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
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
Molecular Formula | C19H14Cl2FN3O |
Molecular Weight | 390.238 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
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
Sources: http://adisinsight.springer.com/drugs/800035252
Curator's Comment: # Novartis
Approval Year
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
161 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25114127 |
10 mg 1 times / day multiple, oral dose: 10 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
CIPARGAMIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
991 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25114127 |
60 mg 1 times / day multiple, oral dose: 60 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
CIPARGAMIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
1170 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25114127 |
100 mg 1 times / day multiple, oral dose: 100 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
CIPARGAMIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
1770 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25114127 |
150 mg 1 times / day multiple, oral dose: 150 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
CIPARGAMIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
468 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25114127 |
30 mg 1 times / day multiple, oral dose: 30 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
CIPARGAMIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.91 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25114127 |
10 mg 1 times / day multiple, oral dose: 10 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
CIPARGAMIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
14.1 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25114127 |
60 mg 1 times / day multiple, oral dose: 60 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
CIPARGAMIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
19.8 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25114127 |
100 mg 1 times / day multiple, oral dose: 100 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
CIPARGAMIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
29.4 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25114127 |
150 mg 1 times / day multiple, oral dose: 150 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
CIPARGAMIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
6.42 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25114127 |
30 mg 1 times / day multiple, oral dose: 30 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
CIPARGAMIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
21.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25114127 |
10 mg 1 times / day multiple, oral dose: 10 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
CIPARGAMIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
28 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25114127 |
60 mg 1 times / day multiple, oral dose: 60 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
CIPARGAMIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
23.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25114127 |
100 mg 1 times / day multiple, oral dose: 100 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
CIPARGAMIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
26.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25114127 |
150 mg 1 times / day multiple, oral dose: 150 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
CIPARGAMIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
22.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25114127 |
30 mg 1 times / day multiple, oral dose: 30 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
CIPARGAMIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
PubMed
Title | Date | PubMed |
---|---|---|
Mechanistic study of the spiroindolones: a new class of antimalarials. | 2012 Aug 24 |
|
The spiroindolone drug candidate NITD609 potently inhibits gametocytogenesis and blocks Plasmodium falciparum transmission to anopheles mosquito vector. | 2012 Jul |
|
Spiroindolone that inhibits PfATPase4 is a potent, cidal inhibitor of Toxoplasma gondii tachyzoites in vitro and in vivo. | 2014 |
|
Spiroindolone KAE609 for falciparum and vivax malaria. | 2014 Jul 31 |
|
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. | 2014 Oct |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://clinicaltrials.gov/ct2/show/NCT01524341
30 mg once a day for three days
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22508309
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
Created
by
admin
on
Edited
Sat Dec 16 09:11:31 GMT 2023
by
admin
on
Sat Dec 16 09:11:31 GMT 2023
|
Record UNII |
Z7Q4FWA04P
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Code | English | ||
|
Code | English | ||
|
Code | English | ||
|
Code | English | ||
|
Common Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
FDA ORPHAN DRUG |
746820
Created by
admin on Sat Dec 16 09:11:31 GMT 2023 , Edited by admin on Sat Dec 16 09:11:31 GMT 2023
|
||
|
FDA ORPHAN DRUG |
595417
Created by
admin on Sat Dec 16 09:11:31 GMT 2023 , Edited by admin on Sat Dec 16 09:11:31 GMT 2023
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
Z7Q4FWA04P
Created by
admin on Sat Dec 16 09:11:31 GMT 2023 , Edited by admin on Sat Dec 16 09:11:31 GMT 2023
|
PRIMARY | |||
|
44469321
Created by
admin on Sat Dec 16 09:11:31 GMT 2023 , Edited by admin on Sat Dec 16 09:11:31 GMT 2023
|
PRIMARY | |||
|
100000163596
Created by
admin on Sat Dec 16 09:11:31 GMT 2023 , Edited by admin on Sat Dec 16 09:11:31 GMT 2023
|
PRIMARY | |||
|
DTXSID70152424
Created by
admin on Sat Dec 16 09:11:31 GMT 2023 , Edited by admin on Sat Dec 16 09:11:31 GMT 2023
|
PRIMARY | |||
|
9865
Created by
admin on Sat Dec 16 09:11:31 GMT 2023 , Edited by admin on Sat Dec 16 09:11:31 GMT 2023
|
PRIMARY | |||
|
1193314-23-6
Created by
admin on Sat Dec 16 09:11:31 GMT 2023 , Edited by admin on Sat Dec 16 09:11:31 GMT 2023
|
PRIMARY | |||
|
DB12306
Created by
admin on Sat Dec 16 09:11:31 GMT 2023 , Edited by admin on Sat Dec 16 09:11:31 GMT 2023
|
PRIMARY | |||
|
Cipargamin
Created by
admin on Sat Dec 16 09:11:31 GMT 2023 , Edited by admin on Sat Dec 16 09:11:31 GMT 2023
|
PRIMARY | |||
|
C169853
Created by
admin on Sat Dec 16 09:11:31 GMT 2023 , Edited by admin on Sat Dec 16 09:11:31 GMT 2023
|
PRIMARY |
Related Record | Type | Details | ||
---|---|---|---|---|
|
TARGET ORGANISM->INHIBITOR |
|
||
|
TARGET ORGANISM->INHIBITOR |
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |
|