Pyronaridine

Pyronaridine
Clinical data
Other names	Pyronaridine tetraphosphate
Routes of; administration	Oral, intramuscular injection, intravenous therapy
ATC code	none;
Legal status
Legal status	CLP (EU): Acute Tox. 3(H301), Eye Dam. 1 (H318), Repr. 2 (H361), Aquatic Chronic 4 (H413)[clarification needed];
Identifiers
	IUPAC name 4-[(7-Chloro-2-methoxy-pyrido[3,2-b]quinolin-10-yl)amino]-2,6-bis(pyrrolidin-1-ylmethyl)phenol;
CAS Number	74847-35-1 N;
PubChem CID	5485198;
ChemSpider	10647812 Y;
UNII	TD3P7Q3SG6;
ChEMBL	ChEMBL35228 Y;
CompTox Dashboard (EPA)	DTXSID60996354 ;
Chemical and physical data
Formula	C29H32ClN5O2
Molar mass	518.06 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES Clc1ccc6c(c1)nc2ccc(OC)nc2c6Nc5cc(CN3CCCC3)c(O)c(CN4CCCC4)c5;
	InChI 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) Y; Key:DJUFPMUQJKWIJB-UHFFFAOYSA-N Y;
	NY (what is this?) (verify)

Chemical compound

Pyronaridine is an antimalarial drug.^[1] It was first made in 1970 and has been in clinical use in China since the 1980s.^[2]

In a small (n=88) malaria study in Camaroon, pyronaridine had a 100% cure rate, compared with 60% for chloroquine.^[3]

It is one of the components of the artemisinin combination therapy pyronaridine/artesunate (Pyramax).^[4]

It has also been studied as a potential anticancer drug,^[5] 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.^[6] The combination of pyronaridine and artesunate is being studied as a possible treatment for moderate to severe SARS-COV-2.^[7]

References

^ Croft SL, Duparc S, Arbe-Barnes SJ, Craft JC, Shin CS, Fleckenstein L, et al. (August 2012). "Review of pyronaridine anti-malarial properties and product characteristics". Malaria Journal. 11: 270. doi:10.1186/1475-2875-11-270. PMC 3483207. PMID 22877082.
^ Chang C, Lin-Hua T, Jantanavivat C (1992). "Studies on a new antimalarial compound: pyronaridine". Transactions of the Royal Society of Tropical Medicine and Hygiene. 86 (1): 7–10. doi:10.1016/0035-9203(92)90414-8. PMID 1566313.
^ Ringwald P, Bickii J, Basco LK (April 1998). "Efficacy of oral pyronaridine for the treatment of acute uncomplicated falciparum malaria in African children". Clinical Infectious Diseases. 26 (4): 946–953. doi:10.1086/513942. PMID 9564481.
^ "Pyramax" (PDF). European Medicines Agency. 2016.
^ Villanueva PJ, Martinez A, Baca ST, DeJesus RE, Larragoity M, Contreras L, et al. (2018). "Pyronaridine exerts potent cytotoxicity on human breast and hematological cancer cells through induction of apoptosis". PLOS ONE. 13 (11): e0206467. Bibcode:2018PLoSO..1306467V. doi:10.1371/journal.pone.0206467. PMC 6218039. PMID 30395606.
^ Lane TR, Massey C, Comer JE, Anantpadma M, Freundlich JS, Davey RA, et al. (November 2019). "Repurposing the antimalarial pyronaridine tetraphosphate to protect against Ebola virus infection". PLOS Neglected Tropical Diseases. 13 (11): e0007890. doi:10.1371/journal.pntd.0007890. PMC 6894882. PMID 31751347.
^ Krishna S, Augustin Y, Wang J, Xu C, Staines HM, Platteeuw H, et al. (January 2021). "Repurposing Antimalarials to Tackle the COVID-19 Pandemic". Trends in Parasitology. 37 (1): 8–11. doi:10.1016/j.pt.2020.10.003. PMC 7572038. PMID 33153922.

This antiinfective drug article is a stub. You can help Wikipedia by expanding it.

[1] Croft SL, Duparc S, Arbe-Barnes SJ, Craft JC, Shin CS, Fleckenstein L, et al. (August 2012). "Review of pyronaridine anti-malarial properties and product characteristics". Malaria Journal. 11: 270. doi:10.1186/1475-2875-11-270. PMC 3483207. PMID 22877082.

[2] Chang C, Lin-Hua T, Jantanavivat C (1992). "Studies on a new antimalarial compound: pyronaridine". Transactions of the Royal Society of Tropical Medicine and Hygiene. 86 (1): 7–10. doi:10.1016/0035-9203(92)90414-8. PMID 1566313.

[3] Ringwald P, Bickii J, Basco LK (April 1998). "Efficacy of oral pyronaridine for the treatment of acute uncomplicated falciparum malaria in African children". Clinical Infectious Diseases. 26 (4): 946–953. doi:10.1086/513942. PMID 9564481.

[4] "Pyramax" (PDF). European Medicines Agency. 2016.

[5] Villanueva PJ, Martinez A, Baca ST, DeJesus RE, Larragoity M, Contreras L, et al. (2018). "Pyronaridine exerts potent cytotoxicity on human breast and hematological cancer cells through induction of apoptosis". PLOS ONE. 13 (11): e0206467. Bibcode:2018PLoSO..1306467V. doi:10.1371/journal.pone.0206467. PMC 6218039. PMID 30395606.

[6] Lane TR, Massey C, Comer JE, Anantpadma M, Freundlich JS, Davey RA, et al. (November 2019). "Repurposing the antimalarial pyronaridine tetraphosphate to protect against Ebola virus infection". PLOS Neglected Tropical Diseases. 13 (11): e0007890. doi:10.1371/journal.pntd.0007890. PMC 6894882. PMID 31751347.

[7] Krishna S, Augustin Y, Wang J, Xu C, Staines HM, Platteeuw H, et al. (January 2021). "Repurposing Antimalarials to Tackle the COVID-19 Pandemic". Trends in Parasitology. 37 (1): 8–11. doi:10.1016/j.pt.2020.10.003. PMC 7572038. PMID 33153922.

Clinical data

Other names	Pyronaridine tetraphosphate
Routes of administration	Oral, intramuscular injection, intravenous therapy
ATC code	none
Legal status
Legal status	CLP (EU): Acute Tox. 3(H301), Eye Dam. 1 (H318), Repr. 2 (H361), Aquatic Chronic 4 (H413)^{[clarification needed]}
Identifiers
IUPAC name 4-[(7-Chloro-2-methoxy-pyrido[3,2-b]quinolin-10-yl)amino]-2,6-bis(pyrrolidin-1-ylmethyl)phenol
CAS Number	74847-35-1^N
PubChem CID	5485198
ChemSpider	10647812^Y
UNII	TD3P7Q3SG6
ChEMBL	ChEMBL35228^Y
CompTox Dashboard (EPA)	DTXSID60996354
Chemical and physical data
Formula	C₂₉H₃₂ClN₅O₂
Molar mass	518.06 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES Clc1ccc6c(c1)nc2ccc(OC)nc2c6Nc5cc(CN3CCCC3)c(O)c(CN4CCCC4)c5
InChI 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)^Y Key:DJUFPMUQJKWIJB-UHFFFAOYSA-N^Y
^NY (what is this?) (verify)