Structure via PubChem · Public domain (PubChem)
etretinate
Sign in to saveAlso known as Ro-109359, Tegison®, Ethyl all-trans-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoate, Ethyl (all-E)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoate, 3,7-Dimethyl-9-(4-methoxy-2,3,6-trimethylphenyl)-2,4,6,8-nonanetetraenoic acid ethyl ester
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.
Chemical data
- Formula
- C23H30O3
- Molecular weight
- 354.5 g/mol
- IUPAC name
- ethyl (2E,4E,6E,8E)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoate
- SMILES
- CCOC(=O)/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C(=C(C=C1C)OC)C)C
- InChIKey
- HQMNCQVAMBCHCO-DJRRULDNSA-N
- XLogP
- 6.8
- Polar surface area
- 35.5 Ų
- H-bond donors
- 0
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
Withdrawn- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1986
- Admin. routes
- oral
- Indications
- psoriasis
via ChEMBL · EBI
Research
3,808 papers- Etretinate therapy.Journal of the American Academy of Dermatology · 1987
- Etretinate and psoriasis.Archives of dermatology · 1987
- Etretinate. A clinician's view.Dermatologic clinics · 1988
- Teratogenic risk with etretinate and acitretin treatment.Dermatology (Basel, Switzerland) · 1994
- Pharmacokinetics of acitretin and etretinate.Journal of the American Academy of Dermatology · 1998
via PubMed
Wikidata facts
- Subclass of
- retinoid
- Mass
- 354.219495
- Has use
- medication
Show 6 more facts
- chemical formula
- C₂₃H₃₀O₃
- canonical SMILES
- CCOC(=O)C=C(C)C=CC=C(C)C=CC1=C(C(=C(C=C1C)OC)C)C
- isomeric SMILES
- CCOC(=O)/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C(=C(C=C1C)OC)C)C
- World Health Organisation international non-proprietary name
- etretinate
- defined daily dose
- 35
- Commons category
- Etretinate
via Wikidata · CC0
~3 min read
Encyclopedic overview
6 sectionsContents
- Pharmacology
- Precautions
- Side effects
- History
- See also
- References
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.
==Pharmacology== 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 (t1/2) of 120 days, which make dosing difficult.
Excerpted from Wikipedia’s “etretinate” article, available under the CC BY-SA 4.0 licence.