Dibucaine (BioDeep_00000002371)

human metabolite blood metabolite

代谢物信息卡片

2-Butoxy-quinoline-4-carboxylic acid (2-diethylamino-ethyl)-amide

化学式: C20H29N3O2 (343.2259654)
中文名称: 地布卡因
谱图信息: 最多检出来源 Homo sapiens(blood) 15.38%

分子结构信息

SMILES: CCCCOC1=NC2=CC=CC=C2C(=C1)C(=O)NCCN(CC)CC
InChI: InChI=1S/C20H29N3O2/c1-4-7-14-25-19-15-17(16-10-8-9-11-18(16)22-19)20(24)21-12-13-23(5-2)6-3/h8-11,15H,4-7,12-14H2,1-3H3,(H,21,24)

描述信息

A local anesthetic of the amide type now generally used for surface anesthesia. It is one of the most potent and toxic of the long-acting local anesthetics and its parenteral use is restricted to spinal anesthesia. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1006)
D - Dermatologicals > D04 - Antipruritics, incl. antihistamines, anesthetics, etc. > D04A - Antipruritics, incl. antihistamines, anesthetics, etc. > D04AB - Anesthetics for topical use
C - Cardiovascular system > C05 - Vasoprotectives > C05A - Agents for treatment of hemorrhoids and anal fissures for topical use > C05AD - Local anesthetics
D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants > D000777 - Anesthetics
S - Sensory organs > S02 - Otologicals > S02D - Other otologicals > S02DA - Analgesics and anesthetics
S - Sensory organs > S01 - Ophthalmologicals > S01H - Local anesthetics > S01HA - Local anesthetics
N - Nervous system > N01 - Anesthetics > N01B - Anesthetics, local > N01BB - Amides
D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents
C78272 - Agent Affecting Nervous System > C245 - Anesthetic Agent

同义名列表

36 个代谢物同义名

2-Butoxy-quinoline-4-carboxylic acid (2-diethylamino-ethyl)-amide; 2-Butoxy-quinoline-4-carboxylate (2-diethylamino-ethyl)-amide; 2-Butoxyquinoline-4-carboxylic acid diethylaminoethylamide; 2-butoxy-N-[2-(diethylamino)ethyl]quinoline-4-carboxamide; alpha-Butyloxycinchonic acid-gamma-diethylethylenediamine; 2-Butoxy-N-[2-(diethylamino)ethyl]-4-quinolinecarboxamide; 2-Butoxyquinoline-4-carboxylate diethylaminoethylamide; alpha-Butyloxycinchoninic acid diethylethylenediamide; alpha-Butyloxycinchonate-gamma-diethylethylenediamine; 2-Butoxy-N-(alpha-diethylaminoethyl)cinchoninamide; Α-butyloxycinchoninic acid diethylethylenediamide; Α-butyloxycinchonic acid-γ-diethylethylenediamine; a-Butyloxycinchonic acid-g-diethylethylenediamine; alpha-Butyloxycinchoninate diethylethylenediamide; 2-Butoxy-N-(beta-diethylaminoethyl)cinchoninamide; a-Butyloxycinchoninic acid diethylethylenediamide; 2-Butoxy-N-(2-(diethylamino)ethyl)cinchoninamide; N-(2-(Diethylamino)ethyl)-2-butoxycinchoninamide; 2-N-Butoxy-N-(2-diethylaminoethyl)cinchoninamide; 2-Butoxy-N-(b-diethylaminoethyl)cinchoninamide; 2-Butoxy-N-(a-diethylaminoethyl)cinchoninamide; 2-Butoxy-N-(β-diethylaminoethyl)cinchoninamide; 2-Butoxy-N-(α-diethylaminoethyl)cinchoninamide; a-Butyloxycinchonate-g-diethylethylenediamine; a-Butyloxycinchoninate diethylethylenediamide; Α-butyloxycinchonate-γ-diethylethylenediamine; Α-butyloxycinchoninate diethylethylenediamide; Dibucaine base; Cinchocainum; Cinchocaine; Nupercainal; Cincocainio; Nupercaine; dibucaine; Sovcaine; Cincain

数据库引用编号

16 个数据库交叉引用编号

ChEBI: CHEBI:247956
KEGG: C07879
KEGGdrug: D00733
PubChem: 3025
HMDB: HMDB0014668
Metlin: METLIN3979
DrugBank: DB00527
ChEMBL: CHEMBL1086
Wikipedia: Dibucaine
MeSH: Dibucaine
chemspider: 2917
CAS: 85-79-0
PMhub: MS000002456
PubChem: 10081
NIKKAJI: J3.887C
RefMet: Dibucaine

分类词条

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

9606 - Homo sapiens: -

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

Yusuke Horizumi, Satoru Goto, Miwa Takatsuka, Hideshi Yokoyama. Effects of Local Anesthetics on Liposomal Membranes Determined by Their Inhibitory Activity of Lipid Peroxidation. Molecular pharmaceutics. 2023 Apr; ?(?):. doi: 10.1021/acs.molpharmaceut.2c01053. [PMID: 37104048]
Malavika Prithviraj, Takehiro Kado, Jacob A Mayfield, David C Young, Annie D Huang, Daisuke Motooka, Shota Nakamura, M Sloan Siegrist, D Branch Moody, Yasu S Morita. Tuberculostearic Acid Controls Mycobacterial Membrane Compartmentalization. mBio. 2023 Mar; ?(?):e0339622. doi: 10.1128/mbio.03396-22. [PMID: 36976029]
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]
Ramachandra S Naik, Tatyana Belinskaya, C R Vinayaka, Ashima Saxena. Monoclonal antibodies to fetal bovine serum acetylcholinesterase distinguish between acetylcholinesterases from ruminant and non-ruminant species. Chemico-biological interactions. 2020 Oct; 330(?):109225. doi: 10.1016/j.cbi.2020.109225. [PMID: 32795450]
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]
S C Lopes, G Ivanova, B de Castro, P Gameiro. Cardiolipin and phosphatidylethanolamine role in dibucaine interaction with the mitochondrial membrane. Biochimica et biophysica acta. Biomembranes. 2019 06; 1861(6):1152-1161. doi: 10.1016/j.bbamem.2019.02.011. [PMID: 30840858]
Raquel M Barbosa, Bruna R Casadei, Evandro L Duarte, Patrícia Severino, Leandro R S Barbosa, Nelson Duran, Eneida de Paula. Electron Paramagnetic Resonance and Small-Angle X-ray Scattering Characterization of Solid Lipid Nanoparticles and Nanostructured Lipid Carriers for Dibucaine Encapsulation. Langmuir : the ACS journal of surfaces and colloids. 2018 11; 34(44):13296-13304. doi: 10.1021/acs.langmuir.8b02559. [PMID: 30299102]
Yan Li, Chang-Feng Li, Li-Ming Du, Jian-Xia Feng, Hai-Long Liu, Yun-Long Fu. A competitive strategy based on cucurbit[7]uril supramolecular interaction for simple and sensitive detection of dibucaine. Talanta. 2015 Jan; 132(?):653-7. doi: 10.1016/j.talanta.2014.09.005. [PMID: 25476359]
Eva Kupetz, Heike Bunjes. Lipid nanoparticles: drug localization is substance-specific and achievable load depends on the size and physical state of the particles. Journal of controlled release : official journal of the Controlled Release Society. 2014 Sep; 189(?):54-64. doi: 10.1016/j.jconrel.2014.06.007. [PMID: 24933601]
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]
Nicole Weizenmann, Daniel Huster, Holger A Scheidt. Interaction of local anesthetics with lipid bilayers investigated by ¹H MAS NMR spectroscopy. Biochimica et biophysica acta. 2012 Dec; 1818(12):3010-8. doi: 10.1016/j.bbamem.2012.07.014. [PMID: 22842001]
Jingqiu Chen, Daniel Korostyshevsky, Sean Lee, Ethan O Perlstein. Accumulation of an antidepressant in vesiculogenic membranes of yeast cells triggers autophagy. PloS one. 2012; 7(4):e34024. doi: 10.1371/journal.pone.0034024. [PMID: 22529904]
T-H Han, J A J Martyn. Neuromuscular pharmacodynamics of mivacurium in adults with major burns. British journal of anaesthesia. 2011 May; 106(5):675-9. doi: 10.1093/bja/aer023. [PMID: 21354998]
Ana Peropadre, Paloma Fernández Freire, Oscar Herrero, José M Pérez Martín, Maria José Hazen. Cellular responses associated with dibucaine-induced phospholipidosis. Chemical research in toxicology. 2011 Feb; 24(2):185-92. doi: 10.1021/tx100262c. [PMID: 21261262]
Antonio Raudino, Maria Grazia Sarpietro, Martina Pannuzzo. The thermodynamics of simple biomembrane mimetic systems. Journal of pharmacy & bioallied sciences. 2011 Jan; 3(1):15-38. doi: 10.4103/0975-7406.76462. [PMID: 21430953]
Daniel Fantozzi Garcia, Ticiano G Oliveira, Greice A Molfetta, Luiz V Garcia, Cristiane A Ferreira, Adriana A Marques, Wilson Araujo Silva. Biochemical and genetic analysis of butyrylcholinesterase (BChE) in a family, due to prolonged neuromuscular blockade after the use of succinylcholine. Genetics and molecular biology. 2011 Jan; 34(1):40-4. doi: 10.1590/s1415-47572011000100008. [PMID: 21637541]
Liliana L Jorge, Caroline C Feres, Vitor Ep Teles. Topical preparations for pain relief: efficacy and patient adherence. Journal of pain research. 2010 Dec; 4(?):11-24. doi: 10.2147/jpr.s9492. [PMID: 21386951]
Nouara Yahi, Anaïs Aulas, Jacques Fantini. How cholesterol constrains glycolipid conformation for optimal recognition of Alzheimer's beta amyloid peptide (Abeta1-40). PloS one. 2010 Feb; 5(2):e9079. doi: 10.1371/journal.pone.0009079. [PMID: 20140095]
R Pizzi, J Cracknell, L Dalrymple. Postmortem Evaluation of Left Flank Laparoscopic Access in an Adult Female Giraffe (Giraffa camelopardalis). Veterinary medicine international. 2010; 2010(?):789465. doi: 10.4061/2010/789465. [PMID: 20445792]
Jamie Nelsen, Michael Holland, Michelle Dougherty, Jason Bernad, Christine Stork, Jeanna Marraffa. Severe central nervous system and cardiovascular toxicity in a pediatric patient after ingestion of an over-the-counter local anesthetic. Pediatric emergency care. 2009 Oct; 25(10):670-3. doi: 10.1097/pec.0b013e3181b91e8c. [PMID: 19834416]
Ljiljana Popović, Lili Mikecin, J Kern. The value of plasma cholinesterase in children with severe liver disease. European journal of anaesthesiology. 2009 Apr; 26(4):352-4. doi: 10.1097/eja.0b013e32831c880c. [PMID: 19401671]
G S Lorite, T M Nobre, M E D Zaniquelli, E de Paula, M A Cotta. Dibucaine effects on structural and elastic properties of lipid bilayers. Biophysical chemistry. 2009 Feb; 139(2-3):75-83. doi: 10.1016/j.bpc.2008.10.006. [PMID: 19010585]
Takeshi Saito, Seiji Morita, Izumi Kishiyama, Shota Miyazaki, Akihiro Nakamoto, Manami Nishida, Akira Namera, Masataka Nagao, Sadaki Inokuchi. Simultaneous determination of dibucaine and naphazoline in human serum by monolithic silica spin column extraction and liquid chromatography-mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2008 Sep; 872(1-2):186-90. doi: 10.1016/j.jchromb.2008.07.007. [PMID: 18657485]
Shanmugam Sivabalan, Shanmugam Renuka, Venugopal P Menon. Fat feeding potentiates the diabetogenic effect of dexamethasone in Wistar rats. International archives of medicine. 2008 May; 1(1):7. doi: 10.1186/1755-7682-1-7. [PMID: 18500989]
Antoine Amado, Apra Sood, James S Taylor. Contact allergy to lidocaine: a report of sixteen cases. Dermatitis : contact, atopic, occupational, drug. 2007 Dec; 18(4):215-20. doi: 10.2310/6620.2007.06059. [PMID: 18021602]
Mustafa M A Elsayed, Ossama Y Abdallah, Viviane F Naggar, Nawal M Khalafallah. PG-liposomes: novel lipid vesicles for skin delivery of drugs. The Journal of pharmacy and pharmacology. 2007 Oct; 59(10):1447-50. doi: 10.1211/jpp.59.10.0017. [PMID: 17910822]
G Schwarz, L Damian, M Winterhalter. Model-free analysis of binding at lipid membranes employing micro-calorimetric measurements. European biophysics journal : EBJ. 2007 Jul; 36(6):571-9. doi: 10.1007/s00249-007-0143-5. [PMID: 17345079]
Asad Vaisi-Raygani, Zohreh Rahimi, Hadi Kharazi, Haidar Tavilani, Mahdi Aminiani, Amir Kiani, Aliakbar Vaisi-Raygani, Tayebeh Pourmotabbed. Determination of butyrylcholinesterase (BChE) phenotypes to predict the risk of prolonged apnea in persons receiving succinylcholine in the healthy population of western Iran. Clinical biochemistry. 2007 Jun; 40(9-10):629-33. doi: 10.1016/j.clinbiochem.2007.01.018. [PMID: 17350607]
Young-Ho Lee, No-Soo Park, Jong-Deok Kwon, Ju-Seok Park, Gye-Beom Shin, Chung-Seob Lee, Tae-Sang Jung, Nak-Jin Choi, Jin-Hyeok Yoon, Jin-Seok Ok, Ung-Chan Yoon, Moon-Kyung Bae, Hye-Ock Jang, Il Yun. Amphiphilic effects of dibucaine HCl on rotational mobility of n-(9-anthroyloxy)stearic acid in neuronal and model membranes. Chemistry and physics of lipids. 2007 Mar; 146(1):33-42. doi: 10.1016/j.chemphyslip.2006.12.002. [PMID: 17241620]
Toshinori Tsuruta, Chunyan Yang, Hiroshi Ueki, Guangying Li, Akiko Maekawa, Hideki Kamikawa, Eisaku Oku, Takao Somehara, Hiroshi Fujito, Hideharu Tatebayashi, Shigeto Yamada. Determination of paroxetine in human saliva by reversed-phase high-performance liquid chromatography with UV detection. Nihon shinkei seishin yakurigaku zasshi = Japanese journal of psychopharmacology. 2007 Feb; 27(1):9-12. doi: . [PMID: 17393774]
Varaporn Buraphacheep Junyaprasert, Prapaporn Boonme, Sarunyoo Songkro, Karen Krauel, Thomas Rades. Transdermal delivery of hydrophobic and hydrophilic local anesthetics from o/w and w/o Brij 97-based microemulsions. Journal of pharmacy & pharmaceutical sciences : a publication of the Canadian Society for Pharmaceutical Sciences, Societe canadienne des sciences pharmaceutiques. 2007; 10(3):288-98. doi: ". [PMID: 17727792]
Natsumi Sawada, Masayoshi Yamaguchi. Involvement of nuclear factor I-A1 in the regulation of regucalcin gene promoter activity in cloned normal rat kidney proximal tubular epithelial cells. International journal of molecular medicine. 2006 Oct; 18(4):665-71. doi: . [PMID: 16964421]
Natsumi Sawada, Masayoshi Yamaguchi. Overexpression of RGPR-p117 enhances regucalcin gene promoter activity in cloned normal rat kidney proximal tubular epithelial cells: involvement of TTGGC motif. Journal of cellular biochemistry. 2006 Oct; 99(2):589-97. doi: 10.1002/jcb.20907. [PMID: 16676356]
Naoki Inagaki, Noriko Shiraishi, Katsuhiro Igeta, Tomokazu Itoh, Takao Chikumoto, Masafumi Nagao, John Fan Kim, Hiroichi Nagai. Inhibition of scratching behavior associated with allergic dermatitis in mice by tacrolimus, but not by dexamethasone. European journal of pharmacology. 2006 Sep; 546(1-3):189-96. doi: 10.1016/j.ejphar.2006.07.019. [PMID: 16914137]
Thaïs Souto-Padrón, Ana Paula Lima, Rachel de Oliveira Ribeiro. Effects of dibucaine on the endocytic/exocytic pathways in Trypanosoma cruzi. Parasitology research. 2006 Sep; 99(4):317-20. doi: 10.1007/s00436-006-0192-1. [PMID: 16612626]
Natsumi Sawada, Masayoshi Yamaguchi. Overexpression of RGPR-p117 enhances regucalcin gene expression in cloned normal rat kidney proximal tubular epithelial cells. International journal of molecular medicine. 2005 Dec; 16(6):1049-55. doi: . [PMID: 16273285]
Mohamed Mahmoud Nounou, Labiba Khalil El-Khordagui, Nawal Khalafallah. Effect of various formulation variables on the encapsulation and stability of dibucaine base in multilamellar vesicles. Acta poloniae pharmaceutica. 2005 Sep; 62(5):369-79. doi: ". [PMID: 16459486]
Masayoshi Yamaguchi, Yuko Daimon. Overexpression of regucalcin suppresses cell proliferation in cloned rat hepatoma H4-II-E cells: involvement of intracellular signaling factors and cell cycle-related genes. Journal of cellular biochemistry. 2005 Aug; 95(6):1169-77. doi: 10.1002/jcb.20490. [PMID: 15962315]
Taeko Nakagawa, Masayoshi Yamaguchi. Hormonal regulation on regucalcin mRNA expression in cloned normal rat kidney proximal tubular epithelial NRK52E cells. Journal of cellular biochemistry. 2005 Jun; 95(3):589-97. doi: 10.1002/jcb.20422. [PMID: 15786489]
Koichi Ishida, Masayoshi Yamaguchi. Role of albumin in osteoblastic cells: enhancement of cell proliferation and suppression of alkaline phosphatase activity. International journal of molecular medicine. 2004 Dec; 14(6):1077-81. doi: . [PMID: 15547677]
Takako Izumi, Masayoshi Yamaguchi. Overexpression of regucalcin suppresses cell death and apoptosis in cloned rat hepatoma H4-II-E cells induced by lipopolysaccharide, PD 98059, dibucaine, or Bay K 8644. Journal of cellular biochemistry. 2004 Oct; 93(3):598-608. doi: 10.1002/jcb.20214. [PMID: 15378600]
Kaiyao Huang, Tim Kunkel, Christoph F Beck. Localization of the blue-light receptor phototropin to the flagella of the green alga Chlamydomonas reinhardtii. Molecular biology of the cell. 2004 Aug; 15(8):3605-14. doi: 10.1091/mbc.e04-01-0010. [PMID: 15155806]
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Nasser Vahdati-Mashhadian, Mohammad K Hassanzadeh, Javad Hosseini, Ali A Saffareshargh. Ethnic differences in the frequency of distribution of serum cholinesterase activity in the Iranian population. Canadian journal of physiology and pharmacology. 2004 May; 82(5):326-30. doi: 10.1139/y04-030. [PMID: 15213732]
Zrinka Kovarik, Vera Simeon-Rudolf. An improvement in segregation of human butyrylcholinesterase phenotypes having the fluoride-resistant variants. Arhiv za higijenu rada i toksikologiju. 2003 Dec; 54(4):239-44. doi: NULL. [PMID: 14994645]
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Brian M Polster, Gorka Basañez, Michael Young, Motoshi Suzuki, Gary Fiskum. Inhibition of Bax-induced cytochrome c release from neural cell and brain mitochondria by dibucaine and propranolol. The Journal of neuroscience : the official journal of the Society for Neuroscience. 2003 Apr; 23(7):2735-43. doi: . [PMID: 12684459]
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