氟膦丙胺

氟膦丙胺
	IUPAC名; [(2R)-3-Amino-2-fluoropropyl]phosphinic acid
别名	AZD-3355
识别
CAS号	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配体	7705
性质
化学式	C3H9FNO2P
摩尔质量	141.08 g·mol−1
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

氟膦丙胺^[1]（英语：Lesogaberan，开发代号AZD-3355^[2]），化学名P-[(2R)-3-氨基-2-氟丙基]次磷酸，是由阿斯利康开发的用于治疗胃食管反流的实验药物^[3]^[4]，属GABA_B受体激动剂^[5]，抗反流作用机制和巴氯芬相似，作用于胃迷走神经反射通路靶点，但副作用比巴氯芬低，因为巴氯芬可通过血脑屏障引起中枢神经副作用而限制其临床应用^[6]^[7]。因在临床II期实验中显示对胃食管反流治疗效果无临床意义而被终止开发^[8]。其可由丝氨酸经氟代和还原得到2-氟-1-羟基丙胺中间体，随后经三苯基膦和碘使中间体的羟基转换成碘原子，随后用双(三甲基硅基)亚磷酸酯[HP(OTMS)₂]进行反应即可得到氟膦丙胺^[9]。

参考文献

^ 吴范宏. 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: 化学工业出版社. 2022. ISBN 978-7-122-42170-8.
^ AstraZeneca. AZD3355. [30 December 2011].
^ Bredenoord, Albert J. Lesogaberan, a GABA_B agonist for the potential treatment of gastroesophageal reflux disease. IDrugs. 2009, 12 (9): 576–584. PMID 19697277.
^ 虞阳、于晓峰. 弱酸反流与难治性胃食管反流病. 国际消化病杂志. 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.
^ 林淳荣. 胃酸相關胃腸疾病之最新診治新進展 (PDF). 内科学志. 2015, 26: 123-132.
^ 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.

这是一篇与消化系统药相关小作品。您可以通过编辑或修订扩充其内容。

[1] 吴范宏. 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: 化学工业出版社. 2022. ISBN 978-7-122-42170-8.

[2] AstraZeneca. AZD3355. [30 December 2011].

[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] 虞阳、于晓峰. 弱酸反流与难治性胃食管反流病. 国际消化病杂志. 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] 林淳荣. 胃酸相關胃腸疾病之最新診治新進展 (PDF). 内科学志. 2015, 26: 123-132.

[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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氟膦丙胺


IUPAC名 [(2R)-3-Amino-2-fluoropropyl]phosphinic acid
别名	AZD-3355
识别
CAS号	344413-67-8 ^Y= ^Y
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配体	7705
性质
化学式	C₃H₉FNO₂P
摩尔质量	141.08 g·mol⁻¹
若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。