惕格列定

惕格列定
Tigloidine
臨床資料
商品名（英語：Drug nomenclature）	托品林; Tropigline
其他名稱	巴豆醯莨菪鹼、惕格醯莨菪鹼、惕格醯假託品（3β-tigloyloxytropane）
識別資訊
	IUPAC命名法 (8-Methyl-8-azabicyclo[3.2.1]octan-3-yl) (E)-2-methylbut-2-enoate; ;
CAS號	495-83-0
PubChem CID	5281865;
ChemSpider	16736065;
UNII	75GK1SV4EI;
KEGG	C10868;
ChEBI	CHEBI:9593;
ChEMBL	ChEMBL2107120;
ECHA InfoCard	100.007.101
化學資訊
化學式	C13H21NO2
摩爾質量	223.32 g·mol−1
3D模型（JSmol（英語：JSmol））	交互式圖像;
	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）是一種托品烷生物鹼，化學式：C₁₃H₂₁NO₂，其作為一種生物鹼廣泛分布於茄科植物中，包括軟木茄（學名：Duboisia myoporoides）^[1]，燈籠果（學名：Physalis peruviana）^[2]，曼陀羅等。為惕格酸與3β-托品醇的酯。臨床上常作抗膽鹼劑，用於治療帕金森等神經退行疾病^[3]。商品名為托品林（Tropigline）^[4]。

生物合成

惕格列定作為茄科植物次級代謝產物托品烷生物鹼的一種^[5]，其生物合成主要由托品酮經還原酶還原成3β-托品醇（假託品醇），然後與惕格醯假託品合成酶催化3β-托品醇與惕格醯輔酶A（tigloyl-CoA）發生酯化反應得到^[6]。

醫學用途

1950年Trautner和McCallum發現惕格列定使反覆刺激的牛蛙縫匠肌產生疲勞，60年代報道其對帕金森病、亨廷頓舞蹈症、痙攣性截癱有效果^[7]。1968年美國批准其用於治療帕金森病^[8]。

惕格列定是阿托品的替代藥物，用於治療帕金森。與阿托品相比，其頭痛、喉嚨乾燥、瞳孔擴大等不良反應率更低^[6]。

參考文獻

^ 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.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

臨床資料

商品名（英語：Drug nomenclature）	托品林 Tropigline
其他名稱	巴豆醯莨菪鹼、惕格醯莨菪鹼、惕格醯假託品（3β-tigloyloxytropane）
識別資訊
IUPAC命名法 (8-Methyl-8-azabicyclo[3.2.1]octan-3-yl) (E)-2-methylbut-2-enoate
CAS號	495-83-0 ^Y
PubChem CID	5281865
ChemSpider	16736065
UNII	75GK1SV4EI
KEGG	C10868
ChEBI	CHEBI:9593
ChEMBL	ChEMBL2107120
ECHA InfoCard	100.007.101
化學資訊
化學式	C₁₃H₂₁NO₂
摩爾質量	223.32 g·mol⁻¹
3D模型（JSmol（英語：JSmol））	交互式圖像
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