Cyclizine (BioDeep_00000002344)

 

Secondary id: BioDeep_00000411071

human metabolite blood metabolite Chemicals and Drugs


代谢物信息卡片


(N-Benzhydryl)(n-methyl)diethylenediamine

化学式: C18H22N2 (266.1782892)
中文名称: 苯甲嗪
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CN1CCN(C(c2ccccc2)c2ccccc2)CC1
InChI: InChI=1S/C18H22N2/c1-19-12-14-20(15-13-19)18(16-8-4-2-5-9-16)17-10-6-3-7-11-17/h2-11,18H,12-15H2,1H3

描述信息

Cyclizine is only found in individuals that have used or taken this drug. It is a histamine H1 antagonist given by mouth or parenterally for the control of postoperative and drug-induced vomiting and in motion sickness. (From Martindale, The Extra Pharmacopoeia, 30th ed, p935)Vomiting (emesis) is essentially a protective mechanism for removing irritant or otherwise harmful substances from the upper GI tract. Emesis or vomiting is controlled by the vomiting centre in the medulla region of the brain, an important part of which is the chemotrigger zone (CTZ). The vomiting centre possesses neurons which are rich in muscarinic cholinergic and histamine containing synapses. These types of neurons are especially involved in transmission from the vestibular apparatus to the vomiting centre. Motion sickness principally involves overstimulation of these pathways due to various sensory stimuli. Hence the action of cyclizine which acts to block the histamine receptors in the vomiting centre and thus reduce activity along these pathways. Furthermore since cyclizine possesses anti-cholinergic properties as well, the muscarinic receptors are similarly blocked.
R - Respiratory system > R06 - Antihistamines for systemic use > R06A - Antihistamines for systemic use > R06AE - Piperazine derivatives
CONFIDENCE standard compound; INTERNAL_ID 1; HBM4EU - science and policy for a healthy future (https://www.hbm4eu.eu)
CONFIDENCE Reference Standard (Level 1); HBM4EU - science and policy for a healthy future (https://www.hbm4eu.eu)
D018377 - Neurotransmitter Agents > D018494 - Histamine Agents > D006633 - Histamine Antagonists
D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents
C78272 - Agent Affecting Nervous System > C267 - Antiemetic Agent
D005765 - Gastrointestinal Agents > D000932 - Antiemetics
D002491 - Central Nervous System Agents

同义名列表

15 个代谢物同义名

(N-Benzhydryl)(n-methyl)diethylenediamine; (+-)-1-Diphenylmethyl-4-methylpiperazine; 1-(Diphenylmethyl)-4-methylpiperazine; N-Methyl-n-benzhydrylpiperazine; N-Benzhydryl-n-methylpiperazine; 1-Benzhydryl-4-methylpiperazin; Hydrochloride, cyclizine; Cyclizine Hydrochloride; Cyclizine chloride; HCL, Cyclizine; Cyclizine HCL; Cyclizinum; Ciclizina; CYCLIZINE; Marezine



数据库引用编号

82 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

  • Michel Y Fares, Nada S Abdelwahab, Ghada M El-Sayed, Maha A Hegazy, Maha M Abdelrahman. Spectrofluorimetric Approach for Quantification of Cyclizine in the Presence of its Toxic Impurities in Human Plasma; in silico Study and ADMET Calculations. Journal of fluorescence. 2022 May; 32(3):993-1003. doi: 10.1007/s10895-022-02897-3. [PMID: 35239065]
  • 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]
  • Danyi Lu, Dong Dong, Qian Xie, Zhijie Li, Baojian Wu. Disposition of Mianserin and Cyclizine in UGT2B10-Overexpressing Human Embryonic Kidney 293 Cells: Identification of UGT2B10 as a Novel N-Glucosidation Enzyme and Breast Cancer Resistance Protein as an N-Glucoside Transporter. Drug metabolism and disposition: the biological fate of chemicals. 2018 07; 46(7):970-979. doi: 10.1124/dmd.118.080804. [PMID: 29691239]
  • Shanshan He, Jingbo Xiao, Andrés E Dulcey, Billy Lin, Adam Rolt, Zongyi Hu, Xin Hu, Amy Q Wang, Xin Xu, Noel Southall, Marc Ferrer, Wei Zheng, T Jake Liang, Juan J Marugan. Discovery, Optimization, and Characterization of Novel Chlorcyclizine Derivatives for the Treatment of Hepatitis C Virus Infection. Journal of medicinal chemistry. 2016 Feb; 59(3):841-53. doi: 10.1021/acs.jmedchem.5b00752. [PMID: 26599718]
  • Marianne Arnestad, Kari Beate Boye Eldor, Arne Stray-Pedersen, Liliana Bachs, Ritva Karinen. Suicide due to cyclizine overdose. Journal of analytical toxicology. 2014 Mar; 38(2):110-2. doi: 10.1093/jat/bkt100. [PMID: 24324230]
  • Berit Packert Jensen, Jane Winifred Ann Vella-Brincat, Evan James Begg. Quantification of cyclizine and norcyclizine in human plasma by liquid chromatography-tandem mass spectrometry (LC-MS/MS). Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2011 Mar; 879(9-10):605-9. doi: 10.1016/j.jchromb.2011.01.021. [PMID: 21333615]
  • Parviz Norouzi, Rassoul Dinarvand, Mohammad Reza Ganjali, Aliakbar Moosavi-Movahedi, Aliakbar Saboury, Atefeh Tamaddon. Application of adsorptive voltammetry for the detection of sub-nano molar cyclizine in biological fluids and tablets using fast Fourier transform continuous cyclic voltammetry in a flowing system. Analytical sciences : the international journal of the Japan Society for Analytical Chemistry. 2009 Apr; 25(4):505-10. doi: 10.2116/analsci.25.505. [PMID: 19359790]
  • M A Martínez-Gómez, M M Carril-Avilés, S Sagrado, R M Villanueva-Camañas, M J Medina-Hernández. Characterization of antihistamine-human serum protein interactions by capillary electrophoresis. Journal of chromatography. A. 2007 Apr; 1147(2):261-9. doi: 10.1016/j.chroma.2007.02.054. [PMID: 17339039]
  • A Mohammadi, I Kanfer, V Sewram, R B Walker. An LC-MS-MS method for the determination of cyclizine in human serum. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2005 Sep; 824(1-2):148-52. doi: 10.1016/j.jchromb.2005.07.015. [PMID: 16054445]
  • Akihito Suzuki, Norio Yasui-Furukori, Kazuo Mihara, Tsuyoshi Kondo, Hanako Furukori, Yoshimasa Inoue, Sunao Kaneko, Koichi Otani. Histamine H1-receptor antagonists, promethazine and homochlorcyclizine, increase the steady-state plasma concentrations of haloperidol and reduced haloperidol. Therapeutic drug monitoring. 2003 Apr; 25(2):192-6. doi: 10.1097/00007691-200304000-00008. [PMID: 12657913]
  • M C Dumasia, L Grainger, E Houghton. Biotransformation of cyclizine in greyhounds. 1: Identification and analysis of cyclizine and some basic metabolites in canine urine by gas chromatography-mass spectrometry. Xenobiotica; the fate of foreign compounds in biological systems. 2002 Sep; 32(9):795-807. doi: 10.1080/00498250210144802. [PMID: 12396276]
  • M C Dumasia. Biotransformation of cyclizine in greyhounds. 2: N(1)-dealkylation and identification of some neutral and phenolic metabolites in canine urine by gas chromatography-mass spectrometry. Xenobiotica; the fate of foreign compounds in biological systems. 2002 Sep; 32(9):809-21. doi: 10.1080/00498250210144794. [PMID: 12396277]
  • Nu He, Wen-Qi Zhang, Dolores Shockley, Timi Edeki. Inhibitory effects of H1-antihistamines on CYP2D6- and CYP2C9-mediated drug metabolic reactions in human liver microsomes. European journal of clinical pharmacology. 2002 Feb; 57(12):847-51. doi: 10.1007/s00228-001-0399-0. [PMID: 11936702]
  • D Simpson, R A Braithwaite, D R Jarvie, M J Stewart, S Walker, I W Watson, B Widdop. Screening for drugs of abuse (II): Cannabinoids, lysergic acid diethylamide, buprenorphine, methadone, barbiturates, benzodiazepines and other drugs. Annals of clinical biochemistry. 1997 Sep; 34 ( Pt 5)(?):460-510. doi: 10.1177/000456329703400502. [PMID: 9293303]
  • R B Walker, I Kanfer. Sensitive high-performance liquid chromatographic determination of cyclizine and its demethylated metabolite, norcyclizine, in biological fluids using coulometric detection. Journal of chromatography. B, Biomedical applications. 1995 Oct; 672(1):172-7. doi: 10.1016/0378-4347(95)00202-t. [PMID: 8590933]
  • H Miyauchi, T Horio. Detection of action, inhibition and augmentation spectra in solar urticaria. Dermatology (Basel, Switzerland). 1995; 191(4):286-91. doi: 10.1159/000246570. [PMID: 8573923]
  • M Nishikata, A Nakai, H Fushida, K Miyake, T Arita, K Iseki, K Miyazaki. Enantioselective pharmacokinetics of homochlorcyclizine: disposition of (+)- and (-)-homochlorcyclizine after intravenous and oral administration of racemic homochlorcyclizine to rats. The Journal of pharmacy and pharmacology. 1994 Jul; 46(7):591-5. doi: 10.1111/j.2042-7158.1994.tb03863.x. [PMID: 7996389]
  • M Nishikata, A Nakai, H Fushida, K Miyake, T Arita, K Iseki, K Miyazaki, A Nomura. Enantioselective pharmacokinetics of homochlorcyclizine. III. Simultaneous determination of (+)- and (-)- homochlorcyclizine in human urine by high-performance liquid chromatography. Journal of chromatography. 1993 Feb; 612(2):239-44. doi: NULL. [PMID: 8096848]
  • M Nishikata, A Nomura, K Iseki, K Miyazaki, A Nakai, H Fushida, K Miyake, T Arita. Enantioselective pharmacokinetics of homochlorcyclizine. II: Disposition and metabolism of (+)-, (-)- and racemic homochlorcyclizine after oral administration to man. European journal of clinical pharmacology. 1992; 43(5):533-8. doi: 10.1007/bf02285097. [PMID: 1362384]
  • C M Moore. Solid-phase cation exchange extraction of basic drugs from the urine of racing greyhounds. Journal - Forensic Science Society. 1990 May; 30(3):123-9. doi: 10.1016/s0015-7368(90)73322-1. [PMID: 2398341]
  • R C Backer, P McFeeley, N Wohlenberg. Fatality resulting from cyclizine overdose. Journal of analytical toxicology. 1989 Sep; 13(5):308-9. doi: 10.1093/jat/13.5.308. [PMID: 2615343]
  • S M Ruben, P C McLean, J Melville. Cyclizine abuse among a group of opiate dependents receiving methadone. British journal of addiction. 1989 Aug; 84(8):929-34. doi: 10.1111/j.1360-0443.1989.tb00766.x. [PMID: 2775912]
  • S Cathapermal, B Caddy. Capillary gas chromatographic determination of cyclizine and dipipanone in biological fluids. The Analyst. 1988 Mar; 113(3):385-8. doi: 10.1039/an9881300385. [PMID: 3377178]
  • P G Blain, R J Lane, D N Bateman, M D Rawlins. Opiate-induced rhabdomyolysis. Human toxicology. 1985 Jan; 4(1):71-4. doi: 10.1177/096032718500400109. [PMID: 3988309]
  • N Hanai. Morphological and immunocytochemical study of rat pancreatic beta cell changes induced by cyclizine. Journal of applied toxicology : JAT. 1984 Dec; 4(6):308-14. doi: 10.1002/jat.2550040606. [PMID: 6394638]
  • M J Ashton, A Ashford, A H Loveless, D Riddell, J Salmon, G V Stevenson. Heterocyclic analogues of chlorcyclizine with potent hypolipidemic activity. Journal of medicinal chemistry. 1984 Oct; 27(10):1245-53. doi: 10.1021/jm00376a002. [PMID: 6148419]
  • D S Griffin, R C Baselt. Blood and urine concentrations of cyclizine by nitrogen-phosphorus gas-liquid chromatography. Journal of analytical toxicology. 1984 Mar; 8(2):97-9. doi: 10.1093/jat/8.2.97. [PMID: 6716982]
  • R S Desowitz, N E Palumbo, S F Perri, M S Sylvester. Inhibition of the adverse reaction to diethylcarbamazine in Dirofilaria immitis-infected dogs by lodoxamide ethyl. The American journal of tropical medicine and hygiene. 1982 Mar; 31(2):309-12. doi: 10.4269/ajtmh.1982.31.309. [PMID: 7072895]
  • G Land, K Dean, A Bye. Determination of cyclizine and norcyclizine in plasma and urine using gas--liquid chromatography with nitrogen selective detection. Journal of chromatography. 1981 Jan; 222(1):135-40. doi: 10.1016/s0378-4347(00)81043-9. [PMID: 7217321]
  • E Zylber-Katz, L Granit, M Levy. Gas-liquid chromatographic determination of bupivacaine and lidocaine in plasma. Clinical chemistry. 1978 Sep; 24(9):1573-5. doi: 10.1093/clinchem/24.9.1573. [PMID: 688620]
  • D J Carson. Fatal dextropropoxyphene poisoning in Northern Ireland. Review of 30 cases. Lancet (London, England). 1977 Apr; 1(8017):894-7. doi: 10.1016/s0140-6736(77)91212-0. [PMID: 67297]
  • R Kuntzman, M Jacobson, I Tsai, J J Burns, J Burchall, A Koch. Certain aspects of drug binding to nonplasma proteins as illustrated by studies with cyclizine, chlorcyclizine, and polymyxin B. Annals of the New York Academy of Sciences. 1973 Nov; 226(?):131-47. doi: 10.1111/j.1749-6632.1973.tb20476.x. [PMID: 4148961]
  • Z Hruban, A Slesers, E Hopkins. Drug-induced and naturally occurring myeloid bodies. Laboratory investigation; a journal of technical methods and pathology. 1972 Jul; 27(1):62-70. doi: NULL. [PMID: 4402449]
  • K Takagi, T Fukao. Effects of some drugs on capillary permeability in the anaphylaxis of the mouse. Japanese journal of pharmacology. 1971 Aug; 21(4):455-65. doi: 10.1254/jjp.21.455. [PMID: 4399090]
  • A J Harrison, A Cook. A case history of drug addiction and a T.L.C. system for the separation and identification of some drugs of addiction in sub-microgramme amounts. Journal - Forensic Science Society. 1969 Dec; 9(3):165-7. doi: 10.1016/s0015-7368(69)70530-8. [PMID: 5383496]
  • C McMartin, P Simpson, N Thorpe. The specific assay of basic drugs in urine by CM-cellulose chromatography using continuous drug-dye complex extraction as a detection system. Journal of chromatography. 1969 Aug; 43(1):72-83. doi: 10.1016/s0021-9673(00)99168-4. [PMID: 5802182]
  • R Kuntzman, I Tsai, J J Burns. Importance of tissue and plasma binding in determining the retention of norchlorcyclizine and norcyclizine in man, dog and rat. The Journal of pharmacology and experimental therapeutics. 1967 Nov; 158(2):332-9. doi: NULL. [PMID: 4383640]
  • R KUNTZMAN, A KLUTCH, I TSAI, J J BURNS. PHYSIOLOGICAL DISTRIBUTION AND METABOLIC INACTIVATION OF CHLORCYCLIZINE AND CYCLIZINE. The Journal of pharmacology and experimental therapeutics. 1965 Jul; 149(?):29-35. doi: NULL. [PMID: 14334288]