Pyronaridine
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MedKoo CAT#: 319915

CAS#: 74847-35-1

Description: Pyronaridine, also known as Malaridine, is an antimalarial drug. It was first synthesized in 1970 and has been in clinical use in China since the 1980s. It is one of the components of the artemisinin combination therapy pyronaridine artesunate (Pyramax). Pyronaridine is a promising agent against erythrocytic stage of malaria parasites. It exhibited low toxicity and had no cross-resistance to chloroquine. Clinical administration in malaria cases showed high efficacy and mild side-effects.

Chemical Structure

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Pyronaridine
CAS# 74847-35-1
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 319915
Name: Pyronaridine
CAS#: 74847-35-1
Chemical Formula: C29H32ClN5O2
Exact Mass: 517.22
Molecular Weight: 518.060
Elemental Analysis: C, 67.24; H, 6.23; Cl, 6.84; N, 13.52; O, 6.18

Price and Availability

Size Price Availability Quantity
5g USD -1
50mg USD 450
100mg USD 650
200mg USD 950
500mg USD 1850
1g USD 2850
2g USD 4150
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Synonym: Pyronaridine; Malaridine; Benzonaphthyridine 7351.

IUPAC/Chemical Name: 2-Methoxy-7-chloro-10-(3',5'-bis(pyrrolin-1-ylmethyl)-4'-hydroxyphenylamino)benzo(b)-1,5-naphthyridine

InChi Key: DJUFPMUQJKWIJB-UHFFFAOYSA-N

InChi Code: InChI=1S/C29H32ClN5O2/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/h6-9,14-16,36H,2-5,10-13,17-18H2,1H3,(H,31,32)

SMILES Code: OC1=C(CN2CCCC2)C=C(NC3=C4N=C(OC)C=CC4=NC5=CC(Cl)=CC=C53)C=C1CN6CCCC6

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

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/

Preparing Stock Solutions

The following data is based on the product molecular weight 518.06 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.

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1: Madamet M, Briolant S, Amalvict R, Benoit N, Bouchiba H, Cren J, Pradines B; French National Centre for Imported Malaria Study Group. The Plasmodium falciparum chloroquine resistance transporter is associated with the ex vivo P. falciparum African parasite response to pyronaridine. Parasit Vectors. 2016 Feb 9;9(1):77. doi: 10.1186/s13071-016-1358-z. PubMed PMID: 26858119; PubMed Central PMCID: PMC4746765.

2: Ayyoub A, Methaneethorn J, Ramharter M, Djimde AA, Tekete M, Duparc S, Borghini-Fuhrer I, Shin JS, Fleckenstein L. Population Pharmacokinetic Parameters of Pyronaridine in Pediatric Malaria Patients. Antimicrob Agents Chemother. 2015 Dec 14. pii: AAC.02004-15. [Epub ahead of print] PubMed PMID: 26666916.

3: Sagara I, Beavogui AH, Zongo I, Soulama I, Borghini-Fuhrer I, Fofana B, Camara D, Somé AF, Coulibaly AS, Traore OB, Dara N, Kabore MJ, Thera I, Compaore YD, Sylla MM, Nikiema F, Diallo MS, Dicko A, Gil JP, Borrmann S, Duparc S, Miller RM, Doumbo OK, Shin J, Bjorkman A, Ouedraogo JB, Sirima SB, Djimdé AA. Safety and efficacy of re-treatments with pyronaridine-artesunate in African patients with malaria: a substudy of the WANECAM randomised trial. Lancet Infect Dis. 2016 Feb;16(2):189-98. doi: 10.1016/S1473-3099(15)00318-7. Epub 2015 Oct 23. PubMed PMID: 26601738; PubMed Central PMCID: PMC4726763.

4: Bélard S, Kurth F. Pyronaridine-artesunate retreatment for malaria. Lancet Infect Dis. 2016 Feb;16(2):136-7. doi: 10.1016/S1473-3099(15)00353-9. Epub 2015 Oct 23. PubMed PMID: 26601737.

5: Pascual A, Madamet M, Briolant S, Gaillard T, Amalvict R, Benoit N, Travers D, Pradines B; French National Reference Centre for Imported Malaria Study Group. Multinormal in vitro distribution of Plasmodium falciparum susceptibility to piperaquine and pyronaridine. Malar J. 2015 Feb 5;14:49. doi: 10.1186/s12936-015-0586-6. PubMed PMID: 25848972; PubMed Central PMCID: PMC4323025.

6: Jittamala P, Pukrittayakamee S, Ashley EA, Nosten F, Hanboonkunupakarn B, Lee SJ, Thana P, Chairat K, Blessborn D, Panapipat S, White NJ, Day NP, Tarning J. Pharmacokinetic interactions between primaquine and pyronaridine-artesunate in healthy adult Thai subjects. Antimicrob Agents Chemother. 2015 Jan;59(1):505-13. doi: 10.1128/AAC.03829-14. Epub 2014 Nov 10. PubMed PMID: 25385096; PubMed Central PMCID: PMC4291381.

7: Sereekhajornjaru N, Somboon C, Rattanajak R, Denny WA, Wilairat P, Auparakkitanon S. Comparison of hematin-targeting properties of pynacrine, an acridine analog of the benzonaphthyridine antimalarial pyronaridine. Acta Trop. 2014 Dec;140:181-3. doi: 10.1016/j.actatropica.2014.09.002. Epub 2014 Sep 16. PubMed PMID: 25220507.

8: Morris CA, Pokorny R, Lopez-Lazaro L, Miller RM, Arbe-Barnes S, Duparc S, Borghini-Fuhrer I, Shin JS, Fleckenstein L. Pharmacokinetic interaction between pyronaridine-artesunate and metoprolol. Antimicrob Agents Chemother. 2014 Oct;58(10):5900-8. doi: 10.1128/AAC.02716-14. Epub 2014 Jul 28. PubMed PMID: 25070091; PubMed Central PMCID: PMC4187956.

9: Bukirwa H, Unnikrishnan B, Kramer CV, Sinclair D, Nair S, Tharyan P. Artesunate plus pyronaridine for treating uncomplicated Plasmodium falciparum malaria. Cochrane Database Syst Rev. 2014 Mar 4;3:CD006404. doi: 10.1002/14651858.CD006404.pub2. Review. PubMed PMID: 24596021; PubMed Central PMCID: PMC4448218.

10: Morris CA, Dueker SR, Lohstroh PN, Wang LQ, Fang XP, Jung D, Lopez-Lazaro L, Baker M, Duparc S, Borghini-Fuhrer I, Pokorny R, Shin JS, Fleckenstein L. Mass balance and metabolism of the antimalarial pyronaridine in healthy volunteers. Eur J Drug Metab Pharmacokinet. 2015 Mar;40(1):75-86. doi: 10.1007/s13318-014-0182-0. Epub 2014 Mar 4. PubMed PMID: 24590312.

11: Henrich PP, O'Brien C, Sáenz FE, Cremers S, Kyle DE, Fidock DA. Evidence for pyronaridine as a highly effective partner drug for treatment of artemisinin-resistant malaria in a rodent model. Antimicrob Agents Chemother. 2014;58(1):183-95. doi: 10.1128/AAC.01466-13. Epub 2013 Oct 21. PubMed PMID: 24145526; PubMed Central PMCID: PMC3910733.

12: Duparc S, Borghini-Fuhrer I, Craft CJ, Arbe-Barnes S, Miller RM, Shin CS, Fleckenstein L. Safety and efficacy of pyronaridine-artesunate in uncomplicated acute malaria: an integrated analysis of individual patient data from six randomized clinical trials. Malar J. 2013 Feb 21;12:70. doi: 10.1186/1475-2875-12-70. PubMed PMID: 23433102; PubMed Central PMCID: PMC3598551.

13: Kayentao K, Doumbo OK, Pénali LK, Offianan AT, Bhatt KM, Kimani J, Tshefu AK, Kokolomami JH, Ramharter M, de Salazar PM, Tiono AB, Ouédraogo A, Bustos MD, Quicho F, Borghini-Fuhrer I, Duparc S, Shin CS, Fleckenstein L. Pyronaridine-artesunate granules versus artemether-lumefantrine crushed tablets in children with Plasmodium falciparum malaria: a randomized controlled trial. Malar J. 2012 Oct 31;11:364. doi: 10.1186/1475-2875-11-364. PubMed PMID: 23113947; PubMed Central PMCID: PMC3566922.

14: Zhang CL, Zhou HN, Wang J, Liu H. [In vitro sensitivity of Plasmodium falciparum isolates from China-Myanmar border region to chloroquine, piperaquine and pyronaridine]. Zhongguo Ji Sheng Chong Xue Yu Ji Sheng Chong Bing Za Zhi. 2012 Feb 29;30(1):41-4. Chinese. PubMed PMID: 22913189.

15: Croft SL, Duparc S, Arbe-Barnes SJ, Craft JC, Shin CS, Fleckenstein L, Borghini-Fuhrer I, Rim HJ. Review of pyronaridine anti-malarial properties and product characteristics. Malar J. 2012 Aug 9;11:270. doi: 10.1186/1475-2875-11-270. PubMed PMID: 22877082; PubMed Central PMCID: PMC3483207.

16: Rueangweerayut R, Phyo AP, Uthaisin C, Poravuth Y, Binh TQ, Tinto H, Pénali LK, Valecha N, Tien NT, Abdulla S, Borghini-Fuhrer I, Duparc S, Shin CS, Fleckenstein L; Pyronaridine–Artesunate Study Team. Pyronaridine-artesunate versus mefloquine plus artesunate for malaria. N Engl J Med. 2012 Apr 5;366(14):1298-309. doi: 10.1056/NEJMoa1007125. PubMed PMID: 22475593.

17: Morris CA, Lopez-Lazaro L, Jung D, Methaneethorn J, Duparc S, Borghini-Fuhrer I, Pokorny R, Shin CS, Fleckenstein L. Drug-drug interaction analysis of pyronaridine/artesunate and ritonavir in healthy volunteers. Am J Trop Med Hyg. 2012 Mar;86(3):489-95. doi: 10.4269/ajtmh.2012.11-0558. PubMed PMID: 22403324; PubMed Central PMCID: PMC3284369.

18: Pascual A, Parola P, Benoit-Vical F, Simon F, Malvy D, Picot S, Delaunay P, Basset D, Maubon D, Faugère B, Ménard G, Bourgeois N, Oeuvray C, Didillon E, Rogier C, Pradines B. Ex vivo activity of the ACT new components pyronaridine and piperaquine in comparison with conventional ACT drugs against isolates of Plasmodium falciparum. Malar J. 2012 Feb 14;11:45. doi: 10.1186/1475-2875-11-45. PubMed PMID: 22333675; PubMed Central PMCID: PMC3305508.

19: Okombo J, Kiara SM, Mwai L, Pole L, Ohuma E, Ochola LI, Nzila A. Baseline in vitro activities of the antimalarials pyronaridine and methylene blue against Plasmodium falciparum isolates from Kenya. Antimicrob Agents Chemother. 2012 Feb;56(2):1105-7. doi: 10.1128/AAC.05454-11. Epub 2011 Nov 28. PubMed PMID: 22123687; PubMed Central PMCID: PMC3264213.

20: Kurth F, Bélard S, Basra A, Ramharter M. Pyronaridine-artesunate combination therapy for the treatment of malaria. Curr Opin Infect Dis. 2011 Dec;24(6):564-9. doi: 10.1097/QCO.0b013e32834cabdb. Review. PubMed PMID: 21986615.