Acitretin (CED0003921)

Record Information
Version1.0
Creation Date2016-05-22 03:36:43 UTC
Update Date2026-05-14 16:39:28 UTC
Accession NumberCHEM016547
Identification
Common NameAcitretin
ClassSmall Molecule
Description
Acitretin belongs to the retinoids, a subclass of prenol lipids within the organic compounds. This lipid-like molecule has the chemical formula C21H26O3 and an average molecular weight of 326.43 g/mol. The compound is recorded as being found in or released from five sources, including healthcare, pharmaceuticals & veterinary products (antipsoriatics), household cleaning & consumer products (other smoking requisites and non electric simulated smoking devices), electrical & electronic equipment (electric hearing aids), and building & construction (floors). The recorded route of exposure for this substance is oral. At the molecular level, acitretin interacts with eight recorded protein targets. It acts as an agonist or inhibitor of retinoic acid receptor alpha (RARA), retinoic acid receptor beta (RARB), retinoic acid receptor gamma (RARG), and retinoic acid receptor RXR-beta (RXRB), as well as four other proteins. Regarding its health effects, acitretin is used as a treatment for psoriasis (PMC11665659, PMC12678558, PMC9310593, PMC9372960) and has been noted to have a therapeutic effect on psoriasis (PMC12678558).
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
13-cis-AcitretinHMDB
13-cis-EtretinHMDB
SoriataneHMDB
AcitretinHMDB
Acitretin andreu brandHMDB
Acitretin roche brandHMDB
Acitretin, (Z,e,e,e)-isomerHMDB
Andreu brand OF acitretinHMDB
EtretinHMDB
Hoffmann la roche brand OF acitretinHMDB
Hoffmann-la roche brand OF acitretinHMDB
IsoetretinHMDB
NeotigasonHMDB
Roche brand OF acitretinHMDB
(2Z,4E,6E,8E)-9-(4-Methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoic acidHMDB
IsoacitretinMeSH
Chemical FormulaC21H26O3
Average Molecular Mass326.429 g/mol
Monoisotopic Mass326.188 g/mol
CAS Registry Number55079-83-9
IUPAC Name(2Z,4E,6E,8E)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid
Traditional Nameacetretin
SMILESCOC1=C(C)C(C)=C(\C=C\C(\C)=C\C=C\C(\C)=C\C(O)=O)C(C)=C1
InChI IdentifierInChI=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+
InChI KeyIHUNBGSDBOWDMA-AQFIFDHZSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassRetinoids
Direct ParentRetinoids
Alternative Parents
Substituents
  • Retinoic acid
  • Retinoid skeleton
  • Sesquiterpenoid
  • Cyclofarsesane sesquiterpenoid
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • Medium-chain fatty acid
  • Styrene
  • Alkyl aryl ether
  • Branched fatty acid
  • Methyl-branched fatty acid
  • Monocyclic benzene moiety
  • Fatty acyl
  • Fatty acid
  • Benzenoid
  • Unsaturated fatty acid
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carbonyl group
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00048 g/LALOGPS
logP5.2ALOGPS
logP5.59ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)5.01ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity104.17 m³·mol⁻¹ChemAxon
Polarizability38.39 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-03di-1279000000-d74bbc0348cfdb3b3732Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-001i-4139000000-85e857f30a345651bb66Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-01t9-0592000000-92a48c620c961fdb430fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-056r-1943000000-77c18bcac662a9f6bdcbNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-056r-2942000000-57cdf186555912258599Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-05r0-0389000000-28f8ff224c8fd7ac1606Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-02t9-0690000000-11440b22373ebd567609Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-114j-4920000000-bf257c11adfb644686f4Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-0059000000-2338c505b394d676d7a4Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0059-0097000000-d73443e0cee4f07fd0d9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-066r-3391000000-8adb8a7f90aecb16b198Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001j-0092000000-da6b1640ed88e8dd0629Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-017j-1291000000-8d03b8e6cfa817060924Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00dj-1494000000-45aa9916567486569a90Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0ke9-0395000000-2d28d3c86a8a16a5adacNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0940000000-2f4d9396336fd697861eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00tf-1900000000-f5a87d3a7b17af3487e6Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
2759.0Log mg/kg[1600:4900]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
psoriasisis_treatment_forNot AvailablePMC11665659 , PMC11665659 , PMC11665659 , PMC12678558 , PMC9310593 , PMC9372960
psoriasishas_therapeutic_effect_onNot AvailablePMC12678558
hepatic fibrosisassociated_withNot AvailablePMC12678558
hepatic fibrosisassociated_withincreasePMC12678558 , PMC12678558
Exposure Sources
Source IDSourceSectorReference
305AntipsoriaticsHealthcare, pharmaceuticals & veterinary productsNot Available
497FloorsBuilding & ConstructionNot Available
516Electric Hearing AidsElectrical & Electronic EquipmentNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
619Manicure PedicurePersonal care & cosmeticsNot Available
Pathways
1 pathway
Acitretin Drug Metabolism Action Pathway
Acitretin Drug Metabolism Action Pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureRetinoic acid receptor alphaP11416Mus musculusPredicted (SEA)0.778492
Click to view 3D structureRetinoic acid receptor gammaP18911Mus musculusPredicted (SEA)0.778492
Click to view 3D structureRetinoic acid receptor betaP22605Mus musculusPredicted (SEA)0.856341
Retinoic acid receptor RXR-alpha structureClick to view 3D structureRetinoic acid receptor RXR-alphaP19793HumansPredicted (SEA)9.6533
Click to view 3D structureRetinoic acid receptor RXR-alphaP28700Mus musculusPredicted (SEA)1.63483
Click to view 3D structureCellular retinoic acid-binding protein 1P62965Mus musculusPredicted (SEA)0.389246
Click to view 3D structureCellular retinoic acid-binding protein 2P22935Mus musculusPredicted (SEA)0.389246
Retinoic acid receptor gamma structureClick to view 3D structureRetinoic acid receptor gammaP13631HumansPredicted (SEA)7.31783
Retinoic acid receptor beta structureClick to view 3D structureRetinoic acid receptor betaP10826HumansPredicted (SEA)4.28171
Retinoic acid receptor alpha structureClick to view 3D structureRetinoic acid receptor alphaP10276HumansPredicted (SEA)8.09632
Retinoic acid receptor RXR-beta structureClick to view 3D structureRetinoic acid receptor RXR-betaP28702HumansPredicted (SEA)3.34752
Retinoic acid receptor RXR-gamma structureClick to view 3D structureRetinoic acid receptor RXR-gammaP48443HumansPredicted (SEA)3.26967
Click to view 3D structureCellular retinoic acid-binding protein 1P40220Gallus gallusPredicted (SEA)0.467095
Click to view 3D structureRetinoic acid receptor RXR-gammaP28705Mus musculusPredicted (SEA)2.49118
Click to view 3D structureRetinoic acid receptor RXR-alphaQ05343Rattus norvegicusPredicted (SEA)0.544945
Click to view 3D structureRetinoic acid receptor RXR-betaP28704Mus musculusPredicted (SEA)3.58106
Click to view 3D structureAldehyde dehydrogenase 1A1P27463Gallus gallusPredicted (SEA)0.622794
Alpha-synuclein structureClick to view 3D structureAlpha-synucleinP37840HumansPredicted (SEA)6.69503
Prosaposin structureClick to view 3D structureProsaposinP07602HumansPredicted (SEA)0.778492
Amyloid-beta precursor protein structureClick to view 3D structureAmyloid-beta precursor proteinP05067HumansPredicted (SEA)84.4664
5-hydroxytryptamine receptor 2B structureClick to view 3D structure5-hydroxytryptamine receptor 2BP41595HumansPredicted (SEA)505.786
Transcription factor EB structureClick to view 3D structureTranscription factor EBP19484HumansPredicted (SEA)13.3901
Mitogen-activated protein kinase 1 structureClick to view 3D structureMitogen-activated protein kinase 1P28482HumansPredicted (SEA)1265.13
Adenosine receptor A3 structureClick to view 3D structureAdenosine receptor A3P0DMS8HumansPredicted (SEA)405.828
Carbonic anhydrase 2 structureClick to view 3D structureCarbonic anhydrase 2P00918HumansPredicted (SEA)666.467
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0003039
FooDB IDFDB023099
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID621
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID4942363
ChEBI ID50174
PubChem Compound ID6437841
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Mestres Quadreny, Ramon; Tortajada Lopez, Desamparados; Arrell Piquer, Maria Jose; Parra Alvarez, Margarita; Gil Grau, Salvador; Cetta Builelo, Luisa; Simo Planells, Ana. Process for the preparation of aromatic retinoic acids [e.g., etretin] and their derivatives. Span. (1992), 14 pp.
2. Al-Mallah NR, Bun H, Coassolo P, Aubert C, Cano JP: Determination of the aromatic retinoids (etretin and isoetretin) in biological fluids by high-performance liquid chromatography. J Chromatogr. 1987 Oct 9;421(1):177-86.
3. Vane FM, Bugge JL, Rodriguez LC: Identification of etretinate metabolites in human blood. Drug Metab Dispos. 1989 May-Jun;17(3):280-5.
4. Fayer BE, Huselton CA, Garland WA, Liberato DJ: Quantification of acitretin in human plasma by microbore liquid chromatography-negative chemical ionization mass spectrometry. J Chromatogr. 1991 Jul 17;568(1):135-44.
5. Vane FM, Bugge CJ, Rodriguez LC: Identification of etretinate metabolites in human bile. Drug Metab Dispos. 1989 May-Jun;17(3):275-9.
6. De Leenheer AP, Lambert WE, De Bersaques JP, Kint AH: High-performance liquid chromatographic determination of etretinate and all-trans- and 13-cis-acitretin in human plasma. J Chromatogr. 1990 Feb 2;500:637-42.
7. Larsen FG, Vahlquist C, Andersson E, Torma H, Kragballe K, Vahlquist A: Oral acitretin in psoriasis: drug and vitamin A concentrations in plasma, skin and adipose tissue. Acta Derm Venereol. 1992;72(2):84-8.