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PF-04447943

PDE9 inhibitor CAS# 1082744-20-4

PF-04447943

2D Structure

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Quality Control of PF-04447943

Quality Control & MSDS

Purity: >98%

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Chemical Properties of PF-04447943

Cas No.	1082744-20-4	SDF	Download SDF
PubChem ID	25115162	Appearance	Powder
Formula	C20H25N7O2	M.Wt	395.46
Type of Compound	N/A	Storage	Desiccate at -20°C
Solubility	DMSO : ≥ 54.6 mg/mL (138.07 mM) *"≥" means soluble, but saturation unknown.
Chemical Name	6-[(3S,4S)-4-methyl-1-(pyrimidin-2-ylmethyl)pyrrolidin-3-yl]-1-(oxan-4-yl)-2H-pyrazolo[3,4-d]pyrimidin-4-one
SMILES	CC1CN(CC1C2=NC(=O)C3=CNN(C3=N2)C4CCOCC4)CC5=NC=CC=N5
Standard InChIKey	ACXPOEVOYNJCHF-CZUORRHYSA-N
Standard InChI	InChI=1S/C20H25N7O2/c1-13-10-26(12-17-21-5-2-6-22-17)11-16(13)18-24-19-15(20(28)25-18)9-23-27(19)14-3-7-29-8-4-14/h2,5-6,9,13-14,16,23H,3-4,7-8,10-12H2,1H3/t13-,16-/m1/s1
General tips	For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging	1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment.
Shipping Condition	Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of PF-04447943

Description

PF-04447943 is a potent inhibitor of human recombinant PDE9A (IC50=12 nM) with >78-fold selectivity, respectively, over other PDE family members (IC50>1000 nM).In Vitro:Using recombinant human, rhesus, and rat PDE9A2 in a cell free assay PF-04447943 is shown to have a Ki of 2.8±0.26, 4.5±0.13, and 18.1±1.9 nM (n=4, 11 and 9 respectively). PF-04447943 is found to be highly selective over other PDE enzymes (PDE1, Ki=8600±2121 nM, n = 5; PDE2A3, Ki>99,000 nM; PDE3A, Ki>50,000 nM; PDE4A, Ki>29,000 nM; PDE5A, Ki=14,980±5025 nM, n=5; PDE6C, Ki=5324±2612 nM, n=4; PDE7A2, Ki>75,000 nM; PDE8A, Ki>50,000 nM; PDE10, Ki>51,250±20,056 nM, n=4; PDE11, Ki>80,000 nM) and no other significant activity at ~60 other receptors/enzymes. In HEK whole cells expressing rhesus PDE9A2, PF-04447943 inhibits ANP (0.3 μM) stimulated cGMP with an IC50 of 375±36.9 nM (n=16)[2].In Vivo:Based on i.v. and p.o. dosing, pharmacokinetic studies with PF-04447943 in the rat indicates a Tmax of 0.3 h, T1/2 of 4.9 h, Cl of 21.7 mL/min/kg and an oral bioavailability of 47%. Thirty minutes following oral administration in rats (1-30 mg/kg), PF-04447943 concentrations dose-dependently increase in blood, brain and cerebrospinal fluid (CSF). The brain:plasma exposure ratios 30 min after dosing range from 0.13 at the 1 mg/kg dose to 0.33 at the 30 mg/kg dose. CSF levels are approximately 50% of brain levels. In mice, PF-04447943 (3, 10, 30 mg/kg p.o.) dose-dependently increases plasma and brain concentrations of PF-04447943 while the brain to plasma ratio ranged from 0.26 to 0.7 although this is not entirely dose dependent. CSF cGMP levels increase in a dose-dependent manner from a basal level of 3 pmol/mL to 13.3 pmol/mL (3.5-fold) at the 30 mg/kg dose. CSF cGMP levels also increase in a dose-dependent manner from a basal level of 3 pmol/mL in vehicle treated animals to 13.3 pmol/mL (3.5-fold) at the 30 mg/kg dose. CSF cGMP levels are elevated at all doses tested with a maximal effect of 3.5 fold increase above controls at 30 mg/kg[2].

References:
[1]. Kleiman RJ, et al. Phosphodiesterase 9A regulates central cGMP and modulates responses to cholinergic and monoaminergic perturbation in vivo. J Pharmacol Exp Ther. 2012 May;341(2):396-409. [2]. Hutson, P. H, et al. The selective phosphodiesterase 9 (PDE9) inhibitor PF-04447943 (6-[(3S,4S)-4-methyl-1-(pyrimidin-2-ylmethyl)pyrrolidin-3-yl]-1-(tetrahydro-2H-pyran-4-yl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one) enhances synaptic plasticity and

Protocol

Kinase Assay [1]
PDE enzyme assays are carried out. PDE1A-C, PDE2A, PDE3A/B, PDE4A-D, PDE7A/B, PDE8A/B, PDE9A, PDE10A, and PDE11 are generated from full-length recombinant clones. PDE5 is isolated from human platelets, and PDE6 is isolated from bovine retina. PDE activity is measured by using a scintillation proximity assay (SPA). The effects of PDE inhibitors are investigated by assaying a fixed amount of enzyme and varying inhibitor concentrations in the presence of substrate concentrations of 1/3 Km values for each enzyme, so that the IC50 value approximates the Ki value. PF-4447943 is dissolved in 100% DMSO and diluted to the required concentrations in 15% DMSO water. The enzyme stocks are all thawed slowly and diluted in assay buffer containing 50 mM Tris-HCl (pH 7.5 at room temperature) and 1.3 mM MgCl2. In addition, the PDE1 assay buffers contain 2.8 mM CaCl2. The PDE1C assay also requires the addition of the activator calmodulin at a final assay concentration of 100 units/mL. Incubations are initiated by the addition of diluted enzyme to 384-well plates containing test drugs and radioligand (50 nM [3H]cGMP for PDE1, PDE2, PDE5, PDE6, PDE9, PDE10, and PDE11 and 20 nM [3H]cAMP for PDE3, PDE4, PDE7, and PDE8). The assays are incubated for 30 min at room temperature (60 min for PDE5 and PDE6). The reactions are stopped by the addition of phosphodiesterase SPA beads at a final assay concentration of 0.2 mg/well. PDE9 requires the extra addition of a high concentration (10 μM) of a potent PDE9 inhibitor before beads to stop the reaction completely. Activities of test compounds are assessed by measuring the amount of [3H]5′-GMP or [3H]5′-AMP produced from [3H]cGMP or [3H]cAMP radioligand, respectively. Levels of [3H]5′-GMP or [3H]5′-AMP binds to SPA beads are determined by paralux counting of the assay plates in a Microbeta Trilux Counter 10 h after bead addition. Nonspecific binding is determined by radioligand binding in the presence of a saturating concentration of a potent PDE inhibitor. The IC50 value of each test compound (concentration at which 50% inhibition of specific binding occurs) is calculated by nonlinear regression (curve fitting) of the concentration response[1].

Cell Assay [2]
The rhesus PDE9A2 construct is subcloned into a pcDNA3.3 TOPO vector and HEK 293 cells, stably transfected to constitutively express rhesus PDE9A2 and hNPR1, are incubated with PF-04447943 (30 μM to 1.5 nM) in assay media at a density of 10,000 cells/well, for 30 min at 37°C. Cyclic GMP formation is stimulated by incubation with 0.3 μM ANP (Atrial Natriuretic Peptide) for another 30 min at 37°C. Following incubation, cells are lysed with Antibody/Lysis buffer and ED Reagent for 1 h at room temperature. After a subsequent incubation with EA Reagent for 30 min at room temperature, followed by incubation with Substrate Reagent for 1 h at room temperature, cGMP concentrations are determined by measuring luminescence on the Envision Microplate Luminometer. The maximal inhibition (100% activity) in the cell based assay is determined using 30 μM PF-04447943 and 0% activity is defined by the DMSO control. PF-04447943 is titrated in quadruplicate, in a 10 point titration. Percentage inhibition is calculated using the maximal inhibition value and IC50 values are calculated from concentration response curves using Prism software[2].

Animal Administration [2]
Mice and Rats[2] For the mouse studies, male C57Bl/6J mice are administered PF-04447943 (3, 10, 30 mg/kg p.o.). For the rat studies rats (strain, weight range and supplier as described in the novel object recognition study below) are administered PF-04447943 10 mg/kg i.v. and p.o. At various times after administration the animals are anesthetized with isoflurane; blood samples are withdrawn via cardiac puncture and placed in EDTA tubes on ice. Plasma is separated and frozen at −70°C until assayed for drug concentration. The animals are decapitated, the brain is removed, then homogenized in 3 mL of water per gram of tissue and centrifuged for 15 min at 13,500 g. Sample analysis is conducted using an Acquity UPLC system coupled with a SCIEX API4000 Q-Trap mass spectrometer. Two μL of the sample extract is analyzed using an Acquity UPLC®BEH C18 column (1.7 μm particle size, 50×2.1 mm I.D.) operated at 60°C. The flow rate is 0.7 mL/min. A gradient mobile phase consisting of solvent A (20/80 Methanol/Water, 10 mM Ammonium Acetate) and solvent B (10 mM Ammonium Acetate in Methanol with 0.6 mL/L 10% acetic Acid) is used. The total run time for each sample is 1.2 min. PF-04447943 and the internal standard eluted at 0.61 and 0.67 min, respectively. PF-04447943 and the internal standard are monitored in the positive ion mode at the transition from m/z 396.2 to 203.1 and m/z 477.3 to 266.2, respectively. Quantification is performed using Analyst 1.4 based on duplicate standard curves.

PF-04447943 Dilution Calculator

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Preparing Stock Solutions of PF-04447943

	1 mg	5 mg	10 mg	20 mg	25 mg
1 mM	2.5287 mL	12.6435 mL	25.287 mL	50.574 mL	63.2175 mL
5 mM	0.5057 mL	2.5287 mL	5.0574 mL	10.1148 mL	12.6435 mL
10 mM	0.2529 mL	1.2644 mL	2.5287 mL	5.0574 mL	6.3218 mL
50 mM	0.0506 mL	0.2529 mL	0.5057 mL	1.0115 mL	1.2644 mL
100 mM	0.0253 mL	0.1264 mL	0.2529 mL	0.5057 mL	0.6322 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on PF-04447943

PF-04447943 is a potent and selective inhibitor of PDE9 [1].

Phosphodiesterase 9 (PDE9) selectively degrades cGMP and limits the cGMP-mediated signal transduction which occurs following glutamate binding to NMDA receptors. PDE9 in cortex and hippocampus of rodents and humans play an important role in memory and learning [1].

PF-04447943 have high affinity with Ki of 2.8, 4.5 and 18 nM for human, rhesus and rat recombinant PDE9 respectively and high selectivity for PDE9 versus PDEs1- 8 and 10 -11. In cultured hippocampal neurons, PF-04447943 (30-100 nM) significantly increased neurite outgrowth and synapse formation. Also, PF-04447943 (100 nM) significantly facilitated hippocampal slice LTP evoked by a weak tetanic stimulus [1].

In mice model, PF-04447943 (1 mg/kg) significantly reduced the time spent interacting with the female mouse during the second encounter 24 h later compared to the first encounter, which suggested that PF-04447943 enhanced recognition memory. While, PF-04447943 (3 or 10 mg/kg) didn’t change the interaction times for each encounter. These results suggested that PF-04447943 enhanced memory with an inverted U-shaped dose-response efficacy curve [1].

Reference:
[1]Hutson PH, Finger EN, Magliaro BC, et al. The selective phosphodiesterase 9 (PDE9) inhibitor PF-04447943(6-[(3S,4S)-4-methyl-1-(pyrimidin-2-ylmethyl)pyrrolidin-3-yl]-1-(tetrahydro-2H-pyran-4-yl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one) enhances synaptic plasticity and cognitive function in rodents. Neuropharmacology, 2011, 61(4): 665-676.

References on PF-04447943

The selective phosphodiesterase 9 (PDE9) inhibitor PF-04447943 attenuates a scopolamine-induced deficit in a novel rodent attention task.[Pubmed:22070409]

J Neurogenet. 2011 Dec;25(4):120-6.

Numerous changes occur during aging and Alzheimer's disease (AD) progression, including a decline in cholinergic functioning and cognition, as well as alterations in gene expression and activity in the nitric oxide/cyclic guanosine monophosphate (NO/cGMP) pathway. Donepezil, the current standard of care for Alzheimer's disease, improves cholinergic functioning and has demonstrated effects on multiple domains of cognition, including memory and attention in both preclinical species and patients. We previously found that increasing activation of the NO/cGMP pathway via phosphodiesterase 9 (PDE9) inhibition also improves memory in rodents and suggested that PDE9 might be a promising target for novel treatments for AD. Here we investigated whether PDE9 inhibition also enhances attention using a novel attention task in rats. We validated this task using several pharmacological manipulations and showed that the selective PDE9 inhibitor PF-04447943 produced effects similar to those of donepezil. These data confirm and extend the hypothesis that PDE9 inhibition might serve as a novel treatment for AD and age-related cognitive decline.

A multicenter, double-blind, placebo-controlled trial of the PDE9A inhibitor, PF-04447943, in Alzheimer's disease.[Pubmed:24801218]

Curr Alzheimer Res. 2014;11(5):413-21.

BACKGROUND: PF-04447943 is a potent, selective phosphodiesterase 9A (PDE9A) inhibitor that elevates guanoscine 3',5' - cyclic monophosphate (cGMP) in brain and cerebrospinal fluid. PDE9A inhibition enhances synaptic plasticity and improves memory in preclinical cognition models, and prevents decreases in dendritic spine density in transgenic mice that overexpress amyloid precursor protein (APP) leading to high levels of amyloid beta (Abeta) production (Tg2576). OBJECTIVE: This Phase 2 multicenter study was designed to assess the efficacy, safety and pharmacokinetics of PF-04447943 compared with placebo in mild to moderate probable Alzheimer's disease (AD). METHODS: Subjects in overall good health with Mini Mental State Examination (MMSE) scores of 14-26 were randomized to 12 weeks treatment with PF-04447943 25 mg q12h (n=91) or placebo (n=100). Concomitant acetylcholinesterase inhibitor or memantine use was excluded. The primary outcome was the Alzheimer's Disease Assessment Scale - cognitive subscale (ADAS-cog). The Neuropsychiatric Inventory (NPI), Clinical Global Impression-Improvement scale (CGI-I) and standard safety measures were secondary outcomes. RESULTS: Completion rates were similar, 87% PF-04447943 vs 92% placebo. At week 12 the mean (SE) baseline adjusted decrease from baseline in ADAS cog for PF-04447943-treated patients was -1.91 (0.54). Placebo treated patients had a change of -1.60 (0.50). The difference between treatments was -0.31 (90% CI of -1.52, 0.90). Corresponding values for the NPI were -2.86 (0.72) vs -2.70 (0.67) with a treatment difference of -0.16 (90% CI of -1.78, 1.48). Neither these changes nor the distribution of CGI-I scores were statistically significantly different between groups. The incidence of serious adverse events (AEs) was similar between groups with 2 deaths in the placebo group. The PF-04447943 group reported more gastrointestinal AEs including diarrhea (5.5% vs 3%) and nausea (5.5% vs 1%) and had a higher rate of discontinuation due to AEs (6.6% vs 2%). CONCLUSIONS: Although generally safe and well-tolerated, 12 weeks PF-04447943 treatment did not improve cognition, behavior, and global change compared with placebo.

The selective phosphodiesterase 9 (PDE9) inhibitor PF-04447943 (6-[(3S,4S)-4-methyl-1-(pyrimidin-2-ylmethyl)pyrrolidin-3-yl]-1-(tetrahydro-2H-py ran-4-yl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one) enhances synaptic plasticity and cognitive function in rodents.[Pubmed:21619887]

Neuropharmacology. 2011 Sep;61(4):665-76.

Inhibition of phosphodiesterase 9 (PDE9) has been reported to enhance rodent cognitive function and may represent a potential novel approach to improving cognitive dysfunction in Alzheimer's disease. PF-04447943, (6-[(3S,4S)-4-methyl-1-(pyrimidin-2-ylmethyl)pyrrolidin-3-yl]-1-(tetrahydro-2H-py ran-4-yl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one), a recently described PDE9 inhibitor, was found to have high affinity (Ki of 2.8, 4.5 and 18 nM) for human, rhesus and rat recombinant PDE9 respectively and high selectivity for PDE9 versus PDEs1-8 and 10-11. PF-04447943 significantly increased neurite outgrowth and synapse formation (as indicated by increased synapsin 1 expression) in cultured hippocampal neurons at low (30-100 nM) but not high (300-1000 nM) concentrations. PF-04447943 significantly facilitated hippocampal slice LTP evoked by a weak tetanic stimulus at a concentration of 100 nM but failed to affect response to the weak tetanus at either 30 or 300 nM, or the LTP produced by a theta burst stimulus. Systemic administration of PF-04447943 (1-30 mg/kg p.o.) dose-dependently increased cGMP in the cerebrospinal fluid 30 min after administration indicating target engagement in the CNS of rats. PF-04447943 (1-3 mg/kg p.o.) significantly improved cognitive performance in three rodent cognition assays (mouse Y maze spatial recognition memory model of natural forgetting, mouse social recognition memory model of natural forgetting and rat novel object recognition with a scopolamine deficit). When administered at a dose of 3 mg/kg p.o., which improved performance in novel object recognition, PF-04447943 significantly increased phosphorylated but not total GluR1 expression in rat hippocampal membranes. Collectively these data indicate that PF-04447943 is a potent, selective brain penetrant PDE9 inhibitor that increased indicators of hippocampal synaptic plasticity and improved cognitive function in a variety of cognition models in both rats and mice. Results with PF-04447943 are consistent with previously published findings using a structurally diverse PDE9 inhibitor, BAY73-6199, and further support the suggestion that PDE9 inhibition may represent a novel approach to the palliative remediation of cognitive dysfunction.

Design and discovery of 6-[(3S,4S)-4-methyl-1-(pyrimidin-2-ylmethyl)pyrrolidin-3-yl]-1-(tetrahydro-2H-pyr an-4-yl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one (PF-04447943), a selective brain penetrant PDE9A inhibitor for the treatment of cognitive disorders.[Pubmed:22780914]

J Med Chem. 2012 Nov 8;55(21):9045-54.

6-[(3S,4S)-4-Methyl-1-(pyrimidin-2-ylmethyl)pyrrolidin-3-yl]-1-(tetrahydro-2H-pyr an-4-yl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one (PF-04447943) is a novel PDE9A inhibitor identified using parallel synthetic chemistry and structure-based drug design (SBDD) and has advanced into clinical trials. Selectivity for PDE9A over other PDE family members was achieved by targeting key residue differences between the PDE9A and PDE1C catalytic site. The physicochemical properties of the series were optimized to provide excellent in vitro and in vivo pharmacokinetics properties in multiple species including humans. It has been reported to elevate central cGMP levels in the brain and CSF of rodents. In addition, it exhibits procognitive activity in several rodent models and synaptic stabilization in an amyloid precursor protein (APP) transgenic mouse model. Recent disclosures from clinical trials confirm that it is well tolerated in humans and elevates cGMP in cerebral spinal fluid of healthy volunteers, confirming that it is a quality pharmacological tool for testing clinical hypotheses in disease states associated with impairment of cGMP signaling or cognition.

Description

PF-04447943 is a potent inhibitor of human recombinant PDE9A (IC50=12 nM) with >78-fold selectivity, respectively, over other PDE family members (IC50>1000 nM).

Keywords:

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PF-04447943

Catalog No. BCC1850----Order now to get a substantial discount!

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Quality Control of PF-04447943

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Chemical Properties of PF-04447943

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References on PF-04447943

The selective phosphodiesterase 9 (PDE9) inhibitor PF-04447943 attenuates a scopolamine-induced deficit in a novel rodent attention task.[Pubmed:22070409]

J Neurogenet. 2011 Dec;25(4):120-6.

A multicenter, double-blind, placebo-controlled trial of the PDE9A inhibitor, PF-04447943, in Alzheimer's disease.[Pubmed:24801218]

Curr Alzheimer Res. 2014;11(5):413-21.

The selective phosphodiesterase 9 (PDE9) inhibitor PF-04447943 (6-[(3S,4S)-4-methyl-1-(pyrimidin-2-ylmethyl)pyrrolidin-3-yl]-1-(tetrahydro-2H-py ran-4-yl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one) enhances synaptic plasticity and cognitive function in rodents.[Pubmed:21619887]

Neuropharmacology. 2011 Sep;61(4):665-76.