 g/mol
 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 Canadian market in 1996 and the United States market in 1998 due to the high risk of birth defects.