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去甲哌替啶

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去甲哌替啶
臨床資料
給藥途徑N/A
ATC碼
  • 未分配
法律規範狀態
法律規範
識別資訊
  • Ethyl 4-phenylpiperidine-4-carboxylate
CAS號77-17-8  checkY
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard英語CompTox Chemicals Dashboard (EPA)
ECHA InfoCard100.000.918 編輯維基數據鏈接
化學資訊
化學式C14H19NO2
摩爾質量233.31 g·mol−1
3D模型(JSmol英語JSmol
  • O=C(OCC)C2(c1ccccc1)CCNCC2
  • InChI=1S/C14H19NO2/c1-2-17-13(16)14(8-10-15-11-9-14)12-6-4-3-5-7-12/h3-7,15H,2,8-11H2,1H3 checkY
  • Key:QKHMFBKXTNQCTM-UHFFFAOYSA-N checkY

去甲哌替啶是一種4-苯基哌啶的衍生物,化學式為C14H19NO2。它是哌替啶前體及有毒代謝物。它被列入聯合國麻醉品單一公約,也被美國列入到受管制物質法案附表II,2014年的生產限額為11克(0.39盎司)。[1]

去甲哌替啶因可用於合成哌替啶及相關的N-取代衍生物(如依託利定英語etoxeridine[2]苄替啶英語benzethidine[3]呋替啶英語furethidine[4])而受到管制。不過,去甲哌替啶本身的類阿片作用低,是一種引起抽搐的興奮劑。[5][6]

當把哌替啶用作鎮痛藥時,就要大劑量使用[7]或靜脈注射哌替啶。[8]這會去甲哌替啶產生的速率比排泄去甲哌替啶的速率快,導致去甲哌替啶累積產生的併發症,包括抽搐、肌陣攣[9]低血鈉症[10]這些併發症可能會很嚴重,甚至可能導致死亡。[11]這些併發症在老年人[12]及肝功能或腎功能受損的人[13]身上更明顯。

哌替啶在體內會被肝臟屬於細胞色素P450CYP2B6CYP2C19CYP3A4代謝成去甲哌替啶。由於這些酶的活性因人而異,且可能受到共服的其它藥物影響,因此很難預測產生去甲哌替啶的速率。[14][15]

參考資料

[編輯]
  1. ^ Conversion Factors for Controlled Substances. Diversion Control Division. Drug Enforcement Administration (DEA), U.S. Department of Justice. [2024-03-13]. (原始內容存檔於2016-03-02). 
  2. ^ US granted 2858316,Henri M,「New piperidine derivatives」,發表於28 October 1958,指定於UCB SA 
  3. ^ Frearson PM, Stern ES. 622. Some new analogues of pethidine. Part III. 1-Aryloxy-alkylnorpethidines, and close analogues.. Journal of the Chemical Society (Resumed). 1958: 3065–7. doi:10.1039/JR9580003065. 
  4. ^ Frearson PM, Hardy DG, Stern ES. 426. Some new analogues of pethidine. Part IV. Substituents at the 1-position incorporating cyclic ether groups.. Journal of the Chemical Society (Resumed). 1960: 2103–7. doi:10.1039/JR9600002103. 
  5. ^ Umans JG, Inturrisi CE. Antinociceptive activity and toxicity of meperidine and normeperidine in mice. The Journal of Pharmacology and Experimental Therapeutics. October 1982, 223 (1): 203–6 [2024-03-13]. PMID 7120119. (原始內容存檔於2024-03-13). 
  6. ^ Plummer JL, Gourlay GK, Cmielewski PL, Odontiadis J, Harvey I. Behavioural effects of norpethidine, a metabolite of pethidine, in rats. Toxicology. January 1995, 95 (1–3): 37–44. PMID 7825188. doi:10.1016/0300-483x(94)02871-q. 
  7. ^ Simopoulos TT, Smith HS, Peeters-Asdourian C, Stevens DS. Use of meperidine in patient-controlled analgesia and the development of a normeperidine toxic reaction. Archives of Surgery (Chicago, Ill.). January 2002, 137 (1): 84–8. PMID 11772223. doi:10.1001/archsurg.137.1.84可免費查閱. 
  8. ^ Stone PA, Macintyre PE, Jarvis DA. Norpethidine toxicity and patient controlled analgesia. British Journal of Anaesthesia. November 1993, 71 (5): 738–40. PMID 8251291. doi:10.1093/bja/71.5.738可免費查閱. 
  9. ^ Reutens DC, Stewart-Wynne EG. Norpethidine induced myoclonus in a patient with renal failure. Journal of Neurology, Neurosurgery, and Psychiatry. December 1989, 52 (12): 1450–1. PMC 1031622可免費查閱. PMID 2614458. doi:10.1136/jnnp.52.12.1450. 
  10. ^ Appel WC. Possible roles of normeperidine and hyponatremia in a postoperative death. Canadian Medical Association Journal. November 1987, 137 (10): 912–3. PMC 1267380可免費查閱. PMID 3676934. 
  11. ^ Jiraki K. Lethal effects of normeperidine. The American Journal of Forensic Medicine and Pathology. March 1992, 13 (1): 42–3. PMID 1585886. S2CID 32005631. doi:10.1097/00000433-199203000-00009. 
  12. ^ Holmberg, L.; Odar-Cederlöf, I.; Boréus, L. O.; Heyner, L.; Ehrnebo, M. Comparative disposition of pethidine and norpethidine in old and young patients. European Journal of Clinical Pharmacology. 1982, 22 (2): 175–179. ISSN 0031-6970. doi:10.1007/BF00542464. 
  13. ^ Pond SM, Tong T, Benowitz NL, Jacob P, Rigod J. Presystemic metabolism of meperidine to normeperidine in normal and cirrhotic subjects. Clinical Pharmacology and Therapeutics. August 1981, 30 (2): 183–8. PMID 7249503. S2CID 10117158. doi:10.1038/clpt.1981.146. 
  14. ^ Ramírez J, Innocenti F, Schuetz EG, Flockhart DA, Relling MV, Santucci R, Ratain MJ. CYP2B6, CYP3A4, and CYP2C19 are responsible for the in vitro N-demethylation of meperidine in human liver microsomes. Drug Metabolism and Disposition: The Biological Fate of Chemicals. September 2004, 32 (9): 930–6. PMID 15319333. 
  15. ^ McHugh GJ. Norpethidine accumulation and generalized seizure during pethidine patient-controlled analgesia. Anaesthesia and Intensive Care. June 1999, 27 (3): 289–91. PMID 10389564. 

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