Laudanosine (BioDeep_00000398001)

 

Secondary id: BioDeep_00000002519

PANOMIX_OTCML-2023


代谢物信息卡片


DL-LAUDANOSINE

化学式: C21H27NO4 (357.19399820000007)
中文名称: 劳丹素
谱图信息: 最多检出来源 Viridiplantae(plant) 0.15%

分子结构信息

SMILES: CN1CCC2=CC(=C(C=C2C1CC3=CC(=C(C=C3)OC)OC)OC)OC
InChI: InChI=1S/C21H27NO4/c1-22-9-8-15-12-20(25-4)21(26-5)13-16(15)17(22)10-14-6-7-18(23-2)19(11-14)24-3/h6-7,11-13,17H,8-10H2,1-5H3

描述信息

D002491 - Central Nervous System Agents
Annotation level-1
relative retention time with respect to 9-anthracene Carboxylic Acid is 0.628
relative retention time with respect to 9-anthracene Carboxylic Acid is 0.624
Acquisition and generation of the data is financially supported by the Max-Planck-Society
IPB_RECORD: 2441; CONFIDENCE confident structure
DL-Laudanosine, an Atracurium and Cisatracurium metabolite, crosses the blood–brain barrier and may cause excitement and seizure activity[1].
DL-Laudanosine, an Atracurium and Cisatracurium metabolite, crosses the blood–brain barrier and may cause excitement and seizure activity[1].

同义名列表

2 个代谢物同义名

DL-LAUDANOSINE; Laudanosine



数据库引用编号

32 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。



文献列表

  • Adrià Aguilar, Anna Andaluz, Xavier Moll, Carles Cristòfol, Fèlix García. Effect of age on cis-atracurium besylate pharmacokinetics following a single 1 mg kg-1 intravenous bolus in young pigs. Veterinary anaesthesia and analgesia. 2019 Sep; 46(5):643-651. doi: 10.1016/j.vaa.2018.11.012. [PMID: 31155378]
  • Ahmed Ma'mun, Mohamed K Abd El-Rahman, Mohamed Abd El-Kawy. Real-time potentiometric sensor; an innovative tool for monitoring hydrolysis of chemo/bio-degradable drugs in pharmaceutical sciences. Journal of pharmaceutical and biomedical analysis. 2018 May; 154(?):166-173. doi: 10.1016/j.jpba.2018.02.007. [PMID: 29549855]
  • Limei Chang, Jillian M Hagel, Peter J Facchini. Isolation and Characterization of O-methyltransferases Involved in the Biosynthesis of Glaucine in Glaucium flavum. Plant physiology. 2015 Oct; 169(2):1127-40. doi: 10.1104/pp.15.01240. [PMID: 26297140]
  • Yingying Yang, Mei Chen, Yushan Kuang, Liming Ye, Wensheng Zhang. [Determination of atracurium and laudanosine in dog plasma during cardiopulmonary bypass by high performance liquid chromatography with fluorometric detection]. Se pu = Chinese journal of chromatography. 2013 Jun; 31(6):572-6. doi: 10.3724/sp.j.1123.2012.12013. [PMID: 24063198]
  • Paul Klausmeyer, Thomas G McCloud, Dominic A Scudiero, Michael J Currens, John H Cardellina Ii, Robert H Shoemaker. Discovery and preliminary SAR of bisbenzylisoquinoline alkaloids as inducers of C/EBPα. Bioorganic & medicinal chemistry. 2012 Aug; 20(15):4646-52. doi: 10.1016/j.bmc.2012.06.017. [PMID: 22766217]
  • Thu-Thuy T Dang, Peter J Facchini. Characterization of three O-methyltransferases involved in noscapine biosynthesis in opium poppy. Plant physiology. 2012 Jun; 159(2):618-31. doi: 10.1104/pp.112.194886. [PMID: 22535422]
  • Xu Han, Marc Lamshöft, Nadja Grobe, Xuan Ren, Anthony J Fist, Toni M Kutchan, Michael Spiteller, Meinhart H Zenk. The biosynthesis of papaverine proceeds via (S)-reticuline. Phytochemistry. 2010 Aug; 71(11-12):1305-12. doi: 10.1016/j.phytochem.2010.04.022. [PMID: 20494383]
  • A Mary Vilay, Mariann D Churchwell, Bruce A Mueller. Clinical review: Drug metabolism and nonrenal clearance in acute kidney injury. Critical care (London, England). 2008; 12(6):235. doi: 10.1186/cc7093. [PMID: 19040780]
  • Somdej Kanokmedhakul, Kwanjai Kanokmedhakul, Ratsami Lekphrom. Bioactive constituents of the roots of Polyalthia cerasoides. Journal of natural products. 2007 Sep; 70(9):1536-8. doi: 10.1021/np070293a. [PMID: 17845001]
  • María A Martínez, Salomé Ballesteros, Elena Almarza. Anesthesiologist suicide with atracurium. Journal of analytical toxicology. 2006 Mar; 30(2):120-4. doi: 10.1093/jat/30.2.120. [PMID: 16620544]
  • Susanne Frick, Julie A Chitty, Robert Kramell, Jürgen Schmidt, Robert S Allen, Philip J Larkin, Toni M Kutchan. Transformation of opium poppy (Papaver somniferum L.) with antisense berberine bridge enzyme gene (anti-bbe) via somatic embryogenesis results in an altered ratio of alkaloids in latex but not in roots. Transgenic research. 2004 Dec; 13(6):607-13. doi: 10.1007/s11248-004-2892-6. [PMID: 15672841]
  • A M Al-Amri, R M Smith, B M El-Haj, M H Juma'a. The GC-MS detection and characterization of reticuline as a marker of opium use. Forensic science international. 2004 May; 142(1):61-9. doi: 10.1016/j.forsciint.2004.02.006. [PMID: 15272474]
  • A M Al-Amri, R M Smith, B M El-Haj, M H Juma'a. The GC-MS detection and characterization of reticuline as a marker of opium use. Forensic science international. 2004 Mar; 140(2-3):175-83. doi: 10.1016/j.forsciint.2003.10.022. [PMID: 15036439]
  • Hervé Sayer, Oscar Quintela, Pierre Marquet, Jean-Louis Dupuy, Jean-Michel Gaulier, Gérard Lachâtre. Identification and quantitation of six non-depolarizing neuromuscular blocking agents by LC-MS in biological fluids. Journal of analytical toxicology. 2004 Mar; 28(2):105-10. doi: 10.1093/jat/28.2.105. [PMID: 15068563]
  • J Y Lefrant, C Farenc, J E De la Coussaye, L Muller, J Ripart, P Cuvillon, G Saissi, J J Eledjam. Pharmacodynamics and atracurium and laudanosine concentrations during a fixed continuous infusion of atracurium in mechanically ventilated patients with acute respiratory distress syndrome. Anaesthesia and intensive care. 2002 Aug; 30(4):422-7. doi: 10.1177/0310057x0203000403. [PMID: 12180578]
  • V Fodale, L B Santamaria. Laudanosine, an atracurium and cisatracurium metabolite. European journal of anaesthesiology. 2002 Jul; 19(7):466-73. doi: 10.1017/s0265021502000777. [PMID: 12113608]
  • G Dhonneur, C Cerf, F Lagneau, J Mantz, C Gillotin, P Duvaldestin. The pharmacokinetics of cisatracurium in patients with acute respiratory distress syndrome. Anesthesia and analgesia. 2001 Aug; 93(2):400-4 , 3rd contents page. doi: 10.1097/00000539-200108000-00033. [PMID: 11473869]
  • C Farenc, J Y Lefrant, M Audran, F Bressolle. Pharmacokinetic-pharmacodynamic modeling of atracurium in intensive care patients. Journal of clinical pharmacology. 2001 Jan; 41(1):44-50. doi: 10.1177/00912700122009827. [PMID: 11144993]
  • B Chow, M I Bowden, E Ho, B C Weatherley, J F Bion. Pharmacokinetics and dynamics of atracurium infusions after paediatric orthotopic liver transplantation. British journal of anaesthesia. 2000 Dec; 85(6):850-5. doi: 10.1093/bja/85.6.850. [PMID: 11732518]
  • F R Stermitz, J Tawara-Matsuda, P Lorenz, P Mueller, L Zenewicz, K Lewis. 5'-Methoxyhydnocarpin-D and pheophorbide A: Berberis species components that potentiate berberine growth inhibition of resistant Staphylococcus aureus. Journal of natural products. 2000 Aug; 63(8):1146-9. doi: 10.1021/np990639k. [PMID: 10978214]
  • C Farenc, M Audran, J Y Lefrant, I Mazerm, F Bressolle. High-performance liquid chromatographic method for the determination of atracurium and laudanosine in human plasma. Application to pharmacokinetics. Journal of chromatography. B, Biomedical sciences and applications. 1999 Mar; 724(1):117-26. doi: 10.1016/s0378-4347(98)00576-3. [PMID: 10202964]
  • E F Kamper, J Siafaka, J Stavridis. Modulation of rat brain synaptosomal plasma membrane achieved by atracurium and its metabolite laudanosine. Intensive care medicine. 1998 May; 24(5):519-25. doi: 10.1007/s001340050605. [PMID: 9660270]
  • A M Grigore, L Brusco, M Kuroda, R Koorn. Laudanosine and atracurium concentrations in a patient receiving long-term atracurium infusion. Critical care medicine. 1998 Jan; 26(1):180-3. doi: 10.1097/00003246-199801000-00037. [PMID: 9428564]
  • C E Smith, M M van Miert, C J Parker, J M Hunter. A comparison of the infusion pharmacokinetics and pharmacodynamics of cisatracurium, the 1R-cis 1'R-cis isomer of atracurium, with atracurium besylate in healthy patients. Anaesthesia. 1997 Sep; 52(9):833-41. doi: 10.1111/j.1365-2044.1997.195-az0331.x. [PMID: 9349062]
  • D F Kisor, V D Schmith, W A Wargin, C A Lien, E Ornstein, D R Cook. Importance of the organ-independent elimination of cisatracurium. Anesthesia and analgesia. 1996 Nov; 83(5):1065-71. doi: 10.1097/00000539-199611000-00029. [PMID: 8895287]
  • A M De Wolf, J A Freeman, V L Scott, W Tullock, D A Smith, D F Kisor, S Kerls, D R Cook. Pharmacokinetics and pharmacodynamics of cisatracurium in patients with end-stage liver disease undergoing liver transplantation. British journal of anaesthesia. 1996 May; 76(5):624-8. doi: 10.1093/bja/76.5.624. [PMID: 8688259]
  • A H Boyd, N B Eastwood, C J Parker, J M Hunter. Comparison of the pharmacodynamics and pharmacokinetics of an infusion of cis-atracurium (51W89) or atracurium in critically ill patients undergoing mechanical ventilation in an intensive therapy unit. British journal of anaesthesia. 1996 Mar; 76(3):382-8. doi: 10.1093/bja/76.3.382. [PMID: 8785138]
  • C A Lien, V D Schmith, M R Belmont, A Abalos, D F Kisor, J J Savarese. Pharmacokinetics of cisatracurium in patients receiving nitrous oxide/opioid/barbiturate anesthesia. Anesthesiology. 1996 Feb; 84(2):300-8. doi: 10.1097/00000542-199602000-00007. [PMID: 8602660]
  • V Nigrovic, J Gaspari, M Banoub. A pharmacokinetic-pharmacodynamic model for a muscle relaxant: atracurium. European journal of clinical pharmacology. 1996; 49(4):325-32. doi: 10.1007/bf00226335. [PMID: 8857080]
  • N B Eastwood, A H Boyd, C J Parker, J M Hunter. Pharmacokinetics of 1R-cis 1'R-cis atracurium besylate (51W89) and plasma laudanosine concentrations in health and chronic renal failure. British journal of anaesthesia. 1995 Oct; 75(4):431-5. doi: 10.1093/bja/75.4.431. [PMID: 7488483]
  • R M Welch, A Brown, J Ravitch, R Dahl. The in vitro degradation of cisatracurium, the R, cis-R'-isomer of atracurium, in human and rat plasma. Clinical pharmacology and therapeutics. 1995 Aug; 58(2):132-42. doi: 10.1016/0009-9236(95)90190-6. [PMID: 7648763]
  • J M Hunter, N B Eastwood, A H Boyd, C J Parker. Pharmacokinetics of 51W89: preliminary data. Acta anaesthesiologica Scandinavica. Supplementum. 1995; 106(?):94. doi: 10.1111/j.1399-6576.1995.tb04318.x. [PMID: 8533555]
  • H Burgmann, H Reckendorfer, M Sperlich, G L Tüchy, P G Spieckermann, M Weindlmayr-Göttel, S Schwarz. Influence of incubated atracurium on rat liver function. British journal of anaesthesia. 1994 Mar; 72(3):324-7. doi: 10.1093/bja/72.3.324. [PMID: 8130052]
  • B K Logan, G A Case. Identification of laudanosine, an atracurium metabolite, following a fatal drug-related shooting. Journal of analytical toxicology. 1993 Mar; 17(2):117-9. doi: 10.1093/jat/17.2.117. [PMID: 8492564]
  • R G Lawhead, M Matsumi, K R Peters, D F Landers, G L Becker, R A Earl. Plasma laudanosine levels in patients given atracurium during liver transplantation. Anesthesia and analgesia. 1993 Mar; 76(3):569-73. doi: 10.1213/00000539-199303000-00021. [PMID: 8452269]
  • J F Bion, M I Bowden, B Chow, L Honisberger, B C Weatherley. Atracurium infusions in patients with fulminant hepatic failure awaiting liver transplantation. Intensive care medicine. 1993; 19 Suppl 2(?):S94-8. doi: 10.1007/bf01708809. [PMID: 8106686]
  • J M Hunter. Atracurium and laudanosine pharmacokinetics in acute renal failure. Intensive care medicine. 1993; 19 Suppl 2(?):S91-3. doi: 10.1007/bf01708808. [PMID: 8106685]
  • L I Eriksson, R H Vandenbrom, C Lennmarken, S Agoston. Atracurium-induced neuromuscular block in the isolated arm. Acta anaesthesiologica Scandinavica. 1992 Oct; 36(7):728-32. doi: 10.1111/j.1399-6576.1992.tb03553.x. [PMID: 1332358]
  • V Nigrovic, M Banoub. Pharmacokinetic modelling of a parent drug and its metabolite. Atracurium and laudanosine. Clinical pharmacokinetics. 1992 May; 22(5):396-408. doi: 10.2165/00003088-199222050-00006. [PMID: 1505145]
  • E S Shearer, E P O'Sullivan, J M Hunter. Clearance of atracurium and laudanosine in the urine and by continuous venovenous haemofiltration. British journal of anaesthesia. 1991 Nov; 67(5):569-73. doi: 10.1093/bja/67.5.569. [PMID: 1751271]
  • I Ramzan. High-performance liquid chromatographic assay for laudanosine in biological fluids and tissue for neurotoxic studies in rats. Journal of chromatography. 1991 Apr; 565(1-2):465-70. doi: 10.1016/0378-4347(91)80411-5. [PMID: 1874895]
  • V Nigrovic, J L Fox. Atracurium decay and the formation of laudanosine in humans. Anesthesiology. 1991 Mar; 74(3):446-54. doi: 10.1097/00000542-199103000-00010. [PMID: 2001023]
  • C L Gwinnutt, J M Eddleston, D Edwards, B J Pollard. Concentrations of atracurium and laudanosine in cerebrospinal fluid and plasma in three intensive care patients. British journal of anaesthesia. 1990 Dec; 65(6):829-32. doi: 10.1093/bja/65.6.829. [PMID: 2265055]
  • R H Vandenbrom, J M Wierda, S Agoston. Pharmacokinetics and neuromuscular blocking effects of atracurium besylate and two of its metabolites in patients with normal and impaired renal function. Clinical pharmacokinetics. 1990 Sep; 19(3):230-40. doi: 10.2165/00003088-199019030-00006. [PMID: 2394062]
  • F Varin, J Ducharme, J G Besner, Y Théorêt. Determination of atracurium and laudanosine in human plasma by high-performance liquid chromatography. Journal of chromatography. 1990 Aug; 529(2):319-27. doi: 10.1016/s0378-4347(00)83838-4. [PMID: 2229251]
  • F Varin, J Ducharme, Y Théorêt, J G Besner, D R Bevan, F Donati. Influence of extreme obesity on the body disposition and neuromuscular blocking effect of atracurium. Clinical pharmacology and therapeutics. 1990 Jul; 48(1):18-25. doi: 10.1038/clpt.1990.112. [PMID: 2369806]
  • A N Thomas, J M Anderton, N J Harper. Anaesthesia for the treatment of a giant cerebral aneurysm under hypothermic circulatory arrest. Anaesthesia. 1990 May; 45(5):383-5. doi: 10.1111/j.1365-2044.1990.tb14782.x. [PMID: 2356934]
  • C Schopfer, A Benakis. Simplified method for the determination of atracurium and laudanosine in pig plasma by high-performance liquid chromatography and fluorimetric detection. Journal of chromatography. 1990 Mar; 526(1):223-7. doi: 10.1016/s0378-4347(00)82502-5. [PMID: 2341536]
  • M R Fahey, P C Canfell, T Taboada, Y Hosobuchi, R D Miller. Cerebrospinal fluid concentrations of laudanosine after administration of atracurium. British journal of anaesthesia. 1990 Jan; 64(1):105-6. doi: 10.1093/bja/64.1.105. [PMID: 2302366]
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  • J F Pittet, E Tassonyi, C Schopfer, D R Morel, G Mentha, M Fathi, C Le Coultre, D A Steinig, A Benakis. Plasma concentrations of laudanosine, but not of atracurium, are increased during the anhepatic phase of orthotopic liver transplantation in pigs. Anesthesiology. 1990 Jan; 72(1):145-52. doi: 10.1097/00000542-199001000-00024. [PMID: 2297117]
  • A P Kent, C J Parker, J M Hunter. Pharmacokinetics of atracurium and laudanosine in the elderly. British journal of anaesthesia. 1989 Dec; 63(6):661-6. doi: 10.1093/bja/63.6.661. [PMID: 2611066]
  • J M Eddleston, N J Harper, B J Pollard, D Edwards, C L Gwinnutt. Concentrations of atracurium and laudanosine in cerebrospinal fluid and plasma during intracranial surgery. British journal of anaesthesia. 1989 Nov; 63(5):525-30. doi: 10.1093/bja/63.5.525. [PMID: 2605068]
  • W Z Shi, M R Fahey, D M Fisher, R D Miller. Modification of central nervous system effects of laudanosine by inhalation anaesthetics. British journal of anaesthesia. 1989 Nov; 63(5):598-600. doi: 10.1093/bja/63.5.598. [PMID: 2605078]
  • G H Beemer, A R Bjorksten, P J Dawson, D P Crankshaw. Production of laudanosine following infusion of atracurium in man and its effects on awakening. British journal of anaesthesia. 1989 Jul; 63(1):76-80. doi: 10.1093/bja/63.1.76. [PMID: 2765346]
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  • A Tateishi, M H Zornow, M S Scheller, P C Canfell. Electroencephalographic effects of laudanosine in an animal model of epilepsy. British journal of anaesthesia. 1989 May; 62(5):548-52. doi: 10.1093/bja/62.5.548. [PMID: 2730827]
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  • C J Parker, J E Jones, J M Hunter. Disposition of infusions of atracurium and its metabolite, laudanosine, in patients in renal and respiratory failure in an ITU. British journal of anaesthesia. 1988 Nov; 61(5):531-40. doi: 10.1093/bja/61.5.531. [PMID: 3207525]
  • S J Peat, D R Potter, J M Hunter. The prolonged use of atracurium in a patient with tetanus. Anaesthesia. 1988 Nov; 43(11):962-3. doi: 10.1111/j.1365-2044.1988.tb05663.x. [PMID: 3213921]
  • V Nigrovic, S Kidney, J B Pandya. Pharmacokinetics of atracurium metabolites. British journal of anaesthesia. 1988 Mar; 60(4):477-9. doi: 10.1093/bja/60.4.477-b. [PMID: 3355746]
  • S Ward, N Boheimer, B C Weatherley, R J Simmonds, T A Dopson. Pharmacokinetics of atracurium and its metabolites in patients with normal renal function, and in patients in renal failure. British journal of anaesthesia. 1987 Jun; 59(6):697-706. doi: 10.1093/bja/59.6.697. [PMID: 3606914]
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  • P M Yate, P J Flynn, R W Arnold, B C Weatherly, R J Simmonds, T Dopson. Clinical experience and plasma laudanosine concentrations during the infusion of atracurium in the intensive therapy unit. British journal of anaesthesia. 1987 Feb; 59(2):211-7. doi: 10.1093/bja/59.2.211. [PMID: 3548792]
  • B W Brandom, R L Stiller, D R Cook, S K Woelfel, S Chakravorti, A Lai. Pharmacokinetics of atracurium in anaesthetized infants and children. British journal of anaesthesia. 1986 Nov; 58(11):1210-3. doi: 10.1093/bja/58.11.1210. [PMID: 3778789]
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  • S Ward, B C Weatherley. Pharmacokinetics of atracurium and its metabolites. British journal of anaesthesia. 1986; 58 Suppl 1(?):6S-10S. doi: 10.1093/bja/58.suppl_1.6s. [PMID: 3754756]
  • W Z Shi, M R Fahey, D M Fisher, R D Miller, C Canfell, E I Eger. Laudanosine (a metabolite of atracurium) increases the minimum alveolar concentration of halothane in rabbits. Anesthesiology. 1985 Dec; 63(6):584-8. doi: 10.1097/00000542-198512000-00006. [PMID: 2932981]
  • R L Stiller, D R Cook, S Chakravorti. In vitro degradation of atracurium in human plasma. British journal of anaesthesia. 1985 Nov; 57(11):1085-8. doi: 10.1093/bja/57.11.1085. [PMID: 3840382]
  • M R Fahey, S M Rupp, C Canfell, D M Fisher, R D Miller, M Sharma, K Castagnoli, P J Hennis. Effect of renal failure on laudanosine excretion in man. British journal of anaesthesia. 1985 Nov; 57(11):1049-51. doi: 10.1093/bja/57.11.1049. [PMID: 3840380]
  • R J Simmonds. Determination of atracurium, laudanosine and related compounds in plasma by high-performance liquid chromatography. Journal of chromatography. 1985 Oct; 343(2):431-6. doi: 10.1016/s0378-4347(00)84615-0. [PMID: 3840807]
  • M R Fahey, S M Rupp, D M Fisher, R D Miller, M Sharma, C Canfell, K Castagnoli, P J Hennis. The pharmacokinetics and pharmacodynamics of atracurium in patients with and without renal failure. Anesthesiology. 1984 Dec; 61(6):699-702. doi: 10.1097/00000542-198412000-00011. [PMID: 6239574]
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