Ibutilide (BioDeep_00000006591)

 

Secondary id: BioDeep_00001868052

human metabolite blood metabolite Chemicals and Drugs


代谢物信息卡片


N-(4-{4-[ethyl(heptyl)amino]-1-hydroxybutyl}phenyl)methanesulfonamide

化学式: C20H36N2O3S (384.2447)
中文名称: 伊布利特
谱图信息: 最多检出来源 Homo sapiens(blood) 93.81%

分子结构信息

SMILES: CCCCCCCN(CC)CCCC(C1=CC=C(C=C1)NS(=O)(=O)C)O
InChI: InChI=1S/C20H36N2O3S/c1-4-6-7-8-9-16-22(5-2)17-10-11-20(23)18-12-14-19(15-13-18)21-26(3,24)25/h12-15,20-21,23H,4-11,16-17H2,1-3H3

描述信息

Ibutilide is only found in individuals that have used or taken this drug. It is a Class III antiarrhythmic agent that is indicated for acute cardioconversion of atrial fibrillation and atrial flutter of a recent onset to sinus rhythm. [Wikipedia]Ibutilide is a pure class III antiarrhythmic drug, used intravenously against atrial flutter and fibrillation. At a cellular level it exerts two main actions: induction of a persistent Na+ current sensitive to dihydropyridine Ca2+ channel blockers and potent inhibition of the cardiac rapid delayed rectifier K+ current, by binding within potassium channel pores. In other words, Ibutilide binds to and alters the activity of hERG potassium channels, delayed inward rectifier potassium (IKr) channels and L-type (dihydropyridine sensitive) calcium channels
C - Cardiovascular system > C01 - Cardiac therapy > C01B - Antiarrhythmics, class i and iii > C01BD - Antiarrhythmics, class iii
C78274 - Agent Affecting Cardiovascular System > C47793 - Antiarrhythmic Agent
D002317 - Cardiovascular Agents > D000889 - Anti-Arrhythmia Agents
C93038 - Cation Channel Blocker

同义名列表

11 个代谢物同义名

N-(4-{4-[ethyl(heptyl)amino]-1-hydroxybutyl}phenyl)methanesulfonamide; N-(4-(4-(ethylheptylamino)-1-Hydroxybutyl)phenyl)methanesulfonamide; Ibutilide, fumarate salt (2:1), (+-)-isomer; Ibutilide, fumarate salt (2:1), (+)-isomer; Ibutilide, (+-)-isomer; Ibutilide, (+)-isomer; Ibutilide, (-)-isomer; Ibutilide fumarate; Ibutilide; Corvert; Ibutilide



数据库引用编号

19 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
Cytoplasm 8 ABCB1, AXIN2, BCL2, CASP12, CASP3, CASP9, GJA1, KCNQ1
Peripheral membrane protein 1 CAV1
Endoplasmic reticulum membrane 6 ATF6, BCL2, CALU, CAV1, GJA1, SLC33A1
Nucleus 6 ATF6, AXIN2, BCL2, CASP3, CASP9, GJA1
cytosol 8 ATF6, AXIN2, BCL2, CASP3, CASP9, GJA1, KCNN4, TNNI3
dendrite 1 KCNH1
centrosome 1 AXIN2
nucleoplasm 4 ATF6, CASP3, GJA1, SCNN1G
RNA polymerase II transcription regulator complex 1 ATF6
Cell membrane 8 ABCB1, CAV1, GJA1, KCNH1, KCNH2, KCNJ2, KCNN4, KCNQ1
ruffle membrane 1 KCNN4
Cell projection, axon 1 KCNH1
Early endosome membrane 2 CAV1, KCNH1
Multi-pass membrane protein 11 ABCB1, CACNA1I, GJA1, KCNA3, KCNH1, KCNH2, KCNJ2, KCNN4, KCNQ1, SCNN1G, SLC33A1
Golgi apparatus membrane 2 ATF6, CAV1
cell cortex 1 CAV1
cell junction 1 GJA1
cell surface 2 ABCB1, KCNH2
glutamatergic synapse 3 CASP3, KCNA3, KCNJ2
Golgi apparatus 4 ATF6, CALU, CAV1, GJA1
Golgi membrane 4 ATF6, CAV1, GJA1, SLC33A1
neuronal cell body 4 CASP3, KCNJ2, KCNN4, KCNQ1
presynaptic membrane 2 KCNA3, KCNH1
Lysosome 1 KCNQ1
endosome 1 CAV1
plasma membrane 13 ABCB1, AXIN2, CACNA1I, CAV1, GJA1, KCNA3, KCNH1, KCNH2, KCNJ2, KCNN4, KCNQ1, SCNN1G, SLC33A1
Membrane 13 ABCB1, ATF6, BCL2, CACNA1I, CALU, CAV1, KCNA3, KCNH1, KCNH2, KCNJ2, KCNN4, KCNQ1, SLC33A1
apical plasma membrane 5 ABCB1, CAV1, GJA1, KCNQ1, SCNN1G
axon 2 KCNA3, KCNH1
basolateral plasma membrane 2 CAV1, KCNQ1
caveola 1 CAV1
extracellular exosome 2 ABCB1, SCNN1G
endoplasmic reticulum 7 ATF6, BCL2, CALU, CASP12, CAV1, GJA1, KCNQ1
perinuclear region of cytoplasm 3 CAV1, KCNA3, KCNH2
gap junction 1 GJA1
intercalated disc 2 GJA1, KCNJ2
mitochondrion 3 BCL2, CASP9, GJA1
protein-containing complex 3 BCL2, CASP9, CAV1
intracellular membrane-bounded organelle 2 GJA1, KCNH1
postsynaptic density 1 CASP3
Secreted 1 CALU
extracellular region 1 CALU
Mitochondrion outer membrane 1 BCL2
Single-pass membrane protein 1 BCL2
mitochondrial outer membrane 1 BCL2
Nucleus membrane 1 BCL2
Bcl-2 family protein complex 1 BCL2
nuclear membrane 1 BCL2
external side of plasma membrane 1 SCNN1G
dendritic spine 1 KCNJ2
T-tubule 1 KCNJ2
perikaryon 1 KCNH1
beta-catenin destruction complex 1 AXIN2
cytoplasmic vesicle 1 CAV1
Early endosome 1 KCNQ1
Single-pass type II membrane protein 1 ATF6
vesicle 1 KCNN4
postsynaptic membrane 2 KCNA3, KCNJ2
Apical cell membrane 3 ABCB1, KCNQ1, SCNN1G
Cell projection, ruffle membrane 1 KCNN4
Membrane raft 4 CAV1, GJA1, KCNA3, KCNQ1
pore complex 1 BCL2
focal adhesion 2 CAV1, GJA1
Cell junction, gap junction 1 GJA1
connexin complex 1 GJA1
contractile muscle fiber 1 GJA1
fascia adherens 1 GJA1
intermediate filament 1 GJA1
lateral plasma membrane 2 GJA1, KCNQ1
Nucleus inner membrane 1 KCNH1
nuclear inner membrane 1 KCNH1
Late endosome 1 KCNQ1
sarcomere 1 TNNI3
neuron projection 2 KCNN4, KCNQ1
ciliary base 1 KCNQ1
cilium 1 CAV1
chromatin 1 ATF6
Golgi apparatus, trans-Golgi network 1 CAV1
Basolateral cell membrane 1 KCNQ1
[Isoform 2]: Cell membrane 1 KCNA3
nuclear envelope 1 ATF6
Lipid droplet 1 CAV1
Membrane, caveola 1 CAV1
monoatomic ion channel complex 3 KCNH1, KCNH2, KCNQ1
Cytoplasmic vesicle membrane 1 KCNQ1
sodium channel complex 1 SCNN1G
Cell projection, dendrite 1 KCNH1
Melanosome 1 CALU
Golgi-associated vesicle membrane 1 GJA1
Presynaptic cell membrane 1 KCNH1
myelin sheath 1 BCL2
inward rectifier potassium channel complex 1 KCNH2
voltage-gated potassium channel complex 6 KCNA3, KCNH1, KCNH2, KCNJ2, KCNN4, KCNQ1
endoplasmic reticulum lumen 1 CALU
voltage-gated calcium channel complex 1 CACNA1I
endocytic vesicle membrane 1 CAV1
transport vesicle 1 KCNQ1
tight junction 1 GJA1
postsynaptic density membrane 1 KCNH1
apoptosome 1 CASP9
calyx of Held 1 KCNA3
Sarcoplasmic reticulum lumen 1 CALU
external side of apical plasma membrane 1 ABCB1
death-inducing signaling complex 1 CASP3
[Isoform 1]: Cell membrane 1 KCNA3
acrosomal membrane 1 CAV1
cell-cell contact zone 1 GJA1
cardiac myofibril 1 TNNI3
troponin complex 1 TNNI3
BAD-BCL-2 complex 1 BCL2
[Processed cyclic AMP-dependent transcription factor ATF-6 alpha]: Nucleus 1 ATF6
cardiac Troponin complex 1 TNNI3
[Isoform 3]: Cytoplasm, perinuclear region 1 KCNA3
NLRP1 inflammasome complex 1 CASP12
lumenal side of membrane 1 KCNQ1
caveolar macromolecular signaling complex 1 CAV1
basolateral part of cell 1 KCNQ1
caspase complex 1 CASP9


文献列表

  • James E Tisdale, Heather A Jaynes, Brian R Overholser, Kevin M Sowinski, Mark D Fisch, Jo E Rodgers, Ahmed Aldemerdash, Chia-Chi Hsu, Nan Wang, Elena Tomaselli Muensterman, Vijay U Rao, Richard J Kovacs. Enhanced Response to Drug-Induced QT Interval Lengthening in Patients with Heart Failure with Preserved Ejection Fraction. Journal of cardiac failure. 2020 Sep; 26(9):781-785. doi: 10.1016/j.cardfail.2020.06.008. [PMID: 32592895]
  • Amit Malviya, Manish Kapoor, Rondeep Kumar Nath Sivam, Shakeel Ahamad Khan, Ruchi Pandey, Utpal Kumar, Tony Ete, Animesh Mishra. Ibutilide with magnesium for conversion of atrial fibrillation or flutter in rheumatic heart disease patients: Ibutilide with magnesium for chemical cardioversion of atrial fibrillation or flutter. Indian heart journal. 2020 Jul; 72(4):283-288. doi: 10.1016/j.ihj.2020.07.008. [PMID: 32861384]
  • 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]
  • James E Tisdale, Brian R Overholser, Kevin M Sowinski, Heather A Wroblewski, Kwadwo Amankwa, Steven Borzak, Joanna R Kingery, Rita Coram, Douglas P Zipes, David A Flockhart, Richard J Kovacs. Pharmacokinetics of ibutilide in patients with heart failure due to left ventricular systolic dysfunction. Pharmacotherapy. 2008 Dec; 28(12):1461-70. doi: 10.1592/phco.28.12.1461. [PMID: 19025427]
  • 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]
  • Yishi Li, Lei Tian, Yiling Huang, Lu Hua. Pharmacokinetic and pharmacodynamic properties of a single intravenous dose of ibutilide fumarate: a phase I, randomized, open-label, increasing-dose study in healthy Chinese men. Clinical therapeutics. 2007 Sep; 29(9):1957-66. doi: 10.1016/j.clinthera.2007.09.010. [PMID: 18035195]
  • Charles M Beasley, Malcolm I Mitchell, Alex A Dmitrienko, Jeffrey T Emmick, Wei Shen, Timothy M Costigan, Alun W Bedding, Michael A Turik, Arash Bakhtyari, Margaret R Warner, Jeremy N Ruskin, Louis R Cantilena, Robert A Kloner. The combined use of ibutilide as an active control with intensive electrocardiographic sampling and signal averaging as a sensitive method to assess the effects of tadalafil on the human QT interval. Journal of the American College of Cardiology. 2005 Aug; 46(4):678-87. doi: 10.1016/j.jacc.2005.05.036. [PMID: 16098435]
  • Lei Tian, Yishi Li, Yiling Huang, Fuhua Kuang, Feiou Li, Lu Hua. Sensitive method for the determination of ibutilide in human plasma by liquid chromatography-tandem mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2005 Feb; 816(1-2):81-5. doi: 10.1016/j.jchromb.2004.11.015. [PMID: 15664337]
  • Johann Reisinger, Edmund Gatterer, Wolfgang Lang, Thetis Vanicek, Geza Eisserer, Theresia Bachleitner, Christopher Niemeth, Friedrich Aicher, Wilhelm Grander, Georg Heinze, Peter Kühn, Peter Siostrzonek. Flecainide versus ibutilide for immediate cardioversion of atrial fibrillation of recent onset. European heart journal. 2004 Aug; 25(15):1318-24. doi: 10.1016/j.ehj.2004.04.030. [PMID: 15288159]
  • Ramesh M Gowda, Gopikrishna Punukollu, Ijaz A Khan, Sabrina L Wilbur, Balendu C Vasavada, Terrence J Sacchi. Ibutilide for pharmacological cardioversion of atrial fibrillation and flutter: impact of race on efficacy and safety. American journal of therapeutics. 2003 Jul; 10(4):259-63. doi: 10.1097/00045391-200307000-00005. [PMID: 12845389]
  • Michael F Caron, Jeffrey Kluger, James P Tsikouris, Arnold Ritvo, James S Kalus, C Michael White. Effects of intravenous magnesium sulfate on the QT interval in patients receiving ibutilide. Pharmacotherapy. 2003 Mar; 23(3):296-300. doi: 10.1592/phco.23.3.296.32109. [PMID: 12627926]
  • Weeranuj Yamreudeewong, Michael DeBisschop, Linda G Martin, Dennis L Lower. Potentially significant drug interactions of class III antiarrhythmic drugs. Drug safety. 2003; 26(6):421-38. doi: 10.2165/00002018-200326060-00004. [PMID: 12688833]
  • Anil Yadav, Melvin Scheinman. Atrial fibrillation in the elderly. The American journal of geriatric cardiology. 2003 Jan; 12(1):49-56. doi: 10.1111/j.1076-7460.2003.01754.x. [PMID: 12502916]
  • Marcus G Hennersdorf, Stefan M Perings, Christian Zühlke, Ulrich E Heidland, Christian Perings, Matthias P Heintzen, Bodo E Strauer. Conversion of recent-onset atrial fibrillation or flutter with ibutilide after amiodarone has failed. Intensive care medicine. 2002 Jul; 28(7):925-9. doi: 10.1007/s00134-002-1317-3. [PMID: 12122531]
  • S J Humphrey, M P Smith, C Y Hsu, R R Walters. Cardiovascular effects of the R- and S-enantiomers of ibutilide in conscious beagle dogs. Methods and findings in experimental and clinical pharmacology. 2001 Oct; 23(8):449-55. doi: 10.1358/mf.2001.23.8.662135. [PMID: 11838320]
  • A Eversole, W Hancock, T Johns, L M Lopez, C R Conti. Ibutilide: efficacy and safety in atrial fibrillation and atrial flutter in a general cardiology practice. Clinical cardiology. 2001 Jul; 24(7):521-5. doi: 10.1002/clc.4960240709. [PMID: 11444644]
  • A Vereckei, E Warman, R Mehra, D P Zipes. Comparison of the effects on drug concentrations, electrophysiologic parameters, and termination of atrial fibrillation in dogs when procainamide and ibutilide are delivered into the right atrium versus intravenously. Journal of cardiovascular electrophysiology. 2001 Mar; 12(3):330-6. doi: 10.1046/j.1540-8167.2001.00330.x. [PMID: 11291807]
  • S S Chugh, S B Johnson, D L Packer. Altered response to ibutilide in a heart failure model. Cardiovascular research. 2001 Jan; 49(1):94-102. doi: 10.1016/s0008-6363(00)00235-2. [PMID: 11121800]
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  • L V Buchanan, R J LeMay, R R Walters, C Y Hsu, M N Brunden, J K Gibson. Antiarrhythmic and electrophysiologic effects of intravenous ibutilide and sotalol in the canine sterile pericarditis model. Journal of cardiovascular electrophysiology. 1996 Feb; 7(2):113-9. doi: 10.1111/j.1540-8167.1996.tb00506.x. [PMID: 8853021]
  • C L Hsu, R R Walters. Assay of the enantiomers of ibutilide and artilide using solid-phase extraction, derivatization, and achiral-chiral column-switching high-performance liquid chromatography. Journal of chromatography. B, Biomedical applications. 1995 May; 667(1):115-28. doi: 10.1016/0378-4347(95)00005-4. [PMID: 7663674]