Pyronaridine: Difference between revisions - Wikipedia
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Line 1: {{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 <!--Clinical data-->| alt = A chemical diagram of a Pyronaridine molecule | synonyms = Pyronaridine tetraphosphate | tradename | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | pregnancy_US = <!-- A / B / C / D / X --> | pregnancy_category = | legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled--> | legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII --> | legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C --> | legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> | legal_status | routes_of_administration = Oral, [[intramuscular injection]], [[intravenous therapy]] <!--Pharmacokinetic data-->| bioavailability = | protein_bound
| metabolism ▲| protein_bound = | elimination_half-life = ▲| metabolism = | excretion = <!--Identifiers-->▼ ▲| elimination_half-life = | CAS_number_Ref = {{cascite|changed|??}}▼
| CAS_number = 74847-35-1▼ | ATC_prefix = none▼ | ATC_suffix | PubChem = 5485198▼ | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank | | ChemSpiderID = 10647812▼ | UNII_Ref = {{fdacite|correct|FDA}}▼ | UNII = TD3P7Q3SG6▼ | ChEMBL_Ref = {{ebicite|correct|EBI}}▼ | ChEMBL = 35228▼ <!--Chemical data-->| C = 29▼ ▲<!--Identifiers--> | H = 32 ▲| CAS_number_Ref = {{cascite|changed|??}} | Cl = 1 ▲| CAS_number = 74847-35-1 | N = 5 ▲| ATC_prefix = none | O = 2 ▲| ATC_suffix = | smiles = Clc1ccc6c(c1)nc2ccc(OC)nc2c6Nc5cc(CN3CCCC3)c(O)c(CN4CCCC4)c5▼ ▲| PubChem = 5485198 | | 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)▼ ▲| DrugBank = | | StdInChIKey = DJUFPMUQJKWIJB-UHFFFAOYSA-N▼ ▲| ChemSpiderID = 10647812 ▲| UNII_Ref = {{fdacite|correct|FDA}} ▲| UNII = TD3P7Q3SG6 ▲| ChEMBL_Ref = {{ebicite|correct|EBI}} ▲| ChEMBL = 35228 ▲<!--Chemical data-->
▲| 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 = DJUFPMUQJKWIJB-UHFFFAOYSA-N }} '''Pyronaridine''' is an [[antimalarial drug]].<ref>{{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 }}</ref> It was first made in 1970 and has been in clinical use in China since the 1980s.<ref>{{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 }}</ref> In a small (n=88) malaria study in Camaroon, pyronaridine had a 100% cure rate, compared with 60% for [[chloroquine]].<ref>{{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 }}</ref> It is one of the components of the [[artemisinin combination therapy]] [[pyronaridine/artesunate]] (Pyramax).<ref>{{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}}</ref> It has also been studied as a potential anticancer drug,<ref>{{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 }}</ref> 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.<ref>{{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 }}</ref> The combination of pyronaridine and artesunate is being studied as a possible treatment for moderate to severe SARS-COV-2.<ref>{{ == References == Line 63 ⟶ 66: [[Category:Antimalarial agents]] [[Category:Chinese discoveries]] {{antiinfective-drug-stub}} | |||