氟膦丙胺

氟膦丙胺
	IUPAC名; [(2R)-3-Amino-2-fluoropropyl]phosphinic acid
別名	AZD-3355
識別
CAS號	344413-67-8 =
PubChem	9833984
ChemSpider	23254384
SMILES	O=[PH](O)C[C@H](F)CN;
InChI	1/C3H9FNO2P/c4-3(1-5)2-8(6)7/h3,8H,1-2,5H2,(H,6,7)/t3-/m1/s1;
InChIKey	LJNUIEQATDYXJH-GSVOUGTGBQ
IUPHAR配體	7705
性質
化學式	C3H9FNO2P
摩爾質量	141.08 g·mol−1
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

氟膦丙胺^[1]（英語：Lesogaberan，開發代號AZD-3355^[2]），化學名P-[(2R)-3-氨基-2-氟丙基]次磷酸，是由阿斯利康開發的用於治療胃食管反流的實驗藥物^[3]^[4]，屬GABA_B受體激動劑^[5]，抗反流作用機制和巴氯芬相似，作用於胃迷走神經反射通路靶點，但副作用比巴氯芬低，因為巴氯芬可通過血腦屏障引起中樞神經副作用而限制其臨床應用^[6]^[7]。因在臨床II期實驗中顯示對胃食管反流治療效果無臨床意義而被終止開發^[8]。其可由絲氨酸經氟代和還原得到2-氟-1-羥基丙胺中間體，隨後經三苯基膦和碘使中間體的羥基轉換成碘原子，隨後用雙(三甲基矽基)亞磷酸酯[HP(OTMS)₂]進行反應即可得到氟膦丙胺^[9]。

參考文獻

^ 吳范宏. 第2章胃肠道系统氟药 02004 氟膦丙胺 Lesogaberan. 氟药与氟代制药技术. 北京: 化學工業出版社. 2022. ISBN 978-7-122-42170-8.
^ AstraZeneca. AZD3355. [30 December 2011]. （原始內容存檔於2012-04-26）.
^ Bredenoord, Albert J. Lesogaberan, a GABA_B agonist for the potential treatment of gastroesophageal reflux disease. IDrugs. 2009, 12 (9): 576–584. PMID 19697277.
^ 虞陽、於曉峰. 弱酸反流与难治性胃食管反流病. 國際消化病雜誌. 2011, 31 (6): 317-320. doi:10.3969/j.issn.1673-534X.2011.06.002.
^ Alstermark; Amin, K; Dinn, SR; et al. Synthesis and Pharmacological Evaluation of Novel γ-Aminobutyric Acid Type B (GABAB) Receptor Agonists as Gastroesophageal Reflux Inhibitors. Journal of Medicinal Chemistry. 2008, 51 (14): 4315–4320. PMID 18578471. doi:10.1021/jm701425k.
^ Brian E. Lacy; Robert Chehade; Michael D. Crowell. Lesogaberan. Drugs of the Future. 2010, 35 (12): 987–992. S2CID 258021903. doi:10.1358/dof.2010.035.012.1540661.
^ 林淳榮. 胃酸相關胃腸疾病之最新診治新進展 (PDF). 內科學誌. 2015, 26: 123-132 [2024-09-16]. （原始內容存檔 (PDF)於2024-09-16）.
^ Hans Rydholm, Christian von Corswant, Hans Denison, Jörgen M Jensen,Anders Lehmann, Magnus Ruth, Erik Söderlind, Ann Aurell-Holmberg. Reducing Adverse Effects During Drug Development: The Example of Lesogaberan and Paresthesia. Clinical Therapeutics. 2016, 38 (4): 946-960. PMID 26947796. doi:10.1016/j.clinthera.2016.02.012.
^ Moaz M. Abdou, Rasha A. El-Saeed. Potential chemical transformation of phosphinic acid derivatives and their applications in the synthesis of drugs. Bioorganic Chemistry. 2019, 90: 103039. doi:10.1016/j.bioorg.2019.103039.

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[1] 吳范宏. 第2章胃肠道系统氟药 02004 氟膦丙胺 Lesogaberan. 氟药与氟代制药技术. 北京: 化學工業出版社. 2022. ISBN 978-7-122-42170-8.

[2] AstraZeneca. AZD3355. [30 December 2011]. （原始內容存檔於2012-04-26）.

[3] Bredenoord, Albert J. Lesogaberan, a GABA_B agonist for the potential treatment of gastroesophageal reflux disease. IDrugs. 2009, 12 (9): 576–584. PMID 19697277.

[4] 虞陽、於曉峰. 弱酸反流与难治性胃食管反流病. 國際消化病雜誌. 2011, 31 (6): 317-320. doi:10.3969/j.issn.1673-534X.2011.06.002.

[5] Alstermark; Amin, K; Dinn, SR; et al. Synthesis and Pharmacological Evaluation of Novel γ-Aminobutyric Acid Type B (GABAB) Receptor Agonists as Gastroesophageal Reflux Inhibitors. Journal of Medicinal Chemistry. 2008, 51 (14): 4315–4320. PMID 18578471. doi:10.1021/jm701425k.

[6] Brian E. Lacy; Robert Chehade; Michael D. Crowell. Lesogaberan. Drugs of the Future. 2010, 35 (12): 987–992. S2CID 258021903. doi:10.1358/dof.2010.035.012.1540661.

[7] 林淳榮. 胃酸相關胃腸疾病之最新診治新進展 (PDF). 內科學誌. 2015, 26: 123-132 [2024-09-16]. （原始內容存檔 (PDF)於2024-09-16）.

[8] Hans Rydholm, Christian von Corswant, Hans Denison, Jörgen M Jensen,Anders Lehmann, Magnus Ruth, Erik Söderlind, Ann Aurell-Holmberg. Reducing Adverse Effects During Drug Development: The Example of Lesogaberan and Paresthesia. Clinical Therapeutics. 2016, 38 (4): 946-960. PMID 26947796. doi:10.1016/j.clinthera.2016.02.012.

[9] Moaz M. Abdou, Rasha A. El-Saeed. Potential chemical transformation of phosphinic acid derivatives and their applications in the synthesis of drugs. Bioorganic Chemistry. 2019, 90: 103039. doi:10.1016/j.bioorg.2019.103039.

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