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MedKoo Cat#: 319620 | Name: Cipargamin
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Cipargamin, 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.

Chemical Structure

Cipargamin
Cipargamin
CAS#1193314-23-6

Theoretical Analysis

MedKoo Cat#: 319620

Name: Cipargamin

CAS#: 1193314-23-6

Chemical Formula: C19H14Cl2FN3O

Exact Mass: 389.0498

Molecular Weight: 390.24

Elemental Analysis: C, 58.48; H, 3.62; Cl, 18.17; F, 4.87; N, 10.77; O, 4.10

Price and Availability

Size Price Availability Quantity
2mg USD 350.00 2 Weeks
5mg USD 650.00 2 Weeks
10mg USD 950.00 2 Weeks
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Related CAS #
No Data
Synonym
NITD609; NITD 609; NITD-609; KAE609; KAE 609; KAE-609; GNF-609; GNF 609; GNF609; Cipargamin
IUPAC/Chemical Name
(1R,3S)-5’,7-Dichloro-6-fluoro-3-methyl-spiro[2,3,4,9-tetrahydropyrido[3,4-b]indole-1,3’-indoline]-2’-one
InChi Key
CKLPLPZSUQEDRT-WPCRTTGESA-N
InChi Code
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
SMILES Code
O=C([C@]12N[C@@H](C)CC3=C1NC4=C3C=C(F)C(Cl)=C4)NC5=C2C=C(Cl)C=C5
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 390.24 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Bouwman SA, Zoleko-Manego R, Renner KC, Schmitt EK, Mombo-Ngoma G, Grobusch MP. The early preclinical and clinical development of cipargamin (KAE609), a novel antimalarial compound. Travel Med Infect Dis. 2020 Jul-Aug;36:101765. doi: 10.1016/j.tmaid.2020.101765. Epub 2020 Jun 16. PMID: 32561392. 2: Schmitt EK, Ndayisaba G, Yeka A, Asante KP, Grobusch MP, Karita E, Mugerwa H, Asiimwe S, Oduro A, Fofana B, Doumbia S, Su G, Csermak Renner K, Venishetty VK, Sayyed S, Straimer J, Demin I, Barsainya S, Boulton C, Gandhi P. Efficacy of Cipargamin (KAE609) in a Randomized, Phase II Dose-Escalation Study in Adults in Sub-Saharan Africa With Uncomplicated Plasmodium falciparum Malaria. Clin Infect Dis. 2022 May 30;74(10):1831-1839. doi: 10.1093/cid/ciab716. PMID: 34410358; PMCID: PMC9155642. 3: McCarthy JS, Abd-Rahman AN, Collins KA, Marquart L, Griffin P, Kümmel A, Fuchs A, Winnips C, Mishra V, Csermak-Renner K, Jain JP, Gandhi P. Defining the Antimalarial Activity of Cipargamin in Healthy Volunteers Experimentally Infected with Blood-Stage Plasmodium falciparum. Antimicrob Agents Chemother. 2021 Jan 20;65(2):e01423-20. doi: 10.1128/AAC.01423-20. PMID: 33199389; PMCID: PMC7849011. 4: Ashley EA, Phyo AP. Drugs in Development for Malaria. Drugs. 2018 Jun;78(9):861-879. doi: 10.1007/s40265-018-0911-9. PMID: 29802605; PMCID: PMC6013505. 5: Ndayisaba G, Yeka A, Asante KP, Grobusch MP, Karita E, Mugerwa H, Asiimwe S, Oduro A, Fofana B, Doumbia S, Jain JP, Barsainya S, Kullak-Ublick GA, Su G, Schmitt EK, Csermak K, Gandhi P, Hughes D. Hepatic safety and tolerability of cipargamin (KAE609), in adult patients with Plasmodium falciparum malaria: a randomized, phase II, controlled, dose-escalation trial in sub-Saharan Africa. Malar J. 2021 Dec 20;20(1):478. doi: 10.1186/s12936-021-04009-1. PMID: 34930267; PMCID: PMC8686384. 6: Yipsirimetee A, Chiewpoo P, Tripura R, Lek D, Day NPJ, Dondorp AM, Pukrittayakamee S, White NJ, Chotivanich K. Assessment In Vitro of the Antimalarial and Transmission-Blocking Activities of Cipargamin and Ganaplacide in Artemisinin-Resistant Plasmodium falciparum. Antimicrob Agents Chemother. 2022 Mar 15;66(3):e0148121. doi: 10.1128/AAC.01481-21. Epub 2022 Jan 3. PMID: 34978886; PMCID: PMC8923224. 7: Qiu D, Pei JV, Rosling JEO, Thathy V, Li D, Xue Y, Tanner JD, Penington JS, Aw YTV, Aw JYH, Xu G, Tripathi AK, Gnadig NF, Yeo T, Fairhurst KJ, Stokes BH, Murithi JM, Kümpornsin K, Hasemer H, Dennis ASM, Ridgway MC, Schmitt EK, Straimer J, Papenfuss AT, Lee MCS, Corry B, Sinnis P, Fidock DA, van Dooren GG, Kirk K, Lehane AM. A G358S mutation in the Plasmodium falciparum Na+ pump PfATP4 confers clinically-relevant resistance to cipargamin. Nat Commun. 2022 Sep 30;13(1):5746. doi: 10.1038/s41467-022-33403-9. PMID: 36180431; PMCID: PMC9525273. 8: 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. 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. Drug Metab Dispos. 2016 May;44(5):672-82. doi: 10.1124/dmd.115.069187. Epub 2016 Feb 26. PMID: 26921387. 9: Dennis ASM, Lehane AM, Ridgway MC, Holleran JP, Kirk K. Cell Swelling Induced by the Antimalarial KAE609 (Cipargamin) and Other PfATP4-Associated Antimalarials. Antimicrob Agents Chemother. 2018 May 25;62(6):e00087-18. doi: 10.1128/AAC.00087-18. PMID: 29555632; PMCID: PMC5971608. 10: Hien TT, White NJ, Thuy-Nhien NT, Hoa NT, Thuan PD, Tarning J, Nosten F, Magnusson B, Jain JP, Hamed K. Estimation of the In Vivo MIC of Cipargamin in Uncomplicated Plasmodium falciparum Malaria. Antimicrob Agents Chemother. 2017 Jan 24;61(2):e01940-16. doi: 10.1128/AAC.01940-16. PMID: 27872070; PMCID: PMC5278730. 11: Rosling JEO, Ridgway MC, Summers RL, Kirk K, Lehane AM. Biochemical characterization and chemical inhibition of PfATP4-associated Na+-ATPase activity in Plasmodium falciparum membranes. J Biol Chem. 2018 Aug 24;293(34):13327-13337. doi: 10.1074/jbc.RA118.003640. Epub 2018 Jul 9. PMID: 29986883; PMCID: PMC6109929. 12: Pance A. Evolve and survive. Nat Rev Microbiol. 2017 May;15(5):258. doi: 10.1038/nrmicro.2017.31. Epub 2017 Mar 27. PMID: 28344347. 13: Zhu J, Huang L, Dong W, Li N, Yu X, Deng WP, Tang W. Enantioselective Rhodium-Catalyzed Addition of Arylboroxines to N-Unprotected Ketimines: Efficient Synthesis of Cipargamin. Angew Chem Int Ed Engl. 2019 Nov 4;58(45):16119-16123. doi: 10.1002/anie.201910008. Epub 2019 Sep 24. PMID: 31468680. 14: 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. Comparative chemical genomics reveal that the spiroindolone antimalarial KAE609 (Cipargamin) is a P-type ATPase inhibitor. Sci Rep. 2016 Jun 13;6:27806. doi: 10.1038/srep27806. PMID: 27291296; PMCID: PMC4904242. 15: Surur AS, Huluka SA, Mitku ML, Asres K. Indole: The After Next Scaffold of Antiplasmodial Agents? Drug Des Devel Ther. 2020 Nov 11;14:4855-4867. doi: 10.2147/DDDT.S278588. PMID: 33204071; PMCID: PMC7666986. 16: Stein DS, Jain JP, Kangas M, Lefèvre G, Machineni S, Griffin P, Lickliter J. Open-label, single-dose, parallel-group study in healthy volunteers to determine the drug-drug interaction potential between KAE609 (cipargamin) and piperaquine. Antimicrob Agents Chemother. 2015;59(6):3493-500. doi: 10.1128/AAC.00340-15. Epub 2015 Apr 6. PMID: 25845867; PMCID: PMC4432206. 17: Greenwood B. Treatment of malaria--a continuing challenge. N Engl J Med. 2014 Jul 31;371(5):474-5. doi: 10.1056/NEJMe1407026. PMID: 25075840. 18: Mathews ES, Odom John AR. Tackling resistance: emerging antimalarials and new parasite targets in the era of elimination. F1000Res. 2018 Aug 1;7:F1000 Faculty Rev-1170. doi: 10.12688/f1000research.14874.1. PMID: 30135714; PMCID: PMC6073090. 19: Wolfard J, Xu J, Zhang H, Chung CK. Synthesis of Chiral Tryptamines via a Regioselective Indole Alkylation. Org Lett. 2018 Sep 7;20(17):5431-5434. doi: 10.1021/acs.orglett.8b02335. Epub 2018 Aug 21. PMID: 30130113. 20: van Schalkwyk DA, Moon RW, Duffey M, Leroy D, Sutherland CJ. Ex vivo susceptibility to new antimalarial agents differs among human-infecting Plasmodium species. Int J Parasitol Drugs Drug Resist. 2021 Dec;17:5-11. doi: 10.1016/j.ijpddr.2021.07.002. Epub 2021 Jul 24. PMID: 34315108; PMCID: PMC8327131.