WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 200730
CAS#: 849550-05-6 (free base)
Description: Cevipabulin, also known as TTI-237, an antimicrotubule agent, is a small synthetic molecule of triazolopyrimidine derivative with potential antitumor activity. With a novel mechanism of action distinct from the action of other vinca alkaloid compounds, TTI-237 specifically binds to tubulin at the vinca site, and promotes the polymerization of tubulin into microtubules. TTI-237 stabilizes tubulin and inhibits microtubule disassembly. This results in cell cycle arrest at the G2/M phase, and leading to cell death.
MedKoo Cat#: 200730
Name: Cevipabulin
CAS#: 849550-05-6 (free base)
Chemical Formula: C18H18ClF5N6O
Exact Mass: 464.11508
Molecular Weight: 464.82
Elemental Analysis: C, 46.51; H, 3.90; Cl, 7.63; F, 20.44; N, 18.08; O, 3.44
Related CAS #: 849550-05-6 (free base) 852954-81-5 (succinate dihydrate)
Synonym: TTI 237; TTI-237; TTI237; D06576; D 06576; D-06576; Cevipabulin.
IUPAC/Chemical Name: 5-chloro-6-[2,6-difluoro-4-[3-(methylamino)propoxy]phenyl]-N-[(1S)-2,2,2-trifluoro-1- methylethyl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine.
InChi Key: ZUZPCOQWSYNWLU-VIFPVBQESA-N
InChi Code: InChI=1S/C18H18ClF5N6O/c1-9(18(22,23)24)28-16-14(15(19)29-17-26-8-27-30(16)17)13-11(20)6-10(7-12(13)21)31-5-3-4-25-2/h6-9,25,28H,3-5H2,1-2H3/t9-/m0/s1
SMILES Code: C[C@H](NC1=C(C2=C(F)C=C(OCCCNC)C=C2F)C(Cl)=NC3=NC=NN13)C(F)(F)F
Related:
849550-05-6 (Cevipabulin free base)
852954-81-5 (Cevipabulin succinate, dihydrate).
1: Wang-Gillam A, Arnold SM, Bukowski RM, Rothenberg ML, Cooper W, Wang KK, Gauthier E, Lockhart AC. A phase I dose escalation study of TTI-237 in patients with advanced malignant solid tumors. Invest New Drugs. 2012 Feb;30(1):266-72. Epub 2010 Aug 10. PubMed PMID: 20697774.
2: Ayral-Kaloustian S, Zhang N, Beyer C. Cevipabulin (TTI-237): preclinical and clinical results for a novel antimicrotubule agent. Methods Find Exp Clin Pharmacol. 2009 Sep;31(7):443-7. Review. PubMed PMID: 19907719.
3: Beyer CF, Zhang N, Hernandez R, Vitale D, Nguyen T, Ayral-Kaloustian S, Gibbons JJ. The microtubule-active antitumor compound TTI-237 has both paclitaxel-like and vincristine-like properties. Cancer Chemother Pharmacol. 2009 Sep;64(4):681-9. Epub 2009 Jan 10. PubMed PMID: 19132373.
4: Beyer CF, Zhang N, Hernandez R, Vitale D, Lucas J, Nguyen T, Discafani C, Ayral-Kaloustian S, Gibbons JJ. TTI-237: a novel microtubule-active compound with in vivo antitumor activity. Cancer Res. 2008 Apr 1;68(7):2292-300. PubMed PMID: 18381436.
5: Zhang N, Ayral-Kaloustian S, Nguyen T, Hernandez R, Beyer C. 2-cyanoaminopyrimidines as a class of antitumor agents that promote tubulin polymerization. Bioorg Med Chem Lett. 2007 Jun 1;17(11):3003-5. Epub 2007 Mar 25. PubMed PMID: 17416524.
