Cipargamin

• CAT Number: I006138
• CAS Number: 1193314-23-6
• Molecular Formula: C19H14Cl2FN3O
• Molecular Weight: 390.23
• Purity: ≥95%
• Target: Plasmodium falciparum growth inhibitor
• Solubility: Soluble in DMSO, not in water
• Storage: Store at -20°C
• IUPAC Name: (3R,3'S)-5,7'-dichloro-6'-fluoro-3'-methylspiro[1H-indole-3,1'-2,3,4,9-tetrahydropyrido[3,4-b]indole]-2-one
• InChI: InChI=1S/C19H14Cl2FN3O/c1-8-4-11-10-6-14(22)13(21)7-16(10)23-17(11)19(25-8)12-5-9(20)2-3-15(12)24-18(19)26/h2-3,5-8,23,25H,4H2,1H3,(H,24,26)/t8-,19+/m0/s1
• InChIKey: CKLPLPZSUQEDRT-WPCRTTGESA-N
• SMILES: C[C@H]1CC2=C([C@]3(N1)C4=C(C=CC(=C4)Cl)NC3=O)NC5=CC(=C(C=C25)F)Cl

Cipargamin (Cat.No:I006138), also known as NITD609, GNF-609 and KAE609, is a potent Spiroindolone inhibitor of Plasmodium falciparum growth with potent, dose-dependent antimalarial activity against asexual and sexual stages of Plasmodium. NITD609 potently inhibits gametocytogenesis and blocks Plasmodium falciparum transmission to anopheles mosquito vector.

Reference

1:Estimation of the In Vivo MIC of Cipargamin in Uncomplicated Plasmodium falciparum Malaria. Hien TT, White NJ, Thuy-Nhien NT, Hoa NT, Thuan PD, Tarning J, Nosten F, Magnusson B, Jain JP, Hamed K.Antimicrob Agents Chemother. 2017 Jan 24;61(2). pii: e01940-16. doi: 10.1128/AAC.01940-16. Print 2017 Feb. PMID: 27872070 Free PMC Article2:Comparative chemical genomics reveal that the spiroindolone antimalarial KAE609 (Cipargamin) is a P-type ATPase inhibitor. Goldgof GM, Durrant JD, Ottilie S, Vigil E, Allen KE, Gunawan F, Kostylev M, Henderson KA, Yang J, Schenken J, LaMonte GM, Manary MJ, Murao A, Nachon M, Stanhope R, Prescott M, McNamara CW, Slayman CW, Amaro RE, Suzuki Y, Winzeler EA.Sci Rep. 2016 Jun 13;6:27806. doi: 10.1038/srep27806. PMID: 27291296 Free PMC Article3:KAE609 (Cipargamin), a New Spiroindolone Agent for the Treatment of Malaria: Evaluation of the Absorption, Distribution, Metabolism, and Excretion of a Single Oral 300-mg Dose of [14C]KAE609 in Healthy Male Subjects. Huskey SE, Zhu CQ, Fredenhagen A, Kühnöl J, Luneau A, Jian Z, Yang Z, Miao Z, Yang F, Jain JP, Sunkara G, Mangold JB, Stein DS.Drug Metab Dispos. 2016 May;44(5):672-82. doi: 10.1124/dmd.115.069187. Epub 2016 Feb 26. PMID: 26921387 Free Article4:Open-label, single-dose, parallel-group study in healthy volunteers to determine the drug-drug interaction potential between KAE609 (cipargamin) and piperaquine. Stein DS, Jain JP, Kangas M, Lefèvre G, Machineni S, Griffin P, Lickliter J.Antimicrob Agents Chemother. 2015;59(6):3493-500. doi: 10.1128/AAC.00340-15. Epub 2015 Apr 6. PMID: 25845867 Free PMC Article5:A first-in-human randomized, double-blind, placebo-controlled, single- and multiple-ascending oral dose study of novel antimalarial Spiroindolone KAE609 (Cipargamin) to assess its safety, tolerability, and pharmacokinetics in healthy adult volunteers. Leong FJ, Li R, Jain JP, Lefèvre G, Magnusson B, Diagana TT, Pertel P.Antimicrob Agents Chemother. 2014 Oct;58(10):6209-14. doi: 10.1128/AAC.03393-14. Epub 2014 Aug 11. PMID: 25114127 Free PMC Article