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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H14Cl2FN3O
Molecular Weight 390.238
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CIPARGAMIN

SMILES

C[C@H]1CC2=C(NC3=C2C=C(F)C(Cl)=C3)[C@@]4(N1)C(=O)NC5=C4C=C(Cl)C=C5

InChI

InChIKey=CKLPLPZSUQEDRT-WPCRTTGESA-N
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

HIDE SMILES / InChI

Molecular Formula C19H14Cl2FN3O
Molecular Weight 390.238
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Cipargamin is an experimental synthetic antimalarial molecule belonging to the spiroindolone class. It possesses both the potency (average IC50 of 550 pM against asexual blood-stage P. falciparum) and favorable pharmacokinetics (elimination half-life of ~24 hours in humans) needed for a single-dose cure, a feature that could help slow the onset of parasite resistance and that is not shared by existing, approved antimalarial drugs. KAE609 is also unique in its ability to block transmission to mosquitoes. Cipargamin is a parasite P-type ATPase4 inhibitor. Cipargamin in phase II clinical trials for the treatment of acute, uncomplicated malaria due to plasmodium falciparum monoinfection. Nausea was the most common reported adverse effect. The adverse events were generally mild and did not lead to any discontinuations of the drug.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
161 ng/mL
10 mg 1 times / day multiple, oral
CIPARGAMIN plasma
Homo sapiens
991 ng/mL
60 mg 1 times / day multiple, oral
CIPARGAMIN plasma
Homo sapiens
1170 ng/mL
100 mg 1 times / day multiple, oral
CIPARGAMIN plasma
Homo sapiens
1770 ng/mL
150 mg 1 times / day multiple, oral
CIPARGAMIN plasma
Homo sapiens
468 ng/mL
30 mg 1 times / day multiple, oral
CIPARGAMIN plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
1.91 μg × h/mL
10 mg 1 times / day multiple, oral
CIPARGAMIN plasma
Homo sapiens
14.1 μg × h/mL
60 mg 1 times / day multiple, oral
CIPARGAMIN plasma
Homo sapiens
19.8 μg × h/mL
100 mg 1 times / day multiple, oral
CIPARGAMIN plasma
Homo sapiens
29.4 μg × h/mL
150 mg 1 times / day multiple, oral
CIPARGAMIN plasma
Homo sapiens
6.42 μg × h/mL
30 mg 1 times / day multiple, oral
CIPARGAMIN plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
21.4 h
10 mg 1 times / day multiple, oral
CIPARGAMIN plasma
Homo sapiens
28 h
60 mg 1 times / day multiple, oral
CIPARGAMIN plasma
Homo sapiens
23.1 h
100 mg 1 times / day multiple, oral
CIPARGAMIN plasma
Homo sapiens
26.9 h
150 mg 1 times / day multiple, oral
CIPARGAMIN plasma
Homo sapiens
22.4 h
30 mg 1 times / day multiple, oral
CIPARGAMIN plasma
Homo sapiens

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
30 mg once a day for three days
Route of Administration: Oral
In Vitro Use Guide
Cipargamin was found to inhibit the early and late development of Plasmodium falciparum gametocytes in vitro in a dose-dependent fashion over a range of 5 to 500 nM.
Substance Class Chemical
Record UNII
Z7Q4FWA04P
Record Status Validated (UNII)
Record Version