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-
| Molecular Formula | C21H26O3 |
| Molecular Weight | 326.4293 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 4 |
| Optical Activity | NONE |
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 Date8.4646081E11 |
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 |
|---|---|---|
| Effects of short-term oral acitretin therapy on peripheral nerve function: a prospective neurological and neurophysiological study. | 2001 Nov-Dec |
|
| Acitretin-associated thrombotic stroke. | 2002 Dec |
|
| Peripheral sensory neuropathy associated with short-term oral acitretin therapy. | 2003 Jan-Feb |
|
| Capillary leak syndrome induced by acitretin. | 2004 Jan |
|
| Acitretin embryopathy: a case report. | 2004 Oct |
|
| Effects of ATRA, acitretin and tazarotene on growth and apoptosis of Tca8113 cells. | 2005 |
|
| [Effects of all-trans-retinoic acid, acitretin and tazarotene on apoptosis and Bax/Bcl-2 expressions of human melanoma cells A375 and the significance]. | 2005 Aug |
|
| Papillon-Lefèvre syndrome treated with acitretin. | 2005 Aug |
|
| Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
|
| [Acitretin induces apoptosis and changes of relative signaling pathway in epidermoid carcinoma cell line A431]. | 2006 Mar |
|
| Acitretin induces capillary leak syndrome in a patient with pustular psoriasis. | 2007 Feb |
|
| Acitretin affects bioenergetics of liver mitochondria and promotes mitochondrial permeability transition: potential mechanisms of hepatotoxicity. | 2013 Apr 5 |
|
| A correlation between the in vitro drug toxicity of drugs to cell lines that express human P450s and their propensity to cause liver injury in humans. | 2014 Jan |
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
| Substance Class |
Chemical
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| Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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| Biological Half-life | PHARMACOKINETIC |
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| Tmax | PHARMACOKINETIC |
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