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

Details

Stereochemistry RACEMIC
Molecular Formula C21H27N3O3
Molecular Weight 369.4574
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of BULAQUINE

SMILES

COC1=CC(NC(C)CCCN\C(C)=C2\CCOC2=O)=C3N=CC=CC3=C1

InChI

InChIKey=ADCOUXIGWFEYJP-SDXDJHTJSA-N
InChI=1S/C21H27N3O3/c1-14(6-4-9-22-15(2)18-8-11-27-21(18)25)24-19-13-17(26-3)12-16-7-5-10-23-20(16)19/h5,7,10,12-14,22,24H,4,6,8-9,11H2,1-3H3/b18-15-

HIDE SMILES / InChI

Molecular Formula C21H27N3O3
Molecular Weight 369.4574
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 1
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
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
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
The effect of primaquine on the ultrastructural morphology of Pneumocystis carinii.
1991 Nov-Dec
Isolation and characterization of rat lung Pneumocystis carinii gp120.
1991 Nov-Dec
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
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
[Hemolysis and primaquine treatment. Preliminary report].
1997
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
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
Imported malaria in a cosmopolitan European city: a mirror image of the world epidemiological situation.
2008 Apr 8
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
[In vitro dissolution profile of primaquine tablets available for malaria treatment in Brazil].
2008 Jan-Feb
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
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
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 Sat Dec 16 17:11:31 UTC 2023
Edited
by admin
on Sat Dec 16 17:11:31 UTC 2023
Record UNII
TSQ6U39Q3G
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BULAQUINE
INN   WHO-DD  
INN  
Official Name English
AABLAQUINE
Brand Name English
Bulaquine [WHO-DD]
Common Name English
bulaquine [INN]
Common Name English
DIHYDRO-3-(1-((4-((6-METHOXY-8-QUINOLYL)AMINO)PENTYL)AMINO)ETHYLIDENE)-2(3H)-FURANONE
Systematic Name English
ELUBAQUINE
Common Name English
CDRI 80/53
Code English
2(3H)-FURANONE, DIHYDRO-3-(1-((4-((6-METHOXY-8-QUINOLINYL)AMINO)PENTYL)AMINO)ETHYLIDENE)-
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C271
Created by admin on Sat Dec 16 17:11:32 UTC 2023 , Edited by admin on Sat Dec 16 17:11:32 UTC 2023
Code System Code Type Description
SMS_ID
100000084833
Created by admin on Sat Dec 16 17:11:32 UTC 2023 , Edited by admin on Sat Dec 16 17:11:32 UTC 2023
PRIMARY
ChEMBL
CHEMBL2106578
Created by admin on Sat Dec 16 17:11:32 UTC 2023 , Edited by admin on Sat Dec 16 17:11:32 UTC 2023
PRIMARY
NCI_THESAURUS
C75997
Created by admin on Sat Dec 16 17:11:32 UTC 2023 , Edited by admin on Sat Dec 16 17:11:32 UTC 2023
PRIMARY
PUBCHEM
9831444
Created by admin on Sat Dec 16 17:11:32 UTC 2023 , Edited by admin on Sat Dec 16 17:11:32 UTC 2023
PRIMARY
FDA UNII
TSQ6U39Q3G
Created by admin on Sat Dec 16 17:11:32 UTC 2023 , Edited by admin on Sat Dec 16 17:11:32 UTC 2023
PRIMARY
CAS
79781-00-3
Created by admin on Sat Dec 16 17:11:32 UTC 2023 , Edited by admin on Sat Dec 16 17:11:32 UTC 2023
PRIMARY
INN
7927
Created by admin on Sat Dec 16 17:11:32 UTC 2023 , Edited by admin on Sat Dec 16 17:11:32 UTC 2023
PRIMARY
CAS
223661-25-4
Created by admin on Sat Dec 16 17:11:32 UTC 2023 , Edited by admin on Sat Dec 16 17:11:32 UTC 2023
SUPERSEDED
MESH
C063469
Created by admin on Sat Dec 16 17:11:32 UTC 2023 , Edited by admin on Sat Dec 16 17:11:32 UTC 2023
PRIMARY
EPA CompTox
DTXSID8040983
Created by admin on Sat Dec 16 17:11:32 UTC 2023 , Edited by admin on Sat Dec 16 17:11:32 UTC 2023
PRIMARY
DRUG CENTRAL
425
Created by admin on Sat Dec 16 17:11:32 UTC 2023 , Edited by admin on Sat Dec 16 17:11:32 UTC 2023
PRIMARY
EVMPD
SUB00894MIG
Created by admin on Sat Dec 16 17:11:32 UTC 2023 , Edited by admin on Sat Dec 16 17:11:32 UTC 2023
PRIMARY
Related Record Type Details
ENANTIOMER -> RACEMATE
ENANTIOMER -> RACEMATE
Related Record Type Details
METABOLITE ACTIVE -> PRODRUG
Related Record Type Details
ACTIVE MOIETY