bis(2-[2-(2,5-dimethyl-1-phenyl-1H-pyrrol-3-yl)ethyl]-6-(dimethylamino)-1-methylquinolin-1-ium) 4-[(3-carboxylato-2-hydroxynaphthalen-1-yl)methyl]-3-hydroxynaphthalene-2-carboxylate hydrate

• ChemBase ID: 154670
• Molecular Formular: C75H76N6O7
• Molecular Mass: 1173.44194
• Monoisotopic Mass: 1172.5775488
• SMILES: Cc1cc(c(n1c1ccccc1)C)CCc1ccc2cc(ccc2[n+]1C)N(C)C.Cc1cc(c(n1c1ccccc1)C)CCc1ccc2cc(ccc2[n+]1C)N(C)C.c1ccc2c(c1)cc(c(c2Cc1c2ccccc2cc(c1O)C(=O)[O-])O)C(=O)[O-].O
• Canonical SMILES: [O-]C(=O)c1cc2ccccc2c(c1O)Cc1c(O)c(cc2c1cccc2)C(=O)[O-].CN(c1ccc2c(c1)ccc([n+]2C)CCc1cc(n(c1C)c1ccccc1)C)C.CN(c1ccc2c(c1)ccc([n+]2C)CCc1cc(n(c1C)c1ccccc1)C)C.O
• InChI: InChI=1S/2C26H30N3.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*6-10,12,14-18H,11,13H2,1-5H3;1-10,24-25H,11H2,(H,26,27)(H,28,29);1H2/q2*+1;;/p-2
• InChIKey: ZUTOEUQXOJGDCJ-UHFFFAOYSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: bis(2-[2-(2,5-dimethyl-1-phenyl-1H-pyrrol-3-yl)ethyl]-6-(dimethylamino)-1-methylquinolin-1-ium) 4-[(3-carboxylato-2-hydroxynaphthalen-1-yl)methyl]-3-hydroxynaphthalene-2-carboxylate hydrate
• IUPAC Traditional name: bis(2-[2-(2,5-dimethyl-1-phenylpyrrol-3-yl)ethyl]-6-(dimethylamino)-1-methylquinolin-1-ium) pamoate(2-) hydrate
• Synonyms: 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; Pyrvinium pamoate salt hydrate

Database IDs

• CAS Number: 3546-41-6(anhydrous)
• PubChem SID: 162248808
• PubChem CID: 71311932

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 0.80117667
• LogD (pH = 7.4): 0.8012252
• Log P: 0.8012258
• Molar Refractivity: 135.0285 cm^3
• Polarizability: 48.578392 Å^3
• Polar Surface Area: 12.05 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL
• Apperance: red powder

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22-36/37/38-40
• Safety Statements: 26-36
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H315-H319-H332-H335-H351
• GHS Precautionary statements: P261-P280-P305 + P351 + P338
• Storage Temperature: room temp

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C26H28N3 · 0.5 C23H14O6 · xH2O

DETAILS

Sigma Aldrich - P0027

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.