Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C21H26O3 |
| Molecular Weight | 326.4293 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 4 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=C(C)C(C)=C(\C=C\C(C)=C\C=C\C(C)=C/C(O)=O)C(C)=C1
InChI
InChIKey=IHUNBGSDBOWDMA-UGOGCBOOSA-N
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-
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/21720660
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/21720660
Acitretin is all-Trans-9-(4-methoxy-2, 3, 6¬ trimethylphenyl)-three, 7-dimethyl-2, 4, 6, 8-nonatetraenoic acid. It is a metabolite of exterminate and is related to both retinoic acid and retinol (vitamin A). It is taken orally, and is typically used for psoriasis. The mechanism of action of is unknown. However it is believed to work by targeting specific receptors (retinoid receptors such as RXR and RAR) in the skin, which help normalize the growth cycle of skin cells. Studies on nuclear retinoic acid receptors have shown that acitretin activates all 3 receptor subtypes (RAR-alpha, -beta, and -gamma) without measurable receptor binding; this paradox remains unexplained.
CNS Activity
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2363072 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Palliative | SORIATANE Approved UseAcitretin Capsules USP are indicated for the treatment of severe psoriasis in adults. Because of significant adverse effects associated with their use, Acitretin Capsules USP should be prescribed only by those knowledgeable in the systemic use of retinoids. In females of reproductive potential, Acitretin Capsules USP should be reserved for non-pregnant patients who are unresponsive to other therapies or whose clinical condition contraindicates the use of other treatments (see boxed CONTRAINDICATIONS AND WARNINGS — Acitretin Capsules USP can cause severe birth defects). Most patients experience relapse of psoriasis after discontinuing therapy. Subsequent courses, when clinically indicated, have produced efficacy results similar to the initial course of therapy. Launch Date1996 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
416 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/2977392 |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
ACITRETIN plasma | Homo sapiens population: HEALTHY age: UNKNOWN sex: MALE food status: FED |
|
416 ng/mL |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
ACITRETIN plasma | Homo sapiens population: HEALTHY age: UNKNOWN sex: UNKNOWN food status: FED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
2249 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/2977392 |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
ACITRETIN plasma | Homo sapiens population: HEALTHY age: UNKNOWN sex: MALE food status: FED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
2.8 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/2977392 |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
ACITRETIN plasma | Homo sapiens population: HEALTHY age: UNKNOWN sex: MALE food status: FED |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Determination of the aromatic retinoids (etretin and isoetretin) in biological fluids by high-performance liquid chromatography. | 1987 Oct 9 |
|
| Identification of etretinate metabolites in human blood. | 1989 May-Jun |
|
| Identification of etretinate metabolites in human bile. | 1989 May-Jun |
|
| High-performance liquid chromatographic determination of etretinate and all-trans- and 13-cis-acitretin in human plasma. | 1990 Feb 2 |
|
| Quantification of acitretin in human plasma by microbore liquid chromatography-negative chemical ionization mass spectrometry. | 1991 Jul 17 |
|
| Oral acitretin in psoriasis: drug and vitamin A concentrations in plasma, skin and adipose tissue. | 1992 |
|
| Severe limb defects and craniofacial anomalies in a fetus conceived during acitretin therapy. | 1995 Oct |
|
| Acitretin-induced myopathy. | 1996 May |
|
| Acitretin-associated thrombotic stroke. | 2002 Dec |
|
| Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
|
| Recurrent dysphonia and acitretin. | 2006 Dec |
|
| Interaction between genetic control of vascular endothelial growth factor production and retinoid responsiveness in psoriasis. | 2006 Feb |
|
| [Acitretin induces apoptosis and changes of relative signaling pathway in epidermoid carcinoma cell line A431]. | 2006 Mar |
|
| Acitretin and sixth nerve palsy. | 2007 Oct |
|
| Acitretin induces apoptosis through CD95 signalling pathway in human cutaneous squamous cell carcinoma cell line SCL-1. | 2009 Sep |
Patents
Sample Use Guides
SORIATANE (acitretin capsules) should be initiated at 25 to 50 mg per day, given as a single dose with the main meal. Maintenance doses of 25 to 50 mg per day may be given dependent upon an individual patient’s response to initial treatment. Relapses may be treated as outlined for initial therapy.
Route of Administration:
Oral
In Vitro Use Guide
Curator's Comment: Acitretin plays an inhibitory role in the tumor cell growth and induces the cell apoptosis in A431 cells. The regulation of the Jak/STAT3 signaling pathway may play an important role in inducing growth inhibition and apoptosis by Acitretin in A431 cells.
A431 (epidermoid carcinoma cell lines) were treated with Acitretin at the concentration of 10(-5)mol/L in different time intervals
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PARENT (METABOLITE)
SUBSTANCE RECORD
