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Revision as of 12:12, 6 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 456808826 of page Pyronaridine for the Chem/Drugbox validation project (updated: 'CAS_number').  Latest revision as of 07:26, 22 October 2023 edit Boghog (talk | contribs)Autopatrolled, Extended confirmed users, IP block exemptions, New page reviewers, Pending changes reviewers, Rollbackers, Template editors137,800 edits consistent citation formatting 
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{{Short description|Chemical compound}}
{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}}
{{Drugbox {{Drugbox
| Verifiedfields = changed | Verifiedfields = changed
| Watchedfields = changed | Watchedfields = changed
| verifiedrevid = 417949402 | verifiedrevid = 464377675
| IUPAC_name = 4-quinolin-10-yl)amino]-2,6-bis(pyrrolidin-1-ylmethyl)phenol | IUPAC_name = 4-quinolin-10-yl)amino]-2,6-bis(pyrrolidin-1-ylmethyl)phenol
| image = Pyronaridine.svg | image = Pyronaridine.svg


<!--Clinical data--> <!--Clinical data-->| alt = A chemical diagram of a Pyronaridine molecule
| synonyms = Pyronaridine tetraphosphate
| tradename =
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | tradename =
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X --> | pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_category = | pregnancy_category =
| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled--> | legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII --> | legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C --> | legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C -->
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> | legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
| legal_status = CLP (EU): Acute Tox. 3(H301), Eye Dam. 1 (H318), Repr. 2 (H361), Aquatic Chronic 4 (H413){{clarify|date=February 2017}}
| legal_status =
| routes_of_administration = Oral, ], ] | routes_of_administration = Oral, ], ]


<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->| bioavailability =
⚫ | protein_bound =
| bioavailability =
⚫ | metabolism =
⚫ | protein_bound =
⚫ | elimination_half-life =
⚫ | metabolism =
⚫ | excretion = <!--Identifiers-->
⚫ | elimination_half-life =
⚫ | CAS_number_Ref = {{cascite|changed|??}}
| excretion =
⚫ | 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


⚫ <!--Chemical data-->| C = 29
⚫ <!--Identifiers-->
| H = 32
⚫ | CAS_number_Ref = {{cascite|correct|??}}
| Cl = 1
⚫ | CAS_number = <!-- blanked - oldvalue: 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
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} | 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)
⚫ | DrugBank =
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
⚫ | StdInChIKey = DJUFPMUQJKWIJB-UHFFFAOYSA-N
⚫ | ChemSpiderID = 10647812
⚫ | UNII_Ref = {{fdacite|changed|FDA}}
⚫ | UNII = TD3P7Q3SG6
⚫ | ChEMBL_Ref = {{ebicite|correct|EBI}}
⚫ | ChEMBL = 35228

⚫ <!--Chemical data-->
| C=29 | H=32 | Cl=1 | N=5 | O=2
| molecular_weight = 518.05 g/mol
⚫ | smiles = Clc1ccc6c(c1)nc2ccc(OC)nc2c6Nc5cc(CN3CCCC3)c(O)c(CN4CCCC4)c5
| InChI = 1/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)
| InChIKey = DJUFPMUQJKWIJB-UHFFFAOYAM
⚫ | 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 ].<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 ].<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 ] ] (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>{{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 }}</ref>

== References ==
{{Reflist}}

{{Antimalarials}}

]
]

{{antiinfective-drug-stub}}