CAS 3546-41-6|Pyrvinium pamoate

Introduction：Basic information about CAS 3546-41-6|Pyrvinium pamoate, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Pyrvinium pamoate BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
MUTATION DATA
5. Safety Information
6. Articles1
7. Synonyms

Common Name	Pyrvinium pamoate
CAS Number	3546-41-6	Molecular Weight	575.70
Density	1.0104 (rough estimate)	Boiling Point	829.27°C (rough estimate)
Molecular Formula	C₂₆H₂₈N_3.1/₂C₂₃H₁₄O₆	Melting Point	210-215° (softens at 190°)
MSDS	/	Flash Point	/
Symbol	GHS07, GHS08	Signal Word	Warning

Names

Name	Pyrvinium pamoate
Synonym	More Synonyms

Pyrvinium pamoate BiologicalActivity

Description	Pyrvinium pamoate is an FDA-approved antihelmintic drug that inhibits WNT pathway signaling.
Related Catalog	Signaling Pathways >>Stem Cell/Wnt >>WntResearch Areas >>Cancer
In Vitro	Pyrvinium pamoate (0-500 nM) inhibits proliferation of MCF-7 (luminal), MDA-MB-231 (claudin-low), MDA-MB-468 (basal-like) and SkBr3 (HER2-OE) cells in a dose-dependent manner, with IC50 value of 1170±105.0 nM against MDA-MB-231 cell line. Pyrvinium pamoate significantly inhibits self-renewal and proliferation of BCSCs, and suppresses BCSC population with a distinct phenotype. Pyrvinium pamoate significantly decreases average expression levels of FZD1, FZD10, WNT1, WNT7B, CTNNB1, MYC, and LRP5 at transcriptional level. Moreover, Pyrvinium pamoate also efficiently down-regulates the expression of other stemness genes including ALDH1, CD44 and ABCG2[1]. Pyrvinium pamoate blocks colon cancer cell growth in vitro in a dose-dependent manner with great differences in the inhibitory concentration (IC50), ranging from 0.6 to 65 μM for colon cancer cells with mutations in WNT signaling. Pyrvinium pamoate decreases messenger RNA (mRNA) and protein levels of known WNT target genes as c-MYC and thereby led to the induction of p21[2]. Pyrvinium pamoate ultimately inhibits Wnt signalling despite its lack of efficacy on CK1[3]. Pyrvinium pamoate imposes specific toxicity on cardiac fibroblasts in ischemia (IC50=9.5 nM). The cytotoxic effect of Pyrvinium pamoate on cardiac fibroblasts specifically under glucose- and glutamine-deficient condition[4].
In Vivo	In the xenograft model, Pyrvinium pamoate (500 nM)-pretreatment strongly delays tumor size and tumor weight, and the tumor volume is markedly decreased[1].
Cell Assay	Pyrvinium pamoate is dissolved in DMSO at a concentration of 1 μM and is stocked in aliquots at -20°C. Cells (1×104) are suspended in 200 μL culture medium and then seeded into 96-well plates in quintuplicate overnight. Cells are treated with indicated concentrations of Pyrvinium pamoate (0-8,000 μM). After incubating for 3 days, CCK8 (10 μL) is added into each well and incubated at 37°C for 1 h. The absorbance is measured using a microplate reader at 450 nm[1].
Animal Admin	Mice: NOD/SCID mice are housed under aseptic conditions in individually ventilated cages. For xenografting, 5×106 Pyrvinium pamoate-pretreated or untreated breast cancer cells (MDA-MB-231) are resuspended in a 1:1 mixture of culture medium and Matrigel and then transplanted into the fourth pair of mammary fat pads of mice (4-6-week-old). After injection, tumor size is measured by calipers each day and tumor growth is plotted. Upon reaching the endpoint, mice are sacrificed and tumors are harvested. All the tumors are formalin-fixed, and paraffin-embedded for hematoxylin and eosin and immunohistochemical staining[1].
References	[1]. Xu L, et al. WNT pathway inhibitor pyrvinium pamoate inhibits the self-renewal and metastasis of breast cancer stem cells. Int J Oncol. 2016 Mar;48(3):1175-86. [2]. Wiegering A, et al. The impact of pyrvinium pamoate on colon cancer cell viability. Int J Colorectal Dis. 2014 Oct;29(10):1189-98. [3]. Venerando A, et al. Pyrvinium pamoate does not activate protein kinase CK1, but promotes Akt/PKB down-regulation and GSK3 activation. Biochem J. 2013 May 15;452(1):131-7. [4]. Murakoshi M, et al. An anthelmintic drug, pyrvinium pamoate, thwarts fibrosis and ameliorates myocardial contractile dysfunction in a mouse model of myocardial infarction. PLoS One. 2013 Nov 4;8(11):e79374.

Chemical & Physical Properties

Density	1.0104 (rough estimate)
Boiling Point	829.27°C (rough estimate)
Melting Point	210-215° (softens at 190°)
Molecular Formula	C₂₆H₂₈N_3.1/₂C₂₃H₁₄O₆
Molecular Weight	575.70
PSA	144.82000
LogP	12.33840
Appearance of Characters	red
Index of Refraction	1.6400 (estimate)
InChIKey	OOPDAHSJBRZRPH-UHFFFAOYSA-L
SMILES	Cc1cc(C=Cc2ccc3cc(N(C)C)ccc3[n+]2C)c(C)n1-c1ccccc1.Cc1cc(C=Cc2ccc3cc(N(C)C)ccc3[n+]2C)c(C)n1-c1ccccc1.O=C(O)c1cc2ccccc2c(Cc2c([O-])c(C(=O)O)cc3ccccc23)c1[O-]
Storage condition	room temp
Water Solubility	DMSO: >10mg/mL

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: VC3543500

CAS REGISTRY NUMBER :: 3546-41-6

LAST UPDATED :: 199512

DATA ITEMS CITED :: 11

MOLECULAR FORMULA :: C75-H70-N6-O6

MOLECULAR WEIGHT :: 1151.51

WISWESSER LINE NOTATION :: T66 BKJ B1 HN1&1 C1U1- CT5NJ AR& B1 E1 &L66J CQ DVO B1- BL66J CQ DVO

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 5 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 200 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - tremor

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 15 gm/kg/30D-C

TOXIC EFFECTS :: Endocrine - other changes Related to Chronic Data - death Related to Chronic Data - changes in testicular weight

MUTATION DATA

TYPE OF TEST :: Gene conversion and mitotic recombination

TEST SYSTEM :: Yeast - Saccharomyces cerevisiae

DOSE/DURATION :: 400 umol/L

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 187,79,1987 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 81965 No. of Facilities: 805 (estimated) No. of Industries: 1 No. of Occupations: 1 No. of Employees: 805 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 81965 No. of Facilities: 19 (estimated) No. of Industries: 1 No. of Occupations: 2 No. of Employees: 774 (estimated) No. of Female Employees: 337 (estimated)

Safety Information

Symbol	GHS07, GHS08
Signal Word	Warning
Hazard Statements	H302 + H312 + H332-H315-H319-H335-H351
Precautionary Statements	P261-P280-P301 + P312 + P330-P305 + P351 + P338
Hazard Codes	Xn
Risk Phrases	20/21/22-36/37/38-40
Safety Phrases	26-36
RIDADR	NONH for all modes of transport

Articles1

Casein kinase 1 suppresses activation of REST in insulted hippocampal neurons and halts ischemia-induced neuronal death.

J. Neurosci. 34(17) , 6030-9, (2014)

Repressor Element-1 (RE1) Silencing Transcription Factor/Neuron-Restrictive Silencer Factor (REST/NRSF) is a gene-silencing factor that is widely expressed during embryogenesis and plays a strategic r...

Synonyms

pyrvinium pamoate

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