惕格列定

惕格列定
Tigloidine
临床资料
商品名（英语：Drug nomenclature）	托品林; Tropigline
其他名称	巴豆酰莨菪碱、惕格酰莨菪碱、惕格酰假托品（3β-tigloyloxytropane）
识别信息
	IUPAC命名法 (8-Methyl-8-azabicyclo[3.2.1]octan-3-yl) (E)-2-methylbut-2-enoate; ;
CAS号	495-83-0
PubChem CID	5281865;
ChemSpider	16736065;
UNII	75GK1SV4EI;
KEGG	C10868;
ChEBI	CHEBI:9593;
ChEMBL	ChEMBL2107120;
ECHA InfoCard	100.007.101
化学信息
化学式	C13H21NO2
摩尔质量	223.32 g·mol−1
3D模型（JSmol（英语：JSmol））	交互式图像;
	SMILES CC=C(C)C(=O)OC1CC2CCC(C1)N2C;
	InChI InChI=1S/C13H21NO2/c1-4-9(2)13(15)16-12-7-10-5-6-11(8-12)14(10)3/h4,10-12H,5-8H2,1-3H3/b9-4+; Key:UVHGSMZRSVGWDJ-RUDMXATFSA-N;

惕格列定（英文：tigloidine）是一种托品烷生物碱，化学式：C₁₃H₂₁NO₂，其作为一种生物碱广泛分布于茄科植物中，包括软木茄（学名：Duboisia myoporoides）^[1]，灯笼果（学名：Physalis peruviana）^[2]，曼陀罗等。为惕格酸与3β-托品醇的酯。临床上常作抗胆碱剂，用于治疗帕金森等神经退行疾病^[3]。商品名为托品林（Tropigline）^[4]。

生物合成

惕格列定作为茄科植物次级代谢产物托品烷生物碱的一种^[5]，其生物合成主要由托品酮经还原酶还原成3β-托品醇（假托品醇），然后与惕格酰假托品合成酶催化3β-托品醇与惕格酰辅酶A（tigloyl-CoA）发生酯化反应得到^[6]。

医学用途

1950年Trautner和McCallum发现惕格列定使反复刺激的牛蛙缝匠肌产生疲劳，60年代报道其对帕金森病、亨廷顿舞蹈症、痉挛性截瘫有效果^[7]。1968年美国批准其用于治疗帕金森病^[8]。

惕格列定是阿托品的替代药物，用于治疗帕金森。与阿托品相比，其头痛、喉咙干燥、瞳孔扩大等不良反应率更低^[6]。

参考文献

^ Barger G, Martin WF, Mitchell W. 383. The minor alkaloids of Duboisia myoporoides. Journal of the Chemical Society (Resumed). 1937: 1820. doi:10.1039/JR9370001820. hdl:1842/35366 .
^ Beresford PJ, Woolley JG. Biosynthesis of ticloidine in Physalis peruviana. Phytochemistry. 1974, 13 (10): 2143–2144. Bibcode:1974PChem..13.2143B. doi:10.1016/0031-9422(74)85016-8.
^ Approved Names. British Medical Journal. 1958, 1 (5080): 1175. PMC 2028565 . doi:10.1136/bmj.1.5080.1175.
^ Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000: 1663–. ISBN 978-3-88763-075-1.
^ S Rodriguez, U Uria, E Reyes, L Prieto, M Rodríguez-Rodríguez, L Carrillo, JL Vicario. Enantioselective construction of the 8-azabicyclo [3.2. 1] octane scaffold: application in the synthesis of tropane alkaloids. Organic & Biomolecular Chemistry. 2021, (19): 3763–3775. PMID 33949549. doi:10.1039/d1ob00143d.
^ ^6.0 ^6.1 Junlan Zeng, Xiaoqiang Liu, Zhaoyue Dong; et al. Discovering a mitochondrion-localized BAHD acyltransferase involved in calystegine biosynthesis and engineering the production of 3β-tigloyloxytropane. Nature Communications. 2024, (15): 3623. doi:10.1038/s41467-024-47968-0.
^ I Sanghvi, E Bindler, S Gershon. Pharmacology of a potential anti-parkinson agent: tigloidine. European Journal of Pharmacology. 1968, 4 (3): 246–253. doi:10.1016/0014-2999(68)90091-5.
^ Parkinson's Disease Information and Research Center (New York, N.Y.). Parkinson's Disease & Related Disorders; Cumulative Bibliography: 1800-1970: Subject index. National Institute of Neurological Diseases and Stroke. 1971: 1988.

[1] Barger G, Martin WF, Mitchell W. 383. The minor alkaloids of Duboisia myoporoides. Journal of the Chemical Society (Resumed). 1937: 1820. doi:10.1039/JR9370001820. hdl:1842/35366 .

[2] Beresford PJ, Woolley JG. Biosynthesis of ticloidine in Physalis peruviana. Phytochemistry. 1974, 13 (10): 2143–2144. Bibcode:1974PChem..13.2143B. doi:10.1016/0031-9422(74)85016-8.

[3] Approved Names. British Medical Journal. 1958, 1 (5080): 1175. PMC 2028565 . doi:10.1136/bmj.1.5080.1175.

[4] Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000: 1663–. ISBN 978-3-88763-075-1.

[5] S Rodriguez, U Uria, E Reyes, L Prieto, M Rodríguez-Rodríguez, L Carrillo, JL Vicario. Enantioselective construction of the 8-azabicyclo [3.2. 1] octane scaffold: application in the synthesis of tropane alkaloids. Organic & Biomolecular Chemistry. 2021, (19): 3763–3775. PMID 33949549. doi:10.1039/d1ob00143d.

[nc-6] 6.0 ^6.1 Junlan Zeng, Xiaoqiang Liu, Zhaoyue Dong; et al. Discovering a mitochondrion-localized BAHD acyltransferase involved in calystegine biosynthesis and engineering the production of 3β-tigloyloxytropane. Nature Communications. 2024, (15): 3623. doi:10.1038/s41467-024-47968-0.

[7] I Sanghvi, E Bindler, S Gershon. Pharmacology of a potential anti-parkinson agent: tigloidine. European Journal of Pharmacology. 1968, 4 (3): 246–253. doi:10.1016/0014-2999(68)90091-5.

[8] Parkinson's Disease Information and Research Center (New York, N.Y.). Parkinson's Disease & Related Disorders; Cumulative Bibliography: 1800-1970: Subject index. National Institute of Neurological Diseases and Stroke. 1971: 1988.

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