(2Z,4E,6E,8E)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid

• ChemBase ID: 342
• Molecular Formular: C21H26O3
• Molecular Mass: 326.42934
• Monoisotopic Mass: 326.18819469
• SMILES: O(c1c(c(c(c(c1)C)/C=C/C(=C/C=C/C(=C\C(=O)O)/C)/C)C)C)C
• Canonical SMILES: COc1cc(C)c(c(c1C)C)/C=C/C(=C/C=C/C(=C\C(=O)O)/C)/C
• InChI: InChI=1S/C21H26O3/c1-14(8-7-9-15(2)12-21(22)23)10-11-19-16(3)13-20(24-6)18(5)17(19)4/h7-13H,1-6H3,(H,22,23)/b9-7+,11-10+,14-8+,15-12-
• InChIKey: IHUNBGSDBOWDMA-UGOGCBOOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2Z,4E,6E,8E)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid
• IUPAC Traditional name: acetretin
• Brand Name: Acetretin; Soriatane
• Synonyms: Acitretin; 9-(4-Methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoic Acid, 13-cis-Etretin, Isoacitretin, Isoetretin, Ro 13-7652; 13-cis Acitretin

Database IDs

• CAS Number: 69427-46-9; 55079-83-9
• PubChem SID: 160963805
• PubChem CID: 6437841

CALCULATED PROPERTIES

JChem

• Acid pKa: 5.011076
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 4.976502
• LogD (pH = 7.4): 3.2266924
• Log P: 5.5870485
• Molar Refractivity: 104.1665 cm^3
• Polarizability: 38.030373 Å^3
• Polar Surface Area: 46.53 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 5.2
• LOG S: -5.83
• Solubility (Water): 4.78e-04 g/l

PROPERTIES

Physical Property

• Solubility: 0.0729 mg/L; Acetone; Chloroform; Dichloromethane; Ethyl Acetate,
• Apperance: Yellow Solid
• Melting Point: 190-193°C
• Hydrophobicity(logP): 5.7

Safety Information

• Storage Condition: Amber Vial, -80°C Freezer

DETAILS

DrugBank - DB00459

• Drug Groups: approved
• Description: An oral retinoid effective in the treatment of psoriasis. It is the major metabolite of etretinate with the advantage of a much shorter half-life when compared with etretinate. [PubChem]
• Indication: For the treatment of severe psoriasis in adults.
• Pharmacology: Acitretin is a retinoid. Retinoids have a structure similar to vitamin A and are involved in the normal growth of skin cells. Acitretin works by inhibiting the excessive cell growth and keratinisation (process by which skin cells become thickened due to the deposition of a protein within them) seen in psoriasis. It therefore reduces the thickening of the skin, plaque formation and scaling.
• Toxicity: Oral, rat: LD₅₀ = >4000 mg/kg. Symptoms of overdose include headache and vertigo.
• Affected Organisms: Humans and other mammals
• Biotransformation: Following oral absorption, acitretin undergoes extensive metabolism and interconversion by simple isomerization to its 13-cis form (cis-acitretin). Both parent compound and isomer are further metabolized into chain-shortened breakdown products and conjugates, which are excreted.
• Absorption: Oral absorption of acitretin is optimal when given with food, and is linear and proportional with increasing doses from 25 to 100 mg. Approximately 72% (range 47% to 109%) of the administered dose was absorbed after a single 50 mg dose of acitretin was given to 12 healthy subjects.
• Half Life: 49 hours (range 33 to 96 hours)
• Protein Binding: Over 99.9% bound to plasma proteins, primarily albumin.
• Elimination: Both parent compound and isomer are further metabolized into chain-shortened breakdown products and conjugates, which are excreted. The chain-shortened metabolites and conjugates of acitretin and cis-acitretin are ultimately excreted in the feces (34% to 54%) and urine (16% to 53%).
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Toronto Research Chemicals - A189925

A synthetic retinoid which is the major metabolite of etretinate (E938000).

REFERENCES

• Sato, T., et al.: J. Med. Chem., 51, 7705 (2008)
• Liu, X., et al.: Cancer Chemother. Pharmacol., 63, 167 (2008)