アニラセタム

アニラセタム
IUPAC命名法による物質名
	IUPAC名 1-[(4-Methoxybenzoyl)]-2-pyrrolidinone;
臨床データ
販売名	Ampamet, Memodrin, Pergamid
Drugs.com	国別販売名(英語); International Drug Names
法的規制	US: Not approved; Unscheduled;
薬物動態データ
半減期	1-2.5時間
識別
CAS番号;	72432-10-1
ATCコード	N06BX11 (WHO)
PubChem	CID: 2196
IUPHAR/BPS	4133
DrugBank	DB04599
ChemSpider	2111
UNII	5L16LKN964
KEGG	D01883
ChEBI	CHEBI:47943
ChEMBL	CHEMBL36994
化学的データ
化学式	C12H13NO3
分子量	219.237 g/mol
	SMILES O=C2N(C(=O)c1ccc(OC)cc1)CCC2;
	InChI InChI=1S/C12H13NO3/c1-16-10-6-4-9(5-7-10)12(15)13-8-2-3-11(13)14/h4-7H,2-3,8H2,1H3 ; Key:ZXNRTKGTQJPIJK-UHFFFAOYSA-N ;
	テンプレートを表示

アニラセタム(Aniracetam)またはN-アニソイル-2-ピロリジノン(N-anisoyl-2-pyrrolidinone)は、欧州で処方箋医薬品として販売されるラセタムである。アメリカ食品医薬品局には認可されていない^[1]。

薬理

アニラセタムは、AMPA型グルタミン酸受容体を正に調節する^[2]。

経口で摂取すると肝臓で初回通過効果によってすぐに代謝される。主要な代謝産物は、N-アニソイル-GABA (70–80%)と2-ピロリドン及びp-アニス酸 (20–30%)である^[3]^[4]^[5]。

経口摂取後数時間の血漿中濃度は、アニラセタムで5–15 μg/L、活性代謝産物のN-アニソイル-GABAで5–15 mg/Lである。これら2種は、液体クロマトグラフィー-質量分析により定量される^[6]^[7]^[8]。

合成

1970年代にエフ・ホフマン・ラ・ロシュにより初めて合成された^[9]^[10]。合成は、トリエチルアミンの存在下で2-ピロリドンを塩化アニソイルと反応させることで行われる^[11]。

別の方法として、γ-アミノ酪酸を塩化アニソイルと反応させることでも得られる。塩化チオニルの存在下で閉環が起こる^[11]。

出典

^ “Piracetam and piracetam-like drugs: from basic science to novel clinical applications to CNS disorders”. Drugs 70 (3): 287-312. (February 2010). doi:10.2165/11319230-000000000-00000. PMID 20166767.
^ “Allosteric potentiation of quisqualate receptors by a nootropic drug aniracetam”. The Journal of Physiology 424: 533-43. (May 1990). doi:10.1113/jphysiol.1990.sp018081. PMC 1189827. PMID 1975272.
^ “Aniracetam. An overview of its pharmacodynamic and pharmacokinetic properties, and a review of its therapeutic potential in senile cognitive disorders”. Drugs & Aging 4 (3): 257-73. (March 1994). doi:10.2165/00002512-199404030-00007. PMID 8199398.
^ Action, Ashton (22 July 2013). Schizophrenia: New Insights for the Healthcare Professional. ScholarlyEditions. pp. 152-. ISBN 978-1-4816-6196-6
^ Testa, Bernard; Mayer, Joachim M. (1 August 2003). Hydrolysis in Drug and Prodrug Metabolism. John Wiley & Sons. pp. 109-. ISBN 978-3-906390-25-3
^ “Determination of aniracetam's main metabolite, N-anisoyl-GABA, in human plasma by LC-MS/MS and its application to a pharmacokinetic study”. Journal of Chromatography B 897: 50-4. (May 2012). doi:10.1016/j.jchromb.2012.04.007. PMID 22552003.
^ “Sensitive and selective liquid chromatography-tandem mass spectrometry method for the quantification of aniracetam in human plasma”. Journal of Chromatography B 858 (1-2): 129-34. (October 2007). doi:10.1016/j.jchromb.2007.08.010. PMID 17826366.
^ Baselt, Randall C. (2014). Disposition of Toxic Drugs and Chemicals in Man (10th ed.). Seal Beach, CA: Biomedical Publications. pp. 142-143. ISBN 978-0-9626523-9-4
^ EP application 44088, Kyburz E, Aschwanden W, "p-Methoxy-benzoyl derivatives", published 9 February 1979, assigned to Hoffmann-La Roche
^ EP 5143, Kyburz E, Aschwanden W, "1-Benzoyl-2-pyrrolidinone derivative, processes for its preparation and medicaments containing it.", published 9 February 1979, assigned to Hoffmann-La Roche
^ ^a ^b Kleemann, Axel; Engels, Jurgen; Kutscher, Bernhard; Reichert, Dietmar (2001). Pharmaceutical substances: syntheses, patents, applications (4th ed.). Stuttgart: Thieme. ISBN 978-3-13-558404-1

[1] “Piracetam and piracetam-like drugs: from basic science to novel clinical applications to CNS disorders”. Drugs 70 (3): 287-312. (February 2010). doi:10.2165/11319230-000000000-00000. PMID 20166767.

[2] “Allosteric potentiation of quisqualate receptors by a nootropic drug aniracetam”. The Journal of Physiology 424: 533-43. (May 1990). doi:10.1113/jphysiol.1990.sp018081. PMC 1189827. PMID 1975272.

[3] “Aniracetam. An overview of its pharmacodynamic and pharmacokinetic properties, and a review of its therapeutic potential in senile cognitive disorders”. Drugs & Aging 4 (3): 257-73. (March 1994). doi:10.2165/00002512-199404030-00007. PMID 8199398.

[4] Action, Ashton (22 July 2013). Schizophrenia: New Insights for the Healthcare Professional. ScholarlyEditions. pp. 152-. ISBN 978-1-4816-6196-6

[TestaMayer2003-5] Testa, Bernard; Mayer, Joachim M. (1 August 2003). Hydrolysis in Drug and Prodrug Metabolism. John Wiley & Sons. pp. 109-. ISBN 978-3-906390-25-3

[Cai_2012-6] “Determination of aniracetam's main metabolite, N-anisoyl-GABA, in human plasma by LC-MS/MS and its application to a pharmacokinetic study”. Journal of Chromatography B 897: 50-4. (May 2012). doi:10.1016/j.jchromb.2012.04.007. PMID 22552003.

[7] “Sensitive and selective liquid chromatography-tandem mass spectrometry method for the quantification of aniracetam in human plasma”. Journal of Chromatography B 858 (1-2): 129-34. (October 2007). doi:10.1016/j.jchromb.2007.08.010. PMID 17826366.

[8] Baselt, Randall C. (2014). Disposition of Toxic Drugs and Chemicals in Man (10th ed.). Seal Beach, CA: Biomedical Publications. pp. 142-143. ISBN 978-0-9626523-9-4

[9] EP application 44088, Kyburz E, Aschwanden W, "p-Methoxy-benzoyl derivatives", published 9 February 1979, assigned to Hoffmann-La Roche

[10] EP 5143, Kyburz E, Aschwanden W, "1-Benzoyl-2-pyrrolidinone derivative, processes for its preparation and medicaments containing it.", published 9 February 1979, assigned to Hoffmann-La Roche

[Kleemann-11] Kleemann, Axel; Engels, Jurgen; Kutscher, Bernhard; Reichert, Dietmar (2001). Pharmaceutical substances: syntheses, patents, applications (4th ed.). Stuttgart: Thieme. ISBN 978-3-13-558404-1

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