Identification
- Summary
Acitretin is an oral retinoid used in the treatment of severe psoriasis.
- Brand Names
- Soriatane
- Generic Name
- Acitretin
- DrugBank Accession Number
- DB00459
- Background
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.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Acitretin (DB00459)
- Weight
- Average: 326.4293
Monoisotopic: 326.188194698 - Chemical Formula
- C21H26O3
- Synonyms
- (all-E)-9-(4-Methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoic acid
- Acitretin
- Acitretina
- Acitretine
- Acitretinum
- all-trans-3,7-Dimethyl-9-(4-methoxy-2,3,6-trimethylphenyl)-2,4,6,8-nonatetraenoic acid
- Etretin
- External IDs
- RO 10-1670
- RO 10-1670/000
- RO-10-1670/000
Pharmacology
- Indication
For the treatment of severe psoriasis in adults.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Management of Keratinization disorders •••••••••••• Management of Severe psoriasis •••••••••••• ••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
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.
- Mechanism of action
The mechanism of action of acitretin 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.
Target Actions Organism ARetinoic acid receptor RXR-alpha agonistHumans ARetinoic acid receptor alpha agonistHumans ARetinoic acid receptor beta agonistHumans ARetinoic acid receptor gamma agonistHumans ARetinoic acid receptor RXR-beta agonistHumans ARetinoic acid receptor RXR-gamma agonistHumans URetinol-binding protein 1 agonistHumans URetinoic acid receptor RXR Not Available - 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.
- Volume of distribution
Not Available
- Protein binding
Over 99.9% bound to plasma proteins, primarily albumin.
- Metabolism
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.
- Route of 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%).
- Half-life
49 hours (range 33 to 96 hours)
- Clearance
Not Available
- Adverse Effects
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Oral, rat: LD50 = >4000 mg/kg. Symptoms of overdose include headache and vertigo.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareCyproterone acetate The therapeutic efficacy of Cyproterone acetate can be decreased when used in combination with Acitretin. Demeclocycline The risk or severity of pseudotumor cerebri can be increased when Acitretin is combined with Demeclocycline. Desogestrel The therapeutic efficacy of Desogestrel can be decreased when used in combination with Acitretin. Dienogest The therapeutic efficacy of Dienogest can be decreased when used in combination with Acitretin. Diethylstilbestrol The therapeutic efficacy of Diethylstilbestrol can be decreased when used in combination with Acitretin. - Food Interactions
- Avoid alcohol. Women of childbearing age should avoid ingesting any alcohol during treatment and two months after discontinuation of acitretin. Alcohol intake increases the duration of risk for birth defects to beyond three years post acitretin discontinuation.
- Take with food. Taking acitretin with the main meal of the day improves oral absorption.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Images
- International/Other Brands
- Neotigason
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Soriatane Capsule 25 mg Oral Allergan 1994-12-31 Not applicable Canada 
Soriatane Capsule 17.5 mg/1 Oral Stiefel Laboratories Inc 2010-01-04 2010-04-01 US 
Soriatane Capsule 17.5 mg/1 Oral GlaxoSmithKline Manufacturing SpA 2010-01-04 2017-11-21 US Soriatane Capsule 10 mg/1 Oral Stiefel Laboratories, Inc. 1996-11-01 2010-01-04 US Soriatane Capsule 25 mg/1 Oral Stiefel Laboratories Inc 1996-11-01 2022-04-30 US 
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Acitretin Capsule 17.5 mg/1 Oral Teva Pharmaceuticals USA, Inc. 2013-07-19 Not applicable US 
Acitretin Capsule 25 mg/1 Oral AvKARE 2017-10-11 Not applicable US Acitretin Capsule 10 mg/1 Oral Prasco Laboratories 2013-07-19 2021-03-31 US Acitretin Capsule 25 mg/1 Oral Mylan Pharmaceuticals Inc. 2016-03-10 Not applicable US Acitretin Capsule 10 mg/1 Oral Sigmapharm Laboratories, LLC 2015-09-16 Not applicable US
Categories
- ATC Codes
- D05BB02 — Acitretin
- Drug Categories
- Alkenes
- Antipsoriatics
- Antipsoriatics for Systemic Use
- Biological Factors
- Carotenoids
- Cyclohexanes
- Cyclohexenes
- Cycloparaffins
- Dermatologicals
- Drugs causing inadvertant photosensitivity
- Hepatotoxic Agents
- Hydrocarbons, Acyclic
- Keratolytic Agents
- Misc. Skin and Mucous Membrane Agents
- Photosensitizing Agents
- Pigments, Biological
- Polyenes
- Retinoids
- Retinoids for Treatment of Psoriasis
- Terpenes
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof.
- Kingdom
- Organic compounds
- Super Class
- Lipids and lipid-like molecules
- Class
- Prenol lipids
- Sub Class
- Retinoids
- Direct Parent
- Retinoids
- Alternative Parents
- Sesquiterpenoids / Styrenes / Phenoxy compounds / Methoxybenzenes / Medium-chain fatty acids / Anisoles / Methyl-branched fatty acids / Alkyl aryl ethers / Unsaturated fatty acids / Monocarboxylic acids and derivatives show 4 more
- Substituents
- Alkyl aryl ether / Anisole / Aromatic homomonocyclic compound / Benzenoid / Branched fatty acid / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Cyclofarsesane sesquiterpenoid / Ether show 18 more
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- retinoid, alpha,beta-unsaturated monocarboxylic acid, acitretin (CHEBI:50173)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- LCH760E9T7
- CAS number
- 55079-83-9
- InChI Key
- IHUNBGSDBOWDMA-AQFIFDHZSA-N
- 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+
- IUPAC Name
- (2E,4E,6E,8E)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid
- SMILES
- COC1=C(C)C(C)=C(\C=C\C(\C)=C\C=C\C(\C)=C\C(O)=O)C(C)=C1
References
- Synthesis Reference
Yatendra Kumar, "Process for the preparation of acitretin." U.S. Patent US20040192949, issued September 30, 2004.
US20040192949- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0014602
- KEGG Drug
- D02754
- PubChem Compound
- 5284513
- PubChem Substance
- 46509178
- ChemSpider
- 4447573
- BindingDB
- 50088429
- 16818
- ChEBI
- 50173
- ChEMBL
- CHEMBL1131
- ZINC
- ZINC000003798734
- Therapeutic Targets Database
- DAP000743
- PharmGKB
- PA448039
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- PDRhealth
- PDRhealth Drug Page
- Wikipedia
- Acitretin
- FDA label
- Download (530 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Active Not Recruiting Treatment Psoriasis 1 4 Completed Not Available Psoriasis 1 4 Completed Treatment Psoriasis 2 4 Completed Treatment Psoriasis, Moderate to Severe 1 4 Not Yet Recruiting Other Psoriasis Vulgaris (Plaque Psoriasis) 1
Pharmacoeconomics
- Manufacturers
- Stiefel laboratories inc
- Packagers
- Murfreesboro Pharmaceutical Nursing Supply
- Pharmaceutics International Inc.
- Stiefel Labs
- Dosage Forms
Form Route Strength Capsule Oral 22.5 mg/1 Capsule Oral Capsule Oral 10 mg Capsule Oral 25 mg Capsule, coated Oral 10 mg Capsule Oral 10.0 mg Capsule Oral 25.0 mg Capsule Oral 10 mg/1 Capsule Oral 17.5 mg/1 Capsule Oral 25 mg/1 - Prices
Unit description Cost Unit Soriatane 17.5 mg capsule 30.21USD capsule Soriatane 22.5 mg capsule 30.21USD capsule Soriatane 25 mg capsule 21.71USD capsule Soriatane 10 mg capsule 13.25USD capsule DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 228-230 °C PhysProp water solubility 0.0729 mg/L Not Available logP 6.40 SANGSTER (1993) - Predicted Properties
Property Value Source Water Solubility 0.000478 mg/mL ALOGPS logP 5.2 ALOGPS logP 5.59 Chemaxon logS -5.8 ALOGPS pKa (Strongest Acidic) 4.77 Chemaxon pKa (Strongest Basic) -4.8 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 46.53 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 104.17 m3·mol-1 Chemaxon Polarizability 38.58 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9885 Blood Brain Barrier - 0.5841 Caco-2 permeable + 0.8628 P-glycoprotein substrate Non-substrate 0.6057 P-glycoprotein inhibitor I Non-inhibitor 0.6973 P-glycoprotein inhibitor II Non-inhibitor 0.9382 Renal organic cation transporter Non-inhibitor 0.8899 CYP450 2C9 substrate Non-substrate 0.7907 CYP450 2D6 substrate Non-substrate 0.8202 CYP450 3A4 substrate Non-substrate 0.5108 CYP450 1A2 substrate Non-inhibitor 0.6804 CYP450 2C9 inhibitor Non-inhibitor 0.9239 CYP450 2D6 inhibitor Non-inhibitor 0.9409 CYP450 2C19 inhibitor Non-inhibitor 0.648 CYP450 3A4 inhibitor Non-inhibitor 0.8768 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.5923 Ames test Non AMES toxic 0.8341 Carcinogenicity Non-carcinogens 0.83 Biodegradation Ready biodegradable 0.714 Rat acute toxicity 1.8804 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9216 hERG inhibition (predictor II) Non-inhibitor 0.9501
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 217.63939 predictedDarkChem Lite v0.1.0 [M-H]- 217.96299 predictedDarkChem Lite v0.1.0 [M-H]- 196.85797 predictedDeepCCS 1.0 (2019) [M+H]+ 217.68559 predictedDarkChem Lite v0.1.0 [M+H]+ 218.07359 predictedDarkChem Lite v0.1.0 [M+H]+ 199.25352 predictedDeepCCS 1.0 (2019) [M+Na]+ 218.41019 predictedDarkChem Lite v0.1.0 [M+Na]+ 218.08969 predictedDarkChem Lite v0.1.0 [M+Na]+ 205.2307 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Zinc ion binding
- Specific Function
- Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expressi...
- Gene Name
- RXRA
- Uniprot ID
- P19793
- Uniprot Name
- Retinoic acid receptor RXR-alpha
- Molecular Weight
- 50810.835 Da
References
- Orfanos CE, Zouboulis CC, Almond-Roesler B, Geilen CC: Current use and future potential role of retinoids in dermatology. Drugs. 1997 Mar;53(3):358-88. [Article]
- Tian K, Norris AW, Lin CL, Li E: The isolation and characterization of purified heterocomplexes of recombinant retinoic acid receptor and retinoid X receptor ligand binding domains. Biochemistry. 1997 May 13;36(19):5669-76. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Zinc ion binding
- Specific Function
- Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expressi...
- Gene Name
- RARA
- Uniprot ID
- P10276
- Uniprot Name
- Retinoic acid receptor alpha
- Molecular Weight
- 50770.805 Da
References
- Saurat JH: Retinoids and psoriasis: novel issues in retinoid pharmacology and implications for psoriasis treatment. J Am Acad Dermatol. 1999 Sep;41(3 Pt 2):S2-6. [Article]
- Orfanos CE, Zouboulis CC, Almond-Roesler B, Geilen CC: Current use and future potential role of retinoids in dermatology. Drugs. 1997 Mar;53(3):358-88. [Article]
- Tian K, Norris AW, Lin CL, Li E: The isolation and characterization of purified heterocomplexes of recombinant retinoic acid receptor and retinoid X receptor ligand binding domains. Biochemistry. 1997 May 13;36(19):5669-76. [Article]
- Tippmann F, Hundt J, Schneider A, Endres K, Fahrenholz F: Up-regulation of the alpha-secretase ADAM10 by retinoic acid receptors and acitretin. FASEB J. 2009 Jun;23(6):1643-54. doi: 10.1096/fj.08-121392. Epub 2009 Jan 14. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Zinc ion binding
- Specific Function
- Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expressi...
- Gene Name
- RARB
- Uniprot ID
- P10826
- Uniprot Name
- Retinoic acid receptor beta
- Molecular Weight
- 50488.63 Da
References
- Berggren Soderlund M, Johannesson G, Fex G: Expression of human all-trans-retinoic acid receptor beta and its ligand-binding domain in Escherichia coli. Biochem J. 1995 May 15;308 ( Pt 1):353-9. [Article]
- Zouboulis CC: Retinoids--which dermatological indications will benefit in the near future? Skin Pharmacol Appl Skin Physiol. 2001 Sep-Oct;14(5):303-15. [Article]
- Tippmann F, Hundt J, Schneider A, Endres K, Fahrenholz F: Up-regulation of the alpha-secretase ADAM10 by retinoic acid receptors and acitretin. FASEB J. 2009 Jun;23(6):1643-54. doi: 10.1096/fj.08-121392. Epub 2009 Jan 14. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Zinc ion binding
- Specific Function
- Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expressi...
- Gene Name
- RARG
- Uniprot ID
- P13631
- Uniprot Name
- Retinoic acid receptor gamma
- Molecular Weight
- 50341.405 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Zinc ion binding
- Specific Function
- Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expressi...
- Gene Name
- RXRB
- Uniprot ID
- P28702
- Uniprot Name
- Retinoic acid receptor RXR-beta
- Molecular Weight
- 56921.38 Da
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Zinc ion binding
- Specific Function
- Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expressi...
- Gene Name
- RXRG
- Uniprot ID
- P48443
- Uniprot Name
- Retinoic acid receptor RXR-gamma
- Molecular Weight
- 50870.72 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Orfanos CE, Zouboulis CC, Almond-Roesler B, Geilen CC: Current use and future potential role of retinoids in dermatology. Drugs. 1997 Mar;53(3):358-88. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- General Function
- Transporter activity
- Specific Function
- Intracellular transport of retinol.
- Gene Name
- RBP1
- Uniprot ID
- P09455
- Uniprot Name
- Retinol-binding protein 1
- Molecular Weight
- 15850.13 Da
References
- Berni R, Clerici M, Malpeli G, Cleris L, Formelli F: Retinoids: in vitro interaction with retinol-binding protein and influence on plasma retinol. FASEB J. 1993 Sep;7(12):1179-84. [Article]
8. Retinoic acid receptor RXR
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Toxic substance binding
- Specific Function
- Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Serum albumin
- Molecular Weight
- 69365.94 Da
References
- Urien S, Claudepierre P, Meyer J, Brandt R, Tillement JP: Comparative binding of etretinate and acitretin to plasma proteins and erythrocytes. Biochem Pharmacol. 1992 Nov 3;44(9):1891-3. [Article]
- Preiss JC, Zouboulis CC, Zeitz M, Duchmann R: [Severe erythrodermic psoriasis in a patient with 22q11 deletion syndrome]. Med Klin (Munich). 2005 May 13;100(5):275-8. [Article]
- Carillet V, Morliere P, Maziere JC, Huppe G, Santus R, Dubertret L: In vitro interactions of the aromatic retinoids Ro 10-9359 (etretinate) and Ro 10-1670 (acitretin), its main metabolite, with human serum lipoproteins and albumin. Biochim Biophys Acta. 1990 Nov 12;1055(2):98-101. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55