N-[4-(1-cyanocyclopentyl)phenyl]-2-[(pyridin-4-ylmethyl)amino]pyridine-3-carboxamide; methanesulfonic acid

• ChemBase ID: 73149
• Molecular Formular: C25H27N5O4S
• Molecular Mass: 493.57798
• Monoisotopic Mass: 493.17837537
• SMILES: S(=O)(=O)(O)C.c1cnc(c(c1)C(=O)Nc1ccc(cc1)C1(CCCC1)C#N)NCc1ccncc1
• Canonical SMILES: CS(=O)(=O)O.N#CC1(CCCC1)c1ccc(cc1)NC(=O)c1cccnc1NCc1ccncc1
• InChI: InChI=1S/C24H23N5O.CH4O3S/c25-17-24(11-1-2-12-24)19-5-7-20(8-6-19)29-23(30)21-4-3-13-27-22(21)28-16-18-9-14-26-15-10-18;1-5(2,3)4/h3-10,13-15H,1-2,11-12,16H2,(H,27,28)(H,29,30);1H3,(H,2,3,4)
• InChIKey: FYJROXRIVQPKRY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[4-(1-cyanocyclopentyl)phenyl]-2-[(pyridin-4-ylmethyl)amino]pyridine-3-carboxamide; methanesulfonic acid
• IUPAC Traditional name: N-[4-(1-cyanocyclopentyl)phenyl]-2-[(pyridin-4-ylmethyl)amino]pyridine-3-carboxamide mesylate
• Synonyms: YN968D1; Apatinib

Database IDs

• CAS Number: 811803-05-1
• PubChem SID: 162038069
• PubChem CID: 45139106

CALCULATED PROPERTIES

• Acid pKa: 11.69911
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 4.0203733
• LogD (pH = 7.4): 4.2874675
• Log P: 4.2916036
• Molar Refractivity: 119.1598 cm^3
• Polarizability: 43.87182 Å^3
• Polar Surface Area: 90.7 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Condition: -20°C

Pharmacology Properties

• Target: EGFR

Product Information

• Salt Data: sulfate

DETAILS

Selleck Chemicals - S2221

Research Area: Cancer
Biological Activity:
Apatinib (YN968D1) is a small-molecule selective multitargeted tyrosine kinase inhibitor with an IC50 of 2.43 nM for the inhibition of VEGFR2. Apatinib (YN968D1) has potential antiangiogenic and antineoplastic activities. It is an orally bioavailable, small molecule agent which is thought to inhibit angiogenesis in cancer cells; specifically apatinib inhibits VEGF-mediated endothelial cell migration and proliferation thus blocking new blood vessel formation in tumor tissue. Apatinib (YN968D1) once daily is orally bioavailable in patients with solid tumors refractory to standard therapy. Apatinib exhibited quick absorption, with Cmax reached in 3 to 4 hours. The mean half-life, estimated to be approximately 9 hours, was constant over all dose groups. Steady-state conditions were achieved within 6 days of dosing, with no accumulation during 56 days of once daily dosing of apatinib. Compared with sorafenib and sunitinib, apatinib (YN968D1) shows good anti-cancer effects for gastric and colorectal cancer. Apatinib (YN968D1) also mildly inhibits c-Kit and c-SRC tyrosine kinases. [1][2][3]References on Apatinib (YN968D1)[2] BMC Cancer, 2010, 10:529[3] Cancer Res, 2010, 70:7981-7991

REFERENCES

• Li J et al. BMC Cancer. 2010 Oct 5; 10:529.