吲達品

吲達品
臨床資料
商品名（英語：Drug nomenclature）	Upstène
其他名稱	LM-5008
識別資訊
	IUPAC命名法 3-(2-Piperidin-4-ylethyl)-1H-indole; ;
CAS號	63758-79-2
PubChem CID	44668;
DrugBank	DB08953 ;
ChemSpider	40643 ;
UNII	V35562QSVT;
ChEMBL	ChEMBL276520 ;
CompTox Dashboard（英語：CompTox Chemicals Dashboard） (EPA)	DTXSID80213196 ;
ECHA InfoCard	100.058.569
化學資訊
化學式	C15H20N2
摩爾質量	228.34 g·mol−1
3D模型（JSmol（英語：JSmol））	交互式圖像;
	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 ;

吲達品是選擇性血清素再攝取抑制劑（SSRI）及抗組胺藥。^[1]他曾是在法國及其它歐洲國家^[2]短暫上市的抗抑鬱藥。^[3]^[1]^[4]^[2]

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吲達品於1977年發現，1983年在法國用作藥物。^[1]^[4]不過，它在兩年後就因其毒性從市場撤回。^[1]^[2]雖然有來源稱吲達品是首個被發現的SSRI，^[1]^[4]但在吲達品之前就已發現另一種SSRI——齊美定（英語：zimelidine）。它在1969年發現，於1981年進入市場，後來於1983年因毒性撤回。^[1]^[5]^[2]

合成

吲哚（1）首先與甲基碘化鎂反應，產生有機鎂化合物（2）。它之後與（3）反應生成（4）。用酸去除（4）的苄氧羰基保護基（Cbz）可得到（5），最後用氫化鋁鋰還原，產生吲達品（6）。^[6]^[7]

參考資料

[1]
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]
'Let Them Eat Prozac' - Introduction: The SSRI Issues (PDF). [2024-08-12].
[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.
[4]
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 Gr: It was withdrawn because of side effects, neutropenia supposedly but that was not all.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had been launched before all the carcinogenicity results were in and when they were all available the drug had to be withdrawn.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.
[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].

[Shorter2008-1] [1]
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]
'Let Them Eat Prozac' - Introduction: The SSRI Issues (PDF). [2024-08-12].

[Elks2014-3] [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]
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] [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] [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] [7]
Indalpine. Pharmaceutical Substances. Georg Thieme Verlag KG. [2024-07-16].

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