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ChemicalBook--->CAS DataBase List--->269390-77-4

269390-77-4

269390-77-4 Structure

269390-77-4 Structure
IdentificationBack Directory
[Name]

AAL-993
[CAS]

269390-77-4
[Synonyms]

AAL-993
CS-2315
2-(Pyridin-4-ylmethylamino)-N-[3-(trifluoromethyl)phenyl]benzamide
2-[(4-Pyridinylmethyl)amino]-N-[3-(trifluoromethyl)phenyl]benzami de
Benzamide, 2-[(4-pyridinylmethyl)amino]-N-[3-(trifluoromethyl)phenyl]-
VEGFR Tyrosine Kinase Inhibitor VI, AAL-993 - CAS 269390-77-4 - Calbiochem
[Molecular Formula]

C20H16F3N3O
[MDL Number]

MFCD18251410
[MOL File]

269390-77-4.mol
[Molecular Weight]

371.36
Chemical PropertiesBack Directory
[Melting point ]

158-160 °C
[Boiling point ]

441.3±45.0 °C(Predicted)
[density ]

1.349±0.06 g/cm3(Predicted)
[storage temp. ]

+2C to +8C
[solubility ]

Soluble in DMSO (up to 25 mg/ml) or in Ethanol (up to 15 mg/ml).
[form ]

Off-white powder
[pka]

12.95±0.70(Predicted)
[color ]

Pale yellow
[Stability:]

Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months.
Hazard InformationBack Directory
[Description]

AAL-993 (269390-77-4) inhibits VEGFR-1 (IC50 = 130 nM), VEGFR-2 (IC50 = 23 nM), and VEGFR-3 (IC50 = 18 nM). PDGFR-β, cKit, and CSF-1R are also inhibited at higher concentrations (IC50‘s 640 nM, 236 nM and 380 nM respectively). Screening studies have shown no inhibitory activity against a range of other kinases. X-Ray crystallography has shown that AAL-993 binds to the catalytic domain of VEGFR-2 when the protein is in an inactive conformation. Cell permeable, active in vivo and in whole animal studies.
[Uses]

AAL-993 is a VEGFR tyrosine kinase inhibitor that possess dual inhibition of VEGFR signaling and HIF-1α expression through ERK inhibition without affecting Akt phosphorylation.
[General Description]

A cell-permeable anthranilamide that acts as a potent VEGFR inhibitor (IC50 = 130, 23, and 18 nM against VEGFR-1, -2, and -3, respectively; IC50 = 1.24 nM against VEGF-induced human VEGFR-2 phosphorylation in CHO cells) by targeting the ATP-binding site of VEGFR in its inactive "DFG-out" conformation and effectively suppresses tumor growths (50 to 100 mg/kg; p.o.) via its anti-angiogenesis activity in mice and rats in vivo, while inhibiting c-kit, CSF-1R/c-Fms, PDGFR-β, and c-Abl only at higher concentrations (IC50 = 236, 380, 640, and 2820 nM, respectively). AAL933 and two other VEGFR inhibitors, KRN633 and SU5416, are also shown to inhibit hypoxia-induced HIF-1α expression (by <90% at 30 M) and transcription activation. Unlike KRN633 and SU5416, AAL933 prevents only hypoxia-induced Erk, but not Akt, phosphorylation in HeLa cells.
[in vitro]

aal-993 was found to be a highly potent and selective inhibitor of the recombinant vegfr-2 and vegfr-3 kinases. at 3- to 5-fold higher concentration, aal-993 also inhibited vegfr-1 and, although it possessed some activity against other members of the pdgfr kinase family at submicromolar concentrations, aal-993 did not significantly inhibit any of the other kinases tested at concentrations
[in vivo]

animal efficacy study found that aal-993 was able to potently inhibit vegf-induced angiogenesis in an implant model, with ed50 values of 7 mg/kg. moreover, in a mouse orthotopic model of melanoma, aal-993 could potently inhibit both the growth of the primary tumor as well as the formation of spontaneous peripheral metastases [1].
[IC 50]

130, 23, and 18 nm for vegfr1, 2, and 3, respectively
[storage]

Store at -20°C
[References]

1) Manley et al. (2002), Anthranilic acid amides: a novel class of antiangiogenic VEGF receptor kinase inhibitors; J. Med. Chem., 45 5687 2) Manley et al. (2004), Advances in the structural biology, design and clinical development of VEGF-R kinase inhibitors for the treatment of angiogenesis; Biochim. Biophys. Acta, 1697 17
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