Artemotil (BioDeep_00000395742)

   

PANOMIX_OTCML-2023


代谢物信息卡片


(1R,4S,5R,8S,9R,10S,12R,13R)-10-ethoxy-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0^{4,13}.0^{8,13}]hexadecane

化学式: C17H28O5 (312.1937)
中文名称: 蒿乙醚
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 95.22%

分子结构信息

SMILES: CCOC1C(C2CCC(C3C24C(O1)OC(CC3)(OO4)C)C)C
InChI: InChI=1S/C17H28O5/c1-5-18-14-11(3)13-7-6-10(2)12-8-9-16(4)20-15(19-14)17(12,13)22-21-16/h10-15H,5-9H2,1-4H3/t10-,11-,12+,13+,14+,15-,16-,17-/m1/s1

描述信息

Artemotil is an artemisinin derivative.
Artemotil, also known as β-arteether, is a semi-synthetic derivative of artemisinin and a fast acting blood schizonticide specifically indicated for the treatment of chloroquine-resistant Plasmodium falciparum malaria and cerebral malaria cases.
P - Antiparasitic products, insecticides and repellents > P01 - Antiprotozoals > P01B - Antimalarials > P01BE - Artemisinin and derivatives, plain
D000890 - Anti-Infective Agents > D000977 - Antiparasitic Agents > D000981 - Antiprotozoal Agents
D000890 - Anti-Infective Agents > D000977 - Antiparasitic Agents > D000871 - Anthelmintics
C254 - Anti-Infective Agent > C276 - Antiparasitic Agent > C277 - Antiprotozoal Agent
D009676 - Noxae > D016877 - Oxidants > D010545 - Peroxides
Artemotil (β-Arteether) has antimalarial activity for the treatment of chloroquine-resistant Plasmodium falciparum malaria with an IC50 of 1.61 nM. Artemotil also has central nervous system (CNS) neurotoxicity and anorectic toxicity in rats, dogs and monkeys[1][2].
Artemotil (β-Arteether) has antimalarial activity for the treatment of chloroquine-resistant Plasmodium falciparum malaria with an IC50 of 1.61 nM. Artemotil also has central nervous system (CNS) neurotoxicity and anorectic toxicity in rats, dogs and monkeys[1][2].

同义名列表

28 个代谢物同义名

(1R,4S,5R,8S,9R,10S,12R,13R)-10-ethoxy-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0^{4,13}.0^{8,13}]hexadecane; (1R,4S,5R,8S,9R,10S,12R,13R)-10-ethoxy-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecane; (3R,5aS,6R,8aS,9R,10S,12R,12aR)-10-Ethoxydecahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano(4,3-j)-1,2-benzodioxepin; (3R,5aS,6R,8aS,9R,10S,12R,12aR)-10-Ethoxy-3,6,9-trimethyldecahydro-3H-3,12-epoxy[1,2]dioxepino[4,3-i]isochromene; arteether, (3R-(3alpha,5abeta,6beta,8abeta,9alpha,10alpha,12beta,12aR*))-isomer; arteether, (3R-(3alpha,5abeta,6beta,8abeta,9alpha,10beta,12beta,12aR*))-isomer; beta-Dihydroartemisinin ethyl ether; ARTEMOTILUM [WHO-IP LATIN]; .BETA.-ARTEETHER [WHO-IP]; alpha,beta Arteether; ARTEMOTIL [WHO-IP]; ARTEETHER [WHO-IP]; ARTEMOTIL [WHO-DD]; ARTEMOTIL [MART.]; .beta.-arteether; Beta-Arteether; ARTEETHER [MI]; (+)-Arteether; beta-artether; Artemotilum; b-Arteether; XGL7GFB9YI; arteether; Artemotil; artether; Artecef; E MAL; β-Arteether



数据库引用编号

8 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。

亚细胞结构定位 关联基因列表


文献列表

  • Akram Taleghani, Seyed Ahmad Emami, Zahra Tayarani-Najaran. Artemisia: a promising plant for the treatment of cancer. Bioorganic & medicinal chemistry. 2020 01; 28(1):115180. doi: 10.1016/j.bmc.2019.115180. [PMID: 31784199]
  • Abhisheak Sharma, Swati Jaiswal, Mahendra Shukla, Jawahar Lal. Effect of arteether and pyrimethamine coadministration on the pharmacokinetic and pharmacodynamic profile of ormeloxifene. Naunyn-Schmiedeberg's archives of pharmacology. 2017 Sep; 390(9):971-976. doi: 10.1007/s00210-017-1401-4. [PMID: 28689253]
  • Sangeeta Dhawan, Sarika Gunjan, Anirban Pal, Renu Tripathi. Potentiation of antimalarial activity of arteether in combination with Vetiver root extract. Indian journal of experimental biology. 2016 May; 54(5):315-21. doi: . [PMID: 27319050]
  • Zulfiqar Ali, Neeraj Mishra, Ashish Baldi. Development and characterization of arteether-loaded nanostructured lipid carriers for the treatment of malaria. Artificial cells, nanomedicine, and biotechnology. 2016; 44(2):545-9. doi: 10.3109/21691401.2014.968821. [PMID: 25340261]
  • Oladapo E Oyinloye, Ayokulehin M Kosoko, Benjamin Emikpe, Catherine O Falade, Olusegun G Ademowo. Potential antimalarial activity of Methyl Jasmonate and its effect on lipid profiles in Plasmodium Berghei infected mice. African health sciences. 2015 Sep; 15(3):841-50. doi: 10.4314/ahs.v15i3.19. [PMID: 26957973]
  • Pankaj Dwivedi, Renuka Khatik, Priyanka Chaturvedi, Kiran Khandelwal, Isha Taneja, Kanumuri Siva Rama Raju, Hemlata Dwivedi, Sunil Kumar Singh, Pramod Kumar Gupta, Prashant Shukla, Priyanka Tripathi, Sarika Singh, Renu Tripathi, Wahajuddin, Sarvesh Kumar Paliwal, Anil Kumar Dwivedi, Prabhat Ranjan Mishra. Arteether nanoemulsion for enhanced efficacy against Plasmodium yoelii nigeriensis malaria: an approach by enhanced bioavailability. Colloids and surfaces. B, Biointerfaces. 2015 Feb; 126(?):467-75. doi: 10.1016/j.colsurfb.2014.12.052. [PMID: 25616971]
  • Rashmi Gaur, Mahendra P Darokar, P V Ajayakumar, Ram Sajiwan Shukla, Rajendra Singh Bhakuni. In vitro antimalarial studies of novel artemisinin biotransformed products and its derivatives. Phytochemistry. 2014 Nov; 107(?):135-40. doi: 10.1016/j.phytochem.2014.08.004. [PMID: 25183484]
  • Aik Jiang Lau, Thomas K H Chang. Fetal bovine serum and human constitutive androstane receptor: evidence for activation of the SV23 splice variant by artemisinin, artemether, and arteether in a serum-free cell culture system. Toxicology and applied pharmacology. 2014 Jun; 277(2):221-30. doi: 10.1016/j.taap.2014.03.023. [PMID: 24721719]
  • Pankaj Dwivedi, Renuka Khatik, Kiran Khandelwal, Isha Taneja, Kanumuri Siva Rama Raju, Wahajuddin, Sarvesh Kumar Paliwal, Anil Kumar Dwivedi, Prabhat Ranjan Mishra. Pharmacokinetics study of arteether loaded solid lipid nanoparticles: an improved oral bioavailability in rats. International journal of pharmaceutics. 2014 May; 466(1-2):321-7. doi: 10.1016/j.ijpharm.2014.03.036. [PMID: 24657144]
  • Patrick B Memvanga, Jérémie K Mbinze, Eric Rozet, Philippe Hubert, Véronique Préat, Roland D Marini. Development of a liquid chromatographic method for the simultaneous quantification of curcumin, β-arteether, tetrahydrocurcumin and dihydroartemisinin. Application to lipid-based formulations. Journal of pharmaceutical and biomedical analysis. 2014 Jan; 88(?):447-56. doi: 10.1016/j.jpba.2013.09.009. [PMID: 24184380]
  • Patrick B Memvanga, Régis Coco, Véronique Préat. An oral malaria therapy: curcumin-loaded lipid-based drug delivery systems combined with β-arteether. Journal of controlled release : official journal of the Controlled Release Society. 2013 Dec; 172(3):904-13. doi: 10.1016/j.jconrel.2013.09.001. [PMID: 24021359]
  • Patrick B Memvanga, Pierre Eloy, Eric M Gaigneaux, Véronique Préat. In vitro lipolysis and intestinal transport of β-arteether-loaded lipid-based drug delivery systems. Pharmaceutical research. 2013 Oct; 30(10):2694-705. doi: 10.1007/s11095-013-1094-4. [PMID: 23739990]
  • Renu Tripathi, Amber Rizvi, Swaroop Kumar Pandey, Hemlata Dwivedi, J K Saxena. Ketoconazole, a cytochrome P(450) inhibitor can potentiate the antimalarial action of α/β arteether against MDR Plasmodium yoelii nigeriensis. Acta tropica. 2013 May; 126(2):150-5. doi: 10.1016/j.actatropica.2013.01.012. [PMID: 23391499]
  • Patrick B Memvanga, Véronique Préat. Formulation design and in vivo antimalarial evaluation of lipid-based drug delivery systems for oral delivery of β-arteether. European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V. 2012 Sep; 82(1):112-9. doi: 10.1016/j.ejpb.2012.05.004. [PMID: 22609572]
  • N P Aditya, Geetanjali Chimote, Karthigayan Gunalan, Rinti Banerjee, Swati Patankar, Basavaraj Madhusudhan. Curcuminoids-loaded liposomes in combination with arteether protects against Plasmodium berghei infection in mice. Experimental parasitology. 2012 Jul; 131(3):292-9. doi: 10.1016/j.exppara.2012.04.010. [PMID: 22561991]
  • Qigui Li, Mark Hickman. Toxicokinetic and toxicodynamic (TK/TD) evaluation to determine and predict the neurotoxicity of artemisinins. Toxicology. 2011 Jan; 279(1-3):1-9. doi: 10.1016/j.tox.2010.09.005. [PMID: 20863871]
  • Cheeraratana Cheeramakara, Vasant Khachonsaksumet, Nopachai Suthisai, Wanyarat Nakosiri, Kriyaporn Songmuaeng, Channarong Saenghirun, Duangduen Phienpicharn, Apichart Nontprasert. Distribution of C14-labelled arteether in kidneys and livers of experimental mice after intramuscular injection. The Southeast Asian journal of tropical medicine and public health. 2008 Mar; 39(2):195-9. doi: NULL. [PMID: 18564701]
  • S Sabarinath, R P Singh, R C Gupta. Simultaneous quantification of alpha-/beta-diastereomers of arteether, sulphadoxine and pyrimethamine: a promising anti-relapse antimalarial therapeutic combination, by liquid chromatography tandem mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2006 Sep; 842(1):36-42. doi: 10.1016/j.jchromb.2006.05.003. [PMID: 16725391]
  • M Sukhija, Bikash Medhi, P Pandhi. Effects of artemisinin, artemether, and arteether on the pharmacokinetics of phenytoin. Methods and findings in experimental and clinical pharmacology. 2006 Mar; 28(2):89-94. doi: 10.1358/mf.2006.28.2.977839. [PMID: 16636718]
  • Manpreet Sukhija, Bikash Medhi, P Pandhi. Effects of artemisinin, artemether, arteether on the pharmacokinetics of carbamazepine. Pharmacology. 2006; 76(3):110-6. doi: 10.1159/000090434. [PMID: 16388199]
  • S Sabarinath, K P Madhusudanan, R C Gupta. Pharmacokinetics of the diastereomers of arteether, a potent antimalarial drug, in rats. Biopharmaceutics & drug disposition. 2005 Sep; 26(6):211-23. doi: 10.1002/bdd.452. [PMID: 15926191]
  • Sreedharan N Sabarinath, Omkar P Asthana, Sunil K Puri, Kumkum Srivastava, Kunnath P Madhusudanan, Ram C Gupta. Clinical pharmacokinetics of the diastereomers of arteether in healthy volunteers. Clinical pharmacokinetics. 2005; 44(11):1191-203. doi: 10.2165/00003088-200544110-00006. [PMID: 16231969]
  • M Rajanikanth, K P Madhusudanan, R C Gupta. An HPLC-MS method for simultaneous estimation of alpha,beta-arteether and its metabolite dihydroartemisinin, in rat plasma for application to pharmacokinetic study. Biomedical chromatography : BMC. 2003 Oct; 17(7):440-6. doi: 10.1002/bmc.261. [PMID: 14598327]
  • S Sabarinath, M Rajanikanth, K P Madhusudanan, R C Gupta. A sensitive and selective liquid chromatographic/electrospray ionization tandem mass spectrometric assay for the simultaneous quantification of alpha-,beta-arteether and its metabolite dihydroartemisinin in plasma, useful for pharmacokinetic studies. Journal of mass spectrometry : JMS. 2003 Jul; 38(7):732-42. doi: 10.1002/jms.487. [PMID: 12898653]
  • M Rajanikanth, K P Madhusudanan, R C Gupta. Liquid chromatographic-mass spectrometric method for the determination of alpha-,beta-arteether in rat serum. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2003 Jan; 783(2):391-9. doi: 10.1016/s1570-0232(02)00701-8. [PMID: 12482482]
  • S Looareesuwan, B Oosterhuis, B M Schilizzi, F A E Sollie, P Wilairatana, S Krudsood, Ch B Lugt, P A M Peeters, J O Peggins. Dose-finding and efficacy study for i.m. artemotil (beta-arteether) and comparison with i.m. artemether in acute uncomplicated P. falciparum malaria. British journal of clinical pharmacology. 2002 May; 53(5):492-500. doi: 10.1046/j.1365-2125.2002.01590.x. [PMID: 11994055]
  • N J Siddiqi, V C Pandey. Studies on hepatic oxidative stress and antioxidant defence systems during arteether treatment of Plasmodium yoelii nigeriensis infected mice. Molecular and cellular biochemistry. 1999 Jun; 196(1-2):169-73. doi: 10.1023/a:1006944313291. [PMID: 10448917]
  • Q G Li, J O Peggins, L L Fleckenstein, K Masonic, M H Heiffer, T G Brewer. The pharmacokinetics and bioavailability of dihydroartemisinin, arteether, artemether, artesunic acid and artelinic acid in rats. The Journal of pharmacy and pharmacology. 1998 Feb; 50(2):173-82. doi: 10.1111/j.2042-7158.1998.tb06173.x. [PMID: 9530985]
  • K Ramu, J K Baker. Identification of the glucuronides of the hydroxylated metabolites of the antimalarial arteether in rat plasma and urine by thermospray high-performance liquid chromatography/mass spectrometry. Journal of pharmaceutical sciences. 1997 Aug; 86(8):915-20. doi: 10.1021/js960424k. [PMID: 9269869]
  • D E Davidson. Role of arteether in the treatment of malaria and plans for further development. Transactions of the Royal Society of Tropical Medicine and Hygiene. 1994 Jun; 88 Suppl 1(?):S51-2. doi: 10.1016/0035-9203(94)90474-x. [PMID: 8053028]
  • S Wanwimolruk, G Edwards, S A Ward, A M Breckenridge. The binding of the antimalarial arteether to human plasma proteins in-vitro. The Journal of pharmacy and pharmacology. 1992 Nov; 44(11):940-2. doi: 10.1111/j.2042-7158.1992.tb03243.x. [PMID: 1361544]
  • G Edwards, S Ward, A Breckenridge. Interaction of arteether with the red blood cell in-vitro and its possible importance in the interpretation of plasma concentrations in-vivo. The Journal of pharmacy and pharmacology. 1992 Mar; 44(3):280-1. doi: 10.1111/j.2042-7158.1992.tb03604.x. [PMID: 1354744]
  • H T Chi, K Ramu, J K Baker, C D Hufford, I S Lee, Y L Zeng, J D McChesney. Identification of the in vivo metabolites of the antimalarial arteether by thermospray high-performance liquid chromatography/mass spectrometry. Biological mass spectrometry. 1991 Oct; 20(10):609-28. doi: 10.1002/bms.1200201006. [PMID: 1793739]
  • A Benakis, C Schopfer, M Paris, C T Plessas, P E Karayannakos, I Dondas, D Kotsarelis, S T Plessas, G Skalkeas. Pharmacokinetics of arteether in dog. European journal of drug metabolism and pharmacokinetics. 1991 Oct; 16(4):325-8. doi: 10.1007/bf03189978. [PMID: 1823877]
  • V Melendez, J O Peggins, T G Brewer, A D Theoharides. Determination of the antimalarial arteether and its deethylated metabolite dihydroartemisinin in plasma by high-performance liquid chromatography with reductive electrochemical detection. Journal of pharmaceutical sciences. 1991 Feb; 80(2):132-8. doi: 10.1002/jps.2600800209. [PMID: 2051315]
  • O R Idowu, G Edwards, S A Ward, M L Orme, A M Breckenridge. Determination of arteether in blood plasma by high-performance liquid chromatography with ultraviolet detection after hydrolysis acid. Journal of chromatography. 1989 Aug; 493(1):125-36. doi: 10.1016/s0378-4347(00)82715-2. [PMID: 2778002]