Pyronaridine

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 464377675

| IUPAC_name = 4-[(7-Chloro-2-methoxy-pyrido[3,2-b]quinolin-10-yl)amino]-2,6-bis(pyrrolidin-1-ylmethyl)phenol

| image = Pyronaridine.svg

| image_class = skin-invert-image

| alt = A chemical diagram of a Pyronaridine molecule

| synonyms = Pyronaridine tetraphosphate

| tradename =

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| legal_status = CLP (EU): Acute Tox. 3(H301), Eye Dam. 1 (H318), Repr. 2 (H361), Aquatic Chronic 4 (H413){{clarify|date=February 2017}}

| routes_of_administration = Oral, intramuscular injection, intravenous therapy

| bioavailability =

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| CAS_number_Ref = {{cascite|changed|??}}

| CAS_number = 74847-35-1

| ATC_prefix = none

| ATC_suffix =

| PubChem = 5485198

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank =

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 10647812

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = TD3P7Q3SG6

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 35228

| C = 29

| H = 32

| Cl = 1

| N = 5

| O = 2

| smiles = Clc1ccc6c(c1)nc2ccc(OC)nc2c6Nc5cc(CN3CCCC3)c(O)c(CN4CCCC4)c5

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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)

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = DJUFPMUQJKWIJB-UHFFFAOYSA-N

}}

Pyronaridine is an antimalarial drug.{{cite journal | vauthors = Croft SL, Duparc S, Arbe-Barnes SJ, Craft JC, Shin CS, Fleckenstein L, Borghini-Fuhrer I, Rim HJ | display-authors = 6 | title = Review of pyronaridine anti-malarial properties and product characteristics | journal = Malaria Journal | volume = 11 | pages = 270 | date = August 2012 | pmid = 22877082 | pmc = 3483207 | doi = 10.1186/1475-2875-11-270 | doi-access = free }} It was first made in 1970 and has been in clinical use in China since the 1980s.{{cite journal | vauthors = Chang C, Lin-Hua T, Jantanavivat C | title = Studies on a new antimalarial compound: pyronaridine | journal = Transactions of the Royal Society of Tropical Medicine and Hygiene | volume = 86 | issue = 1 | pages = 7–10 | year = 1992 | pmid = 1566313 | doi = 10.1016/0035-9203(92)90414-8 }}

In a small (n=88) malaria study in Camaroon, pyronaridine had a 100% cure rate, compared with 60% for chloroquine.{{cite journal | vauthors = Ringwald P, Bickii J, Basco LK | title = Efficacy of oral pyronaridine for the treatment of acute uncomplicated falciparum malaria in African children | journal = Clinical Infectious Diseases | volume = 26 | issue = 4 | pages = 946–953 | date = April 1998 | pmid = 9564481 | doi = 10.1086/513942 | doi-access = free }}

It is one of the components of the artemisinin combination therapy pyronaridine/artesunate (Pyramax).{{Cite web | url = https://www.ema.europa.eu/documents/medicine-outside-eu/pyramax-summary-public_en.pdf | title = Pyramax | publisher = European Medicines Agency | date = 2016}}

It has also been studied as a potential anticancer drug,{{cite journal | vauthors = Villanueva PJ, Martinez A, Baca ST, DeJesus RE, Larragoity M, Contreras L, Gutierrez DA, Varela-Ramirez A, Aguilera RJ | display-authors = 6 | title = Pyronaridine exerts potent cytotoxicity on human breast and hematological cancer cells through induction of apoptosis | journal = PLOS ONE | volume = 13 | issue = 11 | pages = e0206467 | year = 2018 | pmid = 30395606 | pmc = 6218039 | doi = 10.1371/journal.pone.0206467 | doi-access = free | bibcode = 2018PLoSO..1306467V }} and treatment for Ebola. The combination of pyronaridine and artesunate has been evaluated to have a synergistic effect of stronger antiviral effect and less toxicity.{{cite journal | vauthors = Lane TR, Massey C, Comer JE, Anantpadma M, Freundlich JS, Davey RA, Madrid PB, Ekins S | display-authors = 6 | title = Repurposing the antimalarial pyronaridine tetraphosphate to protect against Ebola virus infection | journal = PLOS Neglected Tropical Diseases | volume = 13 | issue = 11 | pages = e0007890 | date = November 2019 | pmid = 31751347 | pmc = 6894882 | doi = 10.1371/journal.pntd.0007890 | doi-access = free }} The combination of pyronaridine and artesunate is being studied as a possible treatment for moderate to severe SARS-COV-2.{{cite journal | vauthors = Krishna S, Augustin Y, Wang J, Xu C, Staines HM, Platteeuw H, Kamarulzaman A, Sall A, Kremsner P | display-authors = 6 | title = Repurposing Antimalarials to Tackle the COVID-19 Pandemic | journal = Trends in Parasitology | volume = 37 | issue = 1 | pages = 8–11 | date = January 2021 | pmid = 33153922 | pmc = 7572038 | doi = 10.1016/j.pt.2020.10.003 | author-link = Sanjeev Krishna }}