吡維銨

吡維銨
臨床資料
AHFS/Drugs.com	Micromedex詳細消費者藥物信息
ATC碼	P02CX01 (WHO) ;
識別資訊
	IUPAC命名法 2-[(E)-2-(2,5-Dimethyl-1-phenylpyrrol-3-yl)ethenyl]-N,N,1-trimethylquinolin-1-ium-6-amine; ;
CAS號	7187-62-4
PubChem CID	5281035;
ChemSpider	21125;
UNII	6B9991FLU3;
ChEBI	CHEBI:8687;
ChEMBL	ChEMBL1201303;
CompTox Dashboard（英語：CompTox Chemicals Dashboard） (EPA)	DTXSID4023545 ;
ECHA InfoCard	100.020.543
化學資訊
化學式	C26H28N3+
摩爾質量	382.53 g·mol−1
3D模型（JSmol（英語：JSmol））	交互式圖像;
	SMILES CC1=CC(=C(N1C2=CC=CC=C2)C)/C=C/C3=[N+](C4=C(C=C3)C=C(C=C4)N(C)C)C;
	InChI InChI=1S/C26H28N3/c1-19-17-21(20(2)29(19)24-9-7-6-8-10-24)11-13-23-14-12-22-18-25(27(3)4)15-16-26(22)28(23)5/h6-18H,1-5H3/q+1; Key:QMHSXPLYMTVAMK-UHFFFAOYSA-N;

吡維銨（英語：Pyrvinium）是一種對蟯蟲有效的驅蟲藥。^[1]吡維銨已幾種方式存在，例如吡維氯銨、對甲苯磺酸吡維銨、三氟甲磺酸吡維銨和雙羥萘酸吡維銨（或叫帕莫酸吡維銨及恩波酸吡維銨）。^[2]^[3]吡維銨被鑑定為一種有效的Wnt抑制劑，通過激活酪蛋白激酶CK1α發揮作用。^[4]^[5]

吡維銨鹽還可以抑制癌細胞的生長。^[6]更具體地說，雙羥萘酸鹽已被證明在葡萄糖飢餓期間對各種癌細胞系具有優先毒性。^[7]

合成

其中一種合成方法基於斯克勞普合成和帕爾-克諾爾合成。^[6]最近，報道了通過弗里德蘭德喹啉合成替代三氟甲磺酸吡維銨的收斂合成策略。^[3]

參考資料

^ Desai AS. Single-dose treatment of oxyuriasis with pyrvinium embonate. British Medical Journal. December 1962, 2 (5319): 1583–5. PMC 1926864  . PMID 14027194. doi:10.1136/bmj.2.5319.1583.
^ Pyrvinium. PubChem. U.S. National Library of Medicine. [2023-02-06]. （原始內容存檔於2016-04-02）.
^ ^3.0 ^3.1 Mao Y, Lin N, Tian W, Huang Z. New Synthesis of Pyrvinium That inhibits the β-Catenin/Tcf4 Pathway. Heterocycles. 2012, 85 (5): 1179–1185. doi:10.3987/COM-12-12446.
^ Saraswati S, Alfaro MP, Thorne CA, Atkinson J, Lee E, Young PP. Pyrvinium, a potent small molecule Wnt inhibitor, promotes wound repair and post-MI cardiac remodeling. PLOS ONE. 2010, 5 (11): e15521. Bibcode:2010PLoSO...515521S. PMC 2993965  . PMID 21170416. doi:10.1371/journal.pone.0015521  .
^ Shen C, Nayak A, Melendez RA, Robbins DJ. Casein Kinase 1α as a Regulator of Wnt-Driven Cancer. International Journal of Molecular Sciences. 2020, 21 (16): 5940. PMC 7460588  . PMID 32824859. doi:10.3390/ijms21165940  .
^ ^6.0 ^6.1 WO 2006078754,Macdonald JE, Hysell MK, Yu D, Li H, Wong-Staal F,「Novel Quinolinium Salts and Derivatives」,發表於2006-07-27
^ Esumi H, Lu J, Kurashima Y, Hanaoka T. Antitumor activity of pyrvinium pamoate, 6-(dimethylamino)-2-[2-(2,5-dimethyl-1-phenyl-1H-pyrrol-3-yl)ethenyl]-1-methyl-quinolinium pamoate salt, showing preferential cytotoxicity during glucose starvation. Cancer Science. August 2004, 95 (8): 685–90. PMID 15298733. doi:10.1111/j.1349-7006.2004.tb03330.x  .

[1] Desai AS. Single-dose treatment of oxyuriasis with pyrvinium embonate. British Medical Journal. December 1962, 2 (5319): 1583–5. PMC 1926864  . PMID 14027194. doi:10.1136/bmj.2.5319.1583.

[2] Pyrvinium. PubChem. U.S. National Library of Medicine. [2023-02-06]. （原始內容存檔於2016-04-02）.

[Heterocycles-3] 3.0 ^3.1 Mao Y, Lin N, Tian W, Huang Z. New Synthesis of Pyrvinium That inhibits the β-Catenin/Tcf4 Pathway. Heterocycles. 2012, 85 (5): 1179–1185. doi:10.3987/COM-12-12446.

[4] Saraswati S, Alfaro MP, Thorne CA, Atkinson J, Lee E, Young PP. Pyrvinium, a potent small molecule Wnt inhibitor, promotes wound repair and post-MI cardiac remodeling. PLOS ONE. 2010, 5 (11): e15521. Bibcode:2010PLoSO...515521S. PMC 2993965  . PMID 21170416. doi:10.1371/journal.pone.0015521  .

[5] Shen C, Nayak A, Melendez RA, Robbins DJ. Casein Kinase 1α as a Regulator of Wnt-Driven Cancer. International Journal of Molecular Sciences. 2020, 21 (16): 5940. PMC 7460588  . PMID 32824859. doi:10.3390/ijms21165940  .

[Macdonald-6] 6.0 ^6.1 WO 2006078754,Macdonald JE, Hysell MK, Yu D, Li H, Wong-Staal F,「Novel Quinolinium Salts and Derivatives」,發表於2006-07-27

[7] Esumi H, Lu J, Kurashima Y, Hanaoka T. Antitumor activity of pyrvinium pamoate, 6-(dimethylamino)-2-[2-(2,5-dimethyl-1-phenyl-1H-pyrrol-3-yl)ethenyl]-1-methyl-quinolinium pamoate salt, showing preferential cytotoxicity during glucose starvation. Cancer Science. August 2004, 95 (8): 685–90. PMID 15298733. doi:10.1111/j.1349-7006.2004.tb03330.x  .

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