Verapamil (BioDeep_00000001523)

 

Secondary id: BioDeep_00000229723, BioDeep_00000398575

human metabolite blood metabolite Chemicals and Drugs natural product


代谢物信息卡片


2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile

化学式: C27H38N2O4 (454.2831)
中文名称: 维拉帕米
谱图信息: 最多检出来源 Homo sapiens(blood) 37.25%

分子结构信息

SMILES: c(c2OC)(OC)ccc(c2)C(CCCN(C)CCc(c1)cc(OC)c(OC)c1)(C(C)C)C#N
InChI: InChI=1S/C27H38N2O4/c1-20(2)27(19-28,22-10-12-24(31-5)26(18-22)33-7)14-8-15-29(3)16-13-21-9-11-23(30-4)25(17-21)32-6/h9-12,17-18,20H,8,13-16H2,1-7H3

描述信息

Verapamil is only found in individuals that have used or taken this drug. Verapamil is a calcium channel blocker that is a class IV anti-arrhythmia agent. [PubChem]Verapamil inhibits voltage-dependent calcium channels. Specifically, its effect on L-type calcium channels in the heart causes a reduction in ionotropy and chronotropy, thuis reducing heart rate and blood pressure. Verapamils mechanism of effect in cluster headache is thought to be linked to its calcium-channel blocker effect, but which channel subtypes are involved is presently not known. [PubChem] Calcium channel antagonists can be quite toxic. In the management of poisoning, early recognition is critical. Calcium channel antagonists are frequently prescribed, and the potential for serious morbidity and mortality with over dosage is significant. Ingestion of these agents should be suspected in any patient who presents in an overdose situation with unexplained hypotension and conduction abnormalities. The potential for toxicity should be noted in patients with underlying hepatic or renal dysfunction who are receiving therapeutic doses. (PMID 8213877).
C - Cardiovascular system > C08 - Calcium channel blockers > C08D - Selective calcium channel blockers with direct cardiac effects > C08DA - Phenylalkylamine derivatives
C78274 - Agent Affecting Cardiovascular System > C270 - Antihypertensive Agent > C333 - Calcium Channel Blocker
A calcium channel blocker that is a class IV anti-arrhythmia agent. -- Pubchem;
COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials
D002317 - Cardiovascular Agents > D002121 - Calcium Channel Blockers
D002317 - Cardiovascular Agents > D000889 - Anti-Arrhythmia Agents
D002317 - Cardiovascular Agents > D014665 - Vasodilator Agents
D000077264 - Calcium-Regulating Hormones and Agents
CONFIDENCE standard compound; INTERNAL_ID 8557
CONFIDENCE standard compound; INTERNAL_ID 2260
CONFIDENCE standard compound; INTERNAL_ID 4081
D049990 - Membrane Transport Modulators
C93038 - Cation Channel Blocker
KEIO_ID V021; [MS2] KO009311
Corona-virus
KEIO_ID V021
Coronavirus
SARS-CoV-2
COVID-19
SARS-CoV
COVID19
SARS2
SARS

同义名列表

122 个代谢物同义名

2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile; Sandoz brand OF verapamil; Hydrochloride, verapamil; Verapamil hydrochloride; Verapamil sandoz brand; Verapamil NM pharma; Verapamil injection; CP-165331Verapamil; Hexasoptin retard; Verapamil henning; D-365Iproveratril; Verapress 240 SR; Verapamil basics; Verapamil nordic; Verapamil ebewe; Verapamil riker; CP-16533-1Calan; Verapamil verla; Calaptin 240 SR; Civicor retard; Verapamil acis; Isoptin retard; Verapamil atid; Vera-sanorania; Manidon retard; Cardioprotect; Dilacoran hta; Verapamil-abz; Verapamil MSD; Veroptinstada; Verapamil HCL; dexverapamil; Iproveratril; Verapamil SR; Verapamil NM; Verapamil PB; Cardiabeltin; Novapamyl LP; Verapamil al; Novo-veramil; Veracaps SR; Cordilox SR; Cardibeltin; Verapamilum; Verelan PM; Veratensin; Isoptin SR; Verapamilo; Verelan SR; Cardiagutt; Durasoptin; Hexasoptin; Arpamyl LP; Verasifar; Covera-HS; delta-365; Verahexal; Magotiron; Apo-verap; Praecicor; Jenapamil; Robatelan; Verapamil; Dilacoran; Berkatens; Hormitol; Verdilac; Dignover; Isoptino; Corpamil; Vasopten; Nu-verap; Calaptin; Verpamil; Isoptine; Lekoptin; Finoptin; Isotopin; Falicard; Cordilox; Ikapress; Vetrimil; Verabeta; Calan SR; Verelan; Vasolan; Caveril; Inselon; Izoptin; Veracor; Manidon; Geangin; Securon; Coraver; Civicor; Veramil; Harteze; Isoptin; Lodixal; Veramex; Veraloc; Verasal; Verapin; Vasomil; Vortac; Univer; Flamon; Akilen; Univex; Ikacor; Calcan; Quasar; Elthon; Anpec; Ormil; veraβ; Calan; Rapam; Tarka; D-365; Verapamil; Verapamil



数据库引用编号

41 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)

6 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 6 ABCB1, ACE, AXIN2, CYP3A4, MYLK, PGP
Endoplasmic reticulum membrane 2 CYP1A2, CYP3A4
Mitochondrion membrane 1 ABCG2
Nucleus 2 AXIN2, PLCZ1
cytosol 4 AXIN2, MYLK, PLCZ1, PRKCQ
mitochondrial membrane 1 ABCG2
centrosome 1 AXIN2
nucleoplasm 4 ABCG2, ATP2B1, PLCZ1, SCNN1G
Cell membrane 7 ABCB1, ABCC1, ABCG2, ACE, ADRB3, ATP2B1, KCNH2
Cleavage furrow 1 MYLK
lamellipodium 1 MYLK
Multi-pass membrane protein 8 ABCB1, ABCC1, ABCG2, ADRB3, ATP2B1, KCNA3, KCNH2, SCNN1G
Synapse 2 ATP2B1, MYLK
cell surface 2 ABCB1, KCNH2
glutamatergic synapse 2 ATP2B1, KCNA3
presynaptic membrane 2 ATP2B1, KCNA3
Lysosome 1 ACE
endosome 1 ACE
plasma membrane 16 ABCB1, ABCC1, ABCG2, ACE, ADRB3, ATP2B1, AXIN2, GCG, IFNLR1, KCNA3, KCNH2, KNG1, MYLK, PRKCQ, REN, SCNN1G
synaptic vesicle membrane 1 ATP2B1
Membrane 10 ABCB1, ABCC1, ABCG2, ACE, ATP2B1, CYP3A4, IFNLR1, KCNA3, KCNH2, REN
apical plasma membrane 4 ABCB1, ABCC1, ABCG2, SCNN1G
axon 1 KCNA3
basolateral plasma membrane 2 ABCC1, ATP2B1
extracellular exosome 6 ABCB1, ABCC1, ACE, ATP2B1, KNG1, SCNN1G
extracellular space 4 ACE, GCG, KNG1, REN
perinuclear region of cytoplasm 3 KCNA3, KCNH2, PLCZ1
intracellular membrane-bounded organelle 3 ATP2B1, CYP1A2, CYP3A4
Microsome membrane 2 CYP1A2, CYP3A4
pronucleus 1 PLCZ1
Single-pass type I membrane protein 2 ACE, IFNLR1
Secreted 3 ACE, GCG, REN
extracellular region 4 ACE, GCG, KNG1, REN
centriolar satellite 1 PRKCQ
Cytoplasmic vesicle, secretory vesicle, synaptic vesicle membrane 1 ATP2B1
external side of plasma membrane 2 ACE, SCNN1G
actin cytoskeleton 1 MYLK
beta-catenin destruction complex 1 AXIN2
nucleolus 1 PLCZ1
apical part of cell 1 REN
postsynaptic membrane 1 KCNA3
Apical cell membrane 3 ABCB1, ABCG2, SCNN1G
Cell projection, lamellipodium 1 MYLK
Cytoplasm, perinuclear region 1 PLCZ1
Membrane raft 2 ABCG2, KCNA3
collagen-containing extracellular matrix 1 KNG1
lateral plasma membrane 2 ABCC1, ATP2B1
receptor complex 1 ADRB3
cell projection 1 ATP2B1
Secreted, extracellular space 1 KNG1
brush border membrane 2 ABCG2, ACE
blood microparticle 1 KNG1
sperm midpiece 1 ACE
Basolateral cell membrane 1 ATP2B1
[Isoform 2]: Cell membrane 1 KCNA3
monoatomic ion channel complex 1 KCNH2
sodium channel complex 1 SCNN1G
Presynaptic cell membrane 1 ATP2B1
stress fiber 1 MYLK
basal plasma membrane 2 ABCC1, ACE
inward rectifier potassium channel complex 1 KCNH2
voltage-gated potassium channel complex 2 KCNA3, KCNH2
secretory granule lumen 1 GCG
endoplasmic reticulum lumen 2 GCG, KNG1
platelet alpha granule lumen 1 KNG1
immunological synapse 2 ATP2B1, PRKCQ
aggresome 1 PRKCQ
calyx of Held 1 KCNA3
Cytoplasm, cytoskeleton, stress fiber 1 MYLK
external side of apical plasma membrane 2 ABCB1, ABCG2
[Isoform 1]: Cell membrane 1 KCNA3
[Glucagon-like peptide 1]: Secreted 1 GCG
sperm head 1 PLCZ1
photoreceptor ribbon synapse 1 ATP2B1
[Angiotensin-converting enzyme, soluble form]: Secreted 1 ACE
[Isoform Testis-specific]: Cell membrane 1 ACE
[Isoform 3]: Cytoplasm, perinuclear region 1 KCNA3
interleukin-28 receptor complex 1 IFNLR1


文献列表

  • Emrah Gün, Mahmut Çiçek, Mustafa Kafalı, Hüsnü Demir, İlknur Arslan, Tanıl Kendirli. Use of Intravenous Lipid Emulsion Therapy and Insulin in a Case of Tarka Intoxication. WMJ : official publication of the State Medical Society of Wisconsin. 2024 May; 123(2):144-146. doi: ". [PMID: 38718248]
  • Najeeb Ur Rehman, Mohd Nazam Ansari, Wasim Ahmad, Abuzer Ali. Calcium Channel Inhibitory Effect of Marjoram (Origanum majorana L.): Its Medicinal Use in Diarrhea and Gut Hyperactivity. Frontiers in bioscience (Landmark edition). 2024 Feb; 29(2):47. doi: 10.31083/j.fbl2902047. [PMID: 38420828]
  • Mohd Nazam Ansari, Najeeb Ur Rehman, Abdul Samad, Wasim Ahmad. Pharmacological Basis for the Antidiarrheal and Antispasmodic Effects of Cuminaldehyde in Experimental Animals: In Silico, Ex Vivo and In Vivo Studies. Frontiers in bioscience (Landmark edition). 2024 Jan; 29(1):43. doi: 10.31083/j.fbl2901043. [PMID: 38287835]
  • Rana Abutaima, Yousef Al-Ebini, Ahmad Alkofahi, Anas Alshishani, Samar Thiab, Kumarappan C Alagammai, Mohammad Khalid. In vivo assessment of black seed oil single dose on prednisolone pharmacokinetics. The Journal of pharmacy and pharmacology. 2024 Jan; 76(1):57-63. doi: 10.1093/jpp/rgad110. [PMID: 37978932]
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  • Bin Bao, Yonglin Zhao, Huan Gong, Songshan Shi, Huijun Wang, Shunchun Wang. Quantification of Paeoniflorin by Fully Validated LC-MS/MS Method: Its Application to Pharmacokinetic Interaction between Paeoniflorin and Verapamil. Molecules (Basel, Switzerland). 2022 Nov; 27(23):. doi: 10.3390/molecules27238337. [PMID: 36500431]
  • Abdul Waheed Khan, Zain Ul Abidin, Muhammad Umar Khayam Sahibzada, Muhammad Faheem, Neelam Gul Qazi, Mahboob Alam, Irfan Ullah, Jalal Uddin, Ajmal Khan, Ahmed Al-Harrasi. Potential biomedical applications of Araucaria araucana as an antispasmodic, bronchodilator, vasodilator, and antiemetic: Involvement of calcium channels. Journal of ethnopharmacology. 2022 Nov; 298(?):115651. doi: 10.1016/j.jep.2022.115651. [PMID: 35998784]
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  • Yogeeta O Agrawal, Muzammil Husain, Kiran D Patil, Vishal Sodgir, Tulshidas S Patil, Vinit V Agnihotri, Hitendra S Mahajan, Charu Sharma, Shreesh Ojha, Sameer N Goyal. Verapamil hydrochloride loaded solid lipid nanoparticles: Preparation, optimization, characterisation, and assessment of cardioprotective effect in experimental model of myocardial infarcted rats. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2022 Oct; 154(?):113429. doi: 10.1016/j.biopha.2022.113429. [PMID: 36007280]
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  • Mouqadus-Un -Nisa, Imran Imran, M Khalid Khan, Amna Shabih, Hassan Ali, Ali M Alqahtani, Taha Alqahtani, Barkat Ali Khan. Pharmacological effects (gastrointestinal, respiratory and vascular) of Calligonum polygonoides: Animal model based studies. Pakistan journal of pharmaceutical sciences. 2022 Jul; 35(4(Special)):1201-1208. doi: . [PMID: 36218098]
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  • Mikael Wallman, Jens Markus Borghardt, Eric Martel, Nicolas Pairet, Michael Markert, Mats Jirstrand. An integrative pharmacokinetic-cardiovascular physiology modelling approach based on in vivo dog studies including five reference compounds. Journal of pharmacological and toxicological methods. 2022 May; 115(?):107171. doi: 10.1016/j.vascn.2022.107171. [PMID: 35398273]
  • Xiaodan Wu, He Gong, Xiaorong Hu, Peipei Shi, Haipeng Cen, Chenchen Li. Effect of verapamil on bone mass, microstructure and mechanical properties in type 2 diabetes mellitus rats. BMC musculoskeletal disorders. 2022 Apr; 23(1):363. doi: 10.1186/s12891-022-05294-w. [PMID: 35436905]
  • Guanlan Xu, Tiffany D Grimes, Truman B Grayson, Junqin Chen, Lance A Thielen, Hubert M Tse, Peng Li, Matt Kanke, Tai-Tu Lin, Athena A Schepmoes, Adam C Swensen, Vladislav A Petyuk, Fernando Ovalle, Praveen Sethupathy, Wei-Jun Qian, Anath Shalev. Exploratory study reveals far reaching systemic and cellular effects of verapamil treatment in subjects with type 1 diabetes. Nature communications. 2022 03; 13(1):1159. doi: 10.1038/s41467-022-28826-3. [PMID: 35241690]
  • S R Vaibavi, Manoj Sivasubramaniapandian, Rahul Vaippully, Privita Edwina, Basudev Roy, Saumendra Kumar Bajpai. Calcium-channel-blockers exhibit divergent regulation of cancer extravasation through the mechanical properties of cancer cells and underlying vascular endothelial cells. Cell biochemistry and biophysics. 2022 Mar; 80(1):171-190. doi: 10.1007/s12013-021-01035-3. [PMID: 34643835]
  • P Lido, D Romanello, M Tesauro, A Bei, M A Perrone, D Palazzetti, A Noce, L Di Lullo, L Calò, G Cice. Verapamil: prevention and treatment of cardio-renal syndromes in diabetic hypertensive patients?. European review for medical and pharmacological sciences. 2022 Mar; 26(5):1524-1534. doi: 10.26355/eurrev_202203_28217. [PMID: 35302215]
  • Taizong Wu, Angela A Salim, Hui Cui, Zeinab G Khalil, Paul V Bernhardt, Robert J Capon. Glenthenamines A-F: Enamine Pyranonaphthoquinones from the Australian Pasture Plant Derived Streptomyces sp. CMB-PB042. Journal of natural products. 2022 02; 85(2):337-344. doi: 10.1021/acs.jnatprod.1c00821. [PMID: 35073486]
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  • Rabia Bibi, Umme Salma, Kashif Bashir, Taous Khan, Abdul Jabbar Shah. Antihypertensive Activity of Sauromatum guttatum Mediated by Vasorelaxation and Myocardial Depressant Effects. Arquivos brasileiros de cardiologia. 2021 12; 117(6):1093-1103. doi: 10.36660/abc.20200055. [PMID: 35613166]
  • Allison Jo Boyer, Rachael Erin Ketcham, Clint Allen Hostetler, Jeffrey Paul Orlowski, Ronald A Squires. Performance of Renal Allografts Perfused With Verapamil-Treated Perfusion Solution. Progress in transplantation (Aliso Viejo, Calif.). 2021 12; 31(4):373-380. doi: 10.1177/15269248211045999. [PMID: 34713753]
  • Lara García-Varela, David Vállez García, Pablo Aguiar, Takeharu Kakiuchi, Hiroyuki Ohba, Norihiro Harada, Shingo Nishiyama, Tetsuro Tago, Philip H Elsinga, Hideo Tsukada, Nicola A Colabufo, Rudi A J O Dierckx, Aren van Waarde, Jun Toyohara, Ronald Boellaard, Gert Luurtsema. Head-to-head comparison of (R)-[11C]verapamil and [18F]MC225 in non-human primates, tracers for measuring P-glycoprotein function. European journal of nuclear medicine and molecular imaging. 2021 12; 48(13):4307-4317. doi: 10.1007/s00259-021-05411-2. [PMID: 34117508]
  • Haihua Shang, Ze Wang, Hong Ma, Yinghui Sun, Xiaoyan Ci, Yuan Gu, Changxiao Liu, Duanyun Si. Influence of verapamil on the pharmacokinetics of rotundic acid in rats and its potential mechanism. Pharmaceutical biology. 2021 Dec; 59(1):200-208. doi: 10.1080/13880209.2021.1871634. [PMID: 33595422]
  • Jian-Lin Lai, Yuan-E Lian, Jun-Yi Wu, Yao-Dong Wang, Yan-Nan Bai. Verapamil induces autophagy to improve liver regeneration in non-alcoholic fatty liver mice. Adipocyte. 2021 12; 10(1):532-545. doi: 10.1080/21623945.2021.1983241. [PMID: 34699301]
  • Yi Song, Feng Guo, Yanyan Zhao, Lin Zhao, Xunjie Fan, Yuanyuan Zhang, Yanling Liu, Guijun Qin. Verapamil ameliorates proximal tubular epithelial cells apoptosis and fibrosis in diabetic kidney. European journal of pharmacology. 2021 Nov; 911(?):174552. doi: 10.1016/j.ejphar.2021.174552. [PMID: 34627808]
  • Laura Burattini, Agnese Sbrollini, Laura Scinocca, Chiara Peroni, Ilaria Marcantoni, Micaela Morettini. Electrocardiogram-based index for the assessment of drug-induced hERG potassium channel block. Journal of electrocardiology. 2021 Nov; 69S(?):55-60. doi: 10.1016/j.jelectrocard.2021.10.005. [PMID: 34736759]
  • Jie Liu, Yi Cheng, Yuanjin Zhang, Shengbo Huang, Zongjun Liu, Xin Wang. Lactobacillus rhamnosus induces CYP3A and changes the pharmacokinetics of verapamil in rats. Toxicology letters. 2021 Nov; 352(?):46-53. doi: 10.1016/j.toxlet.2021.09.010. [PMID: 34600097]
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