Details
Stereochemistry | RACEMIC |
Molecular Formula | C15H21N3O.2H3O4P |
Molecular Weight | 455.3371 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OP(O)(O)=O.OP(O)(O)=O.COC1=CC(NC(C)CCCN)=C2N=CC=CC2=C1
InChI
InChIKey=GJOHLWZHWQUKAU-UHFFFAOYSA-N
InChI=1S/C15H21N3O.2H3O4P/c1-11(5-3-7-16)18-14-10-13(19-2)9-12-6-4-8-17-15(12)14;2*1-5(2,3)4/h4,6,8-11,18H,3,5,7,16H2,1-2H3;2*(H3,1,2,3,4)
Molecular Formula | H3O4P |
Molecular Weight | 97.9952 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | C15H21N3O |
Molecular Weight | 259.3467 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
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.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL3959 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21074425 |
7.5 µM [IC50] | ||
Target ID: CHEMBL1795182 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24900883 |
68.0 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | AABLAQUIN Approved UseTreatment and prevention of p. vivax. Launch Date2000 |
|||
Curative | PRIMAQUINE Approved UsePrimaquine phosphate is indicated for the radical cure (prevention of relapse) of vivax malaria. Launch Date1952 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
53 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4027117/ |
15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered: |
PRIMAQUINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
104 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4027117/ |
30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered: |
PRIMAQUINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
66 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4027118/ |
15 mg 1 times / day multiple, oral dose: 15 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
PRIMAQUINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
65 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4027118/ |
15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered: |
PRIMAQUINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
0.5 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4027117/ |
15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered: |
PRIMAQUINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
1 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4027117/ |
30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered: |
PRIMAQUINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
443 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4027118/ |
15 mg 1 times / day multiple, oral dose: 15 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
PRIMAQUINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
468 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4027118/ |
15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered: |
PRIMAQUINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
5.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4027117/ |
15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered: |
PRIMAQUINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
7.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4027117/ |
30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered: |
PRIMAQUINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
4.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4027118/ |
15 mg 1 times / day multiple, oral dose: 15 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
PRIMAQUINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
4.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4027118/ |
15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered: |
PRIMAQUINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Doses
Dose | Population | Adverse events |
---|---|---|
30 mg 1 times / day steady, oral Highest studied dose Dose: 30 mg, 1 times / day Route: oral Route: steady Dose: 30 mg, 1 times / day Sources: |
unhealthy, adult n = 120 Health Status: unhealthy Condition: Plasmodium vivax parasite Age Group: adult Sex: M Population Size: 120 Sources: |
Other AEs: Malaise, Headache... Other AEs: Malaise (1 patient) Sources: Headache (2 patients) Nausea (1 patient) Pyrexia (1 patient) Vomiting (1 patient) Dizziness (1 patient) Asthenia (1 patient) Pruritus (1 patient) Haemoglobin decreased (1 patient) Dyspepsia (1 patient) |
0.6 mg/kg 1 times / day multiple, oral Highest studied dose Dose: 0.6 mg/kg, 1 times / day Route: oral Route: multiple Dose: 0.6 mg/kg, 1 times / day Co-administed with:: (artesunate) Sources: 50 mg |
unhealthy, adult n = 18 Health Status: unhealthy Condition: acute, symptomatic Plasmodium vivax malaria Age Group: adult Sex: unknown Population Size: 18 Sources: |
Disc. AE: Hematocrit decreased... AEs leading to discontinuation/dose reduction: Hematocrit decreased (4 patients) Sources: |
15 mg 1 times / day steady, oral Recommended Dose: 15 mg, 1 times / day Route: oral Route: steady Dose: 15 mg, 1 times / day Sources: |
unhealthy, adult n = 118 Health Status: unhealthy Condition: Plasmodium vivax parasite Age Group: adult Sex: M Population Size: 118 Sources: |
Other AEs: Malaise, Headache... Other AEs: Malaise (4 patients) Sources: Headache (2 patients) Nausea (1 patient) Decreased appetite (3 patients) Pyrexia (1 patient) Vomiting (1 patient) Dizziness (1 patient) Asthenia (1 patient) Arthralgia (1 patient) Muscle spasms (1 patient) Dyspnoea exertional (1 patient) Diarrhoea (1 patient) |
15 mg 1 times / day steady, oral Recommended Dose: 15 mg, 1 times / day Route: oral Route: steady Dose: 15 mg, 1 times / day Sources: |
unhealthy, adult n = 120 Health Status: unhealthy Condition: Plasmodium vivax parasite Age Group: adult Sex: M Population Size: 120 Sources: |
Other AEs: Malaise, Headache... Other AEs: Malaise (3 patients) Sources: Headache (1 patient) Nausea (2 patients) Pyrexia (1 patient) Vomiting (1 patient) Myalgia (2 patients) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Asthenia | 1 patient | 30 mg 1 times / day steady, oral Highest studied dose Dose: 30 mg, 1 times / day Route: oral Route: steady Dose: 30 mg, 1 times / day Sources: |
unhealthy, adult n = 120 Health Status: unhealthy Condition: Plasmodium vivax parasite Age Group: adult Sex: M Population Size: 120 Sources: |
Dizziness | 1 patient | 30 mg 1 times / day steady, oral Highest studied dose Dose: 30 mg, 1 times / day Route: oral Route: steady Dose: 30 mg, 1 times / day Sources: |
unhealthy, adult n = 120 Health Status: unhealthy Condition: Plasmodium vivax parasite Age Group: adult Sex: M Population Size: 120 Sources: |
Dyspepsia | 1 patient | 30 mg 1 times / day steady, oral Highest studied dose Dose: 30 mg, 1 times / day Route: oral Route: steady Dose: 30 mg, 1 times / day Sources: |
unhealthy, adult n = 120 Health Status: unhealthy Condition: Plasmodium vivax parasite Age Group: adult Sex: M Population Size: 120 Sources: |
Haemoglobin decreased | 1 patient | 30 mg 1 times / day steady, oral Highest studied dose Dose: 30 mg, 1 times / day Route: oral Route: steady Dose: 30 mg, 1 times / day Sources: |
unhealthy, adult n = 120 Health Status: unhealthy Condition: Plasmodium vivax parasite Age Group: adult Sex: M Population Size: 120 Sources: |
Malaise | 1 patient | 30 mg 1 times / day steady, oral Highest studied dose Dose: 30 mg, 1 times / day Route: oral Route: steady Dose: 30 mg, 1 times / day Sources: |
unhealthy, adult n = 120 Health Status: unhealthy Condition: Plasmodium vivax parasite Age Group: adult Sex: M Population Size: 120 Sources: |
Nausea | 1 patient | 30 mg 1 times / day steady, oral Highest studied dose Dose: 30 mg, 1 times / day Route: oral Route: steady Dose: 30 mg, 1 times / day Sources: |
unhealthy, adult n = 120 Health Status: unhealthy Condition: Plasmodium vivax parasite Age Group: adult Sex: M Population Size: 120 Sources: |
Pruritus | 1 patient | 30 mg 1 times / day steady, oral Highest studied dose Dose: 30 mg, 1 times / day Route: oral Route: steady Dose: 30 mg, 1 times / day Sources: |
unhealthy, adult n = 120 Health Status: unhealthy Condition: Plasmodium vivax parasite Age Group: adult Sex: M Population Size: 120 Sources: |
Pyrexia | 1 patient | 30 mg 1 times / day steady, oral Highest studied dose Dose: 30 mg, 1 times / day Route: oral Route: steady Dose: 30 mg, 1 times / day Sources: |
unhealthy, adult n = 120 Health Status: unhealthy Condition: Plasmodium vivax parasite Age Group: adult Sex: M Population Size: 120 Sources: |
Vomiting | 1 patient | 30 mg 1 times / day steady, oral Highest studied dose Dose: 30 mg, 1 times / day Route: oral Route: steady Dose: 30 mg, 1 times / day Sources: |
unhealthy, adult n = 120 Health Status: unhealthy Condition: Plasmodium vivax parasite Age Group: adult Sex: M Population Size: 120 Sources: |
Headache | 2 patients | 30 mg 1 times / day steady, oral Highest studied dose Dose: 30 mg, 1 times / day Route: oral Route: steady Dose: 30 mg, 1 times / day Sources: |
unhealthy, adult n = 120 Health Status: unhealthy Condition: Plasmodium vivax parasite Age Group: adult Sex: M Population Size: 120 Sources: |
Hematocrit decreased | 4 patients Disc. AE |
0.6 mg/kg 1 times / day multiple, oral Highest studied dose Dose: 0.6 mg/kg, 1 times / day Route: oral Route: multiple Dose: 0.6 mg/kg, 1 times / day Co-administed with:: (artesunate) Sources: 50 mg |
unhealthy, adult n = 18 Health Status: unhealthy Condition: acute, symptomatic Plasmodium vivax malaria Age Group: adult Sex: unknown Population Size: 18 Sources: |
Arthralgia | 1 patient | 15 mg 1 times / day steady, oral Recommended Dose: 15 mg, 1 times / day Route: oral Route: steady Dose: 15 mg, 1 times / day Sources: |
unhealthy, adult n = 118 Health Status: unhealthy Condition: Plasmodium vivax parasite Age Group: adult Sex: M Population Size: 118 Sources: |
Asthenia | 1 patient | 15 mg 1 times / day steady, oral Recommended Dose: 15 mg, 1 times / day Route: oral Route: steady Dose: 15 mg, 1 times / day Sources: |
unhealthy, adult n = 118 Health Status: unhealthy Condition: Plasmodium vivax parasite Age Group: adult Sex: M Population Size: 118 Sources: |
Diarrhoea | 1 patient | 15 mg 1 times / day steady, oral Recommended Dose: 15 mg, 1 times / day Route: oral Route: steady Dose: 15 mg, 1 times / day Sources: |
unhealthy, adult n = 118 Health Status: unhealthy Condition: Plasmodium vivax parasite Age Group: adult Sex: M Population Size: 118 Sources: |
Dizziness | 1 patient | 15 mg 1 times / day steady, oral Recommended Dose: 15 mg, 1 times / day Route: oral Route: steady Dose: 15 mg, 1 times / day Sources: |
unhealthy, adult n = 118 Health Status: unhealthy Condition: Plasmodium vivax parasite Age Group: adult Sex: M Population Size: 118 Sources: |
Dyspnoea exertional | 1 patient | 15 mg 1 times / day steady, oral Recommended Dose: 15 mg, 1 times / day Route: oral Route: steady Dose: 15 mg, 1 times / day Sources: |
unhealthy, adult n = 118 Health Status: unhealthy Condition: Plasmodium vivax parasite Age Group: adult Sex: M Population Size: 118 Sources: |
Muscle spasms | 1 patient | 15 mg 1 times / day steady, oral Recommended Dose: 15 mg, 1 times / day Route: oral Route: steady Dose: 15 mg, 1 times / day Sources: |
unhealthy, adult n = 118 Health Status: unhealthy Condition: Plasmodium vivax parasite Age Group: adult Sex: M Population Size: 118 Sources: |
Nausea | 1 patient | 15 mg 1 times / day steady, oral Recommended Dose: 15 mg, 1 times / day Route: oral Route: steady Dose: 15 mg, 1 times / day Sources: |
unhealthy, adult n = 118 Health Status: unhealthy Condition: Plasmodium vivax parasite Age Group: adult Sex: M Population Size: 118 Sources: |
Pyrexia | 1 patient | 15 mg 1 times / day steady, oral Recommended Dose: 15 mg, 1 times / day Route: oral Route: steady Dose: 15 mg, 1 times / day Sources: |
unhealthy, adult n = 118 Health Status: unhealthy Condition: Plasmodium vivax parasite Age Group: adult Sex: M Population Size: 118 Sources: |
Vomiting | 1 patient | 15 mg 1 times / day steady, oral Recommended Dose: 15 mg, 1 times / day Route: oral Route: steady Dose: 15 mg, 1 times / day Sources: |
unhealthy, adult n = 118 Health Status: unhealthy Condition: Plasmodium vivax parasite Age Group: adult Sex: M Population Size: 118 Sources: |
Headache | 2 patients | 15 mg 1 times / day steady, oral Recommended Dose: 15 mg, 1 times / day Route: oral Route: steady Dose: 15 mg, 1 times / day Sources: |
unhealthy, adult n = 118 Health Status: unhealthy Condition: Plasmodium vivax parasite Age Group: adult Sex: M Population Size: 118 Sources: |
Decreased appetite | 3 patients | 15 mg 1 times / day steady, oral Recommended Dose: 15 mg, 1 times / day Route: oral Route: steady Dose: 15 mg, 1 times / day Sources: |
unhealthy, adult n = 118 Health Status: unhealthy Condition: Plasmodium vivax parasite Age Group: adult Sex: M Population Size: 118 Sources: |
Malaise | 4 patients | 15 mg 1 times / day steady, oral Recommended Dose: 15 mg, 1 times / day Route: oral Route: steady Dose: 15 mg, 1 times / day Sources: |
unhealthy, adult n = 118 Health Status: unhealthy Condition: Plasmodium vivax parasite Age Group: adult Sex: M Population Size: 118 Sources: |
Headache | 1 patient | 15 mg 1 times / day steady, oral Recommended Dose: 15 mg, 1 times / day Route: oral Route: steady Dose: 15 mg, 1 times / day Sources: |
unhealthy, adult n = 120 Health Status: unhealthy Condition: Plasmodium vivax parasite Age Group: adult Sex: M Population Size: 120 Sources: |
Pyrexia | 1 patient | 15 mg 1 times / day steady, oral Recommended Dose: 15 mg, 1 times / day Route: oral Route: steady Dose: 15 mg, 1 times / day Sources: |
unhealthy, adult n = 120 Health Status: unhealthy Condition: Plasmodium vivax parasite Age Group: adult Sex: M Population Size: 120 Sources: |
Vomiting | 1 patient | 15 mg 1 times / day steady, oral Recommended Dose: 15 mg, 1 times / day Route: oral Route: steady Dose: 15 mg, 1 times / day Sources: |
unhealthy, adult n = 120 Health Status: unhealthy Condition: Plasmodium vivax parasite Age Group: adult Sex: M Population Size: 120 Sources: |
Myalgia | 2 patients | 15 mg 1 times / day steady, oral Recommended Dose: 15 mg, 1 times / day Route: oral Route: steady Dose: 15 mg, 1 times / day Sources: |
unhealthy, adult n = 120 Health Status: unhealthy Condition: Plasmodium vivax parasite Age Group: adult Sex: M Population Size: 120 Sources: |
Nausea | 2 patients | 15 mg 1 times / day steady, oral Recommended Dose: 15 mg, 1 times / day Route: oral Route: steady Dose: 15 mg, 1 times / day Sources: |
unhealthy, adult n = 120 Health Status: unhealthy Condition: Plasmodium vivax parasite Age Group: adult Sex: M Population Size: 120 Sources: |
Malaise | 3 patients | 15 mg 1 times / day steady, oral Recommended Dose: 15 mg, 1 times / day Route: oral Route: steady Dose: 15 mg, 1 times / day Sources: |
unhealthy, adult n = 120 Health Status: unhealthy Condition: Plasmodium vivax parasite Age Group: adult Sex: M Population Size: 120 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.pmda.go.jp/drugs/2016/P20160309001/780069000_2800AMX00403000_I100_1.pdf#page=30 Page: (PMDA_I100_1 in Japanese) 29-30 |
minor [Km 37000 uM] | |||
Sources: https://www.pmda.go.jp/drugs/2016/P20160309001/780069000_2800AMX00403000_I100_1.pdf#page=30 Page: (PMDA_I100_1 in Japanese) 29-30 |
minor [Km 52000 uM] | |||
Sources: https://www.pmda.go.jp/drugs/2016/P20160309001/780069000_2800AMX00403000_I100_1.pdf#page=30 Page: (PMDA_I100_1 in Japanese) 29-30 |
no | |||
Sources: https://www.pmda.go.jp/drugs/2016/P20160309001/780069000_2800AMX00403000_I100_1.pdf#page=30 Page: (PMDA_I100_1 in Japanese) 29-30 |
weak [Km 37000 uM] | |||
Sources: https://www.pmda.go.jp/drugs/2016/P20160309001/780069000_2800AMX00403000_I100_1.pdf#page=30 Page: (PMDA_I100_1 in Japanese) 29-30 |
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: (PMDA_A100_1 in Japanese) 10, (FDA label) 3 |
PubMed
Title | Date | PubMed |
---|---|---|
Potentiation of the curative action of primaquine in vivax malaria by quinine and chloroquine. | 1955 Aug |
|
The haemolytic effect of various regimens of primaquine with chloroquine in American Negroes with G6PD deficiency and the lack of an effect of various antimalarial suppressive agents on erythrocyte metabolism. | 1967 |
|
The treatment of malaria in glucose-6-phosphate dehydrogenase deficient patients in Sabah. | 1981 Dec |
|
Primaquine-chloroquine prophylaxis against malaria in Southeast-Asian refugees entering South Australia. | 1984 Mar 17 |
|
Pharmacokinetics of primaquine in man. I. Studies of the absolute bioavailability and effects of dose size. | 1985 Jun |
|
[Hemolytic reaction due to administration of primaquine]. | 1986 Apr |
|
Activity of clindamycin with primaquine against Pneumocystis carinii in vitro and in vivo. | 1988 Jun |
|
Detection of antidrug IgG antibodies in patients with adverse drug reactions to amodiaquine. | 1991 |
|
Isolation and characterization of rat lung Pneumocystis carinii gp120. | 1991 Nov-Dec |
|
Acute intravascular haemolysis in Vanuatu following a single dose of primaquine in individuals with glucose-6-phosphate dehydrogenase deficiency. | 1992 Oct |
|
Inhibitors of human immunodeficiency virus integrase. | 1993 Mar 15 |
|
New drug developments for opportunistic infections in immunosuppressed patients: Pneumocystis carinii. | 1995 Nov 24 |
|
Dapsone- and primaquine-induced methemoglobinemia in HIV-infected individuals. | 1996 Aug 15 |
|
Efficacy of 101 antimicrobials and other agents on the development of Cryptosporidium parvum in vitro. | 1996 Dec |
|
[Hemolysis and primaquine treatment. Preliminary report]. | 1997 |
|
Potential inhibitors of HIV integrase. | 1999 Apr-May |
|
Primaquine-induced hemolytic anemia: formation and hemotoxicity of the arylhydroxylamine metabolite 6-methoxy-8-hydroxylaminoquinoline. | 2001 May |
|
Cytochrome P450 1A1/2 induction by antiparasitic drugs: dose-dependent increase in ethoxyresorufin O-deethylase activity and mRNA caused by quinine, primaquine and albendazole in HepG2 cells. | 2002 Nov |
|
Time-dependent transcriptional induction of CYP1A1, CYP1A2 and CYP1B1 mRNAs by H+/K+ -ATPase inhibitors and other xenobiotics. | 2003 Feb |
|
Conductometric and indirect AAS determination of antimalarials. | 2003 Mar 26 |
|
Real-time investigation of the interaction between primaquine phosphate and bovine serum albumin (BSA) by piezoelectric quartz crystal impedance analysis. | 2003 Oct 9 |
|
Identification of human cytochrome P(450)s that metabolise anti-parasitic drugs and predictions of in vivo drug hepatic clearance from in vitro data. | 2003 Sep |
|
Different structural requirements of the ligand binding domain of the aryl hydrocarbon receptor for high- and low-affinity ligand binding and receptor activation. | 2004 Feb |
|
Preparation and in vitro evaluation of primaquine-conjugated gum arabic microspheres. | 2004 Jul-Aug |
|
Piperaquine: a resurgent antimalarial drug. | 2005 |
|
Glucose-6-phosphate dehydrogenase deficiency in two returning Operation Iraqi Freedom soldiers who developed hemolytic anemia while receiving primaquine prophylaxis for malaria. | 2005 Apr |
|
Primaquine-induced hemolytic anemia: role of membrane lipid peroxidation and cytoskeletal protein alterations in the hemotoxicity of 5-hydroxyprimaquine. | 2005 Aug |
|
Glycodendrimeric nanoparticulate carriers of primaquine phosphate for liver targeting. | 2005 May 13 |
|
Combined chloroquine, sulfadoxine/pyrimethamine and primaquine against Plasmodium falciparum in Central Java, Indonesia. | 2006 Nov 14 |
|
Persistent binding of ligands to the aryl hydrocarbon receptor. | 2007 Jul |
|
Drug, dosage, activity, studies of antimalarials by physical methods--II. | 2007 May 20 |
|
Congenital malaria in the United States: a review of cases from 1966 to 2005. | 2007 Nov |
|
Formulation and evaluation of taste masked oral reconstitutable suspension of primaquine phosphate. | 2008 |
|
Identification of differentially expressed genes after acute exposure to bulaquine (CDRI 80/53) in mice liver. | 2008 Dec |
|
HepaRG cells as an in vitro model for evaluation of cytochrome P450 induction in humans. | 2008 Jan |
|
Development and validation of UPLC method for determination of primaquine phosphate and its impurities. | 2008 Jan 22 |
|
Omeprazole transactivates human CYP1A1 and CYP1A2 expression through the common regulatory region containing multiple xenobiotic-responsive elements. | 2008 Jul 1 |
|
Novel triazine JPC-2067-B inhibits Toxoplasma gondii in vitro and in vivo. | 2008 Mar 5 |
|
Formulation and evaluation of primaquine phosphate taste-masked rapidly disintegrating tablet. | 2008 Oct |
|
Monkey malaria in a European traveler returning from Malaysia. | 2008 Sep |
|
Diverse chemicals including aryl hydrocarbon receptor ligands modulate transcriptional activity of the 3'immunoglobulin heavy chain regulatory region. | 2009 Jun 30 |
|
Cytochrome P(450)-dependent toxic effects of primaquine on human erythrocytes. | 2009 Nov 15 |
|
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2. | 2011 Jul 14 |
|
Novel potent metallocenes against liver stage malaria. | 2012 Mar |
|
Characterization of Plasmodium liver stage inhibition by halofuginone. | 2012 May |
|
N-cinnamoylated chloroquine analogues as dual-stage antimalarial leads. | 2013 Jan 24 |
|
Quinolin-4(1H)-imines are potent antiplasmodial drugs targeting the liver stage of malaria. | 2013 Jun 13 |
|
Flavones as isosteres of 4(1H)-quinolones: discovery of ligand efficient and dual stage antimalarial lead compounds. | 2013 Nov |
|
N-cinnamoylation of antimalarial classics: quinacrine analogues with decreased toxicity and dual-stage activity. | 2014 Feb |
|
Elucidating mechanisms of toxicity using phenotypic data from primary human cell systems--a chemical biology approach for thrombosis-related side effects. | 2015 Jan 5 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16969059
Patients recieved 25 mg once daily for 7 days.
Route of Administration:
Oral
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:06:04 GMT 2023
by
admin
on
Fri Dec 15 15:06:04 GMT 2023
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Record UNII |
H0982HF78B
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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FDA ORPHAN DRUG |
74793
Created by
admin on Fri Dec 15 15:06:04 GMT 2023 , Edited by admin on Fri Dec 15 15:06:04 GMT 2023
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NCI_THESAURUS |
C271
Created by
admin on Fri Dec 15 15:06:04 GMT 2023 , Edited by admin on Fri Dec 15 15:06:04 GMT 2023
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Code System | Code | Type | Description | ||
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63-45-6
Created by
admin on Fri Dec 15 15:06:04 GMT 2023 , Edited by admin on Fri Dec 15 15:06:04 GMT 2023
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200-560-8
Created by
admin on Fri Dec 15 15:06:04 GMT 2023 , Edited by admin on Fri Dec 15 15:06:04 GMT 2023
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84902-21-6
Created by
admin on Fri Dec 15 15:06:04 GMT 2023 , Edited by admin on Fri Dec 15 15:06:04 GMT 2023
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CHEMBL506
Created by
admin on Fri Dec 15 15:06:04 GMT 2023 , Edited by admin on Fri Dec 15 15:06:04 GMT 2023
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SUB04039MIG
Created by
admin on Fri Dec 15 15:06:04 GMT 2023 , Edited by admin on Fri Dec 15 15:06:04 GMT 2023
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H0982HF78B
Created by
admin on Fri Dec 15 15:06:04 GMT 2023 , Edited by admin on Fri Dec 15 15:06:04 GMT 2023
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C771
Created by
admin on Fri Dec 15 15:06:04 GMT 2023 , Edited by admin on Fri Dec 15 15:06:04 GMT 2023
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100000085099
Created by
admin on Fri Dec 15 15:06:04 GMT 2023 , Edited by admin on Fri Dec 15 15:06:04 GMT 2023
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149765
Created by
admin on Fri Dec 15 15:06:04 GMT 2023 , Edited by admin on Fri Dec 15 15:06:04 GMT 2023
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DTXSID6045248
Created by
admin on Fri Dec 15 15:06:04 GMT 2023 , Edited by admin on Fri Dec 15 15:06:04 GMT 2023
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DBSALT001188
Created by
admin on Fri Dec 15 15:06:04 GMT 2023 , Edited by admin on Fri Dec 15 15:06:04 GMT 2023
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m9133
Created by
admin on Fri Dec 15 15:06:04 GMT 2023 , Edited by admin on Fri Dec 15 15:06:04 GMT 2023
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PRIMARY | Merck Index | ||
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1561507
Created by
admin on Fri Dec 15 15:06:04 GMT 2023 , Edited by admin on Fri Dec 15 15:06:04 GMT 2023
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H0982HF78B
Created by
admin on Fri Dec 15 15:06:04 GMT 2023 , Edited by admin on Fri Dec 15 15:06:04 GMT 2023
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8689
Created by
admin on Fri Dec 15 15:06:04 GMT 2023 , Edited by admin on Fri Dec 15 15:06:04 GMT 2023
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PRIMARY | RxNorm | ||
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PRIMAQUINE PHOSPHATE
Created by
admin on Fri Dec 15 15:06:04 GMT 2023 , Edited by admin on Fri Dec 15 15:06:04 GMT 2023
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PRIMARY | Description: An orange-red, crystalline powder; odourless or almost odourless. Solubility: Soluble in water; practically insoluble in ethanol (~750 g/l) TS and ether R. Category: Antimalarial. Storage: Primaquine diphosphate should be kept in a well-closed container, protected from light. Definition: Primaquine diphosphate contains not less than 98.0% and not more than 102.0% of C15H21N3O,2H3PO4, calculatedwith reference to the dried substance. | ||
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6135
Created by
admin on Fri Dec 15 15:06:04 GMT 2023 , Edited by admin on Fri Dec 15 15:06:04 GMT 2023
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Related Record | Type | Details | ||
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
USP
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
EP
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ENANTIOMER -> RACEMATE | |||
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PARENT -> SALT/SOLVATE |
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Related Record | Type | Details | ||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
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Related Record | Type | Details | ||
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ACTIVE MOIETY |