U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of PRIMAQUINE PHOSPHATE

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)

HIDE SMILES / InChI

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

Targets

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

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
AABLAQUIN

Approved Use

Treatment and prevention of p. vivax.

Launch Date

9.4668482E11
Curative
PRIMAQUINE

Approved Use

Primaquine phosphate is indicated for the radical cure (prevention of relapse) of vivax malaria.

Launch Date

-5.661792E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
53 ng/mL
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
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
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
0.5 μg × h/mL
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
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
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
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

T1/2

ValueDoseCo-administeredAnalytePopulation
5.9 h
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
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
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
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

Doses

DosePopulationAdverse 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)
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)
Sources:
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)
50 mg
Sources:
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)
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)
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 = 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)
Headache (1 patient)
Nausea (2 patients)
Pyrexia (1 patient)
Vomiting (1 patient)
Myalgia (2 patients)
Sources:
AEs

AEs

AESignificanceDosePopulation
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)
50 mg
Sources:
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

OverviewOther

Drug as perpetrator​Drug as victim

Drug as victim

Tox targets
PubMed

PubMed

TitleDatePubMed
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
Methemoglobinemia provoked by malarial chemoprophylaxis in Vietnam.
1968 Nov 21
Simultaneous drug reactions in the same patient. Chloroquine-Primaquine sensitivity.
1970 Apr 27
Reaction to primaquine.
1980 Mar
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
Drug- and chemical-induced methaemoglobinaemia. Clinical features and management.
1986 Jul-Aug
Activity of clindamycin with primaquine against Pneumocystis carinii in vitro and in vivo.
1988 Jun
Primaquine induced hemolysis in a Thai soldier.
1989 Dec
Immunogenicity of amodiaquine in the rat.
1990
Causal prophylactic activity of a new 8-aminoquinoline derivative against Plasmodium cynomolgi B in rhesus monkeys.
1990 May
Effect of anti-relapse antimalarial compound CDRI 80/53 and primaquine on hepatic mixed function oxidase system of rhesus monkey.
1990 Nov-Dec
Detection of antidrug IgG antibodies in patients with adverse drug reactions to amodiaquine.
1991
Inhibitors of human immunodeficiency virus integrase.
1993 Mar 15
Effect of the antimalarial agents primaquine and (N'-3-acetyl-4-5-dihydro-2-furanyl)-N4-(6-methoxy-8-quinolinyl)1,4-pent ane-diamine on oxidative stress and antioxidant defences in mice.
1993 Nov 17
In vitro effects of artemisinin ether, cycloguanil hydrochloride (alone and in combination with sulfadiazine), quinine sulfate, mefloquine, primaquine phosphate, trifluoperazine hydrochloride, and verapamil on Toxoplasma gondii.
1994 Jun
[Primaquine and travelers from the Arab world. A report and recommendations].
1995
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
Drug-induced methaemoglobinaemia. Treatment issues.
1996 Jun
[Hemolysis and primaquine treatment. Preliminary report].
1997
Prediction of aryl hydrocarbon receptor-mediated enzyme induction of drugs and chemicals by mRNA quantification.
1998 Dec
Exotic diseases of dogs and cats at risk of importation to Ireland.
2005 May 1
In Vitro and In Vivo pharmacokinetic studies of bulaquine (analogue of primaquine), a novel antirelapse antimalarial, in rat, rabbit and monkey--highlighting species similarities and differences.
2007 Jul
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
Formulation and evaluation of primaquine phosphate taste-masked rapidly disintegrating tablet.
2008 Oct
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
Interference with bile salt export pump function is a susceptibility factor for human liver injury in drug development.
2010 Dec
Feline babesiosis.
2010 Feb
The Summary Index of Malaria Surveillance (SIMS): a stable index of malaria within India.
2010 Feb 11
An open-label, randomised study of dihydroartemisinin-piperaquine versus artesunate-mefloquine for falciparum malaria in Asia.
2010 Jul 30
Monitoring for Plasmodium falciparum drug resistance to artemisinin and artesunate in Binh Phuoc Province, Vietnam: 1998-2009.
2010 Jun 24
Blockade of hERG K(+) channel by antimalarial drug, primaquine.
2010 May
In Tanzania, hemolysis after a single dose of primaquine coadministered with an artemisinin is not restricted to glucose-6-phosphate dehydrogenase-deficient (G6PD A-) individuals.
2010 May
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
Understanding the mechanisms for metabolism-linked hemolytic toxicity of primaquine against glucose 6-phosphate dehydrogenase deficient human erythrocytes: evaluation of eryptotic pathway.
2012 Mar 29
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
Primaquine or other 8-aminoquinoline for reducing Plasmodium falciparum transmission.
2015 Feb 19
Elucidating mechanisms of toxicity using phenotypic data from primary human cell systems--a chemical biology approach for thrombosis-related side effects.
2015 Jan 5
Development of HepG2-derived cells expressing cytochrome P450s for assessing metabolism-associated drug-induced liver toxicity.
2016 Aug 5
Patents

Sample Use Guides

Patients recieved 25 mg once daily for 7 days.
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:06:04 UTC 2023
Edited
by admin
on Fri Dec 15 15:06:04 UTC 2023
Record UNII
H0982HF78B
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PRIMAQUINE PHOSPHATE
MART.   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD  
Common Name English
1,4-PENTANEDIAMINE, N4-(6-METHOXY-8-QUINOLINYL)-, PHOSPHATE (1:2)
Systematic Name English
MALQUINE
Brand Name English
PRIMAQUINE PHOSPHATE [USP-RS]
Common Name English
PRIMAQUINE DIPHOSPHATE [EP MONOGRAPH]
Common Name English
PRIMAQUINE PHOSPHATE [MART.]
Common Name English
PRIMAQUINE DIPHOSPHATE [WHO-IP]
Common Name English
PRIMAQUINI DIPHOSPHAS [WHO-IP LATIN]
Common Name English
Primaquine phosphate [WHO-DD]
Common Name English
PRIMAQUINE PHOSPHATE [JAN]
Common Name English
CAMDEN
Brand Name English
PRIMAQUINE PHOSPHATE [ORANGE BOOK]
Common Name English
8-(4-AMINO-1-METHYLBUTYLAMINO)-6-METHOXYQUINOLINE DIPHOSPHATE
Systematic Name English
PRIMAQUINE PHOSPHATE [VANDF]
Common Name English
NSC-149765
Code English
PRIMAQUINE PHOSPHATE [USP MONOGRAPH]
Common Name English
PRIMAQUINE DIPHOSPHATE [MI]
Common Name English
WR 2975
Code English
PRIMAQUINE DIPHOSPHATE
MI   WHO-IP  
Common Name English
QUINOLINE, 8-((4-AMINO-1-METHYLBUTYL)AMINO)-6-METHOXY-, DIPHOSPHATE
Systematic Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 74793
Created by admin on Fri Dec 15 15:06:04 UTC 2023 , Edited by admin on Fri Dec 15 15:06:04 UTC 2023
NCI_THESAURUS C271
Created by admin on Fri Dec 15 15:06:04 UTC 2023 , Edited by admin on Fri Dec 15 15:06:04 UTC 2023
Code System Code Type Description
CAS
63-45-6
Created by admin on Fri Dec 15 15:06:04 UTC 2023 , Edited by admin on Fri Dec 15 15:06:04 UTC 2023
PRIMARY
ECHA (EC/EINECS)
200-560-8
Created by admin on Fri Dec 15 15:06:04 UTC 2023 , Edited by admin on Fri Dec 15 15:06:04 UTC 2023
PRIMARY
CAS
84902-21-6
Created by admin on Fri Dec 15 15:06:04 UTC 2023 , Edited by admin on Fri Dec 15 15:06:04 UTC 2023
SUPERSEDED
ChEMBL
CHEMBL506
Created by admin on Fri Dec 15 15:06:04 UTC 2023 , Edited by admin on Fri Dec 15 15:06:04 UTC 2023
PRIMARY
EVMPD
SUB04039MIG
Created by admin on Fri Dec 15 15:06:04 UTC 2023 , Edited by admin on Fri Dec 15 15:06:04 UTC 2023
PRIMARY
DAILYMED
H0982HF78B
Created by admin on Fri Dec 15 15:06:04 UTC 2023 , Edited by admin on Fri Dec 15 15:06:04 UTC 2023
PRIMARY
NCI_THESAURUS
C771
Created by admin on Fri Dec 15 15:06:04 UTC 2023 , Edited by admin on Fri Dec 15 15:06:04 UTC 2023
PRIMARY
SMS_ID
100000085099
Created by admin on Fri Dec 15 15:06:04 UTC 2023 , Edited by admin on Fri Dec 15 15:06:04 UTC 2023
PRIMARY
NSC
149765
Created by admin on Fri Dec 15 15:06:04 UTC 2023 , Edited by admin on Fri Dec 15 15:06:04 UTC 2023
PRIMARY
EPA CompTox
DTXSID6045248
Created by admin on Fri Dec 15 15:06:04 UTC 2023 , Edited by admin on Fri Dec 15 15:06:04 UTC 2023
PRIMARY
DRUG BANK
DBSALT001188
Created by admin on Fri Dec 15 15:06:04 UTC 2023 , Edited by admin on Fri Dec 15 15:06:04 UTC 2023
PRIMARY
MERCK INDEX
m9133
Created by admin on Fri Dec 15 15:06:04 UTC 2023 , Edited by admin on Fri Dec 15 15:06:04 UTC 2023
PRIMARY Merck Index
RS_ITEM_NUM
1561507
Created by admin on Fri Dec 15 15:06:04 UTC 2023 , Edited by admin on Fri Dec 15 15:06:04 UTC 2023
PRIMARY
FDA UNII
H0982HF78B
Created by admin on Fri Dec 15 15:06:04 UTC 2023 , Edited by admin on Fri Dec 15 15:06:04 UTC 2023
PRIMARY
RXCUI
8689
Created by admin on Fri Dec 15 15:06:04 UTC 2023 , Edited by admin on Fri Dec 15 15:06:04 UTC 2023
PRIMARY RxNorm
WHO INTERNATIONAL PHARMACOPEIA
PRIMAQUINE PHOSPHATE
Created by admin on Fri Dec 15 15:06:04 UTC 2023 , Edited by admin on Fri Dec 15 15:06:04 UTC 2023
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.
PUBCHEM
6135
Created by admin on Fri Dec 15 15:06:04 UTC 2023 , Edited by admin on Fri Dec 15 15:06:04 UTC 2023
PRIMARY
Related Record Type Details
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
USP
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
EP
ENANTIOMER -> RACEMATE
PARENT -> SALT/SOLVATE
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
IMPURITY -> PARENT
IMPURITY -> PARENT
Related Record Type Details
ACTIVE MOIETY