Dyphylline (BioDeep_00000001847)

 

Secondary id: BioDeep_00001867700

human metabolite blood metabolite PANOMIX_OTCML-2023 Chemicals and Drugs


代谢物信息卡片


7-(2,3-dihydroxypropyl)-1,3-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione

化学式: C10H14N4O4 (254.1015004)
中文名称: 二羟丙茶碱
谱图信息: 最多检出来源 Homo sapiens(blood) 0.2%

分子结构信息

SMILES: Cn1c(=O)c2c(ncn2CC(O)CO)n(C)c1=O
InChI: InChI=1S/C10H14N4O4/c1-12-8-7(9(17)13(2)10(12)18)14(5-11-8)3-6(16)4-15/h5-6,15-16H,3-4H2,1-2H3

描述信息

Dyphylline is only found in individuals that have used or taken this drug. It is a theophylline derivative with broncho- and vasodilator properties. It is used in the treatment of asthma, cardiac dyspnea, and bronchitis. [PubChem]The bronchodilatory action of dyphylline, as with other xanthines, is thought to be mediated through competitive inhibition of phosphodiesterase with a resulting increase in cyclic AMP producing relaxation of bronchial smooth muscle as well as antagonism of adenosine receptors.
R - Respiratory system > R03 - Drugs for obstructive airway diseases > R03D - Other systemic drugs for obstructive airway diseases > R03DA - Xanthines
D019141 - Respiratory System Agents > D018927 - Anti-Asthmatic Agents > D001993 - Bronchodilator Agents
C78273 - Agent Affecting Respiratory System > C29712 - Anti-asthmatic Agent > C319 - Bronchodilator
D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents
D004791 - Enzyme Inhibitors > D010726 - Phosphodiesterase Inhibitors
D002317 - Cardiovascular Agents > D014665 - Vasodilator Agents
C471 - Enzyme Inhibitor > C744 - Phosphodiesterase Inhibitor
KEIO_ID D183; [MS2] KO008931
KEIO_ID D183
Diphylline (Diprophylline) is a potent A1/A2 adenosine receptor antagonist and cyclic nucleotide phosphodiesterase inhibitor. Diphylline, a xanthine derivative, is a bronchodilator and vasodilator agent and has the potential for chronic bronchitis and emphysema[1][2].
Diphylline (Diprophylline) is a potent A1/A2 adenosine receptor antagonist and cyclic nucleotide phosphodiesterase inhibitor. Diphylline, a xanthine derivative, is a bronchodilator and vasodilator agent and has the potential for chronic bronchitis and emphysema[1][2].

同义名列表

35 个代谢物同义名

7-(2,3-dihydroxypropyl)-1,3-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione; 7-(2,3-Dihydroxypropyl)-3,7-dihydro-1,3-dimethyl-1H-purine-2,6-dione; 7-(2,3-Dihydroxypropyl)-1,3-dimethylxanthine; 1,3-Dimethyl-7-(2,3-dihydroxypropyl)xanthine; 7-(beta,gamma-Dihydroxypropyl)theophylline; (+-)-7-(2,3-Dihydroxypropyl)theophylline; 7-(Β,γ-dihydroxypropyl)theophylline; (1,2-Dihydroxy-3-propyl)thiophyllin; 7-(2,3-Dihydroxypropyl)theophylline; 7-(b,g-Dihydroxypropyl)theophylline; Dihydroxypropyl theophylline; Dihydroxypropyltheophylline; Wallace brand OF dyphylline; Savage brand OF dyphylline; Lunsco brand OF dyphylline; Hauck brand OF dyphylline; Major brand OF dyphylline; Dihydroxypropyl theopylin; Dilor brand OF dyphylline; (+-)-Diprophylline; (+-)-Dyphylline; Diprophyllinum; Diprophylline; Diprophyllin; Diprofilline; Dipropylline; Neothylline; Diprofillin; Diprofilina; dyphylline; Diphylline; Lufyllin; Dilin; Dylix; dT



数据库引用编号

25 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)

3 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

  • Paul H Hayashi, M Isabel Lucena, Robert J Fontana, Einar S Bjornsson, Guruprasad P Aithal, Huiman Barnhart, Andres Gonzalez-Jimenez, Qinghong Yang, Jiezhun Gu, Raul J Andrade, Jay H Hoofnagle. A revised electronic version of RUCAM for the diagnosis of DILI. Hepatology (Baltimore, Md.). 2022 07; 76(1):18-31. doi: 10.1002/hep.32327. [PMID: 35014066]
  • Jawad Ahmad, Huiman X Barnhart, Maurizio Bonacini, Marwan Ghabril, Paul H Hayashi, Joseph A Odin, Don C Rockey, Simona Rossi, Jose Serrano, Hans L Tillmann, David E Kleiner. Value of liver biopsy in the diagnosis of drug-induced liver injury. Journal of hepatology. 2022 05; 76(5):1070-1078. doi: 10.1016/j.jhep.2021.12.043. [PMID: 35074471]
  • Yining Wang, Sajjan Rajpoot, Pengfei Li, Marla Lavrijsen, Zhongren Ma, Nik Hirani, Uzma Saqib, Qiuwei Pan, Mirza S Baig. Repurposing dyphylline as a pan-coronavirus antiviral therapy. Future medicinal chemistry. 2022 05; 14(10):685-699. doi: 10.4155/fmc-2021-0311. [PMID: 35387498]
  • Naga Chalasani, Herbert L Bonkovsky, Jonathan G Stine, Jiezhun Gu, Huiman Barnhart, Elin Jacobsen, Einar Björnsson, Robert J Fontana, David E Kleiner, Jay H Hoofnagle. Clinical characteristics of antiepileptic-induced liver injury in patients from the DILIN prospective study. Journal of hepatology. 2022 Apr; 76(4):832-840. doi: 10.1016/j.jhep.2021.12.013. [PMID: 34953957]
  • 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]
  • Kerem Teralı, Buket Baddal, Hayrettin Ozan Gülcan. Prioritizing potential ACE2 inhibitors in the COVID-19 pandemic: Insights from a molecular mechanics-assisted structure-based virtual screening experiment. Journal of molecular graphics & modelling. 2020 11; 100(?):107697. doi: 10.1016/j.jmgm.2020.107697. [PMID: 32739642]
  • Tobie D Lee, Olivia W Lee, Kyle R Brimacombe, Lu Chen, Rajarshi Guha, Sabrina Lusvarghi, Bethilehem G Tebase, Carleen Klumpp-Thomas, Robert W Robey, Suresh V Ambudkar, Min Shen, Michael M Gottesman, Matthew D Hall. A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Molecular pharmacology. 2019 11; 96(5):629-640. doi: 10.1124/mol.119.115964. [PMID: 31515284]
  • Daniel J Warner, Hongming Chen, Louis-David Cantin, J Gerry Kenna, Simone Stahl, Clare L Walker, Tobias Noeske. Mitigating the inhibition of human bile salt export pump by drugs: opportunities provided by physicochemical property modulation, in silico modeling, and structural modification. Drug metabolism and disposition: the biological fate of chemicals. 2012 Dec; 40(12):2332-41. doi: 10.1124/dmd.112.047068. [PMID: 22961681]
  • Sinan Güres, Aleksander Mendyk, Renata Jachowicz, Przemysław Dorożyński, Peter Kleinebudde. Application of artificial neural networks (ANNs) and genetic programming (GP) for prediction of drug release from solid lipid matrices. International journal of pharmaceutics. 2012 Oct; 436(1-2):877-9. doi: 10.1016/j.ijpharm.2012.05.021. [PMID: 22728260]
  • Sinan Güres, Florence Siepmann, Juergen Siepmann, Peter Kleinebudde. Drug release from extruded solid lipid matrices: theoretical predictions and independent experiments. European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V. 2012 Jan; 80(1):122-9. doi: 10.1016/j.ejpb.2011.10.002. [PMID: 22008146]
  • Sinan Güres, Peter Kleinebudde. Dissolution from solid lipid extrudates containing release modifiers. International journal of pharmaceutics. 2011 Jun; 412(1-2):77-84. doi: 10.1016/j.ijpharm.2011.04.010. [PMID: 21515350]
  • Xiaofan Sui, Jin Sun, Haiyan Li, Yongjun Wang, Jianfang Liu, Xiaohong Liu, Wenping Zhang, Lijiang Chen, Zhonggui He. Prediction of volume of distribution values in human using immobilized artificial membrane partitioning coefficients, the fraction of compound ionized and plasma protein binding data. European journal of medicinal chemistry. 2009 Nov; 44(11):4455-60. doi: 10.1016/j.ejmech.2009.06.004. [PMID: 19586686]
  • 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]
  • Ping Li. [Clinical observation on shufei granule in improving right ventricular function of patients with chronic pulmonary heart disease]. Zhongguo Zhong xi yi jie he za zhi Zhongguo Zhongxiyi jiehe zazhi = Chinese journal of integrated traditional and Western medicine. 2006 Aug; 26(8):732-5. doi: ". [PMID: 16970099]
  • Hsin-Hua Yeh, Yuan-Han Yang, Su-Hwei Chen. Rapid determination of acyclovir in plasma and cerebrospinal fluid by micellar electrokinetic chromatography with direct sample injection and its clinical application. Electrophoresis. 2006 Feb; 27(4):819-26. doi: 10.1002/elps.200500586. [PMID: 16411274]
  • A De Sarro, S Grasso, M Zappala, F Nava, G De Sarro. Convulsant effects of some xanthine derivatives in genetically epilepsy-prone rats. Naunyn-Schmiedeberg's archives of pharmacology. 1997 Jul; 356(1):48-55. doi: 10.1007/pl00005027. [PMID: 9228189]
  • M Nadai, R Apichartpichean, T Hasegawa, T Nabeshima. Pharmacokinetics and the effect of probenecid on the renal excretion mechanism of diprophylline. Journal of pharmaceutical sciences. 1992 Oct; 81(10):1024-7. doi: 10.1002/jps.2600811014. [PMID: 1432614]
  • J A Morais, M C Neves, J R Silva, R Avila. Absorption of intra-bronchial diprophylline-methodology and preliminary results. European journal of drug metabolism and pharmacokinetics. 1992 Jul; 17(3):187-93. doi: 10.1007/bf03190144. [PMID: 1490487]
  • T Hasegawa, M Nadai, R Apichartpichean, I Muraoka, T Nabeshima, K Takagi. Pharmacokinetic characteristics of N7-substituted theophylline derivatives and their interaction with quinolone in rats. Journal of pharmaceutical sciences. 1991 Oct; 80(10):962-5. doi: 10.1002/jps.2600801012. [PMID: 1664467]
  • S J Czuczwar, M Gasior, W Janusz, B Szczepanik, D Włodarczyk, Z Kleinrok. Influence of different methylxanthines on the anticonvulsant action of common antiepileptic drugs in mice. Epilepsia. 1990 May; 31(3):318-23. doi: 10.1111/j.1528-1157.1990.tb05382.x. [PMID: 2344849]
  • F Tagliaro, R Dorizzi, A Frigerio, M Marigo. Non-extraction HPLC method for simultaneous measurement of dyphylline and doxofylline in serum. Clinical chemistry. 1990 Jan; 36(1):113-5. doi: . [PMID: 2297899]
  • M V Alvarez, A Ceballos, F Gonzalez Velasco, J M Cachaza, E L Mariño. Binding of theophylline, ethophylline and diprophylline to human serum albumin. Il Farmaco; edizione pratica. 1988 Jul; 43(7-8):259-65. doi: NULL. [PMID: 3234537]
  • V E Ryzhenkov, A M Chistiakova, J Wójcicki, L Samochowiec, R Daday. [Hypolipidemic effect of the new diprophylline derivative, [2-hydroxy-3-(theophylline-7-ol] propyl ester of 4-benzylhydroxybenzoic acid]. Voprosy meditsinskoi khimii. 1988 Jul; 34(4):109-12. doi: . [PMID: 3195124]
  • H P Huang, J W Ayres. Dyphylline prodrugs: plasma hydrolysis and dyphylline release in rabbits. Journal of pharmaceutical sciences. 1988 Feb; 77(2):104-9. doi: 10.1002/jps.2600770203. [PMID: 3361424]
  • J Wójcicki, L Samochowiec, R Dadej, M Jaworska, B Gawrońska-Szklarz, A Kownacka, V Ryshenkov, A Chistyakova, N Acsenova. Hypolipemic and potential antiatherosclerotic properties of diprophyllinyl-4-benzyloxybenzoate. Polish journal of pharmacology and pharmacy. 1987 Jul; 39(4):343-51. doi: ". [PMID: 3449807]
  • M Acara, E A Carr, E N Terry. Probenecid inhibition of the renal excretion of dyphylline in chicken, rat and man. The Journal of pharmacy and pharmacology. 1987 Jul; 39(7):526-30. doi: 10.1111/j.2042-7158.1987.tb03171.x. [PMID: 2886621]
  • M B Kester, C L Saccar, H C Mansmann. Microassay for the simultaneous determination of theophylline and dyphylline in serum by high-performance liquid chromatography. Journal of chromatography. 1987 Apr; 416(1):91-7. doi: 10.1016/0378-4347(87)80488-7. [PMID: 3597645]
  • M T Lopez-Vidriero, H Koral, M Clay, R G Taylor, R A Francis, M E Kitler, S W Clarke. Protective effect of methylxanthines against carbachol-induced bronchoconstriction in normal subjects. Respiration; international review of thoracic diseases. 1987; 51(4):277-84. doi: 10.1159/000195214. [PMID: 3310159]
  • H Magnussen, R Jörres, V Hartmann. Bronchodilator effect of theophylline preparations and aerosol fenoterol in stable asthma. Chest. 1986 Nov; 90(5):722-5. doi: 10.1378/chest.90.5.722. [PMID: 3533455]
  • H Magnussen, M Litt, G Reuss, P Stutz, R Jörres. [Comparison of the bronchodilator and protective effect of methylxanthines]. Deutsche medizinische Wochenschrift (1946). 1986 Jan; 111(1):15-9. doi: 10.1055/s-2008-1068392. [PMID: 3940830]
  • J Wójcicki, M Jaworska, L Samochowiec, A Hinek. The effect of amino acid derivative of clofibric acid (WKLB-5), and theophylline monoester of nicotinic acid (ME1) on the development of experimental atherosclerosis in rabbits. Polish journal of pharmacology and pharmacy. 1986 Jan; 38(1):77-84. doi: . [PMID: 3509959]
  • J W Ayres, E G Pearson, T W Riebold, S F Chang. Theophylline and dyphylline pharmacokinetics in the horse. American journal of veterinary research. 1985 Dec; 46(12):2500-6. doi: NULL. [PMID: 4083583]
  • A B Straughn, G C Wood, G Raghow, M C Meyer. Bioavailability of dyphylline and dyphylline-guaifenesin tablets in humans. Journal of pharmaceutical sciences. 1985 Mar; 74(3):335-7. doi: 10.1002/jps.2600740324. [PMID: 4009445]
  • K H Molz, Z B Salama, W Gielsdorf, H Jaeger, G Krejci. [Comparative studies on the tolerance of bioequivalent doses of intravenous methylxanthine preparations in healthy subjects]. Arzneimittel-Forschung. 1985; 35(3):626-9. doi: . [PMID: 4039588]
  • M Wenk, B Eggs, F Follath. Simultaneous determination of diprophylline, proxyphylline and theophylline in serum by reversed-phase high-performance liquid chromatography. Journal of chromatography. 1983 Sep; 276(2):341-8. doi: 10.1016/s0378-4347(00)85100-2. [PMID: 6630383]
  • J J Stablein, S S Samaan, S C Bukantz, R F Lockey. Pharmacokinetics and bioavailability of three dyphylline preparations. European journal of clinical pharmacology. 1983; 25(2):281-3. doi: 10.1007/bf00543805. [PMID: 6628514]
  • G Loytved, K Werdermann, W Jorde, W Petro. Clinical efficiency of neobiphyllineR-studies on lung function and serum levels after rectal application of a combination of methyl-xanthines. Agents and actions. Supplements. 1983; 13(?):131-40. doi: NULL. [PMID: 6346832]
  • N Paterson. High-performance liquid chromatographic method for the determination of diprophylline in human serum. Journal of chromatography. 1982 Nov; 232(2):450-5. doi: 10.1016/s0378-4347(00)84189-4. [PMID: 7153295]
  • C N Ou, V L Frawley. Theophylline, dyphylline, caffeine, acetaminophen, salicylate, acetylsalicylate, procainamide, and N-acetylprocainamide determined in serum with a single liquid-chromatographic assay. Clinical chemistry. 1982 Oct; 28(10):2157-60. doi: . [PMID: 6181911]
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  • C H Jarboe, L N Cook, I Malesic, J Fleischaker. Dyphylline elimination kinetics in lactating women: blood to milk transfer. Journal of clinical pharmacology. 1981 Oct; 21(10):405-10. doi: 10.1002/j.1552-4604.1981.tb01741.x. [PMID: 7309903]
  • J G Ufkes, R S Leeuwin, M Ottenhof, A Zeegers, J Zuidema. Efficacy of theophylline and its N-7-substituted derivatives in experimentally induced bronchial asthma in the guinea-pig. Archives internationales de pharmacodynamie et de therapie. 1981 Oct; 253(2):301-14. doi: . [PMID: 7325766]
  • C A Hirshman, C Lawyer, H Downes, A Farbood, R Rodgers, N Gerber. Dyphylline aerosol attenuates antigen-induced bronchoconstriction in experimental canine asthma. Chest. 1981 Apr; 79(4):454-8. doi: 10.1378/chest.79.4.454. [PMID: 7226910]
  • K H Valia, C A Hartman, N Kucharczyk, R D Sofia. Simultaneous determination of dyphylline and theophylline in human plasma by high-performance liquid chromatography. Journal of chromatography. 1980 Nov; 221(1):170-5. doi: 10.1016/s0378-4347(00)81021-x. [PMID: 7451620]
  • C H Lawyer, E J Bardana, R Rodgers, N Gerber. Utilization of intravenous dihydroxypropyl theophylline (dyphylline) in an aminophylline-sensitive patient, and its pharmacokinetic comparison with theophylline. The Journal of allergy and clinical immunology. 1980 May; 65(5):353-7. doi: 10.1016/0091-6749(80)90212-2. [PMID: 7372953]
  • P K Ng, R A Locock. Comparative pharmacokinetics of theophylline and dyphylline following intravenous injection in rabbits. Research communications in chemical pathology and pharmacology. 1979 Dec; 26(3):509-24. doi: . [PMID: 523786]
  • K J Simons, F E Simons. Urinary excretion of dyphylline in humans. Journal of pharmaceutical sciences. 1979 Oct; 68(10):1327-9. doi: 10.1002/jps.2600681038. [PMID: 512873]
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