Piritramide (BioDeep_00000036563)
human metabolite
代谢物信息卡片
化学式: C27H34N4O (430.2732474)
中文名称: 哌腈米特
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: C1CCN(CC1)C2(CCN(CC2)CCC(C#N)(C3=CC=CC=C3)C4=CC=CC=C4)C(=O)N
InChI: InChI=1S/C27H34N4O/c28-22-26(23-10-4-1-5-11-23,24-12-6-2-7-13-24)14-19-30-20-15-27(16-21-30,25(29)32)31-17-8-3-9-18-31/h1-2,4-7,10-13H,3,8-9,14-21H2,(H2,29,32)
描述信息
Piritramide (R-3365, trade names Dipidolor, Piridolan, Pirium and others) is a synthetic opioid analgesic with a potency 0.65 to 0.75 times that of morphine. A common starting dose is 15 mg IV, equivalent to 10 mg of morphine hydrochloride. Piritramide is commonly used for the treatment of postoperative pain. Piritramide was discovered at Janssen Pharmaceutica in 1960 and is currently manufactured and distributed within continental Europe and some other places by Janssen-Cilag. Piritramide is a strong opioid and therefore is regulated much the same as morphine in all known jurisdictions. It was never introduced in the United States and is therefore a Schedule I/Narcotic controlled substance. It is listed under international treaties and other laws such as the German Betabungsmittelgesetz, the Austrian Suchtgiftmittelgesetz, the Opium Laws of various other European countries, Canadian controlled substances act, UK Misuse of Drugs Act of 1971, and equivalents elsewhere. Strangely enough, bezitramide, which is not currently marketed in the United States is a Schedule II/Narcotic controlled substance. Piritramide is also known as pirinitramide. Its closest chemical relatives amongst well-known drugs are diphenoxylate (Lomotil) and bezitramide (Burgodin). Piritramide is available in tablets and ampoules of sterile solution for injection by all routes, and is used in Patient Controlled Analgesia units. In addition to PCA, piritramide is most often used in post-operative situations and emergency departments; some of its properties would seem to lend it well to chronic pain control as well. It is one of the longer-lasting opioids and has a plasma half-life of 3 to 12 hours. Piritramide tends to cause less respiratory depression than morphine and can take a while to have full effect especially if taken by mouth.
D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants > D009294 - Narcotics
N - Nervous system > N02 - Analgesics > N02A - Opioids > N02AC - Diphenylpropylamine derivatives
D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents
C78272 - Agent Affecting Nervous System > C67413 - Opioid Receptor Agonist
D002491 - Central Nervous System Agents > D000700 - Analgesics
同义名列表
数据库引用编号
9 个数据库交叉引用编号
- ChEBI: CHEBI:135699
- PubChem: 9331
- HMDB: HMDB0041990
- DrugBank: DB12492
- ChEMBL: CHEMBL559288
- Wikipedia: Piritramide
- MeSH: Pirinitramide
- chemspider: 8967
- CAS: 302-41-0
分类词条
相关代谢途径
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代谢反应
0 个相关的代谢反应过程信息。
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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。
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文献列表
- Ruth Verplaetse, Jan Tytgat. Development and validation of a sensitive UPLC-MS/MS method for the analysis of narcotic analgesics in urine and whole blood in forensic context.
Forensic science international.
2012 Feb; 215(1-3):136-45. doi:
10.1016/j.forsciint.2011.01.047. [PMID: 21356580] - S M Dorhout Mees, D Bertens, H B van der Worp, G J E Rinkel, W M van den Bergh. Magnesium and headache after aneurysmal subarachnoid haemorrhage.
Journal of neurology, neurosurgery, and psychiatry.
2010 May; 81(5):490-3. doi:
10.1136/jnnp.2009.181404. [PMID: 19828484] - 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] - Thomas Koch, Anja Seifert, Dai-Fei Wu, Marija Rankovic, Jürgen Kraus, Christine Börner, Lars-Ove Brandenburg, Helmut Schröder, Volker Höllt. mu-opioid receptor-stimulated synthesis of reactive oxygen species is mediated via phospholipase D2.
Journal of neurochemistry.
2009 Aug; 110(4):1288-96. doi:
10.1111/j.1471-4159.2009.06217.x. [PMID: 19519662] - Markus Klimek, Jaap W Hol, Stephan Wens, Claudia Heijmans-Antonissen, Sjoerd Niehof, Arnaud J Vincent, Jan Klein, Freek J Zijlstra. Inflammatory profile of awake function-controlled craniotomy and craniotomy under general anesthesia.
Mediators of inflammation.
2009; 2009(?):670480. doi:
10.1155/2009/670480. [PMID: 19536349] - 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] - F Musshoff, J Trafkowski, U Kuepper, B Madea. An automated and fully validated LC-MS/MS procedure for the simultaneous determination of 11 opioids used in palliative care, with 5 of their metabolites.
Journal of mass spectrometry : JMS.
2006 May; 41(5):633-40. doi:
10.1002/jms.1021. [PMID: 16541404] - W Seeling, L Kneer, B Büchele, J E Gschwend, L Maier, C Nett, T Simmet, P Steffen, M Schneider, M Rockemann. [Delta(9)-tetrahydrocannabinol and the opioid receptor agonist piritramide do not act synergistically in postoperative pain].
Der Anaesthesist.
2006 Apr; 55(4):391-400. doi:
10.1007/s00101-005-0963-6. [PMID: 16389542] - Carsten Müller, Wolf Kremer, Steffi Harlfinger, Oxana Doroshyenko, Alexander Jetter, Fritz Hering, Christoph Hünseler, Bernhard Roth, Martin Theisohn. Pharmacokinetics of piritramide in newborns, infants and young children in intensive care units.
European journal of pediatrics.
2006 Apr; 165(4):229-39. doi:
10.1007/s00431-005-0021-z. [PMID: 16496200] - Rainer Kahlich, Christoph H Gleiter, Stefan Laufer, Bernd Kammerer. Quantitative determination of piritramide in human plasma and urine by off- and on-line solid-phase extraction liquid chromatography coupled to tandem mass spectrometry.
Rapid communications in mass spectrometry : RCM.
2006; 20(2):275-83. doi:
10.1002/rcm.2257. [PMID: 16345132] - F Musshoff, S A Padosch, B Madea. Death during patient-controlled analgesia: piritramide overdose and tissue distribution of the drug.
Forensic science international.
2005 Nov; 154(2-3):247-51. doi:
10.1016/j.forsciint.2004.10.012. [PMID: 16182973] - Ralph Lattermann, Geesche Belohlavek, Sigrid Wittmann, Bernd Füchtmeier, Michael Gruber. The anticatabolic effect of neuraxial blockade after hip surgery.
Anesthesia and analgesia.
2005 Oct; 101(4):1202-1208. doi:
10.1213/01.ane.0000167282.65352.e7. [PMID: 16192545] - Stefan Suttner, Katrin Lang, Swen N Piper, Harald Schultz, Kerstin D Röhm, Joachim Boldt. Continuous intra- and postoperative thoracic epidural analgesia attenuates brain natriuretic peptide release after major abdominal surgery.
Anesthesia and analgesia.
2005 Sep; 101(3):896-903. doi:
10.1213/01.ane.0000160532.77128.89. [PMID: 16116011] - Thomas Koch, Antje Widera, Katharina Bartzsch, Stefan Schulz, Lars-Ove Brandenburg, Nicole Wundrack, Andrea Beyer, Gisela Grecksch, Volker Höllt. Receptor endocytosis counteracts the development of opioid tolerance.
Molecular pharmacology.
2005 Jan; 67(1):280-7. doi:
10.1124/mol.104.004994. [PMID: 15475572] - T Bouillon, P Groeger, D Kietzmann. The pharmacokinetics of piritramide after prolonged administration to intensive care patients.
European journal of anaesthesiology.
2004 Sep; 21(9):673-8. doi:
10.1017/s0265021504009019. [PMID: 15595577] - C Höhne, B Donaubauer, U Kaisers. [Opioids during anesthesia in liver and renal failure].
Der Anaesthesist.
2004 Mar; 53(3):291-303. doi:
10.1007/s00101-004-0651-y. [PMID: 15074320] - O Grottke, J Müller, P J Dietrich, T H Krause, F Wappler. [Comparison of premedication with clonidine and midazolam combined with TCI for orthopaedic shoulder surgery].
Anasthesiologie, Intensivmedizin, Notfallmedizin, Schmerztherapie : AINS.
2003 Dec; 38(12):772-80. doi:
10.1055/s-2003-45396. [PMID: 14666440] - T Bouillon, G Garstka, D Stafforst, S Shafer, H Schwilden, A Hoeft. Piritramide and alfentanil display similar respiratory depressant potency.
Acta anaesthesiologica Scandinavica.
2003 Nov; 47(10):1231-41. doi:
10.1046/j.1399-6576.2003.00251.x. [PMID: 14616320] - André Gottschalk, Marc-Alexander Burmeister, Patricia Radtke, Markus Krieg, Faraneh Farokhzad, Sonja Kreissl, Matthias Strauss, Thomas Standl. Continuous wound infiltration with ropivacaine reduces pain and analgesic requirement after shoulder surgery.
Anesthesia and analgesia.
2003 Oct; 97(4):1086-1091. doi:
10.1213/01.ane.0000081733.77457.79. [PMID: 14500162] - J Martens-Lobenhoffer, W Römhild. Quantitative determination of piritramide in human serum applying liquid chromatography-two-stage mass spectrometry.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2003 Jan; 783(1):53-9. doi:
10.1016/s1570-0232(02)00488-9. [PMID: 12450524] - H A Adams, P Meyer, A Stoppa, A Müller-Goch, P Bayer, H Hecker. [Anaesthesia for caesarean section. Comparison of two general anaesthetic regimens and spinal anaesthesia].
Der Anaesthesist.
2003 Jan; 52(1):23-32. doi:
10.1007/s00101-002-0440-4. [PMID: 12577162] - K Gerlach, Th Uhlig, M Hüppe, E Kraatz, L Saager, A Schmitz, V Dörges, P Schmucker. Remifentanil-clonidine-propofol versus sufentanil-propofol anesthesia for coronary artery bypass surgery.
Journal of cardiothoracic and vascular anesthesia.
2002 Dec; 16(6):703-8. doi:
10.1053/jcan.2002.128415. [PMID: 12486650] - H A Adams, P Saatweber, C S Schmitz, H Hecker. Postoperative pain management in orthopaedic patients: no differences in pain score, but improved stress control by epidural anaesthesia.
European journal of anaesthesiology.
2002 Sep; 19(9):658-65. doi:
10.1017/s0265021502001084. [PMID: 12243289] - Sebastian Reinhardt, Ulrich Burkhardt, Andrei Nestler, Renate Wiedemann. Use of piritramide for analgesia and sedation during peribulbar nerve block for cataract surgery.
Ophthalmologica. Journal international d'ophtalmologie. International journal of ophthalmology. Zeitschrift fur Augenheilkunde.
2002 Jul; 216(4):256-60. doi:
10.1159/000063853. [PMID: 12207128] - Holger Holthusen, Peter Backhaus, Frank Boeminghaus, Maria Breulmann, Peter Lipfert. Preemptive analgesia: no relevant advantage of preoperative compared with postoperative intravenous administration of morphine, ketamine, and clonidine in patients undergoing transperitoneal tumor nephrectomy.
Regional anesthesia and pain medicine.
2002 May; 27(3):249-53. doi:
10.1053/rapm.2002.30669. [PMID: 12016597] - D H Bremerich, G Neidhart, K Heimann, P Kessler, M Behne. Prophylactically-administered rectal acetaminophen does not reduce postoperative opioid requirements in infants and small children undergoing elective cleft palate repair.
Anesthesia and analgesia.
2001 Apr; 92(4):907-12. doi:
10.1097/00000539-200104000-00020. [PMID: 11273923] - T Bouillon, D Kietzmann, R Port, I Meineke, A Hoeft. Population pharmacokinetics of piritramide in surgical patients.
Anesthesiology.
1999 Jan; 90(1):7-15. doi:
10.1097/00000542-199901000-00004. [PMID: 9915307] - G Wiesner, M Gruber, K Wild, K Hoerauf, K Taeger. Protein binding of piritramide: influence of various protein concentrations and the postoperative acute phase response.
European journal of clinical pharmacology.
1999 Jan; 54(11):843-5. doi:
10.1007/s002280050564. [PMID: 10027658] - J Boldt, E Thaler, A Lehmann, M Papsdorf, F Isgro. Pain management in cardiac surgery patients: comparison between standard therapy and patient-controlled analgesia regimen.
Journal of cardiothoracic and vascular anesthesia.
1998 Dec; 12(6):654-8. doi:
10.1016/s1053-0770(98)90237-3. [PMID: 9854662] - D Kietzmann, T Bouillon, C Hamm, K Schwabe, H Schenk, U Gundert-Remy, D Kettler. Pharmacodynamic modelling of the analgesic effects of piritramide in postoperative patients.
Acta anaesthesiologica Scandinavica.
1997 Aug; 41(7):888-94. doi:
10.1111/j.1399-6576.1997.tb04805.x. [PMID: 9265933] - D Kietzmann, I Briede, T Bouillon, U Gundert-Remy, D Kettler. Pharmacokinetics of piritramide after an intravenous bolus in surgical patients.
Acta anaesthesiologica Scandinavica.
1996 Sep; 40(8 Pt 1):898-903. doi:
10.1111/j.1399-6576.1996.tb04557.x. [PMID: 8908225] - E M Tschernko, S Hofer, C Bieglmayer, W Wisser, W Haider. Early postoperative stress: video-assisted wedge resection/lobectomy vs conventional axillary thoracotomy.
Chest.
1996 Jun; 109(6):1636-42. doi:
10.1378/chest.109.6.1636. [PMID: 8769523] - V A Mikhaĭlovich, O Iu Kuznetsova, A D Bulganin, A N Berkovich. [Clofelin in the anesthesiological support system for surgical operations].
Khirurgiia.
1996; ?(6):78-81. doi:
NULL. [PMID: 9173160] - V R Gust, R Weber, A Henn-Beilharz, C Krier. [Patient-controlled analgesia (PCA) after urologic interventions].
Anaesthesiologie und Reanimation.
1995; 20(5):134-8. doi:
NULL. [PMID: 8526966] - C Mappes, U Witzsch, R A Bürger, R Hohenfellner. [Clinical tests on reno-ureteral lithiasis with a new Lithostar 2 model C shock wave generator system].
Annales d'urologie.
1994; 28(2):53-6. doi:
. [PMID: 8210210] - H C Michaelis, D Kietzmann, H Neurath, U Jongepier, B Schilling. Sensitive determination of piritramide in human plasma by gas chromatography.
Journal of chromatography.
1991 Nov; 571(1-2):257-62. doi:
10.1016/0378-4347(91)80453-j. [PMID: 1810954] - G Misztal. [Determination of piritramid in plasma using high pressure liquid chromatography methods].
Acta poloniae pharmaceutica.
1991; 48(5-6):1-2. doi:
NULL. [PMID: 1669334] - G Misztal. [Identification of pentazocine, piritramide and methadone in blood using thin layer chromatography].
Acta poloniae pharmaceutica.
1990; 47(5-6):5-8. doi:
NULL. [PMID: 1669331] - P J Kulka, P M Lauven, H Schwilden, K Rommelsheim. [The efficacy of the benzodiazepine antagonist flumazenil (Ro 15-1788) based on the EEG of mechanically ventilated intensive care patients].
Der Anaesthesist.
1989 Aug; 38(8):424-30. doi:
NULL. [PMID: 2506776] - M Berger, A Brandstetter, E Chowanetz, G Gasser, H Mossig, P Schmidt. [Extracorporeal shockwave lithotripsy in sedation-analgesia].
Der Urologe. Ausg. A.
1988 Mar; 27(2):89-92. doi:
NULL. [PMID: 3376372] - S Kostova, A Boĭcheva, N Gavrilova, B Petrova. [Analgesia in the postoperative period for severely ill children].
Khirurgiia.
1987; 40(3):27-30. doi:
". [PMID: 3626387] - W Seeling, K H Altemeyer, M Butters, H L Fehm, U Loos, R Mayer, M Nabjinsky, J E Schmitz. [Blood glucose, ACTH, cortisol, T4, T3 and rT3 after cholecystectomy. Comparative studies of continuous peridural anesthesia and neuroleptanalgesia].
Regional-Anaesthesie.
1984 Jan; 7(1):1-10. doi:
NULL. [PMID: 6324295] - B von Bormann, B Weidler, R Dennhardt, N Frings, H Lennartz, G Hempelmann. [Plasma-antidiuretic hormone level as indicator of postoperative stress (part II) (author's transl)].
Anasthesie, Intensivtherapie, Notfallmedizin.
1981 Dec; 16(6):319-22. doi:
NULL. [PMID: 7325345] - J Winaver, D B Sylk, P R Teredesai, J S Robertson, J B Puschett. Dissociative effects of piretanide on proximal tubular PO4 and HCO3 transport.
The American journal of physiology.
1980 Jan; 238(1):F60-8. doi:
10.1152/ajprenal.1980.238.1.f60. [PMID: 7356023]