| Identification | Back Directory | [Name]
ROLIPRAM | [CAS]
61413-54-5 | [Synonyms]
ZK-62711
ROLIPRAM
SB 95952
Roliprame
ROLIPRAM 98+%
(R,S)-Rolipram
Rolipram, >=97%
ZK-62711, SB95952, ME-3167
4-(3-(cyclopentyloxy)-4-methoxyphenyl)-2-pyrrolidinon
4-[3-(CYCLOPENTYLOXY)-4-METHOXYPHENYL]-2-PYRROLIDINONE
4-(3-(CYCLOPENTYLOXY)-4-METHOXYPHENYL)PYRROLIDIN-2-ONE
2-Pyrrolidinone, 4-[3-(cyclopentyloxy)-4-methoxyphenyl]-
PYRROLIDIN-2-ONE, 4-(3-(CYCLOPENTYLOXY)-4-METHOXYPHENYL)- (+/-)
4-[3-(Cyclopentyloxy)-4-methoxyphenyl]-2-pyrrolidinone, ZK62711 | [EINECS(EC#)]
262-771-1 | [Molecular Formula]
C16H21NO3 | [MDL Number]
MFCD00270906 | [MOL File]
61413-54-5.mol | [Molecular Weight]
275.34 |
| Chemical Properties | Back Directory | [Appearance]
Yellowish solid | [Melting point ]
127-133 °C
| [Boiling point ]
418.29°C (rough estimate) | [density ]
1.0677 (rough estimate) | [refractive index ]
1.5500 (estimate) | [storage temp. ]
0-6°C | [solubility ]
H2O: 0.2 mg/mL
| [form ]
solid
| [pka]
16.02±0.40(Predicted) | [color ]
white to off-white
| [biological source]
synthetic (organic) | [Water Solubility ]
H2O: 0.2mg/mL
ethanol: 7mg/mL
DMSO: 7.3mg/mL | [Merck ]
14,8251 | [Stability:]
Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months. |
| Hazard Information | Back Directory | [Chemical Properties]
Yellowish solid | [Uses]
A selective, cell permeable inhibitor of cAMP-specific phosphodiesterase (PDE4). | [Uses]
antipsychotic | [Uses]
Pharmacological tool for characterization of phosphodiesterase isoenzymes. | [Biological Activity]
Selective inhibitor of cAMP phosphodiesterase (PDE4) (IC 50 = 2.0 μ M). Discriminates between two conformational states of PDE4 isoenzymes. See separate isomers ((R)-(-)-Rolipram and (S)-(+)-Rolipram). | [Description]
Rolipram (61413-54-5) is a selective inhibitor of cAMP-specific phosphodiesterase (PDE4), IC50 = 1 μM. Displays beneficial effects in neurodegenerative diseases. Rolipram also displays anti-inflammatory activity and synergizes with forskolin (cat.# 10-2073). Cell permeable. | [Definition]
ChEBI: Rolipram is a member of the lclass of pyrrolidin-2-ones that is pyrrolidin-2-one bearing a 3-(cyclopentyloxy)-4-methoxyphenyl substituent at the 4-position. It is a type IV-specific phosphodiesterase (PDE4) inhibitor. It has a role as an antidepressant and an EC 3.1.4.* (phosphoric diester hydrolase) inhibitor. | [General Description]
A cell-permeable, selective inhibitor of cAMP-specific phosphodiesterase (PDE IV; IC50 = 800 nM). A rolipram-insensitive PDE IV subtype is also known to exist. Also inhibits NF-κB and NFAT activation in Jurkat and primary T cells. | [Biochem/physiol Actions]
Cell permeable: yes | [storage]
Store at -20°C | [References]
1) Reeves et al. (1987), The identification of a new cyclic nucleotide phosphodiesterase activity in human and guinea-pig cardiac ventricle. Implications for the mechanism of action of selective phosphodiesterase; Biochem. J., 241 535
2) Nishi et al. (2008), Distinct Roles of PDE4 and PDE10A in the Regulation of cAMP/PKA Signaling in the Striatum; J. Neurosci., 28 10460
3) Christiansen et al. (2011), Combined anti-inflammatory effects of β2-adrenergic agonists and PDE4 inhibitors on astrocytes by upregulation of intracellular cAMP; Neurochem. Int., 59 837 |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
36/37/38-11 | [Safety Statements ]
26-36 | [RIDADR ]
3249 | [WGK Germany ]
3
| [RTECS ]
UY5749237
| [HazardClass ]
6.1(b) | [PackingGroup ]
III | [HS Code ]
29337900 | [Toxicity]
LD50 oral in mouse: > 300mg/kg |
|
|