Tasquinimod

HCID 54682876

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Grundinformationen

CAS: 254964-60-8
Standard-SMILES: COc1cccc2c1c(O)c(C(=O)N(C)c1ccc(C(F)(F)F)cc1)c(=O)n2C
InChIKey: ONDYALNGTUAJDX-UHFFFAOYSA-N
Summenformel: C20H17F3N2O4
Durchschnittliche Molmasse: 406,4 g/mol
Monoisotopische Masse: 406,11404168

Überblick

Tasquinimod is a quinoline-3-carboxamide linomide analogue with antiangiogenic and potential antineoplastic activities. Tasquinimod has been shown to decrease blood vessel density but the exact mechanism of action is not known. This agent has also been shown to augment the antineoplastic effects of docetaxel and androgen ablation in a murine model of prostate cancer involving human prostate cancer xenografts.

Namen und Bezeichner

Bevorzugter Name: Tasquinimod
IUPAC: 4-hydroxy-5-methoxy-N,1-dimethyl-2-oxo-N-[4-(trifluoromethyl)phenyl]quinoline-3-carboxamide
Englischer Name: tasquinimod
Summenformel: C20H17F3N2O4
Molmasse: 406.36

Namen und Synonyme

Tasquinimod254964-60-8ABR-215050TASQ4-hydroxy-5-methoxy-N,1-dimethyl-2-oxo-N-[4-(trifluoromethyl)phenyl]quinoline-3-carboxamide4-Hydroxy-5-methoxy-N,1-dimethyl-2-oxo-N-(4-(trifluoromethyl)phenyl)-1,2-dihydroquinoline-3-carboxamideDTXSID90180183756U07KN1R4-Hydroxy-5-methoxy-N,1-dimethyl-2-oxo-N-[4-(trifluoromethyl)phenyl]-1,2-dihydroquinoline-3-carboxamidetasquinimodum4-hydroxy-5-methoxy-N,1-dimethyl-2-oxo-N-(4-(trifluoromethyl)phenyl)quinoline-3-carboxamideRefChem:891191

Weitere Namen anzeigen

TASQ)Tasquinimod, >98%Tasquinimod (Standard)Tasquinimod(ABR-215050)Tasquinimod, 10 mM in DMSO7-diMethoxy-4-quinolinyl)oxy]-ABR215050ABR 2150507-Dimethoxy-quinolin-4-yloxy)-phenylamine

DTXCID00102674Tasquinimod [INN]MFCD18251454UNII-756U07KN1R4-Hydroxy-5-methoxy-N,1-dimethyl-2-oxo-N-(4-(trifluoromethyl)-phenyl)-1,2-dihydroquinoline-3-carboxamideAC-32481N-Methyl-N-(4-trifluoromethyl-phenyl)-1,2-dihydro-4-hydroxy-5-methoxy-1-methyl-2-oxo-quinoline-3-carboxamide4-Hydroxy-5-methoxy-N

Datenbank-Bezeichner

CAS: 254964-60-8
PubChem CID: 54682876
DTXSID: DTXSID90180183
ChEMBL: CHEMBL2107784
ChEBI: CHEBI:231355
UNII: 756U07KN1R
Nikkaji: J2.975.990A

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 3,5
Polarare Oberfläche (TPSA): 70,1 Å²
H-Brücken-Donoren: 1
H-Brücken-Akzeptoren: 7
Frei drehbare Bindungen: 3
Schwere Atome: 29
Formalladung: 0
Komplexität: 686

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Listed in ZINC15

Physikochemische Eigenschaften

Siedepunkt: 501.5 · 501.5±50.0 °C(Predicted)
Dichte: 1.427 · 1.427±0.06 g/cm3(Predicted)
storage temp.: 2 · 2-8°C
Löslichkeit: 2 O; · insoluble in H2O; ≥20.32 mg/mL in DMSO; ≥4.75 mg/mL in EtOH with gentle warming and ultrasonic
Aggregatzustand: solid
pka: 4.5 · 4.50±1.00(Predicted)
Farbe: White to light yellow
InChI: 1S/C20H17F3N2O4/c1-24(12-9-7-11(8-10-12)20(21,22)23)18(27)16-17(26)15-13(25(2)19(16)28)5-4-6-14(15)29-3/h4-10,26H,1-3H3
InChIKey: ONDYALNGTUAJDX-UHFFFAOYSA-N
SMILES: FC(F)(F)c1ccc(cc1)N(C)C(=O)c2[c]([n](c3c(c2O)c(ccc3)OC)C)=O

Sicherheit und Regulatorisches

Sicherheitsdaten

wgk: WGK 3
Speicherklasse: 11 - Combustible Solids

Chemie und Industrie

Anwendungen · 2 Einträge

BeschreibungTasquinimod is an orally-active quinoline-3-carboxamide derived from roquinimex, an immunomodulatory quinolone with applications in some cancers and autoimmune diseases. Tasquinimod inhibits tumor angiogenesis and supplements radiation or chemotherapy in animal models of prostate cancer. While its precise mechanism of action remains unclear, tasquinimod has been reported to alter signaling through S100A9, thrombospondin-1, HIF-1α, androgen receptor, VEGF, and HDAC3/4.

VerwendenTasquinimod is an orally active antiangiogenic agent which may inhibit HDAC4 signalling. This affects cancer cell survival thus making this compound and anti-cancer agent.