ペチジンペチジンの概要

ペチジン
IUPAC命名法による物質名
	IUPAC名 Ethyl 1-methyl-4-phenylpiperidine-4-carboxylate;
臨床データ
販売名	Demerol
胎児危険度分類	AU: C ; US: C ; ;
法的規制	AU: Controlled (S8) ; CA: Schedule I ; DE: Anlage III ; NZ: Class B ; UK: クラスA ; US: スケジュールII ; UN: Narcotic Schedule I ; Class B3 (NZ);
依存性	High
投与方法	oral, intravenous, intramuscular, subcutaneous
薬物動態データ
生物学的利用能	50–60% (Oral), 80-90% (Oral, in cases of hepatic impairment)
血漿タンパク結合	65-75%
代謝	Liver
半減期	2.5-4 hours, 7-11 hours (liver disease)
排泄	Renal
識別
CAS番号;	57-42-1
ATCコード	N02AB02 (WHO)
PubChem	CID: 4058
IUPHAR/BPS	7221
DrugBank	DB00454
ChemSpider	3918
UNII	9E338QE28F
KEGG	D08343
ChEMBL	CHEMBL607
化学的データ
化学式	C15H21NO2
分子量	247.33g/mol
	SMILES O=C(C1(CCN(CC1)C)C2=CC=CC=C2)OCC;
	InChI InChI=1S/C15H21NO2/c1-3-18-14(17)15(9-11-16(2)12-10-15)13-7-5-4-6-8-13/h4-8H,3,9-12H2,1-2H3 =; Key:XADCESSVHJOZHK-UHFFFAOYSA-N =;
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鎮痛作用、呼吸抑制作用はモルヒネよりも弱い。モルヒネに比べてペチジンはより安全で、依存性が弱く、推定される抗コリン効果によって胆道痙攣や腎疝痛（英語版）への有効性は高い^[3]と思われていたが、これらは後に全て幻想であった事が判明し、少なくとも依存性リスクは同等で、胆道痙攣や腎疝痛への効果は他のオピオイドに優越せず、毒性を持つ代謝物（ノルペチジン（英語版））のために他のオピオイドより毒性、特に長期投与時の毒性が高いことが明らかとなった^[3]。ノルペチジンはセロトニン作用を持つので、他のオピオイドと異なりペチジンの副作用にはセロトニン症候群がある^[3]^[4]。

出典

^ “Demerol, Pethidine (meperidine) dosing, indications, interactions, adverse effects, and more”. Medscape Reference. WebMD. 2014年4月9日閲覧。
^ Shipton, E (March 2006). “Should New Zealand continue signing up to the Pethidine Protocol?” (PDF). The New Zealand Medical Journal 119 (1230): U1875. PMID 16532042. オリジナルの2014年4月8日時点におけるアーカイブ。.
^ ^a ^b ^c ^d Latta, KS; Ginsberg, B; Barkin, RL (January–February 2002). “Meperidine: a critical review.”. American Journal of Therapeutics 9 (1): 53–68. doi:10.1097/00045391-200201000-00010. PMID 11782820.
^ ^a ^b MacPherson, RD; Duguid, MD (2008). “Strategy to Eliminate Pethidine Use in Hospitals” (PDF). Journal of Pharmacy Practice and Research 38 (2): 88–89.
^ Mather, LE; Meffin, PJ (September–October 1978). “Clinical pharmacokinetics of pethidine.”. Clinical Pharmacokinetics 3 (5): 352–68. doi:10.2165/00003088-197803050-00002. PMID 359212.
^ ^a ^b Rossi, S, ed (2013). Australian Medicines Handbook (2013 ed.). Adelaide: The Australian Medicines Handbook Unit Trust. ISBN 978-0-9805790-9-3
^ Michaelis, Martin; Schölkens, Bernward; Rudolphi, Karl (April 2007). “An anthology from Naunyn-Schmiedeberg's archives of pharmacology”. Naunyn-Schmiedeberg's Archives of Pharmacology (Springer Berlin) 375 (2): 81–84. doi:10.1007/s00210-007-0136-z. PMID 17310263.
^ Kaiko, Robert F.; Kathleen M. Foley; Patricia Y. Grabinski; George Heidrich; Ada G. Rogers; Charles E. Inturrisi; Marcus M. Reidenberg (February 1983). “Central Nervous System Excitatory Effects of Meperidine in Cancer Patients”. Annals of Neurology (Wiley Interscience) 13 (2): 180–185. doi:10.1002/ana.410130213. PMID 6187275.
^ ^a ^b ^c ^d ^e “オピスタン原末添付文書” (2015年4月). 2016年4月5日閲覧。
^ ^a ^b ^c ^d ^e “ペチジン塩酸塩注射液35mg／ペチジン塩酸塩注射液50mg 添付文書” (2015年7月). 2016年11月6日閲覧。
^ http://www.deadiversion.usdoj.gov/fed_regs/quotas/2014/fr0825.htm
^ “Parenteral opioids for labor pain relief: A systematic review - American Journal of Obstetrics & Gynecology”. www.ajog.org. 2015年7月11日閲覧。
^ “Narcotics for Pain During Labor: Types & Side Effects”. 2015年6月20日閲覧。
^ “WHO en:Template:! Parenteral opioids for maternal pain relief in labour”. apps.who.int. 2015年6月20日閲覧。
^ “Pain relief in labour - Pregnancy and baby guide - NHS Choices”. www.nhs.uk. 2015年6月20日閲覧。
^ Blueprints - Family Medicine (3rd edition)
^ Baselt, R. (2008). Disposition of Toxic Drugs and Chemicals in Man (8 ed.). Foster City, CA: Biomedical Publications. pp. 911-914.
^ Package insert for meperidine hydrochloride, Boehringer Ingelheim, Ridgefield, CT, 2005.
^ Brody, Jane (2007年2月27日). “A Mix of Medicines That Can Be Lethal”. New York Times 2009年2月13日閲覧. "The death of Libby Zion, an 18-year-old college student, in a New York hospital on March 5, 1984, led to a highly publicized court battle and created a cause célèbre over the lack of supervision of inexperienced and overworked young doctors. But only much later did experts zero in on the preventable disorder that apparently led to Ms. Zion’s death: a form of drug poisoning called serotonin syndrome."
^ Bronwen Bryant and Kathleen Knights (2010). Pharmacology for Health Professionals, 3rd Edition. Chatswood: Mosby Australia. ISBN 978-0-7295-3929-6
^ Koczmara, C; Perri, D; Hyland, S; Rousseaux, L (2005). “Meperidine (Demerol) safety issues”. Official Journal of the Canadian Association of Critical Care Nurses 16 (1): 8–12. ISSN 1201-2580 2014年1月11日閲覧。.
^ Laurence, Brunton (2010). Goodman & Gilman's pharmacological basis of therapeutics (12th ed.). McGraw-Hill. p. 549. ISBN 0071624422
^ http://www.fass.se/LIF/produktfakta/artikel_produkt.jsp?NplID=19741206000040&DocTypeID=3&UserTypeID=0
^ Wagner, Larry E., II; Michael Eaton; Salas S. Sabnis; Kevin J. Gingrich (November 1999). “Meperidine and Lidocaine Block of Recombinant Voltage-Dependent Na⁺ Channels: Evidence that Meperidine is a Local Anesthetic”. Anesthesiology (Lippincott Williams & Wilkins) 91 (5): 1481–1490. doi:10.1097/00000542-199911000-00042. PMID 10551601.
^ ^a ^b ^c Izenwasser, Sari; Amy Hauck Newman; Brian M. Cox; Jonathan L. Katz (January–February 1996). “The cocaine-like behavioral effects of meperidine are mediated by activity at the dopamine transporter”. European Journal of Pharmacology (Elsevier) 297 (1–2): 9–17. doi:10.1016/0014-2999(95)00696-6. PMID 8851160.
^ Lomenzo, Stacey A.; Jill B. Rhoden; Sari Izzenwasser; Dean Wade; Theresa Kopajtic; Jonathan L. Katz; Mark L. Trudell (2005-03-05). “Synthesis and Biological Evaluation of Meperdine Analogs at Monoamine Transporters”. Journal of Medicinal Chemistry (American Chemical Society) 48 (5): 1336–1343. doi:10.1021/jm0401614. PMID 15743177.
^ ^a ^b ^c ^d “Demerol: Is It the Best Analgesic?” (PDF), Pennsylvania Patient Safety Reporting Service Patient Safety Advisory (Pennsylvania Patient Safety Authority) 3 (2), (June 2006) 2013年4月15日閲覧。
^ Davis, Sharon (2004年8月). “Use of pethidine for pain management in the emergency department: a position statement of the NSW Therapeutic Advisory Group”. New South Wales Therapeutic Advisory Group. 2007年1月17日閲覧。
^ ^a ^b ^c Latta, Kenneth S.; Brian Ginsberg; Robert L. Barkin (January–February 2002). “Meperidine: A Critical Review”. American Journal of Therapeutics (Lippincott Williams & Wilkins) 9 (1): 53–68. doi:10.1097/00045391-200201000-00010. PMID 11782820.
^ “In Brief”. NPS Radar. National Prescribing Service (2005年12月). 2009年12月22日閲覧。
^ Walker, Diana J.; James P. Zacny (June 1999). “Subjective, Psychomotor, and Physiological Effects of Cumulative Doses of Opioid µ Agonists in Healthy Volunteers”. The Journal of Pharmacology and Experimental Therapeutics (American Society for Pharmacology and Experimental Therapeutics) 289 (3): 1454–1464. PMID 10336539.
^ Molloy, A (2002). “Does pethidine still have a place in therapy?” (PDF). Australian Prescriber (NPS MedicineWise) 25 (1): 12–13.
^ Gilson AM, Ryan KM, Joranson DE, Dahl JL (2004). “A reassessment of trends in the medical use and abuse of opioid analgesics and implications for diversion control: 1997-2002”. J Pain Symptom Manage 28 (2): 176–188. doi:10.1016/j.jpainsymman.2004.01.003. PMID 15276196.
^ Joranson DE, Gilson AM (2005). “Drug crime is a source of abused pain medications in the United States”. J Pain Symptom Manage 30 (4): 299–301. doi:10.1016/j.jpainsymman.2005.09.001. PMID 16256890.
^ ^a ^b Lexicon of alcohol and drug terms. Geneva: World Health Organization. (1994). ISBN 92-4-154468-6
^ http://pubs.acs.org/doi/suppl/10.1021/jm0401614/suppl_file/jm0401614_s.pdf
^ Lomenzo, S.; Rhoden, J.; Izenwasser, S.; Wade, D.; Kopajtic, T.; Katz, J.; Trudell, M. (2005). “Synthesis and biological evaluation of meperidine analogues at monoamine transporters”. Journal of Medicinal Chemistry 48 (5): 1336–1343. doi:10.1021/jm0401614. PMID 15743177.
^ Lomenzo, S.; Izenwasser, S.; Gerdes, R. M.; Katz, J. L.; Kopajtic, T.; Trudell, M. L. (1999). “Synthesis, dopamine and serotonin transporter binding affinities of novel analogues of meperidine”. Bioorganic & Medicinal Chemistry Letters 9 (23): 3273–3276. doi:10.1016/S0960-894X(99)00606-X.
^ Rhoden, J. B.; Bouvet, M.; Izenwasser, S.; Wade, D.; Lomenzo, S. A.; Trudell, M. L. (2005). “Structure-activity studies of 3'-4'-dichloro-meperidine analogues at dopamine and serotonin transporters”. Bioorganic & Medicinal Chemistry 13 (19): 5623–5634. doi:10.1016/j.bmc.2005.05.025. PMID 15993612.
^ Gu, X.; Izenwasser, S.; Wade, D.; Housman, A.; Gulasey, G.; Rhoden, J. B.; Savoie, C. D.; Mobley, D. L. et al. (2010). “Synthesis and structure–activity studies of benzyl ester meperidine and normeperidine derivatives as selective serotonin transporter ligands”. Bioorganic & Medicinal Chemistry 18 (23): 8356. doi:10.1016/j.bmc.2010.09.060.

[前の解説]

[続きの解説]

「ペチジン」の続きの解説一覧

[1] “Demerol, Pethidine (meperidine) dosing, indications, interactions, adverse effects, and more”. Medscape Reference. WebMD. 2014年4月9日閲覧。

[NZ-2] Shipton, E (March 2006). “Should New Zealand continue signing up to the Pethidine Protocol?” (PDF). The New Zealand Medical Journal 119 (1230): U1875. PMID 16532042. オリジナルの2014年4月8日時点におけるアーカイブ。.

[crit-3] Latta, KS; Ginsberg, B; Barkin, RL (January–February 2002). “Meperidine: a critical review.”. American Journal of Therapeutics 9 (1): 53–68. doi:10.1097/00045391-200201000-00010. PMID 11782820.

[SHPA-4] MacPherson, RD; Duguid, MD (2008). “Strategy to Eliminate Pethidine Use in Hospitals” (PDF). Journal of Pharmacy Practice and Research 38 (2): 88–89.

[5] Mather, LE; Meffin, PJ (September–October 1978). “Clinical pharmacokinetics of pethidine.”. Clinical Pharmacokinetics 3 (5): 352–68. doi:10.2165/00003088-197803050-00002. PMID 359212.

[AMH-6] Rossi, S, ed (2013). Australian Medicines Handbook (2013 ed.). Adelaide: The Australian Medicines Handbook Unit Trust. ISBN 978-0-9805790-9-3

[Michaelis-7] Michaelis, Martin; Schölkens, Bernward; Rudolphi, Karl (April 2007). “An anthology from Naunyn-Schmiedeberg's archives of pharmacology”. Naunyn-Schmiedeberg's Archives of Pharmacology (Springer Berlin) 375 (2): 81–84. doi:10.1007/s00210-007-0136-z. PMID 17310263.

[Kaiko-8] Kaiko, Robert F.; Kathleen M. Foley; Patricia Y. Grabinski; George Heidrich; Ada G. Rogers; Charles E. Inturrisi; Marcus M. Reidenberg (February 1983). “Central Nervous System Excitatory Effects of Meperidine in Cancer Patients”. Annals of Neurology (Wiley Interscience) 13 (2): 180–185. doi:10.1002/ana.410130213. PMID 6187275.

[pio-9] “オピスタン原末添付文書” (2015年4月). 2016年4月5日閲覧。

[pii-10] “ペチジン塩酸塩注射液35mg／ペチジン塩酸塩注射液50mg 添付文書” (2015年7月). 2016年11月6日閲覧。

[11] ttp://www.deadiversion.usdoj.gov/fed_regs/quotas/2014/fr0825.htm

[12] “Parenteral opioids for labor pain relief: A systematic review - American Journal of Obstetrics & Gynecology”. www.ajog.org. 2015年7月11日閲覧。

[13] “Narcotics for Pain During Labor: Types & Side Effects”. 2015年6月20日閲覧。

[14] “WHO en:Template:! Parenteral opioids for maternal pain relief in labour”. apps.who.int. 2015年6月20日閲覧。

[15] “Pain relief in labour - Pregnancy and baby guide - NHS Choices”. www.nhs.uk. 2015年6月20日閲覧。

[16] Blueprints - Family Medicine (3rd edition)

[17] Baselt, R. (2008). Disposition of Toxic Drugs and Chemicals in Man (8 ed.). Foster City, CA: Biomedical Publications. pp. 911-914.

[18] Package insert for meperidine hydrochloride, Boehringer Ingelheim, Ridgefield, CT, 2005.

[brody-19] Brody, Jane (2007年2月27日). “A Mix of Medicines That Can Be Lethal”. New York Times 2009年2月13日閲覧. "The death of Libby Zion, an 18-year-old college student, in a New York hospital on March 5, 1984, led to a highly publicized court battle and created a cause célèbre over the lack of supervision of inexperienced and overworked young doctors. But only much later did experts zero in on the preventable disorder that apparently led to Ms. Zion’s death: a form of drug poisoning called serotonin syndrome."

[20] Bronwen Bryant and Kathleen Knights (2010). Pharmacology for Health Professionals, 3rd Edition. Chatswood: Mosby Australia. ISBN 978-0-7295-3929-6

[ISMP2005-21] Koczmara, C; Perri, D; Hyland, S; Rousseaux, L (2005). “Meperidine (Demerol) safety issues”. Official Journal of the Canadian Association of Critical Care Nurses 16 (1): 8–12. ISSN 1201-2580 2014年1月11日閲覧。.

[Goodman_and_Gilman-22] Laurence, Brunton (2010). Goodman & Gilman's pharmacological basis of therapeutics (12th ed.). McGraw-Hill. p. 549. ISBN 0071624422

[23] ttp://www.fass.se/LIF/produktfakta/artikel_produkt.jsp?NplID=19741206000040&DocTypeID=3&UserTypeID=0

[24] Wagner, Larry E., II; Michael Eaton; Salas S. Sabnis; Kevin J. Gingrich (November 1999). “Meperidine and Lidocaine Block of Recombinant Voltage-Dependent Na⁺ Channels: Evidence that Meperidine is a Local Anesthetic”. Anesthesiology (Lippincott Williams & Wilkins) 91 (5): 1481–1490. doi:10.1097/00000542-199911000-00042. PMID 10551601.

[izenwasser-25] Izenwasser, Sari; Amy Hauck Newman; Brian M. Cox; Jonathan L. Katz (January–February 1996). “The cocaine-like behavioral effects of meperidine are mediated by activity at the dopamine transporter”. European Journal of Pharmacology (Elsevier) 297 (1–2): 9–17. doi:10.1016/0014-2999(95)00696-6. PMID 8851160.

[26] Lomenzo, Stacey A.; Jill B. Rhoden; Sari Izzenwasser; Dean Wade; Theresa Kopajtic; Jonathan L. Katz; Mark L. Trudell (2005-03-05). “Synthesis and Biological Evaluation of Meperdine Analogs at Monoamine Transporters”. Journal of Medicinal Chemistry (American Chemical Society) 48 (5): 1336–1343. doi:10.1021/jm0401614. PMID 15743177.

[psrs-27] “Demerol: Is It the Best Analgesic?” (PDF), Pennsylvania Patient Safety Reporting Service Patient Safety Advisory (Pennsylvania Patient Safety Authority) 3 (2), (June 2006) 2013年4月15日閲覧。

[nsw-28] Davis, Sharon (2004年8月). “Use of pethidine for pain management in the emergency department: a position statement of the NSW Therapeutic Advisory Group”. New South Wales Therapeutic Advisory Group. 2007年1月17日閲覧。

[Latta-29] Latta, Kenneth S.; Brian Ginsberg; Robert L. Barkin (January–February 2002). “Meperidine: A Critical Review”. American Journal of Therapeutics (Lippincott Williams & Wilkins) 9 (1): 53–68. doi:10.1097/00045391-200201000-00010. PMID 11782820.

[30] “In Brief”. NPS Radar. National Prescribing Service (2005年12月). 2009年12月22日閲覧。

[31] Walker, Diana J.; James P. Zacny (June 1999). “Subjective, Psychomotor, and Physiological Effects of Cumulative Doses of Opioid µ Agonists in Healthy Volunteers”. The Journal of Pharmacology and Experimental Therapeutics (American Society for Pharmacology and Experimental Therapeutics) 289 (3): 1454–1464. PMID 10336539.

[32] Molloy, A (2002). “Does pethidine still have a place in therapy?” (PDF). Australian Prescriber (NPS MedicineWise) 25 (1): 12–13.

[33] Gilson AM, Ryan KM, Joranson DE, Dahl JL (2004). “A reassessment of trends in the medical use and abuse of opioid analgesics and implications for diversion control: 1997-2002”. J Pain Symptom Manage 28 (2): 176–188. doi:10.1016/j.jpainsymman.2004.01.003. PMID 15276196.

[34] Joranson DE, Gilson AM (2005). “Drug crime is a source of abused pain medications in the United States”. J Pain Symptom Manage 30 (4): 299–301. doi:10.1016/j.jpainsymman.2005.09.001. PMID 16256890.

[WHOLexicon-35] Lexicon of alcohol and drug terms. Geneva: World Health Organization. (1994). ISBN 92-4-154468-6

[36] ttp://pubs.acs.org/doi/suppl/10.1021/jm0401614/suppl_file/jm0401614_s.pdf

[37] Lomenzo, S.; Rhoden, J.; Izenwasser, S.; Wade, D.; Kopajtic, T.; Katz, J.; Trudell, M. (2005). “Synthesis and biological evaluation of meperidine analogues at monoamine transporters”. Journal of Medicinal Chemistry 48 (5): 1336–1343. doi:10.1021/jm0401614. PMID 15743177.

[38] Lomenzo, S.; Izenwasser, S.; Gerdes, R. M.; Katz, J. L.; Kopajtic, T.; Trudell, M. L. (1999). “Synthesis, dopamine and serotonin transporter binding affinities of novel analogues of meperidine”. Bioorganic & Medicinal Chemistry Letters 9 (23): 3273–3276. doi:10.1016/S0960-894X(99)00606-X.

[39] Rhoden, J. B.; Bouvet, M.; Izenwasser, S.; Wade, D.; Lomenzo, S. A.; Trudell, M. L. (2005). “Structure-activity studies of 3'-4'-dichloro-meperidine analogues at dopamine and serotonin transporters”. Bioorganic & Medicinal Chemistry 13 (19): 5623–5634. doi:10.1016/j.bmc.2005.05.025. PMID 15993612.

[40] Gu, X.; Izenwasser, S.; Wade, D.; Housman, A.; Gulasey, G.; Rhoden, J. B.; Savoie, C. D.; Mobley, D. L. et al. (2010). “Synthesis and structure–activity studies of benzyl ester meperidine and normeperidine derivatives as selective serotonin transporter ligands”. Bioorganic & Medicinal Chemistry 18 (23): 8356. doi:10.1016/j.bmc.2010.09.060.

[3]

[4]

痛み、発熱に用いられる薬物に関連する言葉	ジヒドロコデインオキシコドン(おきしこどん) ペチジンフェンタニル(ふぇんたにる) ブプレノルフィン >>薬学に関連する言葉
オピオイドに関連する言葉	フェンタニル(ふぇんたにる) ブプレノルフィンペチジンヘロイン(へろいん) メタドン >>同じ種類の言葉 >>化合物に関連する言葉

IUPAC命名法による物質名


IUPAC名 Ethyl 1-methyl-4-phenylpiperidine-4-carboxylate
臨床データ
販売名	Demerol
胎児危険度分類	AU: C US: C
法的規制	AU: Controlled (S8) CA: Schedule I DE: Anlage III NZ: Class B UK: クラスA US: スケジュールII UN: Narcotic Schedule I Class B3 (NZ)
依存性	High
投与方法	oral, intravenous, intramuscular, subcutaneous
薬物動態データ
生物学的利用能	50–60% (Oral), 80-90% (Oral, in cases of hepatic impairment)
血漿タンパク結合	65-75%
代謝	Liver
半減期	2.5-4 hours, 7-11 hours (liver disease)
排泄	Renal
識別
CAS番号	57-42-1
ATCコード	N02AB02 (WHO)
PubChem	CID: 4058
IUPHAR/BPS	7221
DrugBank	DB00454
ChemSpider	3918
UNII	9E338QE28F
KEGG	D08343
ChEMBL	CHEMBL607
化学的データ
化学式	C₁₅H₂₁N O₂
分子量	247.33g/mol
SMILES O=C(C1(CCN(CC1)C)C2=CC=CC=C2)OCC
InChI InChI=1S/C15H21NO2/c1-3-18-14(17)15(9-11-16(2)12-10-15)13-7-5-4-6-8-13/h4-8H,3,9-12H2,1-2H3= Key:XADCESSVHJOZHK-UHFFFAOYSA-N=
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ペチジン ペチジンの概要

ペチジン

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「ペチジン」の関連用語

ペチジンペチジンの概要