PRIMAQUINE

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 Search

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

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: http://www.cdri.res.in/Bulaquin.aspx | http://www.insa.nic.in/writereaddata/UpLoadedFiles/PINSA/Vol69B_2003_6_Art02.pdfhttps://www.accessdata.fda.gov/drugsatfda_docs/label/2008/008316s017lbl.pdf

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 Target	Pharmacology	Condition	Potency
Quinone reductase 2 12 Target ID: CHEMBL3959 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21074425	Inhibitor 8504		7.5 µM [IC50]
Chloroquine resistance transporter 3 Target ID: CHEMBL1795182 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24900883	Inhibitor 8504		68.0 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Plasmodium vivax malaria 6 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16969059	Curative		Approved 8583	AABLAQUIN Approved Use Treatment and prevention of p. vivax. Launch Date 2000
Plasmodium vivax malaria 6 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/008316s017lbl.pdf	Curative		Approved 8583	PRIMAQUINE Approved Use Primaquine phosphate is indicated for the radical cure (prevention of relapse) of vivax malaria. Launch Date 1952

C_max

Value	Dose	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
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
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

AUC

Value	Dose	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
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
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

T_1/2

Value	Dose	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
4.4 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
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

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: https://pubmed.ncbi.nlm.nih.gov/26366319/	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/26366319/	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: https://pubmed.ncbi.nlm.nih.gov/26366319/
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 Sources: https://pubmed.ncbi.nlm.nih.gov/12932090/	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://pubmed.ncbi.nlm.nih.gov/12932090/	Disc. AE: Hematocrit decreased... AEs leading to discontinuation/dose reduction: Hematocrit decreased (4 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/12932090/
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: https://pubmed.ncbi.nlm.nih.gov/26366319/	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/26366319/	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: https://pubmed.ncbi.nlm.nih.gov/26366319/
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: https://pubmed.ncbi.nlm.nih.gov/26366319/	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/26366319/	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: https://pubmed.ncbi.nlm.nih.gov/26366319/
75 mg single, oral Highest studied dose Dose: 75 mg Route: oral Route: single Dose: 75 mg Sources: https://pubmed.ncbi.nlm.nih.gov/16448575/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/16448575/	Sources: https://pubmed.ncbi.nlm.nih.gov/16448575/
25 mg 1 times / day multiple, oral Studied dose Dose: 25 mg, 1 times / day Route: oral Route: multiple Dose: 25 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/16969059/	unhealthy Health Status: unhealthy Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/16969059/	Other AEs: Nausea, Dizziness... Other AEs: Nausea (4.3%) Dizziness (8.5%) Headache (4.3%) Sources: https://pubmed.ncbi.nlm.nih.gov/16969059/

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946	substrate 1193	substrate 1388 inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 CYP3A4/5 296 P-gp 1741 OATP1A2 43 OATP1B1 1079	CYP2C19 1119 CYP1A2 1197	CYP1A2 832

Drug as perpetrator

Target	Modality	Activity
CYP3A4/5 357	inhibitor 4027 Sources: https://www.pmda.go.jp/drugs/2016/P20160309001/780069000_2800AMX00403000_I100_1.pdf#page=32 Page: (PMDA_I100_1 in Japanese) 32	yes [IC50 19.4 uM]
OATP1A2 43	inhibitor 4027 Sources: https://www.pmda.go.jp/drugs/2016/P20160309001/780069000_22800AMX00403000_A100_1.pdf#page=16 Page: (PMDA_A100_1 in Japanese) 16	yes [IC50 5.6 uM]
CYP1A2 2333	inhibitor 4027 Sources: https://www.pmda.go.jp/drugs/2016/P20160309001/780069000_2800AMX00403000_I100_1.pdf#page=32 Page: (PMDA_I100_1 in Japanese) 32, 36	yes [Ki 0.22 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://www.pmda.go.jp/drugs/2016/P20160309001/780069000_2800AMX00403000_I100_1.pdf#page=32 Page: (PMDA_I100_1 in Japanese) 32	yes [Ki 23 uM]
CYP1A2 2333	inducer 1966 Sources: https://www.pmda.go.jp/drugs/2016/P20160309001/780069000_2800AMX00403000_I100_1.pdf#page=32 Page: (PMDA_I100_1 in Japanese) 32, 36	yes
OATP1B1 1095	inhibitor 4027 Sources: https://www.pmda.go.jp/drugs/2016/P20160309001/780069000_22800AMX00403000_A100_1.pdf#page=16 Page: (PMDA_A100_1 in Japanese) 16	yes
P-gp 1932	inhibitor 4027 Sources: https://www.pmda.go.jp/drugs/2016/P20160309001/780069000_2800AMX00403000_I100_1.pdf#page=32 Page: (PMDA_I100_1 in Japanese) 32	yes

Drug as victim

Target	Modality	Activity
CYP3A4 1946	substrate 4014 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]
CYP2C19 1119	substrate 4014 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]
CYP2C9 1193	substrate 4014 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
CYP2D6 1388	substrate 4014 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]
CYP1A2 1197	substrate 4014 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
hERG 2263	inhibitor 2237 Sources: https://www.pmda.go.jp/drugs/2016/P20160309001/780069000_22800AMX00403000_A100_1.pdf#page=10, https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/008316s023lbl.pdf#page=3 Page: (PMDA_A100_1 in Japanese) 10, (FDA label) 3

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:8405	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:8405
ChemicalBook	CB0875785	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB0875785
eMolecules	1077024	https://www.emolecules.com/cgi-bin/more?vid=1077024
MolPort	MolPort-001-794-628	https://www.molport.com/shop/molecule-link/MolPort-001-794-628

PubMed

Title	Date	PubMed
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	4864652
Methemoglobinemia provoked by malarial chemoprophylaxis in Vietnam.	1968 Nov 21	5686480
Simultaneous drug reactions in the same patient. Chloroquine-Primaquine sensitivity.	1970 Apr 27	5467364
Reaction to primaquine.	1980 Mar	7356244
The treatment of malaria in glucose-6-phosphate dehydrogenase deficient patients in Sabah.	1981 Dec	7325735
Primaquine-chloroquine prophylaxis against malaria in Southeast-Asian refugees entering South Australia.	1984 Mar 17	6366489
Pharmacokinetics of primaquine in man. I. Studies of the absolute bioavailability and effects of dose size.	1985 Jun	4027117
[Hemolytic reaction due to administration of primaquine].	1986 Apr	3742573
Primaquine induced hemolysis in a Thai soldier.	1989 Dec	2639511
Immunogenicity of amodiaquine in the rat.	1990	2210868
Causal prophylactic activity of a new 8-aminoquinoline derivative against Plasmodium cynomolgi B in rhesus monkeys.	1990 May	2397941
Effect of anti-relapse antimalarial compound CDRI 80/53 and primaquine on hepatic mixed function oxidase system of rhesus monkey.	1990 Nov-Dec	2075158
Detection of antidrug IgG antibodies in patients with adverse drug reactions to amodiaquine.	1991	1959977
Isolation and characterization of rat lung Pneumocystis carinii gp120.	1991 Nov-Dec	1818123
Inhibitors of human immunodeficiency virus integrase.	1993 Mar 15	8460151
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	8250972
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	8092843
[Primaquine and travelers from the Arab world. A report and recommendations].	1995	9813483
New drug developments for opportunistic infections in immunosuppressed patients: Pneumocystis carinii.	1995 Nov 24	7490723
Dapsone- and primaquine-induced methemoglobinemia in HIV-infected individuals.	1996 Aug 15	8757424
Efficacy of 101 antimicrobials and other agents on the development of Cryptosporidium parvum in vitro.	1996 Dec	9039272
Drug-induced methaemoglobinaemia. Treatment issues.	1996 Jun	8828017
[Hemolysis and primaquine treatment. Preliminary report].	1997	9685977
Prediction of aryl hydrocarbon receptor-mediated enzyme induction of drugs and chemicals by mRNA quantification.	1998 Dec	9860486
Glucose-6-phosphate dehydrogenase deficiency in two returning Operation Iraqi Freedom soldiers who developed hemolytic anemia while receiving primaquine prophylaxis for malaria.	2005 Apr	15916292
Exotic diseases of dogs and cats at risk of importation to Ireland.	2005 May 1	21851670
Evaluation of anti-malarial effects of mass chemoprophylaxis in the Republic of Korea army.	2005 Oct	16224140
[Haemolysis due to primaquine in 3 cases].	2006 Feb 28	16866141
Pharmacokinetics of piperaquine after repeated oral administration of the antimalarial combination CV8 in 12 healthy male subjects.	2006 May	16570188
Combined chloroquine, sulfadoxine/pyrimethamine and primaquine against Plasmodium falciparum in Central Java, Indonesia.	2006 Nov 14	17105658
Primaquine: report from CDC expert meeting on malaria chemoprophylaxis I.	2006 Sep	16968913
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	17410524
Persistent binding of ligands to the aryl hydrocarbon receptor.	2007 Jul	17431010
Drug, dosage, activity, studies of antimalarials by physical methods--II.	2007 May 20	18084644
Congenital malaria in the United States: a review of cases from 1966 to 2005.	2007 Nov	17984408
Formulation and evaluation of taste masked oral reconstitutable suspension of primaquine phosphate.	2008	18770047
Identification of differentially expressed genes after acute exposure to bulaquine (CDRI 80/53) in mice liver.	2008 Dec	18684221
HepaRG cells as an in vitro model for evaluation of cytochrome P450 induction in humans.	2008 Jan	17954527
Formulation and evaluation of primaquine phosphate taste-masked rapidly disintegrating tablet.	2008 Oct	18812020
Monkey malaria in a European traveler returning from Malaysia.	2008 Sep	18760013
Diverse chemicals including aryl hydrocarbon receptor ligands modulate transcriptional activity of the 3'immunoglobulin heavy chain regulatory region.	2009 Jun 30	19447539
Cytochrome P(450)-dependent toxic effects of primaquine on human erythrocytes.	2009 Nov 15	19616568
The Summary Index of Malaria Surveillance (SIMS): a stable index of malaria within India.	2010 Feb 11	20181218
An open-label, randomised study of dihydroartemisinin-piperaquine versus artesunate-mefloquine for falciparum malaria in Asia.	2010 Jul 30	20689583
Monitoring for Plasmodium falciparum drug resistance to artemisinin and artesunate in Binh Phuoc Province, Vietnam: 1998-2009.	2010 Jun 24	20573274
Blockade of hERG K(+) channel by antimalarial drug, primaquine.	2010 May	20512476
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.	2011 Jul 14	21599003
Characterization of Plasmodium liver stage inhibition by halofuginone.	2012 May	22438279
Quinolin-4(1H)-imines are potent antiplasmodial drugs targeting the liver stage of malaria.	2013 Jun 13	23701465
Primaquine or other 8-aminoquinoline for reducing Plasmodium falciparum transmission.	2015 Feb 19	25693791

Patents

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 Created by `admin` on `Mon Mar 31 18:08:07 GMT 2025` Edited by `admin` on `Mon Mar 31 18:08:07 GMT 2025`
Record UNII	MVR3634GX1
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

KANAPRIM

Preferred Name

English

PRIMAQUINE

Official Name

English

PRIMAQUINE [VANDF]

Common Name

English

PRIMAQUINE [MI]

Common Name

English

SN-13272

Code

English

(±)-PRIMAQUINE

Common Name

English

Primaquine [WHO-DD]

Common Name

English

WR-2975

Code

English

PRIMACHIN

Common Name

English

NEO-QUIPENYL

Brand Name

English

MALIRIDE

Brand Name

English

NSC-27296

Code

English

primaquine [INN]

Common Name

English

QUINOLINE, 8-((4-AMINO-1-METHYLBUTYL)AMINO)-6-METHOXY-

Systematic Name

English

1,4-PENTANEDIAMINE, N4-(6-METHOXY-8-QUINOLINYL)-

Systematic Name

English

Classification Tree Code System Code

LIVERTOX

NBK548031