Primaquine

Identification

Summary

Primaquine is an antimalarial indicated to prevent relapse of vivax malaria.

Generic Name

Primaquine

DrugBank Accession Number

DB01087

Background

An aminoquinoline that is given by mouth to produce a radical cure and prevent relapse of vivax and ovale malarias following treatment with a blood schizontocide. It has also been used to prevent transmission of falciparum malaria by those returning to areas where there is a potential for re-introduction of malaria. Adverse effects include anemias and GI disturbances. (From Martindale, The Extra Pharmacopeia, 30th ed, p404)

Type

Small Molecule

Groups

Approved

Structure

Similar Structures

Weight: Average: 259.3467
Monoisotopic: 259.168462309
Chemical Formula: C₁₅H₂₁N₃O

Synonyms

6-Methoxy-8-(4-amino-1-methylbutylamino)quinoline
8-((4-Amino-1-methylbutyl)amino)-6-methoxyquinoline
8-(4-Amino-1-methylbutylamino)-6-methoxyquinoline
Primachin
Primachina
Primachinum
Primaquin
Primaquina
Primaquine
Primaquinum

External IDs

SN-13272
WR-2975

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Pharmacology

Indication

For the treatment of malaria.

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Associated Conditions

Indication Type	Indication	Approval Level
Prophylaxis of	Malaria	••• •••••
Treatment of	Malaria caused by plasmodium ovale	••••••••••••
Treatment of	Malaria caused by plasmodium vivax	••••••••••••
Used in combination to treat	Pneumocystis pneumonia	••• •••••

Contraindications & Blackbox Warnings

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Pharmacodynamics

Primaquine is an antimalarial agent and is the essential co-drug with chloroquine in treating all cases of malaria. In the blood, malaria parasites break down a part of the red blood cells known as haemoglobin. When this happens haemoglobin is divided into two parts; haem and globin. Haem is toxic to the malaria parasite. To prevent it from being damaged, the malaria parasite produces an chemical which converts the toxic haem into a non-toxic product. Primaquine acts by interfering with a part of the parasite (mitochondria) that is responsible for supplying it with energy. Without energy the parasite dies. This stops the infection from continuing and allows the person to recover. Primaquine kills the intrahepatic form of Plasmodium vivax and Plasmodium ovale, and thereby prevents the development of the erythrocytic forms that are responsible for relapses (it also kills gametocytes). Primaquine is not used in the prevention of malaria, only in the treatment. It has insignificant activity against the asexual blood forms of the parasite and therefore it is always used in conjunction with a blood schizonticide and never as a single agent. Primaquine has gametocytocidal activity against all plasmodia, including P. falciparum.

Mechanism of action

Primaquine's mechanism of action is not well understood. It may be acting by generating reactive oxygen species or by interfering with the electron transport in the parasite. Also, although its mechanism of action is unclear, primaquine may bind to and alter the properties of protozoal DNA.

Target	Actions	Organism
AFe(II)-protoporphyrin IX	antagonist	Plasmodium falciparum
UKeratin, type II cytoskeletal 7	other/unknown	Humans
URibosyldihydronicotinamide dehydrogenase [quinone]	inhibitor	Humans

Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Not Available

Route of elimination

Not Available

Half-life

3.7-7.4 hours

Clearance

Not Available

Adverse Effects

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Toxicity

Not Available

Pathways

Not Available

Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">

Interacting Gene/Enzyme	Allele name	Genotype(s)	Defining Change(s)	Type(s)	Description	Details
NADH-cytochrome b5 reductase 3	---	Not Available	Exon 2 c.129C>A / Exon 2 c.149G>A … show all	ADR Inferred	Risk of methemglobinemia.	Details
Glucose-6-phosphate 1-dehydrogenase	Villeurbanne	Not Available	1000_1002delACC	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Torun	Not Available	1006A->G	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Sunderland	Not Available	105_107delCAT	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Iwatsuki	Not Available	1081G->A	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Serres	Not Available	1082C->T	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Tondela	Not Available	1084_1101delCTGAACGAGCGCAAGGCC	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Loma Linda	Not Available	1089C->A	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Aachen	Not Available	1089C->G	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Tenri	Not Available	1096A->G	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Montpellier	Not Available	1132G>A	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Calvo Mackenna	Not Available	1138A->G	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Riley	Not Available	1139T->C	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Olomouc	Not Available	1141T->C	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Tomah	Not Available	1153T->C	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Lynwood	Not Available	1154G->T	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Madrid	Not Available	1155C->G	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Iowa, Walter Reed, Springfield	Not Available	1156A->G	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Beverly Hills, Genova, Iwate, Niigata, Yamaguchi	Not Available	1160G->A	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Hartford	Not Available	1162A->G	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Praha	Not Available	1166A->G	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Krakow	Not Available	1175T>C	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Wisconsin	Not Available	1177C->G	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Nashville, Anaheim, Portici	Not Available	1178G->A	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Alhambra	Not Available	1180G->C	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Bari	Not Available	1187C->T	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Puerto Limon	Not Available	1192G->A	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Covao do Lobo	Not Available	1205C>A	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Clinic	Not Available	1215G->A	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Utrecht	Not Available	1225C->T	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Suwalki	Not Available	1226C->G	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Riverside	Not Available	1228G->T	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Japan, Shinagawa	Not Available	1229G->A	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Kawasaki	Not Available	1229G->C	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Munich	Not Available	1231A->G	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Georgia	Not Available	1284C->A	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Sumare	Not Available	1292T->G	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Telti/Kobe	Not Available	1318C->T	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Santiago de Cuba, Morioka	Not Available	1339G->A	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Harima	Not Available	1358T->A	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Figuera da Foz	Not Available	1366G->C	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Amiens	Not Available	1367A>T	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Bangkok Noi	Not Available	1376G->T, 1502T->G	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Fukaya	Not Available	1462G->A	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Campinas	Not Available	1463G->T	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Buenos Aires	Not Available	1465C>T	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Arakawa	Not Available	1466C->T	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Brighton	Not Available	1488_1490delGAA	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Kozukata	Not Available	159G->C	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Amsterdam	Not Available	180_182delTCT	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	No name	Not Available	202G->A, 376A->G, 1264C>G	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Swansea	Not Available	224T->C	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Urayasu	Not Available	281_283delAGA	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Vancouver	Not Available	317C->G544C->T592C->T	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Mt Sinai	Not Available	376A->G, 1159C->T	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Plymouth	Not Available	488G->A	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Volendam	Not Available	514C->T	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Shinshu	Not Available	527A->G	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Chikugo	Not Available	535A->T	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Tsukui	Not Available	561_563delCTC	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Pedoplis-Ckaro	Not Available	573C>G	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Santiago	Not Available	593G->C	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Minnesota, Marion, Gastonia, LeJeune	Not Available	637G->T	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Cincinnati	Not Available	637G->T, 1037A->T	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Harilaou	Not Available	648T->G	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	North Dallas	Not Available	683_685delACA	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Asahikawa	Not Available	695G->A	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Durham	Not Available	713A->G	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Stonybrook	Not Available	724_729delGGCACT	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Wayne	Not Available	769C->G	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Aveiro	Not Available	806G->A	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Cleveland Corum	Not Available	820G->A	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Lille	Not Available	821A>T	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Bangkok	Not Available	825G>C	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Sugao	Not Available	826C->T	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	La Jolla	Not Available	832T->C	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Wexham	Not Available	833C->T	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Piotrkow	Not Available	851T>C	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	West Virginia	Not Available	910G->T	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Omiya	Not Available	921G->C	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Nara	Not Available	953_976delCCACCAAAGGGTACCTGGAC GACC	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Manhattan	Not Available	962G->A	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Rehevot	Not Available	964T->C	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Honiara	Not Available	99A->G / 1360C->T	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Tokyo, Fukushima	Not Available	1246G->A	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Chatham	Not Available	1003G->A	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Fushan	Not Available	1004C->A	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Partenope	Not Available	1052G->T	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Ierapetra	Not Available	1057C->T	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Anadia	Not Available	1193A->G	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Abeno	Not Available	1220A->C	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Surabaya	Not Available	1291G->A	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Pawnee	Not Available	1316G->C	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	S. Antioco	Not Available	1342A->G	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Cassano	Not Available	1347G->C	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Hermoupolis	Not Available	1347G->C / 1360C->T	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Union,Maewo, Chinese-2, Kalo	Not Available	1360C->T	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Andalus	Not Available	1361G->A	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Cosenza	Not Available	1376G->C	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Canton, Taiwan- Hakka, Gifu-like, Agrigento-like	Not Available	1376G->T	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Flores	Not Available	1387C->A	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Kaiping, Anant, Dhon, Sapporo-like, Wosera	Not Available	1388G->A	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Kamogawa	Not Available	169C->T	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Costanzo	Not Available	179T>C	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Amazonia	Not Available	185C->A	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Songklanagarind	Not Available	196T->A	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Hechi	Not Available	202G->A / 871G->A	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Namouru	Not Available	208T->C	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Bao Loc	Not Available	352T>C	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Crispim	Not Available	375G->T, 379G->T383T->C384C>T	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Acrokorinthos	Not Available	376A->G / 463C->G	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Santa Maria	Not Available	376A->G / 542A->T	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Ananindeua	Not Available	376A->G / 871G->A	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Vanua Lava	Not Available	383T->C	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Valladolid	Not Available	406C->T	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Belem	Not Available	409C->T	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Liuzhou	Not Available	442G->A	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Shenzen	Not Available	473G>A	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Taipei ‚ÄúChinese- 3‚Äù	Not Available	493A->G	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Toledo	Not Available	496C>T	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Naone	Not Available	497G->A	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Nankang	Not Available	517T->C	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Miaoli	Not Available	519C->G	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Mediterranean, Dallas, Panama‚ Sassari, Cagliari, Birmingham	Not Available	563C->T	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Coimbra Shunde	Not Available	592C->T	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Nilgiri	Not Available	593G>A	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Radlowo	Not Available	679C->T	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Roubaix	Not Available	811G>C	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Haikou	Not Available	835A->G	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Chinese-1	Not Available	835A->T	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Mizushima	Not Available	848A>G	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Osaka	Not Available	853C->T	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Viangchan, Jammu	Not Available	871G->A	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Seoul	Not Available	916G->A	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Ludhiana	Not Available	929G->A	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Farroupilha	Not Available	977C->A	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Chinese-5	Not Available	1024C->T	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Rignano	Not Available	130G>A	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Orissa	Not Available	131C->G	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	G6PDNice	Not Available	1380G>C	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Kamiube, Keelung	Not Available	1387C->T	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Neapolis	Not Available	1400C->G	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Aures	Not Available	143T->C	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Split	Not Available	1442C->G	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Kambos	Not Available	148C->T	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Palestrina	Not Available	170G>A	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Metaponto	Not Available	172G->A	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Musashino	Not Available	185C->T	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Asahi	Not Available	202G->A	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	A- (202), Ferrara I	Not Available	202G->A / 376A->G	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Murcia Oristano	Not Available	209A->G	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Ube Konan	Not Available	241C->T	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Lagosanto	Not Available	242G->A	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Guangzhou	Not Available	274C->T	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Hammersmith	Not Available	323T->A	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Sinnai	Not Available	34G->T	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	A- (680)	Not Available	376A->G / 680G->T	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	A- (968), Betica,Selma, Guantanamo	Not Available	376A->G / 968T->C	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Salerno Pyrgos	Not Available	383T>G	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Quing Yan	Not Available	392G->T	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Lages	Not Available	40G->A	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Ilesha	Not Available	466G->A	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Mahidol	Not Available	487G->A	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Malaga	Not Available	542A->T	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Sibari	Not Available	634A->G	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Mexico City	Not Available	680G->A	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Nanning	Not Available	703C->T	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Seattle, Lodi, Modena, Ferrara II, Athens-like	Not Available	844G->C	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Bajo Maumere	Not Available	844G->T	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Montalbano	Not Available	854G->A	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Kalyan-Kerala, Jamnaga, Rohini	Not Available	949G->A	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details
Glucose-6-phosphate 1-dehydrogenase	Gaohe	Not Available	95A->G	ADR Inferred	Increased risk of potentially fatal hemolysis. Associated with leukopenia.	Details

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

Drug	Interaction
Integrate drug-drug interactions in your software
1,2-Benzodiazepine	The metabolism of 1,2-Benzodiazepine can be decreased when combined with Primaquine.
Abametapir	The serum concentration of Primaquine can be increased when it is combined with Abametapir.
Abatacept	The metabolism of Primaquine can be increased when combined with Abatacept.
Abemaciclib	The metabolism of Abemaciclib can be decreased when combined with Primaquine.
Abiraterone	The serum concentration of Primaquine can be increased when it is combined with Abiraterone.

Food Interactions

Take with food. Food decreases irritation.

Products

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Product Ingredients

Ingredient	UNII	CAS	InChI Key
Primaquine phosphate	H0982HF78B	63-45-6	GJOHLWZHWQUKAU-UHFFFAOYSA-N

International/Other Brands

Neo-Quipenyl / Primachin

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Primaquine	Tablet	26.3 mg	Oral	Sanofi Aventis	1945-12-31	Not applicable
Primaquine Phosphate	Tablet, film coated	15 mg/1	Oral	PD-Rx Pharmaceuticals, Inc.	2011-04-15	Not applicable
Primaquine Phosphate	Tablet, film coated	15 mg/1	Oral	Avera McKennan Hospital	2015-08-24	2017-05-24
Primaquine Phosphate	Tablet, film coated	15 mg/1	Oral	bryant ranch prepack	2011-04-15	2016-10-30
Primaquine Phosphate	Tablet, film coated	15 mg/1	Oral	sanofi-aventis U.S. LLC	2011-04-15	Not applicable

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Primaquine Phosphate	Tablet	15 mg/1	Oral	PD-Rx Pharmaceuticals, Inc.	2014-08-01	Not applicable
Primaquine Phosphate	Tablet, film coated	15 mg/1	Oral	AvKARE	2019-02-21	Not applicable
Primaquine Phosphate	Tablet, film coated	15 mg/1	Oral	Ingenus Pharmaceuticals Nj, Llc	2016-06-23	2016-06-23
Primaquine Phosphate	Tablet, film coated	26.3 mg/1	Oral	Alvogen Inc.	2014-02-03	2018-02-01
Primaquine Phosphate	Tablet	15 mg/1	Oral	Golden State Medical Supply	2014-02-25	Not applicable

Chemical Identifiers

UNII: MVR3634GX1
CAS number: 90-34-6
InChI Key: INDBQLZJXZLFIT-UHFFFAOYSA-N
InChI: 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
IUPAC Name: N4-(6-methoxyquinolin-8-yl)pentane-1,4-diamine
SMILES: COC1=CC(NC(C)CCCN)=C2N=CC=CC2=C1

References

General References

Mihaly GW, Ward SA, Edwards G, Nicholl DD, Orme ML, Breckenridge AM: Pharmacokinetics of primaquine in man. I. Studies of the absolute bioavailability and effects of dose size. Br J Clin Pharmacol. 1985 Jun;19(6):745-50. [Article]
ALVING AS, ARNOLD J, HOCKWALD RS, CLAYMAN CB, DERN RJ, BEUTLER E, FLANAGAN CL: Potentiation of the curative action of primaquine in vivax malaria by quinine and chloroquine. J Lab Clin Med. 1955 Aug;46(2):301-6. [Article]
Hill DR, Baird JK, Parise ME, Lewis LS, Ryan ET, Magill AJ: Primaquine: report from CDC expert meeting on malaria chemoprophylaxis I. Am J Trop Med Hyg. 2006 Sep;75(3):402-15. [Article]
Cohen RJ, Sachs JR, Wicker DJ, Conrad ME: Methemoglobinemia provoked by malarial chemoprophylaxis in Vietnam. N Engl J Med. 1968 Nov 21;279(21):1127-31. [Article]
Coleman MD, Coleman NA: Drug-induced methaemoglobinaemia. Treatment issues. Drug Saf. 1996 Jun;14(6):394-405. [Article]
Taavitsainen P, Juvonen R, Pelkonen O: In vitro inhibition of cytochrome P450 enzymes in human liver microsomes by a potent CYP2A6 inhibitor, trans-2-phenylcyclopropylamine (tranylcypromine), and its nonamine analog, cyclopropylbenzene. Drug Metab Dispos. 2001 Mar;29(3):217-22. [Article]
Bapiro TE, Andersson TB, Otter C, Hasler JA, Masimirembwa CM: 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. Eur J Clin Pharmacol. 2002 Nov;58(8):537-42. Epub 2002 Oct 2. [Article]
CYP1A2 CTEP document [File]

External Links

Human Metabolome Database: HMDB0015219
KEGG Compound: C07627
PubChem Compound: 4908
PubChem Substance: 46508222
ChemSpider: 4739
BindingDB: 71542
RxNav: 8687
ChEBI: 8405
ChEMBL: CHEMBL506
Therapeutic Targets Database: DAP000216
PharmGKB: PA451103
Drugs.com: Drugs.com Drug Page
Wikipedia: Primaquine

FDA label

Download (105 KB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count
4	Active Not Recruiting	Prevention	Malaria / Parasitic Diseases	1
4	Active Not Recruiting	Treatment	Malaria / Malaria caused by Plasmodium falciparum / Malaria caused by plasmodium vivax	1
4	Completed	Basic Science	Plasmodium Falciparum Clinical Episode / Plasmodium Falciparum Infection / Plasmodium Vivax Clinical Episode / Plasmodium Vivax Infection	1
4	Completed	Diagnostic	Malaria caused by plasmodium vivax	1
4	Completed	Prevention	Malaria	2

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Bayer Healthcare
Dispensing Solutions
Gallipot
Kaiser Foundation Hospital
Sanofi-Aventis Inc.

Dosage Forms

Form	Route	Strength
Tablet	Oral	15 mg
Tablet, film coated	Oral
Tablet	Oral
Tablet, coated	Oral
Tablet	Oral	26.3 mg
Tablet	Oral	15 mg/1
Tablet, film coated	Oral	15 mg/1
Tablet, film coated	Oral	26.3 mg/1
Tablet, film coated	Oral	15 mg

Prices

Unit description	Cost	Unit
Primaquin phosphate powder	18.2USD	g
Primaquine 26.3 mg tablet	1.51USD	tablet
Primaquine Phosphate 15 mg Tablet	0.43USD	tablet

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Not Available

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	< 25 °C	PhysProp
boiling point (°C)	177 °C at 2.00E-01 mm Hg	PhysProp
logP	2.1	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0564 mg/mL	ALOGPS
logP	2.76	ALOGPS
logP	1.64	Chemaxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	17.11	Chemaxon
pKa (Strongest Basic)	10.2	Chemaxon
Physiological Charge	1	Chemaxon
Hydrogen Acceptor Count	4	Chemaxon
Hydrogen Donor Count	2	Chemaxon
Polar Surface Area	60.17 Å²	Chemaxon
Rotatable Bond Count	6	Chemaxon
Refractivity	78.51 m³·mol^-1	Chemaxon
Polarizability	29.92 Å³	Chemaxon
Number of Rings	2	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	Yes	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	No	Chemaxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	0.9776
Blood Brain Barrier	+	0.9787
Caco-2 permeable	-	0.5622
P-glycoprotein substrate	Substrate	0.8018
P-glycoprotein inhibitor I	Non-inhibitor	0.8782
P-glycoprotein inhibitor II	Non-inhibitor	0.7681
Renal organic cation transporter	Inhibitor	0.5501
CYP450 2C9 substrate	Non-substrate	0.8703
CYP450 2D6 substrate	Substrate	0.8918
CYP450 3A4 substrate	Substrate	0.5723
CYP450 1A2 substrate	Inhibitor	0.9107
CYP450 2C9 inhibitor	Non-inhibitor	0.93
CYP450 2D6 inhibitor	Inhibitor	0.8932
CYP450 2C19 inhibitor	Inhibitor	0.8994
CYP450 3A4 inhibitor	Non-inhibitor	0.831
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.5057
Ames test	AMES toxic	0.9106
Carcinogenicity	Non-carcinogens	0.9283
Biodegradation	Not ready biodegradable	1.0
Rat acute toxicity	2.4474 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.7858
hERG inhibition (predictor II)	Inhibitor	0.8162

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	splash10-001l-7390000000-20feb8c491df9e9e6f0d
LC-MS/MS Spectrum - LC-ESI-qTof , Positive	LC-MS/MS	splash10-01r6-0970000000-a3b1021cda642a6141b8
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-01p6-4290000000-d5f33ea098bbcd333ccf
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-000l-9360000000-9f32d7ddbda48f0e2dc5
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-002r-9530000000-5c70a8800c55df1915e7
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-002r-9810000000-89e3b0e2b3cb4d1e9293
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-00n0-5900000000-cbe196964f610f8bf1ff
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-00o9-3900000000-6209d7be74ea608e7fc2
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-03di-0190000000-32ab0ba382901a73b1c0
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-002f-1690000000-82416f4c3f338eece150
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-004i-0920000000-65f7b4135f0db6eee15e
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-004i-0900000000-17b7474db1209213f689
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-001i-0900000000-b2c7e131a6a25d115853
MS/MS Spectrum - , positive	LC-MS/MS	splash10-01r6-0970000000-a3b1021cda642a6141b8
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-001i-2900000000-d3dfd1b72d458ffd07d7
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-01p6-4290000000-314f515d08e6730a1df9
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-000l-9360000000-3933ab4d9c2c3918ecce
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-002r-9530000000-65625d68f98ae8f36ea0
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-002r-7910000000-6c3e274b81107c5e98eb
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-01ox-0090000000-362659f93fcc4d10c147
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0a4i-0190000000-81817deda24aa57a8ff4
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0a4i-0690000000-93d402c5190d97232bef
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0006-1090000000-1bc7c3107a0dc53000c0
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-03fr-1940000000-2cfa21c02b2da8f1a589
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0006-0910000000-20eeadf6660484c1e6a7
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å²)	Source type	Source
[M-H]-	174.4743242	predicted	DarkChem Lite v0.1.0
[M-H]-	162.39983	predicted	DeepCCS 1.0 (2019)
[M+H]+	175.0517242	predicted	DarkChem Lite v0.1.0
[M+H]+	164.75783	predicted	DeepCCS 1.0 (2019)
[M+Na]+	174.2339242	predicted	DarkChem Lite v0.1.0
[M+Na]+	170.85097	predicted	DeepCCS 1.0 (2019)

Targets

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Details1. Fe(II)-protoporphyrin IX

Kind

Small molecule

Organism

Plasmodium falciparum

Pharmacological action

Yes

Actions

Antagonist

References

Dorn A, Vippagunta SR, Matile H, Jaquet C, Vennerstrom JL, Ridley RG: An assessment of drug-haematin binding as a mechanism for inhibition of haematin polymerisation by quinoline antimalarials. Biochem Pharmacol. 1998 Mar 15;55(6):727-36. [Article]
Fitch CD: Ferriprotoporphyrin IX, phospholipids, and the antimalarial actions of quinoline drugs. Life Sci. 2004 Mar 5;74(16):1957-72. [Article]

Details2. Keratin, type II cytoskeletal 7

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Other/unknown

General Function: Structural molecule activity
Specific Function: Blocks interferon-dependent interphase and stimulates DNA synthesis in cells. Involved in the translational regulation of the human papillomavirus type 16 E7 mRNA (HPV16 E7).
Gene Name: KRT7
Uniprot ID: P08729
Uniprot Name: Keratin, type II cytoskeletal 7
Molecular Weight: 51385.11 Da

References

Heard CM, Monk BV, Modley AJ: Binding of primaquine to epidermal membranes and keratin. Int J Pharm. 2003 May 12;257(1-2):237-44. [Article]
Basso LG, Rodrigues RZ, Naal RM, Costa-Filho AJ: Effects of the antimalarial drug primaquine on the dynamic structure of lipid model membranes. Biochim Biophys Acta. 2011 Jan;1808(1):55-64. doi: 10.1016/j.bbamem.2010.08.009. Epub 2010 Aug 14. [Article]

Details3. Ribosyldihydronicotinamide dehydrogenase [quinone]

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Nadph dehydrogenase (quinone) activity
Specific Function: The enzyme apparently serves as a quinone reductase in connection with conjugation reactions of hydroquinones involved in detoxification pathways as well as in biosynthetic processes such as the vi...
Gene Name: NQO2
Uniprot ID: P16083
Uniprot Name: Ribosyldihydronicotinamide dehydrogenase [quinone]
Molecular Weight: 25918.4 Da

References

Graves PR, Kwiek JJ, Fadden P, Ray R, Hardeman K, Coley AM, Foley M, Haystead TA: Discovery of novel targets of quinoline drugs in the human purine binding proteome. Mol Pharmacol. 2002 Dec;62(6):1364-72. [Article]

Enzymes

Details1. Cytochrome P450 3A4

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate
Inhibitor

General Function: Vitamin d3 25-hydroxylase activity
Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name: CYP3A4
Uniprot ID: P08684
Uniprot Name: Cytochrome P450 3A4
Molecular Weight: 57342.67 Da

References

Zhao XJ, Ishizaki T: Metabolic interactions of selected antimalarial and non-antimalarial drugs with the major pathway (3-hydroxylation) of quinine in human liver microsomes. Br J Clin Pharmacol. 1997 Nov;44(5):505-11. [Article]
Bangchang KN, Karbwang J, Back DJ: Primaquine metabolism by human liver microsomes: effect of other antimalarial drugs. Biochem Pharmacol. 1992 Aug 4;44(3):587-90. [Article]
Avula B, Tekwani BL, Chaurasiya ND, Fasinu P, Dhammika Nanayakkara NP, Bhandara Herath HMT, Wang YH, Bae JY, Khan SI, Elsohly MA, McChesney JD, Zimmerman PA, Khan IA, Walker LA: Metabolism of primaquine in normal human volunteers: investigation of phase I and phase II metabolites from plasma and urine using ultra-high performance liquid chromatography-quadrupole time-of-flight mass spectrometry. Malar J. 2018 Aug 13;17(1):294. doi: 10.1186/s12936-018-2433-z. [Article]
Ganesan S, Tekwani BL, Sahu R, Tripathi LM, Walker LA: Cytochrome P(450)-dependent toxic effects of primaquine on human erythrocytes. Toxicol Appl Pharmacol. 2009 Nov 15;241(1):14-22. doi: 10.1016/j.taap.2009.07.012. Epub 2009 Jul 17. [Article]

Details2. Cytochrome P450 1A2

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate
Inducer

General Function: Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name: CYP1A2
Uniprot ID: P05177
Uniprot Name: Cytochrome P450 1A2
Molecular Weight: 58293.76 Da

References

Shoda T, Mitsumori K, Onodera H, Toyoda K, Uneyama C, Takada K, Hirose M: Liver tumor-promoting effect of beta-naphthoflavone, a strong CYP 1A1/2 inducer, and the relationship between CYP 1A1/2 induction and Cx32 decrease in its hepatocarcinogenesis in the rat. Toxicol Pathol. 2000 Jul-Aug;28(4):540-7. doi: 10.1177/019262330002800406. [Article]
Li XQ, Bjorkman A, Andersson TB, Gustafsson LL, Masimirembwa CM: Identification of human cytochrome P(450)s that metabolise anti-parasitic drugs and predictions of in vivo drug hepatic clearance from in vitro data. Eur J Clin Pharmacol. 2003 Sep;59(5-6):429-42. Epub 2003 Aug 12. [Article]
Bapiro TE, Egnell AC, Hasler JA, Masimirembwa CM: Application of higher throughput screening (HTS) inhibition assays to evaluate the interaction of antiparasitic drugs with cytochrome P450s. Drug Metab Dispos. 2001 Jan;29(1):30-5. [Article]
Bapiro TE, Andersson TB, Otter C, Hasler JA, Masimirembwa CM: 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. Eur J Clin Pharmacol. 2002 Nov;58(8):537-42. Epub 2002 Oct 2. [Article]
Krusekopf S, Roots I, Hildebrandt AG, Kleeberg U: Time-dependent transcriptional induction of CYP1A1, CYP1A2 and CYP1B1 mRNAs by H+/K+ -ATPase inhibitors and other xenobiotics. Xenobiotica. 2003 Feb;33(2):107-18. [Article]

Details3. Cytochrome P450 2D6

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Steroid hydroxylase activity
Specific Function: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name: CYP2D6
Uniprot ID: P10635
Uniprot Name: Cytochrome P450 2D6
Molecular Weight: 55768.94 Da

References

Masimirembwa CM, Hasler JA, Johansson I: Inhibitory effects of antiparasitic drugs on cytochrome P450 2D6. Eur J Clin Pharmacol. 1995;48(1):35-8. [Article]

Details4. Cytochrome P450 1A1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inducer

General Function: Vitamin d 24-hydroxylase activity
Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name: CYP1A1
Uniprot ID: P04798
Uniprot Name: Cytochrome P450 1A1
Molecular Weight: 58164.815 Da

References

Bapiro TE, Andersson TB, Otter C, Hasler JA, Masimirembwa CM: 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. Eur J Clin Pharmacol. 2002 Nov;58(8):537-42. Epub 2002 Oct 2. [Article]
Krusekopf S, Roots I, Hildebrandt AG, Kleeberg U: Time-dependent transcriptional induction of CYP1A1, CYP1A2 and CYP1B1 mRNAs by H+/K+ -ATPase inhibitors and other xenobiotics. Xenobiotica. 2003 Feb;33(2):107-18. [Article]
Werlinder V, Backlund M, Zhukov A, Ingelman-Sundberg M: Transcriptional and post-translational regulation of CYP1A1 by primaquine. J Pharmacol Exp Ther. 2001 Apr;297(1):206-14. [Article]

Details5. Cytochrome P450 1B1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inducer

General Function: Oxygen binding
Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name: CYP1B1
Uniprot ID: Q16678
Uniprot Name: Cytochrome P450 1B1
Molecular Weight: 60845.33 Da

References

Krusekopf S, Roots I, Hildebrandt AG, Kleeberg U: Time-dependent transcriptional induction of CYP1A1, CYP1A2 and CYP1B1 mRNAs by H+/K+ -ATPase inhibitors and other xenobiotics. Xenobiotica. 2003 Feb;33(2):107-18. [Article]

Transporters

Details1. P-glycoprotein 1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Xenobiotic-transporting atpase activity
Specific Function: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name: ABCB1
Uniprot ID: P08183
Uniprot Name: Multidrug resistance protein 1
Molecular Weight: 141477.255 Da

References

Kim JH, Choi AR, Kim YK, Yoon S: Co-treatment with the anti-malarial drugs mefloquine and primaquine highly sensitizes drug-resistant cancer cells by increasing P-gp inhibition. Biochem Biophys Res Commun. 2013 Nov 22;441(3):655-60. doi: 10.1016/j.bbrc.2013.10.095. Epub 2013 Oct 26. [Article]
Choi AR, Kim JH, Woo YH, Kim HS, Yoon S: Anti-malarial Drugs Primaquine and Chloroquine Have Different Sensitization Effects with Anti-mitotic Drugs in Resistant Cancer Cells. Anticancer Res. 2016 Apr;36(4):1641-8. [Article]

Drug created at June 13, 2005 13:24 / Updated at December 02, 2023 07:02

Primaquine

Identification

Structure for Primaquine (DB01087)

Pharmacology

Interactions

Products

Categories

Chemical Identifiers

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Clinical Trials

Pharmacoeconomics

Properties

Spectra

Collision Cross Sections (CCS)

Targets

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Enzymes

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Transporters

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