Cediranib
Grundinformationen
- CAS
288383-20-0- Standard-SMILES
COc1cc2c(Oc3ccc4[nH]c(C)cc4c3F)ncnc2cc1OCCCN1CCCC1- InChIKey
XXJWYDDUDKYVKI-UHFFFAOYSA-N- Summenformel
- C25H27FN4O3
- Durchschnittliche Molmasse
- 450,5 g/mol
- Monoisotopische Masse
- 450,2067189
Überblick
4-[(4-fluoro-2-methyl-1H-indol-5-yl)oxy]-6-methoxy-7-[3-(1-pyrrolidinyl)propoxy]quinazoline is an aromatic ether.
Namen und Bezeichner
- Bevorzugter Name
- Cediranib
- IUPAC
- 4-[(4-fluoro-2-methyl-1H-indol-5-yl)oxy]-6-methoxy-7-(3-pyrrolidin-1-ylpropoxy)quinazoline
- Englischer Name
- Cediranib
- Summenformel
- C25H27FN4O3
- Molmasse
- 450.51
Namen und Synonyme
Cediranib288383-20-04-((4-Fluoro-2-methyl-1H-indol-5-yl)oxy)-6-methoxy-7-(3-(pyrrolidin-1-yl)propoxy)quinazolineAZD 2171AZD-2171cediranibumNQU9IPY4K94-[(4-fluoro-2-methyl-1H-indol-5-yl)oxy]-6-methoxy-7-[3-(pyrrolidin-1-yl)propoxy]quinazolineDTXSID101830354-((4-Fluoro-2-methyl-1H-indol-5-yl)oxy)-6-methoxy-7-(3-(pyrrolidin-1-yl)propoxy)quinazoline (2Z)-but-2-enedioateRefChem:574948DTXCID20105526
Weitere Namen anzeigen
Cediranib dihydrochlorideCS-377RecentinCadiranibNSC-732208Cediranib RCediranib, >=99%Cediranib (AZD217)
L01XE324-((4-fluoro-2-methyl-1H-indol-5-yl)oxy)-6-methoxy-7-(3-(pyrrolidin-1-yl)propoxy)quinazoline (2Z)-but-2-enedioate (1:1)AZD2171CedirannibCediranib (AZD2171)Cediranib free baseMFCD099541154-[(4-fluoro-2-methyl-1H-indol-5-yl)oxy]-6-methoxy-7-(3-pyrrolidin-1-ylpropoxy)quinazoline
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 4,9
- Polarare Oberfläche (TPSA)
- 72,5 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 7
- Frei drehbare Bindungen
- 8
- Schwere Atome
- 33
- Formalladung
- 0
- Komplexität
- 624
Experimentelle und physikochemische Eigenschaften
DrugsPharmaceuticals -> Listed in ZINC15
Physikochemische Eigenschaften
- Schmelzpunkt
- 135 · 135-138°C
- Siedepunkt
- 626.6 · 626.6±55.0 °C(Predicted)
- Dichte
- 1.285 · 1.285
- storage temp.
- -20 °C · Sealed in dry,Store in freezer, under -20°C
- Löslichkeit
- Acetone (Slightly), DMSO (Slightly), Methanol (Slightly)
- Aggregatzustand
- Solid
- pka
- 16.14 · 16.14±0.30(Predicted)
- Farbe
- White to Off-White
- InChI
- InChI=1S/C25H27FN4O3/c1-16-12-17-19(29-16)6-7-21(24(17)26)33-25-18-13-22(31-2)23(14-20(18)27-15-28-25)32-11-5-10-30-8-3-4-9-30/h6-7,12-15,29H,3-5,8-11H2,1-2H3
- InChIKey
- XXJWYDDUDKYVKI-UHFFFAOYSA-N
- SMILES
- N1=C2C(C=C(OC)C(OCCCN3CCCC3)=C2)=C(OC2C=CC3=C(C=2F)C=C(C)N3)N=C1
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
Danger
H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]
P203, P260, P264, P270, P273, P280, P301+P316, P302+P352, P317, P318, P319, P321, P330, P332+P317, P362+P364, P391, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 5 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Hazard Classes and CategoriesAcute Tox. 3 (100%)
Sicherheitsdaten
- wgk
- WGK 3
- hs_code
- 2933599590
- Speicherklasse
- 11 - Combustible Solids
Chemie und Industrie
Pharmakologische Informationen
ATC Code
L - Antineoplastic and immunomodulating agents
QL - Antineoplastic and immunomodulating agents
Pharmacodynamics
Cediranib is a once-daily, orally available, highly potent and selective VEGF signalling inhibitor that inhibits all three VEGF receptors. The preclinical profile of Cediranib indicates that it has the potential to be the 'best in class' VEGF signalling inhibitor. Phase I data indicate that Cediranib is generally well tolerated, with the most common dose related adverse events being diarrhoea, hoarseness, headache and hypertension.
Mechanism of Action
Cediranib inhibits vacular endothelial growth factor (VEGF) receptor tyrosine kinase (RTK). By forming a blockade at the VEGF receptors, Cediranib limits the growth of new blood vessels, which are essential to supporting tumor growth. Thus, lacking sufficient blood supply, tumor cells become starved for nutrients, slowing or halting growth and potentially improving the efficacy of other treatments. Preclinical evidence indicated that the drug had a high affinity at these sites, and was well tolerated and efficacious in animal studies.
Biological Half-Life12 to 35 hours
MeSH Pharmacological Classification
Substances that inhibit or prevent the proliferation of NEOPLASMS.
Agents that inhibit PROTEIN KINASES.
Absorption, Distribution and ExcretionAvailable following oral administration.
Anwendungen
BeschreibungReceptors for VEGF have central roles in vasculogenesis and angiogenesis and thus serve as targets for cancer therapy. Cediranib is a potent inhibitor of VEGF receptor tyrosine kinases, including VEGFR1, 2, and 3 (IC50s = 5, 1, and 3 nM, respectively). It also potently inhibits a variety of other receptor and non-receptor tyrosine kinases, including several in the platelet-derived growth factor, fibroblast growth factor, and endothelial growth factor receptor families. Cediranib blocks tubule formation by human umbilical vein endothelial cells in vitro and prevents angiogenesis as well as xenograft tumor growth in vivo. Because of these effects, cediranib has potential use in a range of cancers.
Zugehörige Reaktionen
5
Notizen zur Verbindung
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