Rolipram | CAS#61413-54-5 | antidepressant

MedKoo Cat#: 528828 | Name: Rolipram

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Rolipram is a phosphodiesterase 4 inhibitor potentially for treatment of depression.

Chemical Structure

Rolipram

CAS#61413-54-5

Theoretical Analysis

MedKoo Cat#: 528828

Name: Rolipram

CAS#: 61413-54-5

Chemical Formula: C16H21NO3

Exact Mass: 275.1521

Molecular Weight: 275.34

Elemental Analysis: C, 69.79; H, 7.69; N, 5.09; O, 17.43

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 300.00
25mg	USD 500.00

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Related CAS #

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Synonym

ME-3167; ZK-62711; ME3167; ZK62711; ME 3167; ZK 62711

IUPAC/Chemical Name

4-(3-(cyclopentyloxy)-4-methoxyphenyl)pyrrolidin-2-one

InChi Key

HJORMJIFDVBMOB-UHFFFAOYSA-N

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)

SMILES Code

O=C1NCC(C2=CC=C(OC)C(OC3CCCC3)=C2)C1

Appearance

Solid powder

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 and ethanol

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

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Product Data

Product Data

Instruction

View handling instruction

Biological target:

Rolipram is a selective inhibitor of cAMP phosphodiesterase (PDE4) (IC50 = 2.0 μM). Rolipram discriminates between two conformational states of PDE4 isoenzymes.

In vitro activity:

Rolipram suppressed migration and invasion of human choriocarcinoma cells in vitro, possibly by inhibiting epithelial-mesenchymal transition through PDE4 inhibition. Rolipram and knockdown of PDE4D were efficient to inhibit the migration and invasion of choriocarcinoma cells in vitro, accompanied by decreased expression of MMP9 and TIMP1. Reference: J Biochem Mol Toxicol. 2023 Jul;37(7):e23363. https://pubmed.ncbi.nlm.nih.gov/37020384/

In vivo activity:

The findings of this study suggest that rolipram can be an effective target for treatment of comorbid Alzheimer's disease and depression. In this APP/PS1/tau mice model, rolipram injections may mitigate cognitive deficits and depression-like behavior by reducing amyloid-β pathology, tau phosphorylation, neuroinflammation, and apoptosis. Reference: Int J Neuropsychopharmacol. 2023 Jul 25:pyad042. https://pubmed.ncbi.nlm.nih.gov/37490542/

	Solvent	mg/mL	mM
Solubility
	DMSO	20.7	75.00
	Ethanol	20.7	75.00

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 275.34 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:

1. Huang Y, Zheng Y, Wang Q, Qi C. Rolipram suppresses migration and invasion of human choriocarcinoma cells by inhibiting phosphodiesterase 4-mediated epithelial-mesenchymal transition. J Biochem Mol Toxicol. 2023 Jul;37(7):e23363. doi: 10.1002/jbt.23363. Epub 2023 Apr 5. PMID: 37020384. 2. Ramezani S, Hadjighassem M, Vousooghi N, Parvaresh M, Arbabi F, Amini N, Joghataei MT. The Role of Protein Kinase B Signaling Pathway in Anti-Cancer Effect of Rolipram on Glioblastoma Multiforme: An In Vitro Study. Basic Clin Neurosci. 2017 Jul-Aug;8(4):325-336. doi: 10.18869/nirp.bcn.8.4.325. PMID: 29158883; PMCID: PMC5683690. 3. Cong YF, Liu FW, Xu L, Song SS, Shen XR, Liu D, Hou XQ, Zhang HT. Rolipram ameliorates memory deficits and depression-like behavior in APP/PS1/tau triple transgenic mice: involvement of neuroinflammation and apoptosis via cAMP signaling. Int J Neuropsychopharmacol. 2023 Jul 25:pyad042. doi: 10.1093/ijnp/pyad042. Epub ahead of print. PMID: 37490542. 4. Wimmer ME, Blackwell JM, Abel T. Rolipram treatment during consolidation ameliorates long-term object location memory in aged male mice. Neurobiol Learn Mem. 2020 Mar;169:107168. doi: 10.1016/j.nlm.2020.107168. Epub 2020 Jan 19. PMID: 31962134; PMCID: PMC7106430.

In vitro protocol:

In vivo protocol:

1. Cong YF, Liu FW, Xu L, Song SS, Shen XR, Liu D, Hou XQ, Zhang HT. Rolipram ameliorates memory deficits and depression-like behavior in APP/PS1/tau triple transgenic mice: involvement of neuroinflammation and apoptosis via cAMP signaling. Int J Neuropsychopharmacol. 2023 Jul 25:pyad042. doi: 10.1093/ijnp/pyad042. Epub ahead of print. PMID: 37490542. 2. Wimmer ME, Blackwell JM, Abel T. Rolipram treatment during consolidation ameliorates long-term object location memory in aged male mice. Neurobiol Learn Mem. 2020 Mar;169:107168. doi: 10.1016/j.nlm.2020.107168. Epub 2020 Jan 19. PMID: 31962134; PMCID: PMC7106430.

1: Cong YF, Liu FW, Xu L, Song SS, Shen XR, Liu D, Hou XQ, Zhang HT. Rolipram Ameliorates Memory Deficits and Depression-Like Behavior in APP/PS1/tau Triple Transgenic Mice: Involvement of Neuroinflammation and Apoptosis via cAMP Signaling. Int J Neuropsychopharmacol. 2023 Sep 25;26(9):585-598. doi: 10.1093/ijnp/pyad042. PMID: 37490542; PMCID: PMC10519811. 2: Gobejishvili L, Rodriguez WE, Bauer P, Wang Y, Soni C, Lydic T, Barve S, McClain C, Maldonado C. Novel Liposomal Rolipram Formulation for Clinical Application to Reduce Emesis. Drug Des Devel Ther. 2022 May 3;16:1301-1309. doi: 10.2147/DDDT.S355796. PMID: 35535222; PMCID: PMC9078351. 3: Lu X, Wang J, Chen X, Jiang Y, Pan ZK. Rolipram Protects Mice from Gram- negative Bacterium Escherichia coli-induced Inflammation and Septic Shock. Sci Rep. 2020 Jan 13;10(1):175. doi: 10.1038/s41598-019-56899-6. PMID: 31932743; PMCID: PMC6957694. 4: Huang Y, Zheng Y, Wang Q, Qi C. Rolipram suppresses migration and invasion of human choriocarcinoma cells by inhibiting phosphodiesterase 4-mediated epithelial-mesenchymal transition. J Biochem Mol Toxicol. 2023 Jul;37(7):e23363. doi: 10.1002/jbt.23363. Epub 2023 Apr 5. PMID: 37020384. 5: Dastgheib M, Shetab-Boushehri SV, Baeeri M, Gholami M, Karimi MY, Hosseini A. Rolipram and pentoxifylline combination ameliorates experimental diabetic neuropathy through inhibition of oxidative stress and inflammatory pathways in the dorsal root ganglion neurons. Metab Brain Dis. 2022 Oct;37(7):2615-2627. doi: 10.1007/s11011-022-01060-y. Epub 2022 Aug 4. Erratum in: Metab Brain Dis. 2024 Jan;39(1):253-254. doi: 10.1007/s11011-023-01305-4. PMID: 35922732. 6: Gao J, Khang MK, Liao Z, Webb K, Detloff MR, Lee JS. Rolipram-loaded PgP nanoparticle reduces secondary injury and enhances motor function recovery in a rat moderate contusion SCI model. Nanomedicine. 2023 Sep;53:102702. doi: 10.1016/j.nano.2023.102702. Epub 2023 Aug 11. PMID: 37574117. 7: Dastgheib M, Falak R, Moghaddam MV, Hassanzadeh G, Safa M, Hosseini A. Rolipram and pentoxifylline combination ameliorates the morphological abnormalities of dorsal root ganglion neurons in experimental diabetic neuropathy by reducing mitochondrial dysfunction and apoptosis. J Biochem Mol Toxicol. 2023 Nov;37(11):e23459. doi: 10.1002/jbt.23459. Epub 2023 Jul 11. PMID: 37431890. 8: Maher A, El Sayed N, Nafea H, Gad M. Rolipram Rescues Memory Consolidation Deficits Caused by Sleep Deprivation: Implication of the cAMP/PKA and cAMP/Epac Pathways. CNS Neurol Disord Drug Targets. 2022;21(7):631-639. doi: 10.2174/1871527320666210816105144. PMID: 34397335. 9: Huang H, Xie M, Gao L, Zhang W, Zhu X, Wang Y, Li W, Wang R, Chen K, Boutjdir M, Chen L. Rolipram, a PDE4 Inhibitor, Enhances the Inotropic Effect of Rat Heart by Activating SERCA2a. Front Pharmacol. 2019 Mar 22;10:221. doi: 10.3389/fphar.2019.00221. PMID: 30967774; PMCID: PMC6439224. 10: Wu L, Xu L, Chen Y, Xu G, Guo Q, Meng D, Fan J, Song G, Xu P. Rolipram plays an anti-fibrotic effect in ligamentum flavum fibroblasts by inhibiting the activation of ERK1/2. BMC Musculoskelet Disord. 2021 Sep 23;22(1):818. doi: 10.1186/s12891-021-04712-9. PMID: 34556093; PMCID: PMC8461931. 11: Zhu J, Mix E, Winblad B. The antidepressant and antiinflammatory effects of rolipram in the central nervous system. CNS Drug Rev. 2001 Winter;7(4):387-98. doi: 10.1111/j.1527-3458.2001.tb00206.x. PMID: 11830756; PMCID: PMC6741679. 12: Yuan F, Ren H, Tan W, Wang Y, Luo H. Effect of phosphodiesterase-4 inhibitor rolipram on colonic hypermotility in water avoidance stress rat model. Neurogastroenterol Motil. 2022 Jul;34(7):e14317. doi: 10.1111/nmo.14317. Epub 2022 Jan 17. PMID: 35037375; PMCID: PMC9286810. 13: Sakurai M, Imaizumi M, Sakai Y, Morimoto M. Rolipram promotes hippocampal regeneration in mice after trimethyltin-induced neurodegeneration. Neuroreport. 2024 Sep 4;35(13):832-838. doi: 10.1097/WNR.0000000000002072. Epub 2024 Jul 5. PMID: 38973498. 14: Sims CR, Singh SP, Mu S, Gokden N, Zakaria D, Nguyen TC, Mayeux PR. Rolipram Improves Outcome in a Rat Model of Infant Sepsis-Induced Cardiorenal Syndrome. Front Pharmacol. 2017 May 3;8:237. doi: 10.3389/fphar.2017.00237. PMID: 28515693; PMCID: PMC5413568. 15: Mondal D, Bagchi A, Biswas S, Dagar T, Biswas A, Bagchi A, De S. Vesicle- Encapsulated Rolipram (PDE4 Inhibitor) and Its Anticancer Activity. ACS Appl Bio Mater. 2024 Jan 15;7(1):369-378. doi: 10.1021/acsabm.3c00961. Epub 2023 Dec 27. PMID: 38150107. 16: Kenk M, Thomas A, Lortie M, Dekemp R, Beanlands RS, Dasilva JN. PET measurements of cAMP-mediated phosphodiesterase-4 with (R)-[11C]rolipram. Curr Radiopharm. 2011 Jan;4(1):44-58. doi: 10.2174/1874471011104010044. PMID: 22191614. 17: Ramezani S, Vousooghi N, Ramezani Kapourchali F, Yousefzadeh-Chabok S, Reihanian Z, Alizadeh AM, Khodayari S, Khodayari H. Rolipram optimizes therapeutic effect of bevacizumab by enhancing proapoptotic, antiproliferative signals in a glioblastoma heterotopic model. Life Sci. 2019 Dec 15;239:116880. doi: 10.1016/j.lfs.2019.116880. Epub 2019 Oct 31. PMID: 31678282. 18: Peng Y, Jin J, Fan L, Xu H, He P, Li J, Chen T, Ruan W, Chen G. Rolipram Attenuates Early Brain Injury Following Experimental Subarachnoid Hemorrhage in Rats: Possibly via Regulating the SIRT1/NF-κB Pathway. Neurochem Res. 2018 Apr;43(4):785-795. doi: 10.1007/s11064-018-2480-4. Epub 2018 Feb 3. PMID: 29397536. 19: Ji J, Liu Z, Hong X, Liu Z, Gao J, Liu J. Protective effects of rolipram on endotoxic cardiac dysfunction via inhibition of the inflammatory response in cardiac fibroblasts. BMC Cardiovasc Disord. 2020 May 24;20(1):242. doi: 10.1186/s12872-020-01529-7. PMID: 32448150; PMCID: PMC7247226. 20: Costa LM, Pereira JE, Filipe VM, Magalhães LG, Couto PA, Gonzalo-Orden JM, Raimondo S, Geuna S, Maurício AC, Nikulina E, Filbin MT, Varejão AS. Rolipram promotes functional recovery after contusive thoracic spinal cord injury in rats. Behav Brain Res. 2013 Apr 15;243:66-73. doi: 10.1016/j.bbr.2012.12.056. Epub 2013 Jan 4. PMID: 23295392.