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Details

Stereochemistry RACEMIC
Molecular Formula C15H21N3O
Molecular Weight 259.3467
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PRIMAQUINE

SMILES

COC1=CC(NC(C)CCCN)=C2N=CC=CC2=C1

InChI

InChIKey=INDBQLZJXZLFIT-UHFFFAOYSA-N
InChI=1S/C15H21N3O/c1-11(5-3-7-16)18-14-10-13(19-2)9-12-6-4-8-17-15(12)14/h4,6,8-11,18H,3,5,7,16H2,1-2H3

HIDE SMILES / InChI

Molecular Formula C15H21N3O
Molecular Weight 259.3467
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description

Primaquine is a oral medication used to treat and prevent malaria and to treat Pneumocystis pneumonia. Specifically it is used for malaria due to Plasmodium vivax and Plasmodium ovale along with other medications and for prevention if other options cannot be used. Primaquine is an alternative treatment for Pneumocystis pneumonia together with clindamycin. Primaquine is lethal to P. vivax and P. ovale in the liver stage, and also to P. vivax in the blood stage through its ability to do oxidative damage to the cell. However, the exact mechanism of action is not fully understood. Primaquine is well-absorbed in the gut and extensively distributed in the body without accumulating in red blood cells. Administration of primaquine with food or grapefruit juice increases its oral bioavailibity. In blood, about 20% of circulating primaquine is protein-bound, with preferential binding to the acute phase protein orosomucoid. With a half-life on the order of 6 hours, it is quickly metabolized by liver enzymes to carboxyprimaquine, which does not have anti-malarial activity. Common side effects of primaquine administration include nausea, vomiting, and stomach cramps. Primaquine phosphate is recommended only for the radical cure of vivax malaria, the prevention of relapse in vivax malaria, or following the termination of chloroquine phosphate suppressive therapy in an area where vivax malaria is endemic. Patients suffering from an attack of vivax malaria or having parasitized red blood cells should receive a course of chloroquine phosphate, which quickly destroys the erythrocytic parasites and terminates the paroxysm. Primaquine phosphate should be administered concurrently in order to eradicate the exoerythrocytic parasites in a dosage of 1 tablet (equivalent to 15 mg base) daily for 14 days.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
7.5 µM [IC50]
68.0 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
AABLAQUIN
Curative
PRIMAQUINE

Cmax

ValueDoseCo-administeredAnalytePopulation
53 ng/mL
15 mg single, oral
PRIMAQUINE plasma
Homo sapiens
104 ng/mL
30 mg single, oral
PRIMAQUINE plasma
Homo sapiens
66 ng/mL
15 mg 1 times / day multiple, oral
PRIMAQUINE plasma
Homo sapiens
65 ng/mL
15 mg single, oral
PRIMAQUINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
0.5 μg × h/mL
15 mg single, oral
PRIMAQUINE plasma
Homo sapiens
1 μg × h/mL
30 mg single, oral
PRIMAQUINE plasma
Homo sapiens
443 ng × h/mL
15 mg 1 times / day multiple, oral
PRIMAQUINE plasma
Homo sapiens
468 ng × h/mL
15 mg single, oral
PRIMAQUINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
5.9 h
15 mg single, oral
PRIMAQUINE plasma
Homo sapiens
7.4 h
30 mg single, oral
PRIMAQUINE plasma
Homo sapiens
4.3 h
15 mg 1 times / day multiple, oral
PRIMAQUINE plasma
Homo sapiens
4.4 h
15 mg single, oral
PRIMAQUINE plasma
Homo sapiens

Doses

AEs

Drug as perpetrator​

Drug as victim

Tox targets

PubMed

Sample Use Guides

In Vivo Use Guide
Patients recieved 25 mg once daily for 7 days.
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Record UNII
MVR3634GX1
Record Status Validated (UNII)
Record Version