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SML2375

Sigma-Aldrich

KDU691

≥98% (HPLC)

Synonym(s):

KDU 691, N-(4-Chlorophenyl)-N-methyl-3-[4-(methylcarbamoyl)phenyl]imidazo[1,2-a]pyrazine-6-carboxamide, N-(4-Chlorophenyl)-N-methyl-3-[4-[(methylamino)carbonyl]phenyl]imidazo[1,2-a]pyrazine-6-carboxamide

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About This Item

Empirical Formula (Hill Notation):
C22H18ClN5O2
CAS Number:
1513879-19-0
Molecular Weight:
419.86
MDL number:
MFCD28963927
UNSPSC Code:
12352200

Assay

≥98% (HPLC)

form

powder

color

white to brown

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

SMILES string

O=C(N(C1=CC=C(Cl)C=C1)C)C(N=C2)=CN3C2=NC=C3C4=CC=C(C(NC)=O)C=C4

InChI

1S/C22H18ClN5O2/c1-24-21(29)15-5-3-14(4-6-15)19-11-26-20-12-25-18(13-28(19)20)22(30)27(2)17-9-7-16(23)8-10-17/h3-13H,1-2H3,(H,24,29)

InChI key

TYMFFISSODJRDV-UHFFFAOYSA-N

Biochem/physiol Actions

KDU691 is an orally active imidazopyrazine class antiparasitic that inhibits Plasmodium & Cryptosporidium phosphatidylinositol-4-OH kinase, PI(4)K, in an ATP-competitive, highly potent and selective manner (IC50/[ATP] = 1.5 nM/10 μM/P. vivax & 17 nM/3 μM/C. parvum PI(4)K) with little or no activity against human PI3Kα/β/γ/δ, PI4KIIIβ, VPS34, and 36 human protein kinases. KDU691 is effective against human pathogens P. falciparum, P. vivax, C. parvum and C. hominis, as well as simian parasite P. cynomolgi. KDU691 blocks Plasmodium development in all life-cycle stages and displays in vivo efficacy in murine models of malaria and cryptosporidiosis.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000051038
0000051039
0000042368

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Michelle Yi-Xiu Lim et al.
Nature microbiology, 16166-16166 (2016-09-20)
A molecular understanding of drug resistance mechanisms enables surveillance of the effectiveness of new antimicrobial therapies during development and deployment in the field. We used conventional drug resistance selection as well as a regime of limiting dilution at early stages
L Dembele et al.
Scientific reports, 7(1), 2325-2325 (2017-05-26)
Malaria control and elimination are threatened by the emergence and spread of resistance to artemisinin-based combination therapies (ACTs). Experimental evidence suggests that when an artemisinin (ART)-sensitive (K13 wild-type) Plasmodium falciparum strain is exposed to ART derivatives such as dihydroartemisinin (DHA)
Case W McNamara et al.
Nature, 504(7479), 248-253 (2013-11-29)
Achieving the goal of malaria elimination will depend on targeting Plasmodium pathways essential across all life stages. Here we identify a lipid kinase, phosphatidylinositol-4-OH kinase (PI(4)K), as the target of imidazopyrazines, a new antimalarial compound class that inhibits the intracellular
Koen J Dechering et al.
Scientific reports, 7(1), 17680-17680 (2017-12-17)
Eradication of malaria requires a novel type of drug that blocks transmission from the human to the mosquito host, but selection of such a drug is hampered by a lack of translational models. Experimental mosquito infections yield infection intensities that
Laurent Dembele et al.
Antimicrobial agents and chemotherapy, 62(5) (2018-03-14)
Artemisinin (ART) resistance has spread through Southeast Asia, posing a serious threat to the control and elimination of malaria. ART resistance has been associated with mutations in the Plasmodium falciparum kelch-13 (Pfk13) propeller domain. Phenotypically, ART resistance is defined as
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