- 関
- pyrvinium
Wikipedia preview
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
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Systematic (IUPAC) name |
2-[(E)-2-(2,5-Dimethyl-1-phenylpyrrol-3-yl)ethenyl]-N,N,1-trimethylquinolin-1-ium-6-amine
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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
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CC1=CC(=C(N1C2=CC=CC=C2)C)/C=C/C3=[N+](C4=C(C=C3)C=C(C=C4)N(C)C)C
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InChI
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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
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Key:QMHSXPLYMTVAMK-UHFFFAOYSA-N
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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
Antiparasitics – Anthelmintics (P02) and Endectocides (QP54)
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Antiplatyhelmintic agents |
Antitrematodals
(schistosomicides)
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Binds tubulin
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AI
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Other/unknown
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- quinoline
- Praziquantel#
- Oxamniquine#
- phenol
- thiazole
- arylsulfonate
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Anticestodals
(taeniacides)
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Binds tubulin
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Other/unknown
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- salicylanilide
- aminoacridine
- butyrophenone
- chlorophenol
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Antinematodal agents
(including
macrofilaricides) |
Binds tubulin
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- benzimidazole
- Mebendazole#
- Albendazole#
- Thiabendazole
- Fenbendazole
- Ciclobendazole
- Flubendazole
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Glutamate-gated chloride channel, GABA receptor
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- avermectins
- Abamectin
- Doramectin
- Emamectin
- Ivermectin
- Selamectin
- milbemycins
- Moxidectin
- Milbemycin oxime
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NMDA
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- tetrahydropyrimidine
- Pyrantel#
- Pyrantel pamoate
- Oxantel
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Other/unknown
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- piperazine
- Piperazine
- Diethylcarbamazine#
- thiazole
- quinolinium
- benzylammonium
- naphthalenesulfonate
- Tribendimidine
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
Index of parasites and pests
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Description |
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Disease |
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Treatment |
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UpToDate Contents
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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
Related Links
- CAS Number - Chemical Abstracts Service registry number. Unique identification number assigned to this chemical by the American Chemical Society. UN/NA Number - The United Nations-North America number (also called UN ...
- Pyrvinium pamoate (PP) is an FDA-approved classical anthelmintic, but is now attracting particular attention as an anti-cancer drug after recent findings of its potent cytotoxicity against various cancer cell lines only during ...
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ピルビニウム
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パモ酸、パモ酸塩