吲达品

吲达品
臨床資料
商品名（英语：Drug nomenclature）	Upstène
其他名稱	LM-5008
识别信息
	IUPAC命名法 3-(2-Piperidin-4-ylethyl)-1H-indole; ;
CAS号	63758-79-2
PubChem CID	44668;
DrugBank	DB08953 ;
ChemSpider	40643 ;
UNII	V35562QSVT;
ChEMBL	ChEMBL276520 ;
CompTox Dashboard（英语：CompTox Chemicals Dashboard） (EPA)	DTXSID80213196 ;
ECHA InfoCard	100.058.569
化学信息
化学式	C15H20N2
摩尔质量	228.34 g·mol−1
3D模型（JSmol（英语：JSmol））	交互式图像;
	SMILES c2(c1ccccc1[nH]c2)CCC3CCNCC3;
	InChI InChI=1S/C15H20N2/c1-2-4-15-14(3-1)13(11-17-15)6-5-12-7-9-16-10-8-12/h1-4,11-12,16-17H,5-10H2 ; Key:SADQVAVFGNTEOD-UHFFFAOYSA-N ;

吲达品是选择性血清素再摄取抑制剂（SSRI）及抗组胺药。^[1]他曾是在法国及其它欧洲国家^[2]短暂上市的抗抑郁药。^[3]^[1]^[4]^[2]

吲达品于1977年发现，1983年在法国用作药物。^[1]^[4]不过，它在两年后就因其毒性从市场撤回。^[1]^[2]虽然有来源称吲达品是首个被发现的SSRI，^[1]^[4]但在吲达品之前就已发现另一种SSRI——齐美定（英语：zimelidine）。它在1969年发现，于1981年进入市场，后来于1983年因毒性撤回。^[1]^[5]^[2]

合成

吲哚（1）首先与甲基碘化镁反应，产生有机镁化合物（2）。它之后与（3）反应生成（4）。用酸去除（4）的苄氧羰基保护基（Cbz）可得到（5），最后用氢化铝锂还原，产生吲达品（6）。^[6]^[7]

参考资料

^ ^1.0 ^1.1 ^1.2 ^1.3 ^1.4 ^1.5 Shorter, E. Before Prozac: The Troubled History of Mood Disorders in Psychiatry. Oxford University Press. 2008: 15,175,221 [2024-08-12]. ISBN 978-0-19-970933-5.
^ ^2.0 ^2.1 ^2.2 ^2.3 'Let Them Eat Prozac' - Introduction: The SSRI Issues (PDF). [2024-08-12].
^ Elks J. The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. 2014-11-14: 988–. ISBN 978-1-4757-2085-3.
^ ^4.0 ^4.1 ^4.2 Healy, David. The Psychopharmacologists III (PDF). CRC Press. 2020-10-14. ISBN 978-1-003-05889-2. doi:10.4324/9781003058892-1. It now seems clomipramine is useful for OCD because of its action on the 5HT system. This leads on to a Rhône-Poulenc drug which as I understand it was the first SSRI to be released clinically – Upstene, Indalpine. Can you tell me anything about it? Br: Well it wasn’t made in Rhône-Poulenc. It was Fournier Freres, who were part of Pharmuka, who in turn became part of Rhône-Poulenc. Indalpine was launched in 1983. Gr: It was withdrawn because of side effects, neutropenia supposedly but that was not all. This drug had been launched before all the carcinogenicity results were in and when they were all available the drug had to be withdrawn. [...] Of 500,000 patients treated in 1984, the Pharmacovigilance committee had reports of 30 cases of neutropenia. Upstene in fact won the Prix Galien for pharmaceutical innovation in 1983.
^ Healy, D. Let Them Eat Prozac: The Unhealthy Relationship Between the Pharmaceutical Industry and Depression. NYU Press. 2004: 20–22 [2024-08-12]. ISBN 978-0-8147-7300-0.
^ Gueremy C, Audiau F, Uzan A, Le Fur G, Rataud J. 3-(4-Piperidinylalkyl)indoles, selective inhibitors of neuronal 5-hydroxytryptamine uptake. Journal of Medicinal Chemistry. December 1980, 23 (12): 1306–1310. PMID 7452682. doi:10.1021/jm00186a005.
^ Indalpine. Pharmaceutical Substances. Georg Thieme Verlag KG. [2024-07-16].

[Shorter2008-1] 1.0 ^1.1 ^1.2 ^1.3 ^1.4 ^1.5 Shorter, E. Before Prozac: The Troubled History of Mood Disorders in Psychiatry. Oxford University Press. 2008: 15,175,221 [2024-08-12]. ISBN 978-0-19-970933-5.

[LetThemEatProzacIntro-2] 2.0 ^2.1 ^2.2 ^2.3 'Let Them Eat Prozac' - Introduction: The SSRI Issues (PDF). [2024-08-12].

[Elks2014-3] Elks J. The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. 2014-11-14: 988–. ISBN 978-1-4757-2085-3.

[Healy2020-4] 4.0 ^4.1 ^4.2 Healy, David. The Psychopharmacologists III (PDF). CRC Press. 2020-10-14. ISBN 978-1-003-05889-2. doi:10.4324/9781003058892-1. It now seems clomipramine is useful for OCD because of its action on the 5HT system. This leads on to a Rhône-Poulenc drug which as I understand it was the first SSRI to be released clinically – Upstene, Indalpine. Can you tell me anything about it? Br: Well it wasn’t made in Rhône-Poulenc. It was Fournier Freres, who were part of Pharmuka, who in turn became part of Rhône-Poulenc. Indalpine was launched in 1983. Gr: It was withdrawn because of side effects, neutropenia supposedly but that was not all. This drug had been launched before all the carcinogenicity results were in and when they were all available the drug had to be withdrawn. [...] Of 500,000 patients treated in 1984, the Pharmacovigilance committee had reports of 30 cases of neutropenia. Upstene in fact won the Prix Galien for pharmaceutical innovation in 1983.

[Healy2004-5] Healy, D. Let Them Eat Prozac: The Unhealthy Relationship Between the Pharmaceutical Industry and Depression. NYU Press. 2004: 20–22 [2024-08-12]. ISBN 978-0-8147-7300-0.

[6] Gueremy C, Audiau F, Uzan A, Le Fur G, Rataud J. 3-(4-Piperidinylalkyl)indoles, selective inhibitors of neuronal 5-hydroxytryptamine uptake. Journal of Medicinal Chemistry. December 1980, 23 (12): 1306–1310. PMID 7452682. doi:10.1021/jm00186a005.

[7] Indalpine. Pharmaceutical Substances. Georg Thieme Verlag KG. [2024-07-16].

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