Sitaxentan (CED0009392)

Record Information
Version1.0
Creation Date2016-05-22 07:18:47 UTC
Update Date2026-08-19 23:10:08 UTC
Accession NumberCHEM020672
Identification
Common NameSitaxentan
ClassSmall Molecule
Description
Sitaxentan is an organic compound with the chemical formula C18H15ClN2O6S2 and an average molecular weight of 454.90 g/mol. Sitaxentan belongs to the benzodioxoles, a class of organoheterocyclic compounds within the organic compounds. This compound is identified as an antagonist of the Endothelin-1 receptor (EDNRA) and the Endothelin receptor type B (EDNRB). It has been recorded in 11 different sources, including antihypertensives within the category of healthcare, pharmaceuticals, and veterinary products. Other recorded sources include pipe accessories in household cleaning and consumer products, ladders in building and construction, as well as various electrical and electronic equipment such as antennas, amplifiers, auxiliary devices, discharge lamps, and line transmission systems. The recorded route of exposure for sitaxentan is oral.
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
SitaxsentanHMDB
TBC-11251HMDB
N-(4-Chloro-3-methyl-5-isoxazolyl)-2-(3,4-(methylenedioxy)-6-methyl)phenylacetyl-3-thiophenesulfonamideMeSH
N-(4-Chloro-3-methyl-5-isoxazolyl)-2-((4,5-(methylenedioxy)-O-toly)acetyl)-3-thiophenesulfonamideMeSH
Chemical FormulaC18H15ClN2O6S2
Average Molecular Mass454.905 g/mol
Monoisotopic Mass454.006 g/mol
CAS Registry Number184036-34-8
IUPAC NameN-(4-chloro-3-methyl-1,2-oxazol-5-yl)-2-[2-(6-methyl-2H-1,3-benzodioxol-5-yl)acetyl]thiophene-3-sulfonamide
Traditional Namethelin
SMILESCC1=NOC(NS(=O)(=O)C2=C(SC=C2)C(=O)CC2=CC3=C(OCO3)C=C2C)=C1Cl
InChI IdentifierInChI=1S/C18H15ClN2O6S2/c1-9-5-13-14(26-8-25-13)7-11(9)6-12(22)17-15(3-4-28-17)29(23,24)21-18-16(19)10(2)20-27-18/h3-5,7,21H,6,8H2,1-2H3
InChI KeyPHWXUGHIIBDVKD-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzodioxoles
Sub ClassNot Available
Direct ParentBenzodioxoles
Alternative Parents
Substituents
  • Benzodioxole
  • Aryl alkyl ketone
  • Aryl ketone
  • Aryl chloride
  • Aryl halide
  • Benzenoid
  • Organosulfonic acid amide
  • Azole
  • Isoxazole
  • Heteroaromatic compound
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Aminosulfonyl compound
  • Thiophene
  • Sulfonyl
  • Ketone
  • Oxacycle
  • Acetal
  • Azacycle
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
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 Solubility0.018 g/LALOGPS
logP3.35ALOGPS
logP3.09ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)6.89ChemAxon
pKa (Strongest Basic)0.75ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area107.73 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity105.8 m³·mol⁻¹ChemAxon
Polarizability43.12 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0002-2911100000-bc2a1c237a5d20fc7fddNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0012900000-ce9abb5f9d34eeec4e75Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4r-0953700000-bf4f0740a903bbe272bbNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-052u-3390000000-26c07fb81659836de3aaNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0001900000-89731203423f9c2c4f61Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-1291600000-b346cc1802382a37696aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4l-9410000000-8a91a08da2a0b22f85afNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0001900000-4603fc4b43ea34c94da3Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0900200000-4603223331cb368e057eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-009t-1930100000-1655132c3e1392943c27Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0000900000-c85f93916432b4dbe289Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udj-0136900000-dd6a50653785ff673c2cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-2289500000-62d0e1afc39abb8eb9e8Not 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
644.0Log mg/kg[360:1100]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
289AntihypertensivesHealthcare, pharmaceuticals & veterinary productsNot Available
498LaddersBuilding & ConstructionNot Available
505AmplifiersElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
507Auxiliary DevicesElectrical & Electronic EquipmentNot Available
514Discharge LampsElectrical & Electronic EquipmentNot Available
525Line Transmission SystemsElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
531RelaysElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
562Pipe AccessoriesHousehold cleaning & consumer productsNot Available
592Marine Propulsion Or SteeringMarine, shipping & aquacultureNot Available
601Lawn MowersAgriculture & land managementNot Available
625Racing SportsRecreation & sports surfacesNot Available
627Roulette GamesRecreation & sports surfacesNot Available
630ToysRecreation & sports surfacesNot Available
643HeadwearTextiles, leather & furnishingsNot Available
651Purses Money Bags WalletsTextiles, leather & furnishingsNot Available
653SewingTextiles, leather & furnishingsNot Available
656Snap FastenersTextiles, leather & furnishingsNot Available
Pathways
1 pathway
Sitaxentan Drug Metabolism Action Pathway
Sitaxentan Drug Metabolism Action Pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Endothelin-1 receptor structureClick to view 3D structureEndothelin-1 receptorP25101HumansPredicted (SEA)109.067
Click to view 3D structureATP-dependent 6-phosphofructokinaseQ4E657Trypanosoma cruziPredicted (SEA)32.8524
Click to view 3D structureEndothelin-1 receptorP26684Rattus norvegicusPredicted (SEA)125.96
Type-1 angiotensin II receptor structureClick to view 3D structureType-1 angiotensin II receptorP30556HumansPredicted (SEA)808.308
Click to view 3D structureProteasome subunit betaO96673Trypanosoma cruziPredicted (SEA)31.5289
Kappa-type opioid receptor structureClick to view 3D structureKappa-type opioid receptorP41145HumansPredicted (SEA)2798.13
Mu-type opioid receptor structureClick to view 3D structureMu-type opioid receptorP35372HumansPredicted (SEA)2618.15
Delta-type opioid receptor structureClick to view 3D structureDelta-type opioid receptorP41143HumansPredicted (SEA)2071.02
Induced myeloid leukemia cell differentiation protein Mcl-1 structureClick to view 3D structureInduced myeloid leukemia cell differentiation protein Mcl-1Q07820HumansPredicted (SEA)1459.21
Click to view 3D structureProbable nicotinate-nucleotide adenylyltransferaseP65502Staphylococcus aureus (strain N315)Predicted (SEA)293.336
Dual specificity tyrosine-phosphorylation-regulated kinase 1A structureClick to view 3D structureDual specificity tyrosine-phosphorylation-regulated kinase 1AQ13627HumansPredicted (SEA)4320.01
Dual specificity protein kinase CLK2 structureClick to view 3D structureDual specificity protein kinase CLK2P49760HumansPredicted (SEA)4031.27
Dual specificity protein kinase CLK4 structureClick to view 3D structureDual specificity protein kinase CLK4Q9HAZ1HumansPredicted (SEA)4017.56
Sodium channel protein type 8 subunit alpha structureClick to view 3D structureSodium channel protein type 8 subunit alphaQ9UQD0HumansPredicted (SEA)437.98
Sodium channel protein type 5 subunit alpha structureClick to view 3D structureSodium channel protein type 5 subunit alphaQ14524HumansPredicted (SEA)1176.3
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform structureClick to view 3D structurePhosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoformP48736HumansPredicted (SEA)2889.22
Sodium channel protein type 9 subunit alpha structureClick to view 3D structureSodium channel protein type 9 subunit alphaQ15858HumansPredicted (SEA)1081.95
Dual specificity tyrosine-phosphorylation-regulated kinase 1B structureClick to view 3D structureDual specificity tyrosine-phosphorylation-regulated kinase 1BQ9Y463HumansPredicted (SEA)3390.65
Click to view 3D structureType-1 angiotensin II receptor BP29089Rattus norvegicusPredicted (SEA)349.154
Click to view 3D structureProtein kinase C zeta typeQ05513HumansPredicted (SEA)4056.18
Phosphatidylinositol 3-kinase catalytic subunit type 3 structureClick to view 3D structurePhosphatidylinositol 3-kinase catalytic subunit type 3Q8NEB9HumansPredicted (SEA)843.185
Click to view 3D structurePhosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit beta isoformP42338HumansPredicted (SEA)2936.94
Dual specificity protein kinase CLK1 structureClick to view 3D structureDual specificity protein kinase CLK1P49759HumansPredicted (SEA)2670.31
Dual specificity protein kinase CLK3 structureClick to view 3D structureDual specificity protein kinase CLK3P49761HumansPredicted (SEA)2036.77
Dual specificity protein phosphatase 3 structureClick to view 3D structureDual specificity protein phosphatase 3P51452HumansPredicted (SEA)1176.22
Concentrations
Not Available
External Links
DrugBank IDDB06268
HMDB IDHMDB0015629
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkSitaxentan
Chemspider ID187436
ChEBI ID123417
PubChem Compound ID216235
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References