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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/08/21 16:47:53」(JST)

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Pyrvinium is an anthelmintic effective for pinworms.^[1] Several forms of pyrvinium have been prepared with variable counter anions, such as halides, tosylate, triflate and pamoate.^[2]^[3]

Pyrvinium salts can also inhibit the growth of cancer cells.^[4] More specifically, the pamoate salt has been shown to have preferential toxicity for various cancer cell lines during glucose starvation.^[5]

Synthesis

One synthetic method is based on Skraup synthesis and Paal-Knorr synthesis.^[4] More recently, an alternative convergent, synthetic strategy to pyrvinium triflate salts through Friedländer synthesis was reported.^[3]

References

^ Desai, A. S. (1962). "Single-dose treatment of oxyuriasis with pyrvinium embonate". British medical journal 2 (5319): 1583–1585. doi:10.1136/bmj.2.5319.1583. PMC 1926864. PMID 14027194. edit
^ PubChem: Pyrvinium
^ ^a ^b An, Jing; Mao, Yongjun; Lin, Nan; Tian, Wang; Huang, Ziwei (2012). "New Synthesis of Pyrvinium That inhibits the β-Catenin/Tcf4 Pathway". Heterocycles 85 (5): 1179–1185. doi:10.3987/COM-12-12446.
^ ^a ^b WO 2006078754, J. E. Macdonald, M. K. Hysell, D. Yu, H. Li, and F. Wong-Staal, "Novel Quinolinium Salts and Derivatives", published 2006-07-27
^ Esumi, H.; Lu, J.; Kurashima, Y.; Hanaoka, T. (2004). "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 95 (8): 685–690. doi:10.1111/j.1349-7006.2004.tb03330.x. PMID 15298733. edit

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UpToDate Contents

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1. Enterobiasis (pinworm) and trichuriasis (whipworm)
2. 鉤虫感染 hookworm infection
3. 回虫症 ascariasis
4. その他の線虫 miscellaneous nematodes
5. 集団寄生虫駆除 population deworming

English Journal

An anticancer agent, pyrvinium pamoate inhibits the NADH-fumarate reductase system--a unique mitochondrial energy metabolism in tumour microenvironments.

Tomitsuka E, Kita K, Esumi H.SourceCancer Physiology Project, Research Center for Innovative Oncology, National Cancer Center Hospital East, 6-5-1 Kashiwanoha, Kashiwa, Chiba 277-8577, Japan. e-tomi@humeco.m.u-tokyo.ac.jp
Journal of biochemistry.J Biochem.2012 Aug;152(2):171-83. Epub 2012 Apr 23.
Increased glycolysis is the principal explanation for how cancer cells generate energy in the absence of oxygen. However, in actual human tumour microenvironments, hypoxia is often associated with hypoglycemia because of the poor blood supply. Therefore, glycolysis cannot be the sole mechanism for t
PMID 22528668

Pyrvinium pamoate inhibits proliferation of myeloma/erythroleukemia cells by suppressing mitochondrial respiratory complex I and STAT3.

Harada Y, Ishii I, Hatake K, Kasahara T.SourceDepartment of Biochemistry, Keio University Graduate School of Pharmaceutical Sciences, Tokyo 105-8512, Japan.
Cancer letters.Cancer Lett.2012 Jun 1;319(1):83-8. Epub 2011 Dec 27.
Pyrvinium pamoate (PP), a classical anthelminthic, potently inhibited proliferation and STAT3 Tyr705 phosphorylation of human myeloma (U266B1 and PCM6)/erythroleukemia (HEL 92.1.7) cells. PCM6 cell proliferation was markedly impaired by STAT3 siRNA knockdown. PP inhibited ATP production/O(2) consump
PMID 22210382

Japanese Journal

An anticancer agent, pyrvinium pamoate inhibits the NADH-fumarate reductase system : a unique mitochondrial energy metabolism in tumour microenvironments

Tomitsuka Eriko,Kita Kiyoshi,Esumi Hiroyasu
Journal of Biochemistry 152(2), 171-183, 2012-08
NAID 40019378119

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

ESUMI Hiroyasu,LU Jie,KURASHIMA Yukiko,HANAOKA Tomoyuki
Cancer science 95(8), 685-690, 2004-08-10
NAID 10013570573

Sex-related Different Efficacy of Chemotherapy on Human Strongyloidiasis in Okinawa, Japan

小林潤,佐藤良也,當眞弘 [他],田崎力,高良政弘,城間祥行
寄生虫学雑誌 = Japanese journal of parasitology 45(5), 350-354, 1996-10-01
NAID 10009009114

「ピルビニウム」

Pyrvinium
Systematic (IUPAC) name
	2-[(E)-2-(2,5-Dimethyl-1-phenylpyrrol-3-yl)ethenyl]-N,N,1-trimethylquinolin-1-ium-6-amine
Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Identifiers
CAS Registry Number	7187-62-4
ATC code	P02CX01
PubChem	CID: 5281035
ChemSpider	21125
UNII	6B9991FLU3
ChEBI	CHEBI:8687
ChEMBL	CHEMBL1201303
Chemical data
Formula	C26H28N3+
Molecular mass	382.52 g/mol
	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 ;