Penciclovir (BioDeep_00000002476)

 

Secondary id: BioDeep_00000405981

human metabolite blood metabolite Chemicals and Drugs Antibiotics


代谢物信息卡片


2-amino-9-[4-hydroxy-3-(hydroxymethyl)butyl]-6,9-dihydro-3H-purin-6-one

化学式: C10H15N5O3 (253.11748400000002)
中文名称: 喷昔洛韦
谱图信息: 最多检出来源 Homo sapiens(urine) 1.85%

分子结构信息

SMILES: C(Cn1cnc2c1nc(N)[nH]c2=O)C(CO)CO
InChI: InChI=1S/C10H15N5O3/c11-10-13-8-7(9(18)14-10)12-5-15(8)2-1-6(3-16)4-17/h5-6,16-17H,1-4H2,(H3,11,13,14,18)

描述信息

Penciclovir is only found in individuals that have used or taken this drug. It is a guanine analogue antiviral drug used for the treatment of various herpesvirus infections. It is a nucleoside analogue which exhibits low toxicity and good selectivity. [Wikipedia]Penciclovir has in vitro activity against herpes simplex virus types 1 (HSV-1) and 2 (HSV-2). In cells infected with HSV-1 or HSV-2, viral thymidine kinase phosphorylates penciclovir to a monophosphate form. The monophosphate form of the drug is then converted to penciclovir triphosphate by cellular kinases. The intracellular triphosphate of penciclovir is retained in vitro inside HSV-infected cells for 10-20 hours, compared with 0.7-1 hour for acyclovir. in vitro studies show that penciclovir triphosphate selectively inhibits viral DNA polymerase by competing with deoxyguanosine triphosphate. Inhibition of DNA synthesis of virus-infected cells inhibits viral replication. In cells not infected with HSV, DNA synthesis is unaltered. Resistant mutants of HSV can occur from qualitative changes in viral thymidine kinase or DNA polymerase. The most commonly encountered acyclovir-resistant mutants that are deficient in viral thymidine kinase are also resistant to penciclovir.
J - Antiinfectives for systemic use > J05 - Antivirals for systemic use > J05A - Direct acting antivirals > J05AB - Nucleosides and nucleotides excl. reverse transcriptase inhibitors
D - Dermatologicals > D06 - Antibiotics and chemotherapeutics for dermatological use > D06B - Chemotherapeutics for topical use > D06BB - Antivirals
D000890 - Anti-Infective Agents > D000998 - Antiviral Agents
C471 - Enzyme Inhibitor > C29575 - DNA Polymerase Inhibitor
C254 - Anti-Infective Agent > C281 - Antiviral Agent
CONFIDENCE standard compound; EAWAG_UCHEM_ID 3288
KEIO_ID P157; [MS2] KO009149
KEIO_ID P157
Penciclovir (VSA 671) is a potent and selective anti-herpesvirus agent with EC50 values of 0.5, 0.8 μg/ml for HSV-1 (HFEM), HSV-2 (MS), respectively. Penciclovir shows anti-herpesvirus activity with no-toxic. Penciclovir preventes mortality in mouse[1][2].

同义名列表

20 个代谢物同义名

2-amino-9-[4-hydroxy-3-(hydroxymethyl)butyl]-6,9-dihydro-3H-purin-6-one; 9-[2-Hydroxy-1-(hydroxymethyl)-ethoxymethyl]guanine; 9-[4-Hydroxy-3-(hydroxymethyl)but-1-yl]guanine; 9-(4-Hydroxy-3-hydroxymethylbut-1-yl)-guanine; 9-(4-Hydroxy-3-hydroxymethylbut-1-yl)guanine; 9-(4-Hydroxy-3-(hydroxymethyl)butyl)guanine; Penciclovir, monosodium salt, monohydrate; Novartis brand OF penciclovir; Penciclovir, monosodium salt; Visfarm brand OF penciclovir; SB-CH Brand OF penciclovir; Penciclovir visfarm; Penciclovirum; penciclovir; Vectavir; Denavir; PE2; PCV; BRL 39123; VSA 671



数据库引用编号

37 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

  • Andreas Ärlemalm, Anders Helldén, Louise Karlsson, Björn Carlsson. Rapid determination of acyclovir, its main metabolite 9-carboxymethoxymethylguanine, ganciclovir, and penciclovir in human serum using LC-MS/MS. Biomedical chromatography : BMC. 2022 Apr; 36(4):e5315. doi: 10.1002/bmc.5315. [PMID: 34981553]
  • Khaled M Hosny, Amal M Sindi, Hala M Alkhalidi, Mallesh Kurakula, Nabil K Alruwaili, Nabil A Alhakamy, Walaa A Abualsunun, Rana B Bakhaidar, Rahaf H Bahmdan, Waleed Y Rizg, Sarah A Ali, Wesam H Abdulaal, Majed S Nassar, Mohammed S Alsuabeyl, Adel F Alghaith, Sultan Alshehri. Oral gel loaded with penciclovir-lavender oil nanoemulsion to enhance bioavailability and alleviate pain associated with herpes labialis. Drug delivery. 2021 Dec; 28(1):1043-1054. doi: 10.1080/10717544.2021.1931561. [PMID: 34060397]
  • Dallas Bednarczyk. Passive Influx and Ion Trapping Are More Relevant to the Cellular Accumulation of Highly Permeable Low-Molecular-Weight Acidic Drugs than Is Organic Anion Transporter 2. Drug metabolism and disposition: the biological fate of chemicals. 2021 08; 49(8):648-657. doi: 10.1124/dmd.121.000425. [PMID: 34031139]
  • Alexander Simonis, Sebastian J Theobald, Gerd Fätkenheuer, Jan Rybniker, Jakob J Malin. A comparative analysis of remdesivir and other repurposed antivirals against SARS-CoV-2. EMBO molecular medicine. 2021 01; 13(1):e13105. doi: 10.15252/emmm.202013105. [PMID: 33015938]
  • Santosh K Maurya, Akhilesh Kumar Maurya, Nidhi Mishra, Hifzur R Siddique. Virtual screening, ADME/T, and binding free energy analysis of anti-viral, anti-protease, and anti-infectious compounds against NSP10/NSP16 methyltransferase and main protease of SARS CoV-2. Journal of receptor and signal transduction research. 2020 Dec; 40(6):605-612. doi: 10.1080/10799893.2020.1772298. [PMID: 32476594]
  • Namrta Choudhry, Xin Zhao, Dan Xu, Mark Zanin, Weisan Chen, Zifeng Yang, Jianxin Chen. Chinese Therapeutic Strategy for Fighting COVID-19 and Potential Small-Molecule Inhibitors against Severe Acute Respiratory Syndrome Coronavirus 2 (SARS-CoV-2). Journal of medicinal chemistry. 2020 11; 63(22):13205-13227. doi: 10.1021/acs.jmedchem.0c00626. [PMID: 32845145]
  • Carmen Gil, Tiziana Ginex, Inés Maestro, Vanesa Nozal, Lucía Barrado-Gil, Miguel Ángel Cuesta-Geijo, Jesús Urquiza, David Ramírez, Covadonga Alonso, Nuria E Campillo, Ana Martinez. COVID-19: Drug Targets and Potential Treatments. Journal of medicinal chemistry. 2020 11; 63(21):12359-12386. doi: 10.1021/acs.jmedchem.0c00606. [PMID: 32511912]
  • Qianni Duan, Tong Liu, Ping Yuan, Cong Huang, Qingqing Shao, Lijun Xu, Jun Sun, Guangyin Huang, Zhuo Chen. Antiviral effect of Chinese herbal prescription JieZe-1 on adhesion and penetration of VK2/E6E7 with herpes simplex viruses type 2. Journal of ethnopharmacology. 2020 Mar; 249(?):112405. doi: 10.1016/j.jep.2019.112405. [PMID: 31743766]
  • Jill C Covert, Sara M Thomasy, Helen Kado-Fong, Leslie N Kon, Philip H Kass, Christopher M Reilly, Michael R Lappin, Barry J Margulies, David J Maggs. Pilot Study of the Safety and Tolerability of a Subconjunctival Penciclovir Implant in Cats Experimentally Infected with Herpesvirus. Journal of ocular pharmacology and therapeutics : the official journal of the Association for Ocular Pharmacology and Therapeutics. 2019 Jan; 35(1):38-49. doi: 10.1089/jop.2018.0043. [PMID: 30562134]
  • Caroline Gracielle Torres Ferreira, Mateus Gandra Campos, Daniele Mendes Felix, Marcus Rebouças Santos, Otávio Valério de Carvalho, Marisa Alves Nogueira Diaz, Juliana Lopes Rangel Fietto, Gustavo Costa Bressan, Abelardo Silva-Júnior, Márcia Rogéria de Almeida. Evaluation of the antiviral activities of Bacharis dracunculifolia and quercetin on Equid herpesvirus 1 in a murine model. Research in veterinary science. 2018 Oct; 120(?):70-77. doi: 10.1016/j.rvsc.2018.09.001. [PMID: 30267998]
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  • Ali S Abdelhameed, Ahmed H Bakheit, Fahad M Almutairi, Haitham AlRabiah, Adnan A Kadi. Biophysical and In Silico Studies of the Interaction between the Anti-Viral Agents Acyclovir and Penciclovir, and Human Serum Albumin. Molecules (Basel, Switzerland). 2017 Nov; 22(11):. doi: 10.3390/molecules22111906. [PMID: 29113080]
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  • A Paige Brock, Ramiro Isaza, Robert P Hunter, Laura K Richman, Richard J Montali, Dennis L Schmitt, David E Koch, William A Lindsay. Estimates of the pharmacokinetics of famciclovir and its active metabolite penciclovir in young Asian elephants (Elephas maximus). American journal of veterinary research. 2012 Dec; 73(12):1996-2000. doi: 10.2460/ajvr.73.12.1996. [PMID: 23176429]
  • Sara M Thomasy, Jill C Covert, Scott D Stanley, David J Maggs. Pharmacokinetics of famciclovir and penciclovir in tears following oral administration of famciclovir to cats: a pilot study. Veterinary ophthalmology. 2012 Sep; 15(5):299-306. doi: 10.1111/j.1463-5224.2011.00984.x. [PMID: 22339892]
  • Sara M Thomasy, Ted Whittem, Jerry L Bales, Marcus Ferrone, Scott D Stanley, David J Maggs. Pharmacokinetics of penciclovir in healthy cats following oral administration of famciclovir or intravenous infusion of penciclovir. American journal of veterinary research. 2012 Jul; 73(7):1092-9. doi: 10.2460/ajvr.73.7.1092. [PMID: 22738064]
  • Yaofeng Cheng, Arpine Vapurcuyan, Mohammad Shahidullah, Lauren M Aleksunes, Ryan M Pelis. Expression of organic anion transporter 2 in the human kidney and its potential role in the tubular secretion of guanine-containing antiviral drugs. Drug metabolism and disposition: the biological fate of chemicals. 2012 Mar; 40(3):617-24. doi: 10.1124/dmd.111.042036. [PMID: 22190696]
  • Lucila Cassino, Silvina Benetti, Fabian Fay, Hugo Tanno, Jorge Quarleri. Unsuccessful therapy with adefovir and entecavir-tenofovir in a patient with chronic hepatitis B infection with previous resistance to lamivudine: a fourteen-year evolution of hepatitis B virus mutations. BMC infectious diseases. 2011 Jun; 11(?):178. doi: 10.1186/1471-2334-11-178. [PMID: 21696601]
  • Stan L Block, Ram Yogev, Felix Waldmeier, Kamal Hamed. Safety and pharmacokinetics of a single 1500-mg dose of famciclovir in adolescents with recurrent herpes labialis. The Pediatric infectious disease journal. 2011 Jun; 30(6):525-8. doi: 10.1097/inf.0b013e3182067cee. [PMID: 21178655]
  • Ravi Kanneti, Dasandi Bhavesh, Dharmesh Paramar, R Shivaprakash, Parloop A Bhatt. Determination of penciclovir in human plasma by liquid chromatography-electrospray ionization tandem mass spectrometry: application to a clinical pharmacokinetic study. Biomedical chromatography : BMC. 2011 Apr; 25(4):458-65. doi: 10.1002/bmc.1468. [PMID: 21374647]
  • Sara M Thomasy, Christine C Lim, Christopher M Reilly, Philip H Kass, Michael R Lappin, David J Maggs. Evaluation of orally administered famciclovir in cats experimentally infected with feline herpesvirus type-1. American journal of veterinary research. 2011 Jan; 72(1):85-95. doi: 10.2460/ajvr.72.1.85. [PMID: 21194340]
  • Karl Y Hostetler. Synthesis and early development of hexadecyloxypropylcidofovir: an oral antipoxvirus nucleoside phosphonate. Viruses. 2010 Oct; 2(10):2213-2225. doi: 10.3390/v2102213. [PMID: 21994617]
  • Koji Tsujimura, Masayuki Yamada, Shun-ichi Nagata, Takashi Yamanaka, Manabu Nemoto, Takashi Kondo, Masahiko Kurosawa, Tomio Matsumura. Pharmacokinetics of penciclovir after oral administration of its prodrug famciclovir to horses. The Journal of veterinary medical science. 2010 Mar; 72(3):357-61. doi: 10.1292/jvms.09-0350. [PMID: 19959884]
  • Kayode Ogungbenro, Ivan Matthews, Michael Looby, Guenther Kaiser, Gordon Graham, Leon Aarons. Population pharmacokinetics and optimal design of paediatric studies for famciclovir. British journal of clinical pharmacology. 2009 Oct; 68(4):546-60. doi: 10.1111/j.1365-2125.2009.03479.x. [PMID: 19843058]
  • Manthena V S Varma, Bo Feng, R Scott Obach, Matthew D Troutman, Jonathan Chupka, Howard R Miller, Ayman El-Kattan. Physicochemical determinants of human renal clearance. Journal of medicinal chemistry. 2009 Aug; 52(15):4844-52. doi: 10.1021/jm900403j. [PMID: 19445515]
  • Dennis R Weller, Henry H Balfour, Heather E Vezina. Simultaneous determination of acyclovir, ganciclovir, and (R)-9-[4-hydroxy-2-(hydroxymethyl)butyl]guanine in human plasma using high-performance liquid chromatography. Biomedical chromatography : BMC. 2009 Aug; 23(8):822-7. doi: 10.1002/bmc.1192. [PMID: 19358150]
  • Deborah Y Chong, Mark W Johnson, Tony H Huynh, Edward F Hall, Grant M Comer, Douglas N Fish. Vitreous penetration of orally administered famciclovir. American journal of ophthalmology. 2009 Jul; 148(1):38-42.e1. doi: 10.1016/j.ajo.2009.02.010. [PMID: 19375688]
  • Qingzhi Lv, Aihua Yu, Yanwei Xi, Houli Li, Zhimei Song, Jing Cui, Fengliang Cao, Guangxi Zhai. Development and evaluation of penciclovir-loaded solid lipid nanoparticles for topical delivery. International journal of pharmaceutics. 2009 May; 372(1-2):191-8. doi: 10.1016/j.ijpharm.2009.01.014. [PMID: 19429280]
  • Charles G Knutson, Emily H Rubinson, Dapo Akingbade, Carolyn S Anderson, Donald F Stec, Katya V Petrova, Ivan D Kozekov, F Peter Guengerich, Carmelo J Rizzo, Lawrence J Marnett. Oxidation and glycolytic cleavage of etheno and propano DNA base adducts. Biochemistry. 2009 Feb; 48(4):800-9. doi: 10.1021/bi801654j. [PMID: 19132922]
  • Yongyu Pan, Xinxing Gao, Na Guo, Junming Li, Xingjie Guo. HPLC method for the determination of penciclovir in human plasma and application to a bioequivalence study. Journal of chromatographic science. 2008 Oct; 46(9):819-22. doi: 10.1093/chromsci/46.9.819. [PMID: 19007485]
  • R Scott Obach, Franco Lombardo, Nigel J Waters. Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds. Drug metabolism and disposition: the biological fate of chemicals. 2008 Jul; 36(7):1385-405. doi: 10.1124/dmd.108.020479. [PMID: 18426954]
  • Islam T M Hussein, Rebecca V Menashy, Hugh J Field. Penciclovir is a potent inhibitor of feline herpesvirus-1 with susceptibility determined at the level of virus-encoded thymidine kinase. Antiviral research. 2008 Jun; 78(3):268-74. doi: 10.1016/j.antiviral.2007.10.015. [PMID: 18325606]
  • Yi-jun Dao, Zheng Jiao, Ming-kang Zhong. Simultaneous determination of aciclovir, ganciclovir, and penciclovir in human plasma by high-performance liquid chromatography with fluorescence detection. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2008 May; 867(2):270-6. doi: 10.1016/j.jchromb.2008.04.022. [PMID: 18468495]
  • Sara M Thomasy, David J Maggs, Nicole K Moulin, Scott D Stanley. Pharmacokinetics and safety of penciclovir following oral administration of famciclovir to cats. American journal of veterinary research. 2007 Nov; 68(11):1252-8. doi: 10.2460/ajvr.68.11.1252. [PMID: 17975982]
  • Heon-Woo Lee, Ji-Hyung Seo, Kyung-Tae Lee. Development and validation of a high-performance liquid chromatography-tandem mass spectrometry for the determination of penciclovir in human plasma: application to a bioequivalence study. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2007 Jun; 852(1-2):382-8. doi: 10.1016/j.jchromb.2007.01.044. [PMID: 17324644]
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