Details of the Drug

General Information of Drug (ID: DMT70RC)

Drug Name

Piperaquine

Synonyms

Piperaquinoline; Quinoline, 4,4'-(1,3-propanediyldi-4,1-piperazinediyl)bis(7-chloro-); Quinoline, 4,4'-(1,3-propanediyldi-4,1-piperazinediyl)bis(7-chloro-(9CI); 1,3-bis(1-(7-chloro-4'-quinolyl)-4'-piperazinyl)propane; 1,3-bis(4-(7'-chloro-4'-quinoline)-1-piperazine); 4,4'-(propane-1,3-diyldipiperazine-4,1-diyl)bis(7-chloroquinoline); 7-chloro-4-[4-[3-[4-(7-chloroquinolin-4-yl)piperazin-1-yl]propyl]piperazin-1-yl]quinoline

Indication

Disease Entry	ICD 11	Status	REF
Malaria	1F40-1F45	Approved	[1]
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Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 2

Molecular Weight (mw)

535.5

Logarithm of the Partition Coefficient (xlogp)

5.6

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Absorption AUC: The area under the plot of plasma concentration (AUC) of drug is 0.225-0.290 micromolh/L [2]
Absorption Cmax: The maximum plasma concentration (Cmax) of drug is 0.283 micromol/L [2]
Absorption Tmax: The time to maximum plasma concentration (Tmax) is 90 min [2]
Bioavailability: The bioavailability of drug is 80-100% [2]
Clearance: The total clearance of drug is 1.12 L/h/kg [3]
Half-life: The concentration or amount of drug in body reduced by one-half in 576 hours or 24 days [3]
Metabolism: The drug is metabolized via N-oxidation of one of the nitrogens in the quinoline groups at either side of the molecule [4]
Vd: The volume of distribution (Vd) of drug is 26.7 L/kg [3]

Chemical Identifiers

Formula: C29H32Cl2N6
IUPAC Name: 7-chloro-4-[4-[3-[4-(7-chloroquinolin-4-yl)piperazin-1-yl]propyl]piperazin-1-yl]quinoline
Canonical 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
InChIKey: UCRHFBCYFMIWHC-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 122262
ChEBI ID: CHEBI:91231
CAS Number: 4085-31-8
DrugBank ID: DB13941
TTD ID: D0P0SZ
INTEDE ID: DR1296

Combinatorial Drugs (CBD)

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Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Sarcoplasmic/endoplasmic reticulum calcium ATPase (ATP2A)	TTZVSJ2	NOUNIPROTAC	Inhibitor	[1]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 2C9 (CYP2C9)	DE5IED8	CP2C9_HUMAN	Substrate	[5]
Mephenytoin 4-hydroxylase (CYP2C19)	DEGTFWK	CP2CJ_HUMAN	Substrate	[6]

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Molecular Interaction Atlas (MIA)

MIA Detail

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References

1	The fight against drug-resistant malaria: novel plasmodial targets and antimalarial drugs. Curr Med Chem. 2008;15(2):161-71.
2	Hoskin PJ, Hanks GW: Morphine: pharmacokinetics and clinical practice. Br J Cancer. 1990 Nov;62(5):705-7.
3	EMA: Eurartesim Assessment Report
4	Gelotte CK, Zimmerman BA: Pharmacokinetics, safety, and cardiovascular tolerability of phenylephrine HCl 10, 20, and 30 mg after a single oral administration in healthy volunteers. Clin Drug Investig. 2015 Sep;35(9):547-58. doi: 10.1007/s40261-015-0311-9.
5	Eurartesim - European Medicines Agency
6	Open-label crossover study of primaquine and dihydroartemisinin-piperaquine pharmacokinetics in healthy adult thai subjects. Antimicrob Agents Chemother. 2014 Dec;58(12):7340-6.