Tazarotene (CED0005853)

Record Information
Version1.0
Creation Date2016-05-22 05:53:07 UTC
Update Date2026-08-21 18:38:08 UTC
Accession NumberCHEM019179
Identification
Common NameTazarotene
ClassSmall Molecule
Description
Tazarotene is an organic compound with the formula C21H21NO2S and an average molecular weight of 351.46 g/mol. Tazarotene belongs to the retinoids, a subclass of prenol lipids within the organic compounds. In industrial applications, it serves as a softener and conditioner. Within the healthcare and pharmaceutical sectors, it is utilized as an antipsoriatic. The compound is found in or released from 19 recorded sources. These include electrical and electronic equipment, such as electrodes, hybrid capacitors, antennas, conductors or conductive bodies characterised by the conductive materials, and electrically stimulated smoking devices. In the category of household cleaning and consumer products, it is associated with soap detergents, perfumes within detergents and soaps, cigar cigarettes, non electric simulated smoking devices, and other smoking requisites. Additionally, it is found in building and construction materials, specifically floors, stairs and ramps, as well as in food processing and cookware related to food preservation and the preparation of vinegar. Recorded exposure routes for the compound include oral, topical, and cutaneous paths. Tazarotene acts on four recorded protein targets, functioning as an agonist of Retinoic acid receptor alpha (RARA), Retinoic acid receptor beta (RARB), Retinoic acid receptor gamma (RARG), and Retinoic acid receptor RXR-beta (RXRB).
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
AvageChEBI
TazarotenoChEBI
TazarotenumChEBI
TazoracChEBI
ZoracChEBI
FabiorKegg
Chemical FormulaC21H21NO2S
Average Molecular Mass351.462 g/mol
Monoisotopic Mass351.129 g/mol
CAS Registry Number118292-40-3
IUPAC Nameethyl 6-[2-(4,4-dimethyl-3,4-dihydro-2H-1-benzothiopyran-6-yl)ethynyl]pyridine-3-carboxylate
Traditional Nametazarotene
SMILESCCOC(=O)C1=CN=C(C=C1)C#CC1=CC2=C(SCCC2(C)C)C=C1
InChI IdentifierInChI=1S/C21H21NO2S/c1-4-24-20(23)16-7-9-17(22-14-16)8-5-15-6-10-19-18(13-15)21(2,3)11-12-25-19/h6-7,9-10,13-14H,4,11-12H2,1-3H3
InChI KeyOGQICQVSFDPSEI-UHFFFAOYSA-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
  • Tazarotene
  • Thiochromane
  • Pyridine carboxylic acid
  • Pyridine carboxylic acid or derivatives
  • Benzothiopyran
  • 1-benzothiopyran
  • Aryl thioether
  • Alkylarylthioether
  • Pyridine
  • Thiopyran
  • Benzenoid
  • Heteroaromatic compound
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Azacycle
  • Thioether
  • Organoheterocyclic compound
  • Organopnictogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organic oxide
  • Organic oxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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 Solubility0.00075 g/LALOGPS
logP5.15ALOGPS
logP5.22ChemAxon
logS-5.7ALOGPS
pKa (Strongest Basic)1.23ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area39.19 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity97.88 m³·mol⁻¹ChemAxon
Polarizability40.31 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-004i-5059000000-5dfdf4638fc629294fd7Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-1590000000-a511655f5e07f3ab2179Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0uk9-0129000000-2db71aa7cf68c539db6dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0009000000-72f9d63158d045736501Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0pb9-5439000000-3f943199dee72abc55c8Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-056s-3392000000-396babafcb01632299a7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0019000000-4cc7d0367627910edc39Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-2039000000-83fa4db6d6d4f8c813ffNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-5093000000-acd348facabd958ebaaeNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0009000000-c9f64427c199d6d00c50Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0ab9-0009000000-50dae41cf3fd9aca5f7fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0lfr-0391000000-efdadade0fc0c9f5b093Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0009000000-085c255d17aa534d26deNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0019000000-d4c78dc93ef4adcb2fffNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-1193000000-201b838185adb6fb2e67Not 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
2224.0Log mg/kg[1300:4000]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
233BrushesPersonal care & cosmeticsNot Available
305AntipsoriaticsHealthcare, pharmaceuticals & veterinary productsNot Available
497FloorsBuilding & ConstructionNot Available
500Stairs And RampsBuilding & ConstructionNot Available
506AntennasElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
525Line Transmission SystemsElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
532SelectorsElectrical & Electronic EquipmentNot Available
545Food PreservationFood, food processing & cookwareNot Available
548Preparation Of VinegarFood, food processing & cookwareNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
578Making CigarsIndustrial manufacturing & chemical processingNot Available
579Manufacture Of Iron Or SteelIndustrial manufacturing & chemical processingNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
583Anchoring EquipmentMarine, shipping & aquacultureNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
612Body Washing Or Cleaning ImplementsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
616Face Mask CosmeticsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
624Merry Go RoundsRecreation & sports surfacesNot Available
632ApparelTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
652RopesTextiles, leather & furnishingsNot Available
653SewingTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
1 pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Fibroblast growth factor receptor 1 structureClick to view 3D structureFibroblast growth factor receptor 1P11362HumansPredicted (SEA)3235.96
Mast/stem cell growth factor receptor Kit structureClick to view 3D structureMast/stem cell growth factor receptor KitP10721HumansPredicted (SEA)3077.22
Click to view 3D structureStreptokinase AP10520Streptococcus pyogenes serotype M1Predicted (SEA)1391.94
Click to view 3D structurePhospholipase A2 group VP51433Rattus norvegicusPredicted (SEA)84.3886
Glycogen synthase kinase-3 beta structureClick to view 3D structureGlycogen synthase kinase-3 betaP49841HumansPredicted (SEA)3981.29
Cyclin-dependent kinase 2 structureClick to view 3D structureCyclin-dependent kinase 2P24941HumansPredicted (SEA)3625.59
Hepatocyte growth factor receptor structureClick to view 3D structureHepatocyte growth factor receptorP08581HumansPredicted (SEA)3519.02
Retinoic acid receptor beta structureClick to view 3D structureRetinoic acid receptor betaP10826HumansPredicted (SEA)2.10193
Retinoic acid receptor alpha structureClick to view 3D structureRetinoic acid receptor alphaP10276HumansPredicted (SEA)3.26967
Retinoic acid receptor gamma structureClick to view 3D structureRetinoic acid receptor gammaP13631HumansPredicted (SEA)4.04816
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansPredicted (SEA)91.0836
Cellular retinoic acid-binding protein 2 structureClick to view 3D structureCellular retinoic acid-binding protein 2P29373HumansPredicted (SEA)1.79053
Retinoic acid receptor RXR-alpha structureClick to view 3D structureRetinoic acid receptor RXR-alphaP19793HumansPredicted (SEA)23.1212
Click to view 3D structureRetinoic acid receptor RXR-gammaP28705Mus musculusPredicted (SEA)4.7488
Click to view 3D structureRetinoic acid receptor RXR-betaP28704Mus musculusPredicted (SEA)4.7488
Retinoic acid receptor RXR-beta structureClick to view 3D structureRetinoic acid receptor RXR-betaP28702HumansPredicted (SEA)8.56341
Retinoic acid receptor RXR-gamma structureClick to view 3D structureRetinoic acid receptor RXR-gammaP48443HumansPredicted (SEA)6.77288
Click to view 3D structureRetinoic acid receptor RXR-alphaP28700Mus musculusPredicted (SEA)6.30579
Click to view 3D structureCytochrome P450 26B1Q9NR63HumansPredicted (SEA)5.91654
Click to view 3D structureCytochrome P450 26A1O43174HumansPredicted (SEA)16.4262
Click to view 3D structureAquaporin-9Q9JJJ3Mus musculusPredicted (SEA)41.4936
Click to view 3D structureAquaporin-3Q8R2N1Mus musculusPredicted (SEA)41.4936
Vascular endothelial growth factor receptor 2 structureClick to view 3D structureVascular endothelial growth factor receptor 2P35968HumansPredicted (SEA)3046.86
Proto-oncogene tyrosine-protein kinase Src structureClick to view 3D structureProto-oncogene tyrosine-protein kinase SrcP12931HumansPredicted (SEA)3182.16
Click to view 3D structureProtein RecAP9WHJ3Mycobacterium tuberculosisPredicted (SEA)941.197
Concentrations
Not Available
External Links
DrugBank IDDB00799
HMDB IDHMDB0014937
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkTazarotene
Chemspider ID5188
ChEBI ID32184
PubChem Compound ID5381
Kegg Compound IDC12531
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
5. The lipid handbook with CD-ROM