Synonym
PF-03716556; PF 03716556; PF03716556; PF-3716556; PF 3716556; PF3716556.
IUPAC/Chemical Name
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
InChi Key
YBHKBMJREUZHOV-QGZVFWFLSA-N
InChi Code
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
SMILES Code
O=C(C1=CN2C(C(N[C@@H]3CCOC4=C3C(C)=CC=C4)=C1)=NC(C)=C2)N(CCO)C
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
PF-03716556 is a potent, and selective acid pump antagonist for the treatment of gastroesophageal reflux disease.
In vitro activity:
PF-03716556 demonstrated 3-fold greater inhibitory activity than 5,6-dimethyl-2-(4-fluorophenylamino)-4-(1-methyl-1,2,3,4-tetrahydroisoquinoline-2-yl)pyrimidine (revaprazan), the only acid pump antagonist that has been available on the market, in ion-tight assay. Kinetics experiments revealed that PF-03716556 has a competitive and reversible mode of action.
Reference: J Pharmacol Exp Ther. 2009 Feb;328(2):671-9. https://pubmed.ncbi.nlm.nih.gov/18981288/
|
Solvent |
mg/mL |
mM |
comments |
| Solubility |
| DMF |
30.0 |
76.05 |
|
| DMSO |
54.0 |
136.89 |
|
| DMSO:PBS (pH 7.2) (1:20) |
0.0 |
0.10 |
|
| Ethanol |
44.0 |
111.54 |
|
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
394.48
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
Mori H, Tonai-Kachi H, Ochi Y, Taniguchi Y, Ohshiro H, Takahashi N, Aihara T, Hirao A, Kato T, Sakakibara M, Kurebayashi Y. 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), a novel, potent, and selective acid pump antagonist for the treatment of gastroesophageal reflux disease. J Pharmacol Exp Ther. 2009 Feb;328(2):671-9. doi: 10.1124/jpet.108.146415. Epub 2008 Nov 3. PMID: 18981288.
In vitro protocol:
Mori H, Tonai-Kachi H, Ochi Y, Taniguchi Y, Ohshiro H, Takahashi N, Aihara T, Hirao A, Kato T, Sakakibara M, Kurebayashi Y. 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), a novel, potent, and selective acid pump antagonist for the treatment of gastroesophageal reflux disease. J Pharmacol Exp Ther. 2009 Feb;328(2):671-9. doi: 10.1124/jpet.108.146415. Epub 2008 Nov 3. PMID: 18981288.
1: Mori H, Tonai-Kachi H, Ochi Y, Taniguchi Y, Ohshiro H, Takahashi N, Aihara T,
Hirao A, Kato T, Sakakibara M, Kurebayashi Y.
N-(2-hydroxyethyl)-N,2-dimethyl-8-{[(4R)-5-methyl-3,4-dihydro-2H-chromen-4-yl]ami
no}imidazo[1,2-a]pyridine-6-carboxamide (PF-03716556), a novel, potent, and
selective acid pump antagonist for the treatment of gastroesophageal reflux
disease. J Pharmacol Exp Ther. 2009 Feb;328(2):671-9. doi:
10.1124/jpet.108.146415. Epub 2008 Nov 3. PubMed PMID: 18981288.
Tanaka S, Morita M, Yamagishi T, Madapally HV, Hayashida K, Khandelia H, Gerle C, Shigematsu H, Oshima A, Abe K. Structural Basis for Binding of Potassium-Competitive Acid Blockers to the Gastric Proton Pump. J Med Chem. 2022 Jun 9;65(11):7843-7853. doi: 10.1021/acs.jmedchem.2c00338. Epub 2022 May 23. PMID: 35604136.
