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| 25mg |
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| 50mg |
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| 100mg |
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Purity: ≥98%
(R)-(-)-Rolipram is the R-enantiomer of Rolipram with potent anti-inflammatory and anti-depressant activity in the central nervous system, and it is more potent than its S enantiomer. Rolipram (also known as ZK-62711 and SB 95952, the racemic mixture of R- and S-rolipram) is a novel, potent and selective phosphodiesterases PDE4 inhibitor with IC50s of 3 nM, 130 nM and 240 nM for PDE4A, PDE4B, and PDE4D, respectively. PDE4 inhibitor Rolipram has anti-inflammatory activity. Rolipram inhibits human monocyte. Rolipram inhibits human monocyte cyclic AMP-specific PDE4 with IC50 of 0.75 μM. It has potent anti-inflammatory and anti-depressant activity in the central nervous system, and the S-(+)-Rolipram is less potent than its R enantiomer.
| Targets |
Phosphodiesterases/PDE4
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| ln Vitro |
In a dose-dependent manner, caspase-1 cleavage and IL-1β secretion are suppressed by increasing cAMP synthesis with the adenylate cyclase activator forskolin or decreasing cAMP hydrolysis with the phosphodiesterase inhibitors Isobutylmethylxanthine (IBMX) and (R)-(-)-Rolipram.
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| ln Vivo |
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| Enzyme Assay |
PDE4 inhibition with rolipram boosts P2Y11/IL-1R-induced upregulation of CXCR7 expression and CCL20 production in an epidermal growth factor receptor dependent manner. Using an astrocytoma cell line, naturally expressing CXCR7 but lacking CXCR4, P2Y11/IL-1R activation effectively induced and CXCR7 agonist TC14012 enhanced CCL20 production even in the absence of PDE4 inhibition. Moreover, CXCR7 depletion by RNA interference suppressed CCL20 production. In macrophages, the simultaneous activation of P2Y11 and CXCR7 by their respective agonists was sufficient to induce CCL20 production with no need of PDE4 inhibition, as CXCR7 activation increased its own and eliminated CXCR4 expression. Finally, analysis of multiple CCL chemokines in the macrophage secretome revealed that CXCR4 inactivation and CXCR7 activation selectively enhanced P2Y11/IL-1R-mediated secretion of CCL20. Altogether, our data establish CXCR7 as an integral component of the P2Y11/IL-1R-initiated signaling cascade and CXCR4-associated PDE4 as a regulatory checkpoint. Cell Mol Life Sci. 2024 Mar 13;81(1):132.
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| Cell Assay |
The entrapment and subsequent release of the important cAMP-specific PDE4 inhibitor/drug Rolipram, which has antibreast cancer properties, was assessed on the breast cancer cell line MCF-7. Rolipram has important therapeutic applications, one of the most significant in recent times being the treatment of Covid-19-triggered pneumonia and cytokine storms. As for cancer chemotherapy, the localization of drug, targeted delivery, and sustained release are extremely important issues, and it seemed worthwhile to explore the potential of the bilosomes and niosomes to entrap and release Rolipram. The important finding is that niosomes perform much better than bilosomes in the hormone-responsive breast cancer mileau MCF-7. Moreover, there was a 4-fold decrease in the IC50 of Rolipram encapsulated in niosomes compared to Rolipram alone. On the other hand, bilosome-encapsulated Rolipram shows higher IC50 value. The results can be further understood by molecular docking studies. ACS Appl Bio Mater. 2024 Jan 15;7(1):369-378.
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| References | |||
| Additional Infomation |
(-)-rolipram is the (R)-enantiomer of rolipram. It is an enantiomer of a (+)-rolipram.
The (R)-enantiomer of rolipram, it is a phosphodiesterase inhibitor with antidepressant properties. |
| Molecular Formula |
C16H21NO3
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| Molecular Weight |
275.34
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| Exact Mass |
275.152
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| Elemental Analysis |
C, 69.79; H, 7.69; N, 5.09; O, 17.43
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| CAS # |
85416-75-7
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| Related CAS # |
Rolipram;61413-54-5;(S)-(+)-Rolipram;85416-73-5
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| PubChem CID |
448055
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| Appearance |
Off-white to light yellow solid powder
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| Density |
1.2±0.1 g/cm3
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| Boiling Point |
472.7±45.0 °C at 760 mmHg
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| Melting Point |
134 °C
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| Flash Point |
239.7±28.7 °C
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| Vapour Pressure |
0.0±1.2 mmHg at 25°C
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| Index of Refraction |
1.552
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| LogP |
1.43
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
4
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| Heavy Atom Count |
20
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| Complexity |
341
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| Defined Atom Stereocenter Count |
1
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| SMILES |
COC1=C(C=C(C=C1)[C@H]2CC(=O)NC2)OC3CCCC3
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| InChi Key |
HJORMJIFDVBMOB-LBPRGKRZSA-N
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| InChi Code |
InChI=1S/C16H21NO3/c1-19-14-7-6-11(12-9-16(18)17-10-12)8-15(14)20-13-4-2-3-5-13/h6-8,12-13H,2-5,9-10H2,1H3,(H,17,18)/t12-/m0/s1
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| Chemical Name |
(4R)-4-(3-cyclopentyloxy-4-methoxyphenyl)pyrrolidin-2-one
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| Synonyms |
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
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| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (9.08 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (9.08 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (9.08 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. Solubility in Formulation 4: 30% PEG400+0.5% Tween80+5% propylene glycol:10 mg/L |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.6319 mL | 18.1594 mL | 36.3187 mL | |
| 5 mM | 0.7264 mL | 3.6319 mL | 7.2637 mL | |
| 10 mM | 0.3632 mL | 1.8159 mL | 3.6319 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
| NCT Number | Recruitment | interventions | Conditions | Sponsor/Collaborators | Start Date | Phases |
| NCT05522673 | Terminated Has Results | Drug: 11(R)-rolipram | Depression | National Institute of Mental Health (NIMH) |
February 8, 2023 | Phase 1 |
| NCT00011375 | Completed | Drug: Rolipram | Multiple Sclerosis | National Institute of Neurological Disorders and Stroke (NINDS) |
February 2001 | Phase 2 |
| NCT01215552 | Terminated | Drug: HT-0712 | Healthy Elderly Volunteers | Dart NeuroScience, LLC | September 2010 | Phase 1 |
| NCT00250172 | Completed | Drug: [C-11](R)-rolipram | Dosimetry Healthy |
National Institute of Mental Health (NIMH) |
October 31, 2005 | Phase 1 |
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