P0027

Pyrvinium pamoate salt hydrate

≥98% (HPLC)

• Synonym(s): 6-(Dimethylamino)-2-[2-(2,5-dimethyl-1-phenyl-1H-pyrrol-3-yl)ethenyl]-1-methyl-4,4′-methylenebis[3-hydroxy-2-naphthalenecarboxylate] (2:1)-quinolinium, Alnoxin, Altolat, NSC 223622, PP, Pamovin, Vermitibier, Vipyrvinium embonate
• Empirical Formula (Hill Notation): C₂₆H₂₈N₃ · 0.5 C₂₃H₁₄O₆ · xH₂O
• CAS Number: 3546-41-6
• Molecular Weight: 575.70 (anhydrous basis)
• UNSPSC Code: 51111800
• PubChem Substance ID: 329819982
• NACRES: NA.77

Properties

• Assay: ≥98% (HPLC)
• form: powder
• color: red
• solubility: DMSO: >10 mg/mL
• storage temp.: room temp
• SMILES string: O.CN(C)c1ccc2[n+](C)c(\C=C\c3cc(C)n(c3C)-c4ccccc4)ccc2c1.CN(C)c5ccc6[n+](C)c(\C=C\c7cc(C)n(c7C)-c8ccccc8)ccc6c5.Oc9c(cc%10ccccc%10c9Cc%11c(O)c(cc%12ccccc%11%12)C([O-])=O)C([O-])=O
• InChI: 1S/2C26H28N3.C23H16O6.H2O/c2*1-19-17-21(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;24-20-16(14-7-3-1-5-12(14)9-18(20)22(26)27)11-17-15-8-4-2-6-13(15)10-19(21(17)25)23(28)29;/h2*6-18H,1-5H3;1-10,24-25H,11H2,(H,26,27)(H,28,29);1H2/q2*+1;;/p-2
• InChI key: FGNOZQNUEDSSTR-UHFFFAOYSA-L

Description

Application

Pyrvinium pamoate salt hydrate has been used as an activator of casein kinase 1α (CK1α) in terminal blast phase of chronic myeloid leukemia (BP-CML) and human embryonic kidney (HEK293) cells. It has also been used as an inhibitor of β-catenin in Wilms tumor

Biochem/physiol Actions

Pyrvinium pamoate is a potent androgen receptor inhibitor. Androgen receptors (ARs) are nuclear hormone receptors/transcription factors that reside in the cytoplasm and activated by testosterone and dihydrotestosterone. AR inhibitors have potential therapeutic benefit in prostate cancer; competitive inhibitors and chemical castration methods have been discovered, but both therapies have undesirable side effects and/or resistance potential. A screen for non-competitive inhibitors was performed, resulting in the discovery of pyrvinium as an AR inhibitor. In comparison to competitive inhibitors, this compound does not bind to the ligand-binding domain of AR or block DNA occupancy by AR, but it inhibits AR-dependent gene expression via a distinct signaling mechanism. It is more potent than classical competitive AR antagonists and exhibits synergy with other AR inhibitors.

Features and Benefits

This compound is featured on the Nuclear Receptors (Steroids) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Safety Information

• Pictograms: GHS08,GHS07
• Signal Word: Warning
• Hazard Statements: H302 + H312 + H332,H315,H319,H335,H351
• Precautionary Statements: P280 - P301 + P312 - P302 + P352 + P312 - P304 + P340 + P312 - P305 + P351 + P338 - P308 + P313
• Hazard Classifications: Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Carc. 2 - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• Target Organs: Respiratory system
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable