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-AQFIFDHZSA-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
Originator
Sources: http://adisinsight.springer.com/drugs/800004586
Curator's Comment: # by Roche
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2363072 Sources: https://www.ncbi.nlm.nih.gov/pubmed/?term=10459139 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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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 |
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Identification of etretinate metabolites in human blood. | 1989 May-Jun |
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High-performance liquid chromatographic determination of etretinate and all-trans- and 13-cis-acitretin in human plasma. | 1990 Feb 2 |
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Quantification of acitretin in human plasma by microbore liquid chromatography-negative chemical ionization mass spectrometry. | 1991 Jul 17 |
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Oral acitretin in psoriasis: drug and vitamin A concentrations in plasma, skin and adipose tissue. | 1992 |
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Severe limb defects and craniofacial anomalies in a fetus conceived during acitretin therapy. | 1995 Oct |
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Acitretin-induced myopathy. | 1996 May |
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Severe cholestatic hepatitis in a patient taking acitretin. | 2002 Mar |
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Sensorimotor polyneuropathy after a three-month oral acitretin therapy. | 2002 Nov-Dec |
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Acitretin embryopathy: a case report. | 2004 Oct |
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[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 |
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Papillon-Lefèvre syndrome treated with acitretin. | 2005 Aug |
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Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
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Recurrent dysphonia and acitretin. | 2006 Dec |
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Acitretin affects bioenergetics of liver mitochondria and promotes mitochondrial permeability transition: potential mechanisms of hepatotoxicity. | 2013 Apr 5 |
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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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16610086
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
Created
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Record UNII |
LCH760E9T7
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Record Status |
Validated (UNII)
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NDF-RT |
N0000007700
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NDF-RT |
N0000175607
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N0000007700
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WHO-ATC |
D05BB02
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NDF-RT |
N0000007700
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WHO-VATC |
QD05BB02
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NDF-RT |
N0000007700
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NCI_THESAURUS |
C804
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LIVERTOX |
NBK548784
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NDF-RT |
N0000007700
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Acitretin
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X-94
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ACITRETIN
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LCH760E9T7
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C985
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55079-83-9
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TARGET -> INHIBITOR |
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TARGET -> INHIBITOR |
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BINDER->LIGAND |
BINDING
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TARGET -> INHIBITOR |
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Related Record | Type | Details | ||
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METABOLITE -> PARENT |
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PRODRUG -> METABOLITE ACTIVE |
URINE
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METABOLITE -> PARENT |
Clinical evidence has shown that etretinate (a retinoid with a much longer half-life, see below) can be formed with concurrent ingestion of acitretin and ethanol.
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
MAJOR
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
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Related Record | Type | Details | ||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Tmax | PHARMACOKINETIC |
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Biological Half-life | PHARMACOKINETIC |
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Volume of Distribution | PHARMACOKINETIC |
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