Piperaquine

Piperaquine
Identifiers

IUPAC name 1,3-bis[4-(7-chloroquinolin-4-yl)piperazin-1-yl]propane
CAS Number	4085-31-8^Y
PubChem (CID)	122262
ChemSpider	109031^N
UNII	A0HV2Q956Y^N
ChEBI	CHEBI:91231^N
ChEMBL	CHEMBL303933^N
Chemical and physical data
Formula	C₂₉H₃₂Cl₂N₆
Molar mass	535.51
3D model (Jmol)	Interactive image
SMILES C1CN(CCN1CCCN2CCN(CC2)C3=C4C=CC(=CC4=NC=C3)Cl)C5=C6C=CC(=CC6=NC=C5)Cl
InChI InChI=1S/C29H32Cl2N6/c30-22-2-4-24-26(20-22)32-8-6-28(24)36-16-12-34(13-17-36)10-1-11-35-14-18-37(19-15-35)29-7-9-33-27-21-23(31)3-5-25(27)29/h2-9,20-21H,1,10-19H2^N Key:UCRHFBCYFMIWHC-UHFFFAOYSA-N^N
^NY (what is this?) (verify)

Piperaquine is an antimalarial drug, a bisquinoline first synthesised in the 1960s, and used extensively in China and Indochina as prophylaxis and treatment during the next 20 years. Usage declined in the 1980s as piperaquine-resistant strains of P. falciparum arose and artemisinin-based antimalarials became available. However, Chinese scientists have been studying whether piperaquine can still be used therapeutically in combination with artemisinin.^[1]

Piperaquine is characterized by slow absorption and a long biological half-life,^[2] making it a good partner drug with artemisinin derivatives which are fast acting but have a short biological half-life.^[3]

The fixed-dose combination dihydroartemisinin-piperaquine (Eurartesim) was submitted for approval to the European Medicines Agency in 2009.^[4]

References

↑ Davis TM, Hung TY, Sim IK, Karunajeewa HA, Ilett KF (2005). "Piperaquine: a resurgent antimalarial drug". Drugs. 65 (1): 75–87. doi:10.2165/00003495-200565010-00004. PMID 15610051.
↑ D'alessandro U. (2009). "Progress in the development of piperaquine combinations for the treatment of malaria". Curr Opin Infect Dis. 22 (6): 588–92. doi:10.1097/QCO.0b013e328332674a. PMID 19773652.
↑ http://apps.who.int/prequal/info_applicants/Guidelines/Nonclinical_Overview_Artemisinin-Derivatives.pdf"
↑ Medicines for Malaria. "Registration". Retrieved 2010-06-20.

Antiparasitics – antiprotozoal agents – Chromalveolate antiparasitics (P01)

Alveo-
late

Apicom-
plexa

Conoidasida/
(Coccidiostats)

Cryptosporidiosis	thiazolides (nitazoxanide)

Isosporiasis	trimethoprim/sulfamethoxazole^#

Toxoplasmosis	pyrimethamine sulfadiazine

Aconoidasida

Malaria

Individual
agents

Hemozoin
inhibitors

Aminoquinolines	(4-): amodiaquine^# chloroquine^# hydroxychloroquine^# (8-): primaquine^# pamaquine^‡ tafenoquine^†

4-Methanolquinolines	mefloquine^# quinine^# quinidine

Other	lumefantrine + artemether^# halofantrine

Antifolates

DHFR inhibitors	pyrimethamine biguanides chlorproguanil proguanil^#

Sulfonamides	sulfadoxine sulfalene

Co-formulation	sulfadoxine/pyrimethamine (SP)^#

Sesquiterpene
lactones

Other

Combi-
nations

Fixed-dose (co-formulated) ACTs	artemether/lumefantrine^# arterolane/piperaquine artesunate/amodiaquine (ASAQ) artesunate/mefloquine (ASMQ) artesunate/pyronaridine dihydroartemisinin/piperaquine

Other combinations (not co-formulated)	artesunate/mefloquine artesunate/SP quinine/clindamycin quinine/doxycycline quinine/tetracycline

Babesiosis

clindamycin

Cilio-
phora

Balantidiasis: tetracycline

Hetero-
kont

Blastocystosis: metronidazole

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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