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MedKoo Cat#: 318568 | Name: Primaquine Phosphate
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Primaquine is an established antimalarial drug used in the treatment of persistent liver forms of P. vivax or P. ovale infection for its ability to kill late-stage gametocytes and hypnozoites. In historical terms, this aminoquinoline was the stimulus for the discovery of glucose-6-phosphate (G6P) dehydrogenase deficiency as it induced hemolytic anemia in patients lacking the G6P-metabolizing enzyme.

Chemical Structure

Primaquine Phosphate
CAS#63-45-6

Theoretical Analysis

MedKoo Cat#: 318568

Name: Primaquine Phosphate

CAS#: 63-45-6

Chemical Formula: C15H24N3O5P

Exact Mass: 0.0000

Molecular Weight: 357.35

Elemental Analysis: C, 50.42; H, 6.77; N, 11.76; O, 22.39; P, 8.67

Price and Availability

Size Price Availability Quantity
1g USD 350.00 2 Weeks
2g USD 450.00 2 Weeks
5g USD 750.00 2 Weeks
10g USD 1,350.00 2 Weeks
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Synonym
Primaquine Phosphate; PRIMAQUINE PHOSPHATE; Primaquine (Diphosphate); Primaquine bis(phosphate); Primaquine bisphosphate; Primaquine Diphosphate; Primaquine Phosphate; Boucher and Muir Brand of Primaquine Phosphate; Diphosphate, Primaquine; Phosphate, Primaquine;
IUPAC/Chemical Name
4-N-(6-methoxyquinolin-8-yl)pentane-1,4-diamine;phosphoric acid
InChi Key
GJOHLWZHWQUKAU-UHFFFAOYSA-N
InChi Code
InChI=1S/C15H21N3O.2H3O4P/c1-11(5-3-7-16)18-14-10-13(19-2)9-12-6-4-8-17-15(12)14;2*1-5(2,3)4/h4,6,8-11,18H,3,5,7,16H2,1-2H3;2*(H3,1,2,3,4)
SMILES Code
CC(CCCN)NC1=C2C(=CC(=C1)OC)C=CC=N2.OP(=O)(O)O.OP(=O)(O)O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Primaquine Diphosphate (Primaquine phosphate), an 8-aminoquinoline, exerts a broad spectrum of activities against various stages of parasitic malaria.
In vitro activity:
This study shows that PQ (primaquine) had a significant inhibitory effect on the metabolic activity of all tested cryptococcal strains, with 60 µM, defined as MIC50 in this preliminary study, as it reduced the metabolic activity by more than 50%. Moreover, at this concentration, the drug was able to affect mitochondrial function adversely, as treated cells displayed significant (p < 0.05) loss of mitochondrial membrane potential, cytochrome c (cyt c) leakage and overproduction of reactive oxygen species (ROS) when compared to non-treated cells. Reference: J Mycol Med. 2023 May;33(2):101361. https://pubmed.ncbi.nlm.nih.gov/36812704/
In vivo activity:
In the present study, toxicopathological studies were conducted on a rat model to determine the effect of PQ (primaquine) on affected tissues and mitochondrial toxicity. The results indicated that the LD50 for PQ is 200 mg/kg. A high dose of PQ induced hemolytic anemia, elevated a hepatic enzyme (SGPT), and induced proximal tubular degeneration, ventricular cardiomyopathy, and mitochondrial dysregulation. In addition, PQ induced the upregulation of apoptosis-related proteins Drp-1 and caspase-3, with a positive correlation, as well as the pro-apoptotic mitochondrial gene expression of Bax, reflecting the toxic effect of high doses of PQ on cellular damage and mitochondrial apoptosis in terms of hepatotoxicity, nephrotoxicity, and cardiotoxicity. Reference: Toxics. 2023 Feb 2;11(2):146. https://pubmed.ncbi.nlm.nih.gov/36851021/
Solvent mg/mL mM comments
Solubility
DMF 0.5 1.10
DMSO 117.0 327.41
PBS (pH 7.2) 10.0 21.96
Water 58.0 162.31
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 357.35 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Madu UL, Ogundeji AO, Pohl CH, Albertyn J, Sebolai OM. Primaquine, an antimalarial drug that controls the growth of cryptococcal cells. J Mycol Med. 2023 May;33(2):101361. doi: 10.1016/j.mycmed.2023.101361. Epub 2023 Feb 11. PMID: 36812704. 2. Kim JH, Choi HS, Lee DS. Primaquine Inhibits the Endosomal Trafficking and Nuclear Localization of EGFR and Induces the Apoptosis of Breast Cancer Cells by Nuclear EGFR/Stat3-Mediated c-Myc Downregulation. Int J Mol Sci. 2021 Nov 30;22(23):12961. doi: 10.3390/ijms222312961. PMID: 34884765; PMCID: PMC8657416. 3. Rabiablok A, Hanboonkunupakarn B, Tuentam K, Fongsodsri K, Kanjanapruthipong T, Ampawong S. High-Dose Primaquine Induces Proximal Tubular Degeneration and Ventricular Cardiomyopathy Linked to Host Cells Mitochondrial Dysregulation. Toxics. 2023 Feb 2;11(2):146. doi: 10.3390/toxics11020146. PMID: 36851021; PMCID: PMC9962680. 4. Ma L, Chen L, Li H, Ge L, Wang S, Zhang Z, Huang H, Shi L, Li T, Gu H, Lyu J, He L. Primaquine phosphate induces the apoptosis of ATRA-resistant acute promyelocytic leukemia cells by inhibition of the NF-κB pathway. J Leukoc Biol. 2020 Apr;107(4):685-693. doi: 10.1002/JLB.3A0120-061RR. Epub 2020 Mar 3. PMID: 32125014.
In vitro protocol:
1. Madu UL, Ogundeji AO, Pohl CH, Albertyn J, Sebolai OM. Primaquine, an antimalarial drug that controls the growth of cryptococcal cells. J Mycol Med. 2023 May;33(2):101361. doi: 10.1016/j.mycmed.2023.101361. Epub 2023 Feb 11. PMID: 36812704. 2. Kim JH, Choi HS, Lee DS. Primaquine Inhibits the Endosomal Trafficking and Nuclear Localization of EGFR and Induces the Apoptosis of Breast Cancer Cells by Nuclear EGFR/Stat3-Mediated c-Myc Downregulation. Int J Mol Sci. 2021 Nov 30;22(23):12961. doi: 10.3390/ijms222312961. PMID: 34884765; PMCID: PMC8657416.
In vivo protocol:
1. Rabiablok A, Hanboonkunupakarn B, Tuentam K, Fongsodsri K, Kanjanapruthipong T, Ampawong S. High-Dose Primaquine Induces Proximal Tubular Degeneration and Ventricular Cardiomyopathy Linked to Host Cells Mitochondrial Dysregulation. Toxics. 2023 Feb 2;11(2):146. doi: 10.3390/toxics11020146. PMID: 36851021; PMCID: PMC9962680. 2. Ma L, Chen L, Li H, Ge L, Wang S, Zhang Z, Huang H, Shi L, Li T, Gu H, Lyu J, He L. Primaquine phosphate induces the apoptosis of ATRA-resistant acute promyelocytic leukemia cells by inhibition of the NF-κB pathway. J Leukoc Biol. 2020 Apr;107(4):685-693. doi: 10.1002/JLB.3A0120-061RR. Epub 2020 Mar 3. PMID: 32125014.
1: Jakhan J, Kojom Foko LP, Narang G, Singh V. Glucose-6-phosphate Dehydrogenase Variants: Analysing in Indian Plasmodium vivax Patients. Acta Parasitol. 2024 Aug 20. doi: 10.1007/s11686-024-00883-2. Epub ahead of print. PMID: 39164542. 2: Silva AT, Oliveira I, Duarte D, Moita D, Prudêncio M, Nogueira F, Ferraz R, Marques EF, Gomes P. "Seasoning" antimalarial drugs' action: chloroquine bile salts as novel triple-stage antiplasmodial hits. RSC Med Chem. 2024 May 10;15(8):2657-2662. doi: 10.1039/d4md00007b. PMID: 39149112; PMCID: PMC11324038. 3: Bi B, Wu L, Liu Y, Zhou XN, Shen T, Cao L, White M, Yang GJ. Intervention portfolios analysis of Plasmodium vivax control in central China. Malar J. 2024 Aug 13;23(1):242. doi: 10.1186/s12936-024-05063-1. PMID: 39138510; PMCID: PMC11321059. 4: Ma D, Sekiguchi K, Galon EM, Liu M, Ji S, Xuan X. Evaluation of the inhibitory effects of sitamaquine on Babesia infections. Parasitol Int. 2024 Aug 3;103:102941. doi: 10.1016/j.parint.2024.102941. Epub ahead of print. PMID: 39098655. 5: Dziewulska-Cronk KH, Reisz JA, Hay AM, Nemkov T, Cendali FI, Issaian A, Lamb DR, Palha MS, Legenzov EA, Kao JPY, Walker LA, Tekwani BL, Buehler PW, D'Alessandro A, Zimring JC. Primaquine-5,6-orthoquinone is directly hemolytic to older G6PD deficient RBCs in a humanized mouse model. J Pharmacol Exp Ther. 2024 Aug 2:JPET-AR-2024-002218. doi: 10.1124/jpet.124.002218. Epub ahead of print. PMID: 39095205. 6: Celis-Giraldo D, Fajardo MA, Romo Arteaga DC, Faccini-Martínez ÁA. Primaquine-induced hemolysis in a Colombian patient with glucose-6-phosphate dehydrogenase deficiency. Travel Med Infect Dis. 2024 Jul 30;61:102748. doi: 10.1016/j.tmaid.2024.102748. Epub ahead of print. PMID: 39084311. 7: Ba Konko Ciré EH, Roh ME, Diallo A, Gadiaga T, Seck A, Thiam S, Gaye S, Diallo I, Lo AC, Diouf E, Ba OG, Gueye AB, Fogelson A, Wu X, Milligan P, Kibuka T, Hama M, Eckert E, Thwing J, Bennett A, Gosling R, Hwang J, Sene D, Ba F, Cissé B, Sturm-Ramirez K, Hsiang MS, Ndiaye JL. Mass drug administration to reduce malaria incidence in a low-to-moderate endemic setting: short-term impact results from a cluster randomised controlled trial in Senegal. medRxiv [Preprint]. 2024 Jul 18:2024.07.17.24310593. doi: 10.1101/2024.07.17.24310593. PMID: 39072042; PMCID: PMC11275686. 8: Sharma G, Sharma CS. Tetrahydropyridine appended 8-aminoquinoline derivatives: Design, synthesis, in silico, and in vitro antimalarial studies. Bioorg Chem. 2024 Jul 24;151:107674. doi: 10.1016/j.bioorg.2024.107674. Epub ahead of print. PMID: 39059071. 9: Chaumeau V, Wasisakun P, Watson JA, Oo T, Aryalamloed S, Sue MP, Htoo GN, Tha NM, Archusuksan L, Sawasdichai S, Gornsawun G, Mehra S, White NJ, Nosten FH. Transmission-blocking activities of artesunate, chloroquine, and methylene blue on Plasmodium vivax gametocytes. Antimicrob Agents Chemother. 2024 Jul 26:e0085324. doi: 10.1128/aac.00853-24. Epub ahead of print. PMID: 39058023. 10: Manh ND, Thanh NV, Quang HH, Van NTT, San NN, Phong NC, Birrell GW, Edgel KA, Martin NJ, Edstein MD, Chavchich M. Therapeutic efficacy of pyronaridine- artesunate (Pyramax) in treating Plasmodium vivax malaria in the central highlands of Vietnam. Antimicrob Agents Chemother. 2024 Jul 24:e0004424. doi: 10.1128/aac.00044-24. Epub ahead of print. PMID: 39046237. 11: Valadbeigi Y, Causon T. Computational and Experimental IM-MS Determination of the Protonated Structures of Antimalarial Drugs. J Am Soc Mass Spectrom. 2024 Aug 7;35(8):1930-1939. doi: 10.1021/jasms.4c00207. Epub 2024 Jul 23. PMID: 39041666; PMCID: PMC11311536. 12: Cassidy-Seyoum SA, Chheng K, Chanpheakdey P, Meershoek A, Hsiang MS, von Seidlein L, Tripura R, Adhikari B, Ley B, Price RN, Lek D, Engel N, Thriemer K. Implementation of Glucose-6-Phosphate Dehydrogenase (G6PD) testing for Plasmodium vivax case management, a mixed method study from Cambodia. PLOS Glob Public Health. 2024 Jul 19;4(7):e0003476. doi: 10.1371/journal.pgph.0003476. PMID: 39028699; PMCID: PMC11259306. 13: Drugs and Lactation Database (LactMed®) [Internet]. Bethesda (MD): National Institute of Child Health and Human Development; 2006–. Primaquine. 2024 Jul 15. PMID: 30000766. 14: Drugs and Lactation Database (LactMed®) [Internet]. Bethesda (MD): National Institute of Child Health and Human Development; 2006–. Chloroquine. 2024 Jul 15. PMID: 30000205. 15: Habtamu K, Getachew H, Abossie A, Demissew A, Tsegaye A, Degefa T, Wang X, Lee MC, Zhou G, Kibret S, King CL, Kazura JW, Petros B, Yewhalaw D, Yan G. The effect of single low-dose primaquine treatment for uncomplicated Plasmodium falciparum malaria on haemoglobin levels in Ethiopia: a longitudinal cohort study. Malar J. 2024 Jul 12;23(1):208. doi: 10.1186/s12936-024-05021-x. PMID: 38997771; PMCID: PMC11245871. 16: Hanboonkunupakarn B, Mukaka M, Jittamala P, Poovorawan K, Pongsuwan P, Stockdale L, Provstgaard-Morys S, Chotivanich K, Tarning J, Hoglund RM, Chimjinda N, Ewer K, Ramos-Lopez F, Day NPJ, Dondorp AM, Hill AV, White NJ, von Seidlein L, Pukrittayakamee S. A randomised trial of malaria vaccine R21/Matrix-M™ with and without antimalarial drugs in Thai adults. NPJ Vaccines. 2024 Jul 6;9(1):124. doi: 10.1038/s41541-024-00920-1. PMID: 38971837; PMCID: PMC11227592. 17: Gebrie H, Yimer M, Ayehu A, Mohammed H, Hailgiorgis H, Wuletaw Y, Hailu M, Tolera G, Tasew G, Kassa M, Gidey B. Efficacy and safety of chloroquine plus primaquine for the treatment of Plasmodium vivax malaria in Hamusit site, Northwestern Ethiopia. Malar J. 2024 Jul 6;23(1):202. doi: 10.1186/s12936-024-05031-9. PMID: 38971786; PMCID: PMC11227712. 18: Kaewkungwal J, Roobsoong W, Lawpoolsri S, Nguitragool W, Thammapalo S, Prikchoo P, Khamsiriwatchara A, Pawarana R, Jarujareet P, Parker DM, Sripoorote P, Kengganpanich M, Ngamjarus C, Sattabongkot J, Cui L. Effectiveness, Safety, and Acceptability of Primaquine Mass Drug Administration in Low-Endemicity Areas in Southern Thailand: Proof-of-Concept Study. JMIR Public Health Surveill. 2024 Jun 26;10:e51993. doi: 10.2196/51993. PMID: 38922648; PMCID: PMC11237773. 19: Wu Y, Liu X, Yao C, Chen J, Wu X, Zhu M. Fluorescent hyaluronic acid nanoprodrug: A tumor-activated autophagy inhibitor for synergistic cancer therapy. Int J Biol Macromol. 2024 Aug;274(Pt 1):133360. doi: 10.1016/j.ijbiomac.2024.133360. Epub 2024 Jun 21. PMID: 38909736. 20: Puça MCSB, Rodrigues DF, Salazar YEAR, Louzada J, Fontes CJF, Daher A, Pereira DB, Fernandes Vieira JL, Carvalho LH, Alves de Brito CF, Gil JP, Nobrega de Sousa T. Monoamine oxidase-A (MAO-A) low-expression variants and increased risk of Plasmodium vivax malaria relapses. J Antimicrob Chemother. 2024 Aug 1;79(8):1985-1989. doi: 10.1093/jac/dkae196. PMID: 38870082; PMCID: PMC11290872.