Sitaxentan
Grundinformationen
- CAS
184036-34-8- Standard-SMILES
Cc1cc2c(cc1CC(=O)c1sccc1S(=O)(=O)Nc1onc(C)c1Cl)OCO2- InChIKey
PHWXUGHIIBDVKD-UHFFFAOYSA-N- Summenformel
- C18H15ClN2O6S2
- Durchschnittliche Molmasse
- 454,9 g/mol
- Monoisotopische Masse
- 454,0060062
Namen und Bezeichner
- Bevorzugter Name
- Sitaxentan
- IUPAC
- N-(4-chloro-3-methyl-1,2-oxazol-5-yl)-2-[2-(6-methyl-1,3-benzodioxol-5-yl)acetyl]thiophene-3-sulfonamide
- Englischer Name
- N-(4-chloro-3-methyl-oxazol-5-yl)-2-[2-(6-methylbenzo[1,3]dioxol-5-yl)acetyl]thiophene-3-sulfonamide
- Summenformel
- C18H15ClN2O6S2
- Molmasse
- 0
Namen und Synonyme
SitaxsentanSitaxentan184036-34-8TBC-11251TBC11251TBC 11251DTXSID0057673N-(4-chloro-3-methyl-1,2-oxazol-5-yl)-2-[2-(6-methyl-1,3-benzodioxol-5-yl)acetyl]thiophene-3-sulfonamideIPI 1040IPI-1040J9QH779MEMDTXCID1031462
Weitere Namen anzeigen
Unii-J9qh779memSitaxentan [INN]3-Thiophenesulfonamide, N-(4-chloro-3-methyl-5-isoxazolyl)-2-((6-methyl-1,3-benzodioxol-5-yl)acetyl)-N-(4-Chloro-3-methyl-5-isoxazolyl)-2-((2-methyl-4,5-methylenedioxyphenyl)acetyl)thiophene-3-sulfonamideN-(4-Chloro-3-methyl-5-isoxazolyl)-2-((3,4-(methylenedioxy)-6-methylphenyl)acetyl)-3-thiophenesulfonamide
N-(4-Chloro-3-methyl-5-isoxazolyl)-2-((4,5-(methylenedioxy)-o-toly)acetyl)-3-thiophenesulfonamideN-(4-chloro-3-methyl-5-isoxazolyl)-2-(3,4-(methylenedioxy)-6-methyl)phenylacetyl-3-thiophenesulfonamideN-(4-chloro-3-methyl-1,2-oxazol-5-yl)-2-[2-(6-methyl-2H-1,3-benzodioxol-5-yl)acetyl]thiophene-3-sulfonamidesitaxentanumN-(4-chloro-3-methyl-1,2-oxazol-5-yl)-2-(2-(6-methyl-1,3-benzodioxol-5-yl)acetyl)thiophene-3-sulfonamideN-(4-chloro-3-methyl-1,2-oxazol-5-yl)-2-(2-(6-methyl-2H-1,3-benzodioxol-5-yl)acetyl)thiophene-3-sulfonamideRefChem:886377C02KX03
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 3,7
- Polarare Oberfläche (TPSA)
- 144 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 9
- Frei drehbare Bindungen
- 6
- Schwere Atome
- 29
- Formalladung
- 0
- Komplexität
- 720
Experimentelle und physikochemische Eigenschaften
Physical DescriptionSolid
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
Toxikologische Informationen
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Sitaxsentan
vMost-DILI-concern
8
Withdrawn
DOI:10.1016/j.drudis.2016.02.015
Chemie und Industrie
Pharmakologische Informationen
ATC Code
C - Cardiovascular system；C02 - Antihypertensives；C02K - Other antihypertensives；C02KX - Antihypertensives for pulmonary arterial hypertension；C02KX03 - Sitaxentan
QC - Cardiovascular system；QC02 - Antihypertensives；QC02K - Other antihypertensives；QC02KX - Antihypertensives for pulmonary arterial hypertension；QC02KX03 - Sitaxentan
Protein Binding99% +
Pharmacodynamics
Sitaxentan belongs to a class of drugs known as endothelin receptor antagonists (ERAs). Patients with PAH have elevated levels of endothelin, a potent blood vessel constrictor, in their plasma and lung tissue. Sitaxentan blocks the binding of endothelin to its receptors, thereby negating endothelin's deleterious effects.
Mechanism of Action
Sitaxentan is a competitive antagonist of endothelin-1 at the endothelin-A (ET-A) and endothelin-B (ET-B) receptors. Under normal conditions, endothelin-1 binding of ET-A or ET-B receptors causes pulmonary vasoconstriction. By blocking this interaction, Sitaxentan decreases pulmonary vascular resistance. Sitaxentan has a higher affinity for ET-A than ET-B.
Biological Half-Life10 hours
Metabolism/MetabolitesHepatic (CYP2C9- and CYP3A4-mediated)
MeSH Pharmacological ClassificationCompounds and drugs that bind to and inhibit or block the activation of ENDOTHELIN RECECPTORS.
Absorption, Distribution and Excretion
70-100%
Renal (50 to 60%) Fecal (40 to 50%)
Cellular LocationsMembrane
Zugehörige Reaktionen
1
Notizen zur Verbindung
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