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MedKoo Cat#: 527036 | Name: Pyronaridine Tetraphosphate
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Description:

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

Pyronaridine is a Mannich base antimalarial drug that exhibits potent activity against Plasmodium species, including chloroquine-resistant strains. It functions by inhibiting hemozoin formation, disrupting hemoglobin digestion in the parasite, and inducing oxidative stress. Pyronaridine shows IC₅₀ values in the low nanomolar range (typically 1–10 nM) against P. falciparum in vitro and demonstrates strong in vivo efficacy in murine malaria models. When combined with artesunate (Pyramax®), it exhibits synergistic effects, enhancing parasite clearance and reducing resistance development. The combination has an estimated cure rate of over 95% in clinical trials, making it an effective treatment for uncomplicated P. falciparum and P. vivax malaria. Additionally, pyronaridine has been investigated for potential antiviral and anticancer activities due to its ability to interfere with nucleic acid metabolism and protein synthesis pathways.

Chemical Structure

Pyronaridine Tetraphosphate
Pyronaridine Tetraphosphate
CAS#76748-86-2 (phosphate)

Theoretical Analysis

MedKoo Cat#: 527036

Name: Pyronaridine Tetraphosphate

CAS#: 76748-86-2 (phosphate)

Chemical Formula: C29H44ClN5O18P4

Exact Mass: 0.0000

Molecular Weight: 910.03

Elemental Analysis: C, 38.28; H, 4.87; Cl, 3.90; N, 7.70; O, 31.65; P, 13.61

Price and Availability

Size Price Availability Quantity
100mg USD 90.00 Ready to ship
200mg USD 150.00 Ready to ship
500mg USD 250.00 Ready to ship
1g USD 450.00 Ready to ship
2g USD 750.00 Ready to ship
10g USD 3,850.00 2 Weeks
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Related CAS #
76748-86-2 (phosphate) 74847-35-1 (free base)
Synonym
Pyronaridine Tetraphosphate
IUPAC/Chemical Name
Phenol, 4-[(7-chloro-2-methoxybenzo[b]-1,5-naphthyridin-10-yl)amino]-2,6-bis(1-pyrrolidinylmethyl)-, phosphate (1:4)
InChi Key
YKUQEKXHQFYULM-UHFFFAOYSA-N
InChi Code
InChI=1S/C29H32ClN5O2.4H3O4P/c1-37-26-9-8-24-28(33-26)27(23-7-6-21(30)16-25(23)32-24)31-22-14-19(17-34-10-2-3-11-34)29(36)20(15-22)18-35-12-4-5-13-35;4*1-5(2,3)4/h6-9,14-16,36H,2-5,10-13,17-18H2,1H3,(H,31,32);4*(H3,1,2,3,4)
SMILES Code
OC1=C(CN2CCCC2)C=C(NC3=C4N=C(OC)C=CC4=NC5=CC(Cl)=CC=C53)C=C1CN6CCCC6.O=P(O)(O)O.O=P(O)(O)O.O=P(O)(O)O.O=P(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 and 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
Biological target:
Pyronaridine is active against P. falciparum and Echinococcus granulosus infection. At equivalent molar concentrations, both the salt and free forms of a compound exhibit comparable biological activity.
In vitro activity:
This study established pyronaridine's pharmacokinetic profile and tissue distribution in the context of repurposing it for COVID-19 treatment. The researchers assessed the concentration levels of pyronaridine in various tissues, including the lung and trachea. Pyronaridine was distributed to the lung and trachea with the lung-to-blood and trachea-to-blood concentration ratios of 25.83 and 12.41 at the steady state, respectively. Reference: Pharmaceutics. 2023 Mar 3;15(3):838. https://pubmed.ncbi.nlm.nih.gov/36986698/
In vivo activity:
Pyronaridine is a potential therapeutic candidate for COVID-19. In a K18-hACE transgenic mouse model of COVID-19, pyronaridine treatment demonstrated a statistically significant reduction of viral load in the lungs of SARS-CoV-2-infected mice, reducing lung pathology, which was also associated with significant reduction in the levels of pro-inflammatory cytokines/chemokine and cell infiltration. Reference: ACS Infect Dis. 2022 Jun 10;8(6):1147-1160. https://pubmed.ncbi.nlm.nih.gov/35609344/
Solvent mg/mL mM
Solubility
DMSO 12.5 13.74
Water 25.0 27.47
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 910.03 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. Kang DW, Kim KM, Kim JH, Cho HY. Application of Minimal Physiologically-Based Pharmacokinetic Model to Simulate Lung and Trachea Exposure of Pyronaridine and Artesunate in Hamsters. Pharmaceutics. 2023 Mar 3;15(3):838. doi: 10.3390/pharmaceutics15030838. PMID: 36986698; PMCID: PMC10058671. 2. Puhl AC, Fritch EJ, Lane TR, Tse LV, Yount BL, Sacramento CQ, Fintelman-Rodrigues N, Tavella TA, Maranhão Costa FT, Weston S, Logue J, Frieman M, Premkumar L, Pearce KH, Hurst BL, Andrade CH, Levi JA, Johnson NJ, Kisthardt SC, Scholle F, Souza TML, Moorman NJ, Baric RS, Madrid PB, Ekins S. Repurposing the Ebola and Marburg Virus Inhibitors Tilorone, Quinacrine, and Pyronaridine: In Vitro Activity against SARS-CoV-2 and Potential Mechanisms. ACS Omega. 2021 Mar 10;6(11):7454-7468. doi: 10.1021/acsomega.0c05996. PMID: 33778258; PMCID: PMC7992063. 3. Puhl AC, Gomes GF, Damasceno S, Godoy AS, Noske GD, Nakamura AM, Gawriljuk VO, Fernandes RS, Monakhova N, Riabova O, Lane TR, Makarov V, Veras FP, Batah SS, Fabro AT, Oliva G, Cunha FQ, Alves-Filho JC, Cunha TM, Ekins S. Pyronaridine Protects against SARS-CoV-2 Infection in Mouse. ACS Infect Dis. 2022 Jun 10;8(6):1147-1160. doi: 10.1021/acsinfecdis.2c00091. Epub 2022 May 24. PMID: 35609344. 4. Lane TR, Massey C, Comer JE, Freiberg AN, Zhou H, Dyall J, Holbrook MR, Anantpadma M, Davey RA, Madrid PB, Ekins S. Pyronaridine tetraphosphate efficacy against Ebola virus infection in guinea pig. Antiviral Res. 2020 Sep;181:104863. doi: 10.1016/j.antiviral.2020.104863. Epub 2020 Jul 16. PMID: 32682926; PMCID: PMC8194506.
In vitro protocol:
1. Kang DW, Kim KM, Kim JH, Cho HY. Application of Minimal Physiologically-Based Pharmacokinetic Model to Simulate Lung and Trachea Exposure of Pyronaridine and Artesunate in Hamsters. Pharmaceutics. 2023 Mar 3;15(3):838. doi: 10.3390/pharmaceutics15030838. PMID: 36986698; PMCID: PMC10058671. 2. Puhl AC, Fritch EJ, Lane TR, Tse LV, Yount BL, Sacramento CQ, Fintelman-Rodrigues N, Tavella TA, Maranhão Costa FT, Weston S, Logue J, Frieman M, Premkumar L, Pearce KH, Hurst BL, Andrade CH, Levi JA, Johnson NJ, Kisthardt SC, Scholle F, Souza TML, Moorman NJ, Baric RS, Madrid PB, Ekins S. Repurposing the Ebola and Marburg Virus Inhibitors Tilorone, Quinacrine, and Pyronaridine: In Vitro Activity against SARS-CoV-2 and Potential Mechanisms. ACS Omega. 2021 Mar 10;6(11):7454-7468. doi: 10.1021/acsomega.0c05996. PMID: 33778258; PMCID: PMC7992063.
In vivo protocol:
1. Puhl AC, Gomes GF, Damasceno S, Godoy AS, Noske GD, Nakamura AM, Gawriljuk VO, Fernandes RS, Monakhova N, Riabova O, Lane TR, Makarov V, Veras FP, Batah SS, Fabro AT, Oliva G, Cunha FQ, Alves-Filho JC, Cunha TM, Ekins S. Pyronaridine Protects against SARS-CoV-2 Infection in Mouse. ACS Infect Dis. 2022 Jun 10;8(6):1147-1160. doi: 10.1021/acsinfecdis.2c00091. Epub 2022 May 24. PMID: 35609344. 2. Lane TR, Massey C, Comer JE, Freiberg AN, Zhou H, Dyall J, Holbrook MR, Anantpadma M, Davey RA, Madrid PB, Ekins S. Pyronaridine tetraphosphate efficacy against Ebola virus infection in guinea pig. Antiviral Res. 2020 Sep;181:104863. doi: 10.1016/j.antiviral.2020.104863. Epub 2020 Jul 16. PMID: 32682926; PMCID: PMC8194506.
1: Siqueira-Neto JL, Lane TR, Bernatchez JA, Calvet Alvarez CM, Barbosa da Silva E, Giardini MA, Ekins S. Oral Pyronaridine Tetraphosphate Reduces Tissue Presence of Parasites in a Mouse Model of Chagas Disease. ACS Omega. 2024 Aug 20;9(35):37288-37298. doi: 10.1021/acsomega.4c05060. PMID: 39246496; PMCID: PMC11375811. 2: Ramharter M, Djimde AA, Borghini-Fuhrer I, Miller R, Shin J, Aspinall A, Richardson N, Wibberg M, Fleckenstein L, Arbe-Barnes S, Duparc S. Safety and efficacy of pyronaridine-artesunate paediatric granules in the treatment of uncomplicated malaria in children: insights from randomized clinical trials and a real-world study. Malar J. 2024 Feb 28;23(1):61. doi: 10.1186/s12936-024-04885-3. PMID: 38418982; PMCID: PMC10902982. 3: Djimde M, Tshiongo JK, Muhindo HM, Tinto H, Sevene E, Traore M, Vala A, Macuacua S, Kabore B, Dabira ED, Erhart A, Diakite H, Keita M, Piqueras M, González R, Menendez C, Dorlo TP, Sagara I, Mens P, Schallig H, D'Alessandro U, Kayentao K. Efficacy and safety of pyronaridine-artesunate (PYRAMAX) for the treatment of P. falciparum uncomplicated malaria in African pregnant women (PYRAPREG): study protocol for a phase 3, non-inferiority, randomised open-label clinical trial. BMJ Open. 2023 Oct 9;13(10):e065295. doi: 10.1136/bmjopen-2022-065295. PMID: 37813539; PMCID: PMC10565244. 4: Ardanuy J, Johnson R, Dillen C, Taylor L, Hammond H, Weston S, Frieman M. Pyronaridine tetraphosphate is an efficacious antiviral and anti-inflammatory active against multiple highly pathogenic coronaviruses. mBio. 2023 Oct 31;14(5):e0158723. doi: 10.1128/mbio.01587-23. Epub 2023 Aug 15. PMID: 37581442; PMCID: PMC10653794. 5: Puhl AC, Lane TR, Ekins S. Learning from COVID-19: How drug hunters can prepare for the next pandemic. Drug Discov Today. 2023 Oct;28(10):103723. doi: 10.1016/j.drudis.2023.103723. Epub 2023 Jul 22. PMID: 37482237; PMCID: PMC10994687. 6: Alebachew M, Gelaye W, Abate MA, Sime H, Hailgiorgis H, Gidey B, Haile M, Assefa G, Bekele W, Belay H, Parr JB, Tasew G, Mohammed H, Assefa A. Therapeutic efficacy of pyronaridine-artesunate (Pyramax®) against uncomplicated Plasmodium falciparum infection at Hamusit Health Centre, Northwest Ethiopia. Malar J. 2023 Jun 17;22(1):186. doi: 10.1186/s12936-023-04618-y. PMID: 37330475; PMCID: PMC10276904. 7: Falade CO, Orimadegun AE, Olusola FI, Michael OS, Anjorin OE, Funwei RI, Adedapo AD, Olusanya AL, Orimadegun BE, Mokuolu OA. Efficacy and safety of pyronaridine-artesunate versus artemether-lumefantrine in the treatment of acute uncomplicated malaria in children in South-West Nigeria: an open-labelled randomized controlled trial. Malar J. 2023 May 13;22(1):154. doi: 10.1186/s12936-023-04574-7. PMID: 37179349; PMCID: PMC10182553. 8: Rizk MA, El-Sayed SAE, Igarashi I. Diminazene aceturate and imidocarb dipropionate-based combination therapy for babesiosis - A new paradigm. Ticks Tick Borne Dis. 2023 Jul;14(4):102145. doi: 10.1016/j.ttbdis.2023.102145. Epub 2023 Apr 1. PMID: 37011497. 9: Rizk MA, El-Sayed SAE, Igarashi I. Diminazene aceturate and imidocarb dipropionate-based combination therapy for babesiosis - a new paradigm. Ticks Tick Borne Dis. 2023 Feb 20;14(1F1):102141. doi: 10.1016/j.ttbdis.2023.102141. Epub ahead of print. PMID: 36812788. 10: Mohammed H, Sime H, Hailgiorgis H, Chernet M, Alebachew M, Solomon H, Assefa G, Haile M, Girma S, Bekele W, Tasew G, Gidey B, Commons RJ, Assefa A. Efficacy and safety of pyronaridine-artesunate (Pyramax®) for the treatment of uncomplicated Plasmodium vivax malaria in Northwest Ethiopia. Malar J. 2022 Dec 31;21(1):401. doi: 10.1186/s12936-022-04422-0. PMID: 36587210; PMCID: PMC9805271. 11: Rizk MA, El-Sayed SAE, Igarashi I. In Vitro Inhibitory Effects and Bioinformatic Analysis of Norfloxacin and Ofloxacin on Piroplasm. Acta Parasitol. 2023 Mar;68(1):213-222. doi: 10.1007/s11686-022-00648-9. Epub 2022 Dec 21. PMID: 36539677. 12: Funwei RI, Uyaiabasi GN, Hammed WA, Ojurongbe O, Walker O, Falade CO. High prevalence of persistent residual parasitemia on days 3 and 14 after artemether- lumefantrine or pyronaridine-artesunate treatment of uncomplicated Plasmodium falciparum malaria in Nigeria. Parasitol Res. 2023 Feb;122(2):519-526. doi: 10.1007/s00436-022-07753-8. Epub 2022 Dec 13. PMID: 36510009. 13: Maketa V, Kabalu J, Kabena M, Luzolo F, Muhindo-Mavoko H, Schallig HDFH, Kayentao K, Mens PF, Lutumba P, Tinto H. Comparison of intermittent screening (using ultra-sensitive malaria rapid diagnostic test) and treatment (using a newly registered antimalarial pyronaridine-artesunate-PYRAMAX®) to standard intermittent preventive treatment with sulfadoxine-pyrimethamine for the prevention of malaria in pregnant women living in endemic areas: ULTRAPYRAPREG. Trials. 2022 Nov 28;23(1):963. doi: 10.1186/s13063-022-06884-8. PMID: 36443882; PMCID: PMC9706843. 14: Rouamba T, Sondo P, Yerbanga IW, Compaore A, Traore-Coulibaly M, Hien FS, Diande NA, Valea I, Tahita MC, Baiden R, Binka F, Tinto H. Prospective observational study to evaluate the clinical and biological safety profile of pyronaridine-artesunate in a rural health district in Burkina Faso. Pharmacol Res Perspect. 2022 Aug;10(4):e00987. doi: 10.1002/prp2.987. PMID: 35855566; PMCID: PMC9297024. 15: Hien D, Kaboré JMT, Siribié M, Soulama I, Barry N, Baguiya A, Tiono AB, Tchouatieu AM, Sirima SB. Stakeholder perceptions on the deployment of multiple first-line therapies for uncomplicated malaria: a qualitative study in the health district of Kaya, Burkina Faso. Malar J. 2022 Jun 27;21(1):202. doi: 10.1186/s12936-022-04225-3. PMID: 35761273; PMCID: PMC9235275. 16: Pryce J, Taylor M, Fox T, Hine P. Pyronaridine-artesunate for treating uncomplicated Plasmodium falciparum malaria. Cochrane Database Syst Rev. 2022 Jun 21;6(6):CD006404. doi: 10.1002/14651858.CD006404.pub4. PMID: 35726133; PMCID: PMC9209011. 17: Groger M, Tona Lutete G, Mombo-Ngoma G, Ntamabyaliro NY, Kahunu Mesia G, Muena Mujobu TB, Dimessa Mbadinga LB, Zoleko Manego R, Egger-Adam D, Borghini- Fuhrer I, Shin J, Miller R, Arbe-Barnes S, Duparc S, Ramharter M. Effectiveness of pyronaridine-artesunate against Plasmodium malariae, Plasmodium ovale spp, and mixed-Plasmodium infections: a post-hoc analysis of the CANTAM-Pyramax trial. Lancet Microbe. 2022 Aug;3(8):e598-e605. doi: 10.1016/S2666-5247(22)00092-1. Epub 2022 May 30. PMID: 35654079; PMCID: PMC9329129. 18: Stone W, Mahamar A, Sanogo K, Sinaba Y, Niambele SM, Sacko A, Keita S, Youssouf A, Diallo M, Soumare HM, Kaur H, Lanke K, Ter Heine R, Bradley J, Issiaka D, Diawara H, Traore SF, Bousema T, Drakeley C, Dicko A. Pyronaridine- artesunate or dihydroartemisinin-piperaquine combined with single low-dose primaquine to prevent Plasmodium falciparum malaria transmission in Ouélessébougou, Mali: a four-arm, single-blind, phase 2/3, randomised trial. Lancet Microbe. 2022 Jan;3(1):e41-e51. doi: 10.1016/S2666-5247(21)00192-0. PMID: 35028628; PMCID: PMC8721154. 19: Manh ND, Thanh NV, Quang HH, Van NTT, San NN, Phong NC, Birrell GW, Edstein MD, Edgel KA, Martin NJ, Chavchich M. Pyronaridine-Artesunate (Pyramax) for Treatment of Artemisinin- and Piperaquine-Resistant Plasmodium falciparum in the Central Highlands of Vietnam. Antimicrob Agents Chemother. 2021 Nov 17;65(12):e0027621. doi: 10.1128/AAC.00276-21. Epub 2021 Sep 27. PMID: 34570647; PMCID: PMC8597783. 20: Tona Lutete G, Mombo-Ngoma G, Assi SB, Bigoga JD, Koukouikila-Koussounda F, Ntamabyaliro NY, Ntoumi F, Agnandji ST, Groger M, Shin J, Borghini-Fuhrer I, Arbe-Barnes S, Allen SJ, Kremsner PG, Miller R, Duparc S, Ramharter M; CANTAM study group. Pyronaridine-artesunate real-world safety, tolerability, and effectiveness in malaria patients in 5 African countries: A single-arm, open- label, cohort event monitoring study. PLoS Med. 2021 Jun 15;18(6):e1003669. doi: 10.1371/journal.pmed.1003669. PMID: 34129601; PMCID: PMC8205155.

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