N-(2-hydroxyethyl)-N,2-dimethyl-8-{[(4R)-5-methyl-3,4-dihydro-2H-1-benzopyran-4-yl]amino}imidazo[1,2-a]pyridine-6-carboxamide

• ChemBase ID: 72830
• Molecular Formular: C22H26N4O3
• Molecular Mass: 394.46684
• Monoisotopic Mass: 394.20049071
• SMILES: c1cc(c2c(c1)OCC[C@H]2Nc1cc(cn2c1nc(c2)C)C(=O)N(CCO)C)C
• Canonical SMILES: OCCN(C(=O)c1cc(N[C@@H]2CCOc3c2c(C)ccc3)c2n(c1)cc(n2)C)C
• InChI: InChI=1S/C22H26N4O3/c1-14-5-4-6-19-20(14)17(7-10-29-19)24-18-11-16(22(28)25(3)8-9-27)13-26-12-15(2)23-21(18)26/h4-6,11-13,17,24,27H,7-10H2,1-3H3/t17-/m1/s1
• InChIKey: YBHKBMJREUZHOV-QGZVFWFLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(2-hydroxyethyl)-N,2-dimethyl-8-{[(4R)-5-methyl-3,4-dihydro-2H-1-benzopyran-4-yl]amino}imidazo[1,2-a]pyridine-6-carboxamide
• IUPAC Traditional name: N-(2-hydroxyethyl)-N,2-dimethyl-8-{[(4R)-5-methyl-3,4-dihydro-2H-1-benzopyran-4-yl]amino}imidazo[1,2-a]pyridine-6-carboxamide
• Synonyms: 8-[[(4R)-3,4-Dihydro-5-methyl-2H-1-benzopyran-4-yl]amino]-N-(2-hydroxyethyl)-N,2-dimethylimidazo[1,2-a]pyridine-6-carboxamide; N-(2-Hydroxyethyl)-N,2-dimethyl-8-{[(4R)-5-methyl-3,4-dihydro-2H-chromen-4-yl]amino}imidazo[1,2-a]pyridine-6-carboxamide; PF 3716556; PF-03716556; PF-3716556; PF-03716556; PF 3716556; [N-(2-Hydroxyethyl)-N,2-dimethyl-8-{[(4R)-5-methyl-3,4-dihydro-2H-chromen-4-yl]amino}imidazo[1,2-a]pyridine-6-carboxamide]; PF-03716556

Database IDs

• CAS Number: 928774-43-0
• MDL Number: MFCD19690947
• PubChem SID: 162037751
• PubChem CID: 25134521

CALCULATED PROPERTIES

• Acid pKa: 15.574108
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 0.15962853
• LogD (pH = 7.4): 0.9624813
• Log P: 1.0000132
• Molar Refractivity: 114.5694 cm^3
• Polarizability: 42.00518 Å^3
• Polar Surface Area: 79.1 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; DMSO: ≥10 mg/mL; Methanol
• Apperance: Light Tan Solid; white to tan powder
• Melting Point: 143-145°C

Safety Information

• Storage Condition: -20°C; Refrigerator
• German water hazard class: 3
• Storage Temperature: 2-8°C

Pharmacology Properties

• Target: ATPase

Product Information

• Purity: ≥98% (HPLC)
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C22H26N4O3

DETAILS

Selleck Chemicals - S2222

Research Area: Cancer
Biological Activity:
PF-03716556 is a potent, and selective acid pump antagonist with pIC50 of 6.026 ± 0.112, 6.038 ± 0.039 and 6.009 ± 0.209 at pH 6.4 for the inhibition of H+, K+-ATPase activity of porcine, canine and human ion-leaky membrane vesicles, respectively.PF-03716556 is used for the treatment of gastroesophageal reflux disease. PF-03716556 is highly selective for H+, K+-ATPase in vitro. PF-03716556 displays no activity at Na+, K+-ATPase. PF-03716556 inhibits gastric acid secretion in rat and dog models. PF-03716556 has no species differences among the porcine, canine and human enzymes. PF-03716556 produced greater inhibition than revaprazan in both the in vitro (ion-tight assay) and in vivo conditions. PF-03716556 offers long-lasting and maximal efficacy within 30 min of a single dosing with responses that are maintained for at least 5 days of repeated dosing with no signs of tolerance. PF-03716556 did not exhibit any biologically relevant activity against any of the tested more than 50 (e.g., adenosine receptor) receptors, ion channels, or enzymes expressed in naïve tissues, cell lines and transfectants. [1]References on PF 3716556[1] J Pharmacol Exp Ther., 2009 Feb, 328(2):671-9.

Sigma Aldrich - PZ0155

Biochem/physiol Actions
potent, selective and reversible acid pump antagonist (H, K-ATPase)
Legal Information
Sold for research purposes under agreement from Pfizer Inc.

Toronto Research Chemicals - P293980

A novel, potent, and selective acid pump antagonist for the treatment of gastroesophageal reflux disease.

REFERENCES

• Mori H et al. J Pharmacol Exp Ther. 2009 Feb;328(2):671-9.
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