| Synonyms |
ZK-62711; SB 95952; 4-(3-cyclopentyloxy-4-methoxyphenyl)pyrrolidin-2-one |
| IUPAC Name |
4-(3-cyclopentyloxy-4-methoxyphenyl)pyrrolidin-2-one |
| Molecular Weight |
275.34 |
| Molecular Formula |
C16H21NO3 |
| Canonical SMILES |
COC1=C(C=C(C=C1)C2CC(=O)NC2)OC3CCCC3 |
| InChI |
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) |
| InChIKey |
HJORMJIFDVBMOB-UHFFFAOYSA-N |
| Boiling Point |
472.7±45.0 °C at 760 mmHg |
| Melting Point |
127-133°C |
| Flash Point |
239.7°C |
| Purity |
>98% |
| Density |
1.155 g/cm³ |
| Solubility |
In vitro:
10 mM in DMSO |
| Appearance |
Solid |
| Application |
Antidepressive Agents |
| Storage |
0-6°C |
| Animal Admin |
Mice Inbred C57BL/6 MKP-1(-/-) mice are used. C57BL/6 mice (20-25 g) are divided into groups of six mice and treated with 200 μL of PBS or Rolipram (100 mg/kg in PBS) by an i.p. injection 2 h before applying carrageenan. Before the administration of carrageenan, the mice are anaesthetized by i.p. injection of 0.5 mg/kg of medetomidine and 75 mg/kg of ketamine. The mice receive a 30 μL i.d. injection of carrageenan (1.5%, dissolved in normal saline) in one hind paw. The contralateral paw receive 30 μL of saline and it is used as a control. Paw volume is measured before and 3 h after the carrageenan injection with a plethysmometer. Oedema is expressed as a change in paw volume over time. |
| Complexity |
341 |
| Exact Mass |
275.15214353 |
| Index Of Refraction |
1.552 |
| In Vitro |
The PDE4 selective inhibitor, Rolipram, inhibits immunopurified PDE4B and PDE4D activities similarly, with IC50s of approx. 130 nM and 240 nM respectively. In contrast, Rolipram inhibits immunopurified PDE4A activity with a dramatically lower IC50 of around 3 nM. Rolipram increases phosphorylation of cAMP-response-element-binding protein (CREB) in U937 cells in a dose-dependent fashion, which implies the presence of both high affinity (IC50 approx. 1 nM) and low affinity (IC50 approx. 120 nM) components. Rolipram dose-dependently inhibits the IFN-gamma-stimulated phosphorylation of p38 MAPK in a simple monotonic fashion with an IC50 of approx. 290 nM. Rolipram is a selective PDE4 inhibitor that inhibits all PDE4 isoforms A, B, C and D. Rolipram inhibits LPS-induced TNF production in a dose-dependent manner (IC50 25.9 nM), and maximal/submaximal inhibition is observed with 2 μM drug concentration in J774 cells. |
| In Vivo |
TNF mRNA and protein expression is induced by LPS in peritoneal macrophages (PM) from WT mice, and that is clearly (by 74 and 63% for TNF mRNA and TNF protein, respectively) inhibited by Rolipram. LPS-induced TNF production is enhanced in PM from MKP-1(-/-) mice as compared to that in PM from WT mice, which is in line with the published results. Interestingly, the inhibition of TNF mRNA and protein expression by Rolipram is markedly attenuated in PM from MKP-1(-/-) mice and does not reach statistical significance. Repeated administration of Rolipram (1.25 mg/kg, i.p.) reduces the number of escape failures in learned helplessness rats. |
| PSA |
47.56 |
| Target |
IC50: 3 nM (PDE4A), 130 nM (PDE4B), 240 nM (PDE4D) |
| Vapor Pressure |
0.0±1.2 mmHg at 25°C |
| XLogP3-AA |
2.2 |
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