Primaquine

Antimalarial — ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS

Key facts

Primaquine is an ofp drug in the Antimalarial class catalogued in DrugCentral. It was first approved by the FDA in 1952. DrugCentral lists 14 molecular targets, including HSP90AA1, SLC6A4 and CYP1A2. Recorded indications include Vivax malaria.

• Approval status: ofp (first approved 1952 by the FDA).
• Drug class: Antimalarial.
• Molecular targets: HSP90AA1, SLC6A4, CYP1A2 and SHMT2 (14 listed in DrugCentral).
• Indications: Vivax malaria.
• ATC code: P01BA03 (Aminoquinolines).
• Molecular formula: C15H21N3O; molecular weight 259.35 g/mol.

Indications & contraindications

Drug–disease relationships curated by DrugCentral (OMOP / SNOMED concepts).

Indications (1)

• Vivax malaria

Off-label uses (3)

• Ovale malaria
• Plasmodium Ovale Malaria Prevention
• Pneumocystosis jiroveci pneumonia

Contraindications (7)

• Anemia due to enzyme deficiency
• Bone marrow depression
• Deficiency of cytochrome-b>5< reductase
• Deficiency of glucose-6-phosphate dehydrogenase
• Hemolytic anemia
• Neutropenic disorder
• Pregnancy, function

Mechanism & targets

• Established pharmacologic class: Antimalarial

Molecular targets (14)

Target	Gene	Action	Activity
Heat shock protein HSP 90-alpha	HSP90AA1	unknown	IC50 8.22
Sodium-dependent serotonin transporter	SLC6A4	unknown	Ki 8.07
Cytochrome P450 1A2	CYP1A2	unknown	IC50 6.74
Serine hydroxymethyltransferase, mitochondrial	SHMT2	unknown	IC50 6.36
Aryl hydrocarbon receptor	AHR	unknown	IC50 5.33
Ribosyldihydronicotinamide dehydrogenase [quinone]	NQO2	unknown	IC50 5.12
Potassium voltage-gated channel subfamily H member 2	KCNH2	unknown	IC50 4.67
Chloroquine resistance transporter	CRT	unknown	IC50 4.17
Amine oxidase [flavin-containing] A	MAOA	unknown	IC50 4.12
Amine oxidase [flavin-containing] B	MAOB	unknown	IC50 4.02
Reverse transcriptase/RNaseH	pol	unknown	IC50 4.00
Reverse transcriptase	reverse transcriptas	unknown	IC50 4.00
Glucose-6-phosphate 1-dehydrogenase	G6PD	unknown	—
Hemoglobin subunit alpha	HBA1	unknown	—

Regulatory approvals (1)

Date	Agency	Marketed as	Applicant	Orphan
1952-01-23	FDA	—	SANOFI AVENTIS US

ATC classification

ATC code	Therapeutic hierarchy
P01BA03	ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS › ANTIPROTOZOALS › ANTIMALARIALS › Aminoquinolines

Pharmacogenomics

Drug-label and guideline annotations from PharmGKB and CPIC.

• FDA label: G6PD · Testing Required
• FDA label: CYB5R1, CYB5R2, CYB5R3, CYB5R4 · Actionable PGx
• HCSC label: CYB5R1, CYB5R2, CYB5R3, CYB5R4, CYP2D6 · Actionable PGx
• HCSC label: G6PD · Testing Required

Reported adverse-event signals

Strongest FDA FAERS disproportionality signals (log-likelihood ratio). A signal is a statistical association in spontaneous reports, not proof that the drug causes the event.

MedDRA term	LLR
Methaemoglobinaemia	356.3
Plasmodium vivax infection	72.3
Haemolysis	58.5
Drug interaction	47.3
Cyanosis	45.8

Chemical structure

Full physicochemical, ADMET and 3D-structure analysis of Primaquine is on its molecule page.

• Molecular formula: C₁₅H₂₁N₃O
• Molecular weight: 259.35 g/mol
• CAS number: 90-34-6
• InChIKey: INDBQLZJXZLFIT-UHFFFAOYSA-N
• PubChem CID: 4908

COC1=CC(NC(C)CCCN)=C2N=CC=CC2=C1

Frequently asked questions

Answers are generated from the structured data on this page, not written by hand.

What is Primaquine used for?

DrugCentral lists the following indications for Primaquine: Vivax malaria.

How does Primaquine work?

Its molecular targets in DrugCentral include HSP90AA1, SLC6A4, CYP1A2 and SHMT2.

When was Primaquine first approved?

Primaquine was first approved by the FDA in 1952.

What drug class does Primaquine belong to?

Primaquine is in the Antimalarial class.

What is the chemical formula of Primaquine?

Primaquine has the molecular formula C15H21N3O and a molecular weight of 259.35 g/mol.

Sources

• DrugCentral drug card 2266 — structure, indications, targets, approvals, pharmacologic classes (CC BY-SA 4.0)
• ChEMBL CHEMBL43128 — compound record and bioactivity
• PubChem CID 4908 — chemical identifiers
• DrugBank DB01087 — drug record
• FDA UNII MVR3634GX1 — substance identity
• DailyMed: FDA labels for Primaquine — current prescribing information (label search)
• UniProt P07900 (HSP90AA1) — target protein
• UniProt P31645 (SLC6A4) — target protein
• UniProt P05177 (CYP1A2) — target protein
• UniProt P34897 (SHMT2) — target protein
• UniProt P35869 (AHR) — target protein
• UniProt P16083 (NQO2) — target protein
• FDA Adverse Event Reporting System (openFDA FAERS) — adverse-event signals, as aggregated by DrugCentral
• PharmGKB / CPIC — pharmacogenomic label annotations

How this page is built: methodology · editorial policy & corrections.