Primaquine
Overview
Description
Primaquine is a medication primarily used to treat and prevent malaria, specifically targeting the dormant liver forms of the parasite Plasmodium vivax and Plasmodium ovale . It is also used in combination with other medications to treat Pneumocystis pneumonia . This compound was first synthesized in 1946 and is included in the World Health Organization’s List of Essential Medicines .
Mechanism of Action
Target of Action
Primaquine, an 8-aminoquinoline, primarily targets the liver stages of the malaria parasites, specifically Plasmodium vivax and Plasmodium ovale . It is also effective against the sexual stage of the Plasmodium parasite .
Mode of Action
It is believed to interfere with a part of the parasite (mitochondria) that is responsible for supplying it with energy . Without energy, the parasite dies, stopping the infection from continuing and allowing the person to recover .
Pharmacokinetics
This compound is well-absorbed in the gut and extensively distributed in the body without accumulating in red blood cells . Its elimination half-life is reported to be around 6 hours . This compound’s bioavailability is increased when taken with food or grapefruit juice .
Result of Action
The result of this compound’s action is the death of the malaria parasite. By interfering with the parasite’s energy supply, this compound stops the infection from continuing, allowing the person to recover . It also prevents the relapse of vivax and ovale malarias following treatment with a blood schizontocide .
Biochemical Analysis
Biochemical Properties
Primaquine interacts with various enzymes, proteins, and other biomolecules. It is metabolized in humans via three pathways . The first pathway involves direct glucuronide/glucose/carbamate/acetate conjugation of this compound. The second pathway involves hydroxylation (likely cytochrome P450-mediated) at different positions on the quinoline ring, with mono-, di-, or even tri-hydroxylations possible, and subsequent glucuronide conjugation of the hydroxylated metabolites . The third pathway involves the monoamine oxidase catalyzed oxidative deamination of this compound resulting in the formation of this compound-aldehyde, this compound alcohol, and carboxy this compound (cPQ), which are further metabolized through additional phase I hydroxylations and/or phase II glucuronide conjugations .
Cellular Effects
This compound has significant effects on various types of cells and cellular processes. It interferes with a part of the parasite (mitochondria) that is responsible for supplying it with energy . Without energy, the parasite dies, stopping the infection from continuing and allowing the person to recover .
Molecular Mechanism
It may be acting by generating reactive oxygen species or by interfering with the electron transport in the parasite . This compound may also bind to and alter the properties of protozoal DNA .
Temporal Effects in Laboratory Settings
In laboratory settings, the effects of this compound change over time. A single low-dose of this compound was found to be haematologically safe in a population of G6PD-normal and G6PD-deficient African males without malaria . The study observed haemoglobin levels up to 28 days after drug administration .
Dosage Effects in Animal Models
In animal models, the effects of this compound vary with different dosages . The plasma AUC 0-last (µg h/mL) (1.6 vs. 0.6), T 1/2 (h) (1.9 vs. 0.45), and T max (h) (1 vs. 0.5) were greater for S-Primaquine as compared to R-Primaquine .
Metabolic Pathways
This compound is involved in various metabolic pathways. As mentioned earlier, it is metabolized in humans via three pathways . These pathways involve various enzymes and cofactors, and can also affect metabolic flux or metabolite levels .
Transport and Distribution
This compound is transported and distributed within cells and tissues . The concentration of S-Primaquine was found to be higher in all tissues . At T max, (0.5–1 h in all tissues), the level of S-Primaquine was 3 times that of R-Primaquine in the liver .
Preparation Methods
Synthetic Routes and Reaction Conditions
Primaquine is synthesized through a multi-step process starting from 8-aminoquinoline. . The reaction conditions typically involve the use of strong bases and organic solvents to facilitate the substitution reactions.
Industrial Production Methods
Industrial production of this compound involves large-scale synthesis using similar reaction conditions as in the laboratory synthesis but optimized for higher yields and purity. The process includes rigorous purification steps to ensure the final product meets pharmaceutical standards .
Chemical Reactions Analysis
Types of Reactions
Primaquine undergoes various chemical reactions, including:
Reduction: The compound can also undergo reduction reactions, particularly in the presence of reducing agents.
Substitution: This compound can participate in substitution reactions, especially at the amino and methoxy groups.
Common Reagents and Conditions
Common reagents used in the reactions of this compound include oxidizing agents like hydrogen peroxide, reducing agents such as sodium borohydride, and various organic solvents . The reactions are typically carried out under controlled temperature and pH conditions to ensure the desired products are formed.
Major Products Formed
The major products formed from the reactions of this compound include its oxidized and reduced forms, as well as various substituted derivatives . These products are often studied for their potential pharmacological activities.
Scientific Research Applications
Primaquine has a wide range of scientific research applications:
Comparison with Similar Compounds
Primaquine belongs to the class of 8-aminoquinoline compounds. Similar compounds include:
Tafenoquine: Like this compound, tafenoquine is used to treat and prevent malaria.
Chloroquine: Although not an 8-aminoquinoline, chloroquine is another antimalarial drug that targets the blood stages of the parasite.
This compound’s uniqueness lies in its ability to eliminate the dormant liver forms of malaria parasites, making it essential for preventing relapses .
Properties
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 | |
| URL | https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0000090346 | |
| Description | ChemIDplus is a free, web search system that provides access to the structure and nomenclature authority files used for the identification of chemical substances cited in National Library of Medicine (NLM) databases, including the TOXNET system. | |
DSSTOX Substance ID |
DTXSID8023509 |
Source
|
| Record name | Primaquine | |
| Source | EPA DSSTox | |
| 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. | |
| 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. | |
Boiling Point |
175-179 °C |
Source
|
| Record name | Primaquine | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB01087 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
| Record name | PRIMAQUINE | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/6516 | |
| Description | The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel. | |
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. | |
| 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. | |
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 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
| Record name | PRIMAQUINE | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/6516 | |
| Description | The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel. | |
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 | |
| Description | CAS Common Chemistry is an open community resource for accessing chemical information. Nearly 500,000 chemical substances from CAS REGISTRY cover areas of community interest, including common and frequently regulated chemicals, and those relevant to high school and undergraduate chemistry classes. This chemical information, curated by our expert scientists, is provided in alignment with our mission as a division of the American Chemical Society. | |
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| Record name | Primaquine [INN:BAN] | |
| Source | ChemIDplus | |
| URL | https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0000090346 | |
| Description | ChemIDplus is a free, web search system that provides access to the structure and nomenclature authority files used for the identification of chemical substances cited in National Library of Medicine (NLM) databases, including the TOXNET system. | |
| Record name | Primaquine | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB01087 | |
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| Record name | Primaquine | |
| Source | EPA DSSTox | |
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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 | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| 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 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
| 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
Retrosynthesis Analysis
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| Precursor scoring | Relevance Heuristic |
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| Template Set | Pistachio/Bkms_metabolic/Pistachio_ringbreaker/Reaxys/Reaxys_biocatalysis |
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Feasible Synthetic Routes
Q1: How does primaquine exert its antimalarial effects?
A1: While the exact mechanism of action remains incompletely understood, this compound is known to target the liver stages of Plasmodium vivax and Plasmodium ovale malaria, specifically the dormant hypnozoites responsible for relapses. This compound'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 this compound metabolites in its antimalarial activity?
A2: this compound 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, this compound-5,6-orthoquinone (5,6-POQ), has been identified as a key mediator of this compound's activity against Plasmodium parasites. []
Q3: Is this compound effective against the blood stages of malaria parasites?
A3: this compound 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 this compound?
A4: The molecular formula of this compound is C15H21N3O, and its molecular weight is 259.34 g/mol.
Q5: How is this compound metabolized in the body?
A5: this compound 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 this compound?
A6: Pharmacokinetic studies indicated comparable this compound disposition between men and women, suggesting no need for dose adjustments based on sex. [, ]
Q7: How effective is this compound in preventing relapses of Plasmodium vivax malaria?
A7: this compound 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 this compound doses (≥5 mg/kg). []
Q8: Is there evidence of this compound resistance?
A8: While widespread this compound 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 this compound regimens. [, , ]
Q9: What is the role of CYP2D6 polymorphisms in this compound efficacy?
A9: CYP2D6 genetic variations, particularly those resulting in decreased enzyme activity, can significantly impact this compound metabolism and reduce its efficacy. This highlights the importance of understanding the pharmacogenetics of this compound for personalized treatment strategies. []
Q10: What are the major safety concerns associated with this compound 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 this compound and other 8-aminoquinolines. [, , , , ]
Q11: Are there strategies to improve this compound delivery to its target sites?
A11: Researchers have explored nanoparticle formulations of this compound 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 this compound-loaded chitosan nanoparticles achieved a threefold increase in liver this compound concentrations compared to conventional this compound in rats. [, ]
Q12: What analytical methods are employed to quantify this compound and its metabolites?
A12: Liquid chromatography coupled with mass spectrometry (LC-MS) is commonly utilized for the sensitive and specific quantification of this compound 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 this compound and its metabolites achieved?
A13: Chiral chromatography, employing specialized stationary phases designed to separate enantiomers, is used to isolate and quantify individual enantiomers of this compound and its metabolites. This technique is crucial for understanding potential differences in the pharmacological and toxicological profiles of individual enantiomers. []
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