Proguanil (BioDeep_00000002125)

 

Secondary id: BioDeep_00001868401

human metabolite blood metabolite Chemicals and Drugs


代谢物信息卡片


(E)-1-({amino[(4-chlorophenyl)amino]methylidene}amino)-N-(propan-2-yl)methenimidamide

化学式: C11H16ClN5 (253.10941659999997)
中文名称: 氯胍
谱图信息: 最多检出来源 Mentha canadensis(plant) 91.18%

分子结构信息

SMILES: CC(C)N=C(N)N=C(N)NC1=CC=C(C=C1)Cl
InChI: InChI=1S/C11H16ClN5/c1-7(2)15-10(13)17-11(14)16-9-5-3-8(12)4-6-9/h3-7H,1-2H3,(H5,13,14,15,16,17)

描述信息

Proguanil is a prophylactic antimalarial drug, which works by stopping the malaria parasite, Plasmodium falciparum and Plasmodium vivax, from reproducing once it is in the red blood cells. It does this by inhibiting the enzyme, dihydrofolate reductase, which is involved in the reproduction of the parasite.
P - Antiparasitic products, insecticides and repellents > P01 - Antiprotozoals > P01B - Antimalarials > P01BB - Biguanides
D000890 - Anti-Infective Agents > D000977 - Antiparasitic Agents > D000981 - Antiprotozoal Agents
C254 - Anti-Infective Agent > C276 - Antiparasitic Agent > C277 - Antiprotozoal Agent
C471 - Enzyme Inhibitor > C2153 - Dihydrofolate Reductase Inhibitor
D007004 - Hypoglycemic Agents > D001645 - Biguanides
D009676 - Noxae > D000963 - Antimetabolites

同义名列表

9 个代谢物同义名

(E)-1-({amino[(4-chlorophenyl)amino]methylidene}amino)-N-(propan-2-yl)methenimidamide; (1E)-1-[amino-(4-chloroanilino)methylidene]-2-propan-2-ylguanidine; 1-[amino-(4-chloroanilino)methylidene]-2-propan-2-ylguanidine; N-(4-Chlorophenyl)-n-(isopropyl)-imidodicarbonimidic diamide; 1-(p-Chlorophenyl)-5-isopropylbiguanide; Chloroguanide; Chlorguanide; Proguanilum; Proguanil



数据库引用编号

17 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

1 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。



文献列表

  • Stephan Chalon, M Farouk Chughlay, Nada Abla, Andre Marie Tchouatieu, Amina Haouala, Ben Hutter, Ulrike Lorch, Fiona Macintyre. Unanticipated CNS Safety Signal in a Placebo-Controlled, Randomized Trial of Co-Administered Atovaquone-Proguanil and Amodiaquine. Clinical pharmacology and therapeutics. 2022 04; 111(4):867-877. doi: 10.1002/cpt.2404. [PMID: 34453327]
  • Bruno A Rodriguez-Rodriguez, Maria G Noval, Maria E Kaczmarek, Kyung Ku Jang, Sara A Thannickal, Angelica Cifuentes Kottkamp, Rebecca S Brown, Margaret Kielian, Ken Cadwell, Kenneth A Stapleford. Atovaquone and Berberine Chloride Reduce SARS-CoV-2 Replication In Vitro. Viruses. 2021 12; 13(12):. doi: 10.3390/v13122437. [PMID: 34960706]
  • Namshik Han, Woochang Hwang, Konstantinos Tzelepis, Patrick Schmerer, Eliza Yankova, Méabh MacMahon, Winnie Lei, Nicholas M Katritsis, Anika Liu, Ulrike Felgenhauer, Alison Schuldt, Rebecca Harris, Kathryn Chapman, Frank McCaughan, Friedemann Weber, Tony Kouzarides. Identification of SARS-CoV-2-induced pathways reveals drug repurposing strategies. Science advances. 2021 06; 7(27):. doi: 10.1126/sciadv.abh3032. [PMID: 34193418]
  • Mark J Henderson, Kathleen A Trychta, Shyh-Ming Yang, Susanne Bäck, Adam Yasgar, Emily S Wires, Carina Danchik, Xiaokang Yan, Hideaki Yano, Lei Shi, Kuo-Jen Wu, Amy Q Wang, Dingyin Tao, Gergely Zahoránszky-Kőhalmi, Xin Hu, Xin Xu, David Maloney, Alexey V Zakharov, Ganesha Rai, Fumihiko Urano, Mikko Airavaara, Oksana Gavrilova, Ajit Jadhav, Yun Wang, Anton Simeonov, Brandon K Harvey. A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome. Cell reports. 2021 04; 35(4):109040. doi: 10.1016/j.celrep.2021.109040. [PMID: 33910017]
  • John Oludele Olanlokun, Folashade Abimbola Balogun, Olufunso Olabode Olorunsogo. Chemotherapeutic and prophylactic antimalarial drugs induce cell death through mitochondrial-mediated apoptosis in murine models. Drug and chemical toxicology. 2021 Jan; 44(1):47-57. doi: 10.1080/01480545.2018.1536139. [PMID: 30486696]
  • Ryohkan Funakoshi, Yukana Tomoda, Toshiyuki Kudo, Kenichi Furihata, Hiroyuki Kusuhara, Kiyomi Ito. Effects of proton pump inhibitors, esomeprazole and vonoprazan, on the disposition of proguanil, a CYP2C19 substrate, in healthy volunteers. British journal of clinical pharmacology. 2019 07; 85(7):1454-1463. doi: 10.1111/bcp.13914. [PMID: 30845361]
  • Pablo Villoslada, Gemma Vila, Valeria Colafrancesco, Beatriz Moreno, Begoña Fernandez-Diez, Raquel Vazquez, Inna Pertsovskaya, Irati Zubizarreta, Irene Pulido-Valdeolivas, Joaquin Messeguer, Gloria Vendrell-Navarro, Jose Maria Frade, Noelia López-Sánchez, Meritxell Teixido, Ernest Giralt, Mar Masso, Jason C Dugas, Dmitri Leonoudakis, Karen D Lariosa-Willingham, Lawrence Steinman, Angel Messeguer. Axonal and Myelin Neuroprotection by the Peptoid BN201 in Brain Inflammation. Neurotherapeutics : the journal of the American Society for Experimental NeuroTherapeutics. 2019 07; 16(3):808-827. doi: 10.1007/s13311-019-00717-4. [PMID: 30815844]
  • Maarten van der Velden, Albert Bilos, Jeroen J M W van den Heuvel, Sanna R Rijpma, Evelien G E Hurkmans, Robert W Sauerwein, Frans G M Russel, Jan B Koenderink. Proguanil and cycloguanil are organic cation transporter and multidrug and toxin extrusion substrates. Malaria journal. 2017 10; 16(1):422. doi: 10.1186/s12936-017-2062-y. [PMID: 29061131]
  • Maxime G Corral, Julie Leroux, Keith A Stubbs, Joshua S Mylne. Herbicidal properties of antimalarial drugs. Scientific reports. 2017 03; 7(?):45871. doi: 10.1038/srep45871. [PMID: 28361906]
  • Fabrice Bruneel, Florence Tubach, Jean-Paul Mira, Sandrine Houze, Sebastien Gibot, Marie-Genevieve Huisse, Bruno Megarbane, Christophe Choquet, Philippe Corne, Eric Peytel, Daniel Villers, Christophe Camus, Olivier Bouchaud, Eric Caumes, Pierre-Marie Girard, Fabrice Simon, Antoine Kalloumeh, Carine Roy, Remy Durand, Jacques Le Bras, Sophie Matheron, Michel Wolff. Imported falciparum malaria in adults: host- and parasite-related factors associated with severity. The French prospective multicenter PALUREA cohort study. Intensive care medicine. 2016 Oct; 42(10):1588-1596. doi: 10.1007/s00134-016-4356-x. [PMID: 27169586]
  • Domagoj Dinter, Goran Gajski, Ana-Marija Domijan, Vera Garaj-Vrhovac. Cytogenetic and oxidative status of human lymphocytes after exposure to clinically relevant concentrations of antimalarial drugs atovaquone and proguanil hydrochloride in vitro. Fundamental & clinical pharmacology. 2015 Dec; 29(6):575-85. doi: 10.1111/fcp.12153. [PMID: 26434663]
  • Mario Thevis, Hans Geyer, Andreas Thomas, Laura Tretzel, Isabelle Bailloux, Corinne Buisson, Francoise Lasne, Maximilian S Schaefer, Peter Kienbaum, Irmela Mueller-Stoever, Wilhelm Schänzer. Formation of the diuretic chlorazanil from the antimalarial drug proguanil--implications for sports drug testing. Journal of pharmaceutical and biomedical analysis. 2015 Nov; 115(?):208-13. doi: 10.1016/j.jpba.2015.07.017. [PMID: 26226108]
  • Andrea K Boggild, Rachel Lau, Denis Reynaud, Kevin C Kain, Marvin Gerson. Failure of atovaquone-proguanil malaria chemoprophylaxis in a traveler to Ghana. Travel medicine and infectious disease. 2015 Jan; 13(1):89-93. doi: 10.1016/j.tmaid.2014.12.010. [PMID: 25582377]
  • Martin Lochner, Andrew J Thompson. The antimalarial drug proguanil is an antagonist at 5-HT3 receptors. The Journal of pharmacology and experimental therapeutics. 2014 Dec; 351(3):674-84. doi: 10.1124/jpet.114.218461. [PMID: 25277140]
  • Aiko Iguchi, Nobuyuki Shiranaga, Aya Matsuu, Yoshiaki Hikasa. Efficacy of Malarone(®) in dogs naturally infected with Babesia gibsoni. The Journal of veterinary medical science. 2014 Sep; 76(9):1291-5. doi: 10.1292/jvms.14-0139. [PMID: 24909969]
  • Qigui Li, Shon Remich, Scott R Miller, Bernhards Ogutu, Walter Otieno, Victor Melendez, Paktiya Teja-Isavadharm, Peter J Weina, Mark R Hickman, Bryan Smith, Mark Polhemus. Pharmacokinetic evaluation of intravenous artesunate in adults with uncomplicated falciparum malaria in Kenya: a phase II study. Malaria journal. 2014 Jul; 13(?):281. doi: 10.1186/1475-2875-13-281. [PMID: 25047305]
  • Carmelina Calitri, Silvia Garazzino, Roberta Camilla, Licia Peruzzi, Alessandro Amore, Pier-Angelo Tovo. 'Collateral' effect of artemether in an atypical kidney involvement by Plasmodium falciparum malaria: a case report. Journal of vector borne diseases. 2014 Jun; 51(2):147-8. doi: NULL. [PMID: 24947225]
  • Eleri Wallace, Charlene M Y Ong, Charles M Heard. Delivery of atovaquone and proguanil across sublingual membranes, in vitro. Pharmaceutical development and technology. 2012 Nov; 17(6):770-6. doi: 10.3109/10837450.2011.580760. [PMID: 21612571]
  • M Cella, F Kloprogge, M Danhof, O Della Pasqua. Dosing rationale for fixed-dose combinations in children: shooting from the hip?. Clinical pharmacology and therapeutics. 2012 Apr; 91(4):718-25. doi: 10.1038/clpt.2011.297. [PMID: 22398964]
  • Akinsomisoye Olumide Stephen, Raji Yinusa. Prolonged administration of proguanil induces reproductive toxicity in male rats. The Journal of toxicological sciences. 2011 Oct; 36(5):587-99. doi: 10.2131/jts.36.587. [PMID: 22008534]
  • Chiara Tommasi, Rita Bellagamba, Massimo Tempestilli, Antonio D'Avolio, Anna L Gallo, Jelena Ivanovic, Emanuele Nicastri, Leopoldo P Pucillo, Pasquale Narciso. Marked increase in etravirine and saquinavir plasma concentrations during atovaquone/proguanil prophylaxis. Malaria journal. 2011 May; 10(?):141. doi: 10.1186/1475-2875-10-141. [PMID: 21600016]
  • Carrie A Morris, Marie A Onyamboko, Edmund Capparelli, Matthew A Koch, Joseph Atibu, Vicky Lokomba, Macaya Douoguih, Jennifer Hemingway-Foday, David Wesche, Robert W Ryder, Carl Bose, Linda Wright, Antoinette K Tshefu, Steven Meshnick, Lawrence Fleckenstein. Population pharmacokinetics of artesunate and dihydroartemisinin in pregnant and non-pregnant women with malaria. Malaria journal. 2011 May; 10(?):114. doi: 10.1186/1475-2875-10-114. [PMID: 21548983]
  • Philippe Rasoanaivo, Colin W Wright, Merlin L Willcox, Ben Gilbert. Whole plant extracts versus single compounds for the treatment of malaria: synergy and positive interactions. Malaria journal. 2011 Mar; 10 Suppl 1(?):S4. doi: 10.1186/1475-2875-10-s1-s4. [PMID: 21411015]
  • Yan Pan, Badrul Amini Abd-Rashid, Zakiah Ismail, Rusli Ismail, Joon Wah Mak, Peter C K Pook, Hui Meng Er, Chin Eng Ong. In vitro modulatory effects of Andrographis paniculata, Centella asiatica and Orthosiphon stamineus on cytochrome P450 2C19 (CYP2C19). Journal of ethnopharmacology. 2011 Jan; 133(2):881-7. doi: 10.1016/j.jep.2010.11.026. [PMID: 21093571]
  • Kirti Mishra, Aditya P Dash, Nrisingha Dey. Andrographolide: A Novel Antimalarial Diterpene Lactone Compound from Andrographis paniculata and Its Interaction with Curcumin and Artesunate. Journal of tropical medicine. 2011; 2011(?):579518. doi: 10.1155/2011/579518. [PMID: 21760808]
  • Goran Gajski, Domagoj Dinter, Vera Garaj-Vrhovac. In vitro effect of the antimalarial drug proguanil hydrochloride on viability and DNA damage in human peripheral blood lymphocytes. Environmental toxicology and pharmacology. 2010 Nov; 30(3):257-63. doi: 10.1016/j.etap.2010.07.001. [PMID: 21787658]
  • Robert L Clark, William E Gristwood, Richard Lewsley, Robert Wilson, Andrew W Harrell. Localization of artesunate and its derivatives in the pregnant rat and fetus following oral administration and relationship to developmental toxicity. Birth defects research. Part B, Developmental and reproductive toxicology. 2010 Oct; 89(5):364-75. doi: 10.1002/bdrb.20256. [PMID: 20717981]
  • Hetty Jolink, Jan den Hartigh, Leo G Visser, Cees van Nieuwkoop. Pancytopenia due to proguanil toxicity in a returning traveller with fever. European journal of clinical pharmacology. 2010 Aug; 66(8):811-2. doi: 10.1007/s00228-010-0824-3. [PMID: 20407763]
  • Matthijs van Luin, Marchina E Van der Ende, Clemens Richter, Mirjam Visser, Diari Faraj, Andre Van der Ven, Luc Gelinck, Frank Kroon, Ferdinand W Wit, Ron H N Van Schaik, Paul F M Kuks, David M Burger. Lower atovaquone/proguanil concentrations in patients taking efavirenz, lopinavir/ritonavir or atazanavir/ritonavir. AIDS (London, England). 2010 May; 24(8):1223-6. doi: 10.1097/qad.0b013e3283389129. [PMID: 20299957]
  • Julius Olugbenga Soyinka, Cyprian Ogbonna Onyeji. Alteration of pharmacokinetics of proguanil in healthy volunteers following concurrent administration of efavirenz. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences. 2010 Feb; 39(4):213-8. doi: 10.1016/j.ejps.2009.11.012. [PMID: 19961932]
  • Beesan Tan, Himanshu Naik, In-Jin Jang, Kyung-Sang Yu, Lee E Kirsch, Chang-Sik Shin, J Carl Craft, Lawrence Fleckenstein. Population pharmacokinetics of artesunate and dihydroartemisinin following single- and multiple-dosing of oral artesunate in healthy subjects. Malaria journal. 2009 Dec; 8(?):304. doi: 10.1186/1475-2875-8-304. [PMID: 20021657]
  • Reinhold Kerb, Richard Fux, Klaus Mörike, Peter G Kremsner, José Pedro Gil, Christoph H Gleiter, Matthias Schwab. Pharmacogenetics of antimalarial drugs: effect on metabolism and transport. The Lancet. Infectious diseases. 2009 Dec; 9(12):760-74. doi: 10.1016/s1473-3099(09)70320-2. [PMID: 19926036]
  • Manish Sadarangani, Julie Makani, Albert N Komba, Tolu Ajala-Agbo, Charles R Newton, Kevin Marsh, Thomas N Williams. An observational study of children with sickle cell disease in Kilifi, Kenya. British journal of haematology. 2009 Sep; 146(6):675-82. doi: 10.1111/j.1365-2141.2009.07771.x. [PMID: 19650883]
  • David J Bell, Dan Wootton, Mavuto Mukaka, Jacqui Montgomery, Noel Kayange, Phillips Chimpeni, Dyfrig A Hughes, Malcolm E Molyneux, Steve A Ward, Peter A Winstanley, David G Lalloo. Measurement of adherence, drug concentrations and the effectiveness of artemether-lumefantrine, chlorproguanil-dapsone or sulphadoxine-pyrimethamine in the treatment of uncomplicated malaria in Malawi. Malaria journal. 2009 Aug; 8(?):204. doi: 10.1186/1475-2875-8-204. [PMID: 19709418]
  • Kirti Mishra, Aditya P Dash, Bijay K Swain, Nrisingha Dey. Anti-malarial activities of Andrographis paniculata and Hedyotis corymbosa extracts and their combination with curcumin. Malaria journal. 2009 Feb; 8(?):26. doi: 10.1186/1475-2875-8-26. [PMID: 19216765]
  • Chakradhara Rao Uppugunduri Satyanarayana, Anichavezhi Devendran, Muthukumaran Jayaraman, Jayakanthan Mannu, Premendu P Mathur, Shewade Deepak Gopal, Krishnamoorthy Rajagopal, Adithan Chandrasekaran. Influence of the genetic polymorphisms in the 5' flanking and exonic regions of CYP2C19 on proguanil oxidation. Drug metabolism and pharmacokinetics. 2009; 24(6):537-48. doi: 10.2133/dmpk.24.537. [PMID: 20045989]
  • Christine Payen, Luc Monnin, Corine Pulce, Jacques Descotes. Bone marrow aplasia following acute poisoning with chloroquine-proguanil. Clinical toxicology (Philadelphia, Pa.). 2008 Dec; 46(10):1085-7. doi: 10.1080/15563650601182925. [PMID: 19065311]
  • Florence Gardella, Serge Assi, Fabrice Simon, Hervé Bogreau, Teunis Eggelte, Fatou Ba, Vincent Foumane, Marie-Claire Henry, Pélagie Traore Kientega, Léonardo Basco, Jean-François Trape, Richard Lalou, Maryse Martelloni, Marc Desbordes, Meïli Baragatti, Sébastien Briolant, Lionel Almeras, Bruno Pradines, Thierry Fusai, Christophe Rogier. Antimalarial drug use in general populations of tropical Africa. Malaria journal. 2008 Jul; 7(?):124. doi: 10.1186/1475-2875-7-124. [PMID: 18611279]
  • . Artemether + lumefantrine: new drug. An alternative to atovaquone + proguanil. Prescrire international. 2008 Apr; 17(94):54-6. doi: . [PMID: 18516806]
  • N Thorogood, S Atwal, W Mills, M Jenner, D A Lewis, J D Cavenagh, S G Agrawal. The risk of antimalarials in patients with renal failure. Postgraduate medical journal. 2007 Dec; 83(986):e8. doi: 10.1136/pgmj.2007.063735. [PMID: 18057166]
  • Pilar Foronda, María A Santana-Morales, Jorge Orós, Néstor Abreu-Acosta, Antonio Ortega-Rivas, Jacob Lorenzo-Morales, Basilio Valladares. Clinical efficacy of antiparasite treatments against intestinal helminths and haematic protozoa in Gallotia caesaris (lizards). Experimental parasitology. 2007 Aug; 116(4):361-5. doi: 10.1016/j.exppara.2007.02.004. [PMID: 17399704]
  • Tewari Tushar, Thomas Vinod, Sundaram Rajan, Chanolean Shashindran, Chandrasekaran Adithan. Effect of honey on CYP3A4, CYP2D6 and CYP2C19 enzyme activity in healthy human volunteers. Basic & clinical pharmacology & toxicology. 2007 Apr; 100(4):269-72. doi: 10.1111/j.1742-7843.2006.00039.x. [PMID: 17371531]
  • Ranjan K Singh. Hyperreactive malarial splenomegaly in expatriates. Travel medicine and infectious disease. 2007 Jan; 5(1):24-9. doi: 10.1016/j.tmaid.2006.01.018. [PMID: 17161315]
  • Lise Musset, Olivier Bouchaud, Sophie Matheron, Laurent Massias, Jacques Le Bras. Clinical atovaquone-proguanil resistance of Plasmodium falciparum associated with cytochrome b codon 268 mutations. Microbes and infection. 2006 Sep; 8(11):2599-604. doi: 10.1016/j.micinf.2006.07.011. [PMID: 16962361]
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  • Nathalie L Leveque, William N Charman, Francis C K Chiu. Sensitive method for the quantitative determination of proguanil and its metabolites in rat blood and plasma by liquid chromatography-mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2006 Jan; 830(2):314-21. doi: 10.1016/j.jchromb.2005.11.004. [PMID: 16310420]
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  • R McGready, K Stepniewska, M D Edstein, T Cho, G Gilveray, S Looareesuwan, N J White, F Nosten. The pharmacokinetics of atovaquone and proguanil in pregnant women with acute falciparum malaria. European journal of clinical pharmacology. 2003 Oct; 59(7):545-52. doi: 10.1007/s00228-003-0652-9. [PMID: 12955371]
  • R McGready, K Stepniewska, E Seaton, T Cho, D Cho, A Ginsberg, M D Edstein, E Ashley, S Looareesuwan, N J White, F Nosten. Pregnancy and use of oral contraceptives reduces the biotransformation of proguanil to cycloguanil. European journal of clinical pharmacology. 2003 Oct; 59(7):553-7. doi: 10.1007/s00228-003-0651-x. [PMID: 12955370]
  • Kristian Kofoed, Eskild Petersen. The efficacy of chemoprophylaxis against malaria with chloroquine plus proguanil, mefloquine, and atovaquone plus proguanil in travelers from Denmark. Journal of travel medicine. 2003 May; 10(3):150-4. doi: 10.2310/7060.2003.35746. [PMID: 12757688]
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  • Timothy M E Davis, David A Syed, Kenneth F Ilett, P Hugh R Barrett. Toxicity related to chloroquine treatment of resistant vivax malaria. The Annals of pharmacotherapy. 2003 Apr; 37(4):526-9. doi: 10.1345/aph.1c311. [PMID: 12659609]
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