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Merck
CN

SML2375

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
UNSPSC Code:
12352200
MDL number:
MFCD28963927
NACRES:
NA.21

Key Documents

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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

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

assay

≥98% (HPLC)

form

powder

color

white to brown

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

Related Categories

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.
Orally active antiparasitic (antimalarial & anti-cryptosporidial), Plasmodium & Cryptosporidium phosphatidylinositol-4-OH kinase, PI(4)K, inhibitor.

Storage Class

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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Pamela Orjuela-Sanchez et al.
ACS infectious diseases, 4(4), 531-540 (2018-03-16)
To develop new drugs and vaccines for malaria elimination, it will be necessary to discover biological interventions, including small molecules that act against Plasmodium vivax exoerythrocytic forms. However, a robust in vitro culture system for P. vivax is still lacking. Thus
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
Pamela A Magistrado et al.
ACS infectious diseases, 2(11), 816-826 (2016-12-10)
MMV007564 is a novel antimalarial benzimidazolyl piperidine chemotype identified in cellular screens. To identify the genetic determinant of MMV007564 resistance, parasites were cultured in the presence of the compound to generate resistant lines. Whole genome sequencing revealed distinct mutations in
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
Nil Gural et al.
Cell host & microbe, 23(3), 395-406 (2018-02-27)
The unique relapsing nature of Plasmodium vivax infection is a major barrier to malaria eradication. Upon infection, dormant liver-stage forms, hypnozoites, linger for weeks to months and then relapse to cause recurrent blood-stage infection. Very little is known about hypnozoite
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