IUPAC Name	4-N-(6-methoxyquinolin-8-yl)pentane-1,4-diamine	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

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	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

InChI Key	INDBQLZJXZLFIT-UHFFFAOYSA-N	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

Canonical SMILES	CC(CCCN)NC1=C2C(=CC(=C1)OC)C=CC=N2	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

Molecular Formula	C15H21N3O	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

Related CAS	63-45-6 (1:2 PO4)	Source
Record name	Primaquine [INN:BAN]
Source	ChemIDplus
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DSSTOX Substance ID	DTXSID8023509	Source
Record name	Primaquine
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URL	https://comptox.epa.gov/dashboard/DTXSID8023509
Description	DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology.

Molecular Weight	259.35 g/mol	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

Physical Description	Solid	Source
Record name	Primaquine
Source	Human Metabolome Database (HMDB)
URL	http://www.hmdb.ca/metabolites/HMDB0015219
Description	The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body.
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Boiling Point	175-179 °C	Source
Record name	Primaquine
Source	DrugBank
URL	https://www.drugbank.ca/drugs/DB01087
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Record name	PRIMAQUINE
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Solubility	5.64e-02 g/L	Source
Record name	Primaquine
Source	Human Metabolome Database (HMDB)
URL	http://www.hmdb.ca/metabolites/HMDB0015219
Description	The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body.
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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., The precise mechanism of action has not been determined, but may be based on primaquine's ability to bind to and alter the properties of DNA. Primaquine is highly active against the exoeryhrocytic stages of plasmodium vivax and plasmodium ovale and against the primary exoerythrocytic stages of plasmodium falciparum. It is also highly active against the sexual forms of (gametocytes) plasmodia, especially P. falciparum, disrupting transmission of the disease by eliminating the reservoir from which the mosquito carrier is infected., /Primaquine/ disrupts the parasitic mitochondria, thereby interrupting metabolic processes requiring energy., ... /Primaquine is one/ of /aromatic amine-containing/ xenobiotics ... capable to inducing oxidative injury in erythrocytes. These agents appear to potentiate the normal redox reactions and are capable of overwhelming the usual protective mechanisms. The interaction between these xenobiotics and hemoglobin leads to the formation of free radicals that denature critical proteins, including hemoglobin, thiol-dependent enzymes, and components of the erythrocyte membrane ... Oxidative denaturation of the globin chain decreases its affinity for the heme group, which may dissociate from the globin chain during oxidative injury ... The generation of free radicals may also lead to peroxidation of membrane lipids. This may affect the deformability of the erythrocyte and the permeability of the membrane to potassium. The alteration of the Na(+)/K(+) gradient is ... potentially lethal to the affected erythrocyte. Oxidative injury also impairs the metabolic machinery of the erythrocyte, resulting in a decrease in the concentration of ATP. Damage to the membrane can also permit leakage of denatured hemoglobin from the cell. Such free denatured hemoglobin can be toxic on its own. Free hemoglobin may irreversibly bind nitric oxide, resulting in vasoconstriction. Released hemoglobin may form nephrotoxic hemoglobin dimers, leading to kidney damage. /Oxidative hemolysis/	Source
Record name	Primaquine
Source	DrugBank
URL	https://www.drugbank.ca/drugs/DB01087
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Record name	PRIMAQUINE
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Color/Form	Viscous liquid
CAS No.	90-34-6	Source
Record name	Primaquine
Source	CAS Common Chemistry
URL	https://commonchemistry.cas.org/detail?cas_rn=90-34-6
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Record name	Primaquine [INN:BAN]
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Record name	Primaquine
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Record name	PRIMAQUINE
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Record name	Primaquine
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Record name	Primaquine
Source	European Chemicals Agency (ECHA)
URL	https://echa.europa.eu/substance-information/-/substanceinfo/100.001.807
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Record name	PRIMAQUINE
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Record name	PRIMAQUINE
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URL	https://pubchem.ncbi.nlm.nih.gov/source/hsdb/6516
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Record name	Primaquine
Source	Human Metabolome Database (HMDB)
URL	http://www.hmdb.ca/metabolites/HMDB0015219
Description	The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body.
Explanation	HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.

Melting Point	< 25 °C	Source
Record name	Primaquine
Source	DrugBank
URL	https://www.drugbank.ca/drugs/DB01087
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Record name	Primaquine
Source	Human Metabolome Database (HMDB)
URL	http://www.hmdb.ca/metabolites/HMDB0015219
Description	The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body.
Explanation	HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.

Synthesis routes and methods

Procedure details

Primaquine diphosphate solution was used for swelling DDPC/Ch/DCP mixture into liposomes, and the resulting liposomes were washed by centrifugation, and then suspended in a volume of saline four times of that used in swelling the vesicles. The concentration of drug was equivalent to 25 mg/kg primaquine diphosphate for 35 g mice when 0.1 ml was injected, or 376 mg/kg for 0.15 ml, or 50 mg/kg for 0.2 ml.

Name

Primaquine diphosphate

Quantity

0 (± 1) mol

Type

reactant

Reaction Step One

Name

DDPC

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Two

Name

Primaquine

Details

Retrosynthesis Analysis

AI-Powered Synthesis Planning: Our tool employs the Template_relevance Pistachio, Template_relevance Bkms_metabolic, Template_relevance Pistachio_ringbreaker, Template_relevance Reaxys, Template_relevance Reaxys_biocatalysis model, leveraging a vast database of chemical reactions to predict feasible synthetic routes.

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Strategy Settings

Precursor scoring	Relevance Heuristic
Min. plausibility	0.01
Model	Template_relevance
Template Set	Pistachio/Bkms_metabolic/Pistachio_ringbreaker/Reaxys/Reaxys_biocatalysis
Top-N result to add to graph	6

Feasible Synthetic Routes

Reactant of Route 1

Primaquine

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Primaquine

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Primaquine

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Primaquine

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Customer

Q & A

Q1: How does primaquine exert its antimalarial effects?

A1: While the exact mechanism of action remains incompletely understood, primaquine is known to target the liver stages of Plasmodium vivax and Plasmodium ovale malaria, specifically the dormant hypnozoites responsible for relapses. Primaquine's activity is believed to stem from its metabolites, which are thought to generate reactive oxygen species, leading to oxidative damage within the parasite. [, , ]

Q2: What is the role of primaquine metabolites in its antimalarial activity?

A2: Primaquine itself is a prodrug requiring bioactivation to exert its antimalarial effects. This bioactivation process involves enzymatic conversion, likely by cytochrome P450 enzymes, into active metabolites. [, ] One such metabolite, primaquine-5,6-orthoquinone (5,6-POQ), has been identified as a key mediator of primaquine's activity against Plasmodium parasites. []

Q3: Is primaquine effective against the blood stages of malaria parasites?

A3: Primaquine exhibits limited activity against the asexual blood stages of Plasmodium falciparum compared to its potent activity against liver-stage hypnozoites. [, , ]

Q4: What is the molecular formula and weight of primaquine?

A4: The molecular formula of primaquine is C15H21N3O, and its molecular weight is 259.34 g/mol.

Q5: How is primaquine metabolized in the body?

A5: Primaquine undergoes extensive metabolism in the liver, primarily via cytochrome P450 enzymes, particularly CYP2D6. This metabolism leads to the formation of various metabolites, some of which contribute to its antimalarial activity while others are associated with its toxicity. [, , ]

Q6: Does gender influence the pharmacokinetics of primaquine?

A6: Pharmacokinetic studies indicated comparable primaquine disposition between men and women, suggesting no need for dose adjustments based on sex. [, ]

Q7: How effective is primaquine in preventing relapses of Plasmodium vivax malaria?

A7: Primaquine is highly effective in preventing P. vivax relapses when administered at appropriate doses and durations. Clinical trials have demonstrated a significant reduction in relapse rates with higher total primaquine doses (≥5 mg/kg). []

Q8: Is there evidence of primaquine resistance?

A8: While widespread primaquine resistance has not been conclusively documented, several factors can impact treatment outcomes. These include variations in parasite susceptibility, host factors such as G6PD deficiency, and suboptimal adherence to prescribed primaquine regimens. [, , ]

Q9: What is the role of CYP2D6 polymorphisms in primaquine efficacy?

A9: CYP2D6 genetic variations, particularly those resulting in decreased enzyme activity, can significantly impact primaquine metabolism and reduce its efficacy. This highlights the importance of understanding the pharmacogenetics of primaquine for personalized treatment strategies. []

Q10: What are the major safety concerns associated with primaquine use?

A10: The primary concern is hemolytic anemia in individuals with G6PD deficiency. This enzyme is crucial for protecting red blood cells from oxidative damage, and its deficiency can lead to drug-induced hemolysis, particularly with primaquine and other 8-aminoquinolines. [, , , , ]

Q11: Are there strategies to improve primaquine delivery to its target sites?

A11: Researchers have explored nanoparticle formulations of primaquine to enhance its delivery to the liver, aiming to improve its efficacy against liver-stage parasites while potentially minimizing systemic exposure and associated toxicity. One study demonstrated that primaquine-loaded chitosan nanoparticles achieved a threefold increase in liver primaquine concentrations compared to conventional primaquine in rats. [, ]

Q12: What analytical methods are employed to quantify primaquine and its metabolites?

A12: Liquid chromatography coupled with mass spectrometry (LC-MS) is commonly utilized for the sensitive and specific quantification of primaquine and its metabolites in biological samples. This technique allows for the separation and detection of different chemical entities based on their mass-to-charge ratio, enabling comprehensive pharmacokinetic analyses. [, ]

Q13: How is the enantiomeric separation of primaquine and its metabolites achieved?

A13: Chiral chromatography, employing specialized stationary phases designed to separate enantiomers, is used to isolate and quantify individual enantiomers of primaquine and its metabolites. This technique is crucial for understanding potential differences in the pharmacological and toxicological profiles of individual enantiomers. []

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