MW 275.34 Da, Purity >98%. Selective PDE4 inhibitor (IC50 = 0.22 μM). More active enantiomer: 2-10-fold more potent that the (S)-(+)-enantiomer (ab120030).
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- Journal of nuclear medicine : official publication, Society of Nuclear Medicine 52:263-92011PET of (R)-11C-rolipram binding to phosphodiesterase-4 is reproducible and sensitive to increased norepinephrine in the rat heart.Applications:Unspecified applicationReactive species:Unspecified reactive speciesAdam J Thomas,Jean N DaSilva,Mireille Lortie,Jennifer M Renaud,Miran Kenk,Rob S Beanlands,Robert A deKempPubMed 21270457
Key facts
- CAS number
- 85416-75-7
- Purity
- > 98%
- Form
- Solid
- Molecular weight
- 275.34 Da
- Molecular formula
- C16H21NO3
- PubChem identifier
- 448055
- Nature
- Synthetic
Target data
Alternative names
1,8-cineole 2-exo-monooxygenase, 2EL, 5''-cyclic phosphodiesterase 4A, 5''-cyclic phosphodiesterase 4B, 5''-cyclic phosphodiesterase 4C, 5''-cyclic phosphodiesterase 4D, Albendazole monooxygenase, Albendazole sulfoxidase, CBP_HUMAN, CP33, CP34, CP3A4_HUMAN, CREB-binding protein, CYP3, CYP3A, CYP3A3, CYP3A4, CYPIIIA3, CYPIIIA4, Cyclic AMP responsive enhancer binding protein, Cytochrome P450 3A3, Cytochrome P450 3A4, Cytochrome P450 HLp, Cytochrome P450 NF-25, Cytochrome P450 family 3 subfamily A polypeptide 4, Cytochrome P450 subfamily IIIA polypeptide 4, Cytochrome P450-PCN1, DKFZp686F2182, DKFZp686M11213, DPDE 1, DPDE2, DPDE3, DPDE4, Dunce like phosphodiesterase E3, FLJ97311, Glucocorticoid inducible P450, HLP, HSPDE4D, KAT3A, MGC126222, MGC126529, MGC126680, NF 25, Nifedipine oxidase, OTTHUMP00000010652, OTTHUMP00000010653, OTTHUMP00000010654, OTTHUMP00000010656, OTTHUMP00000232365, P450 III steroid inducible, P450 PCN1, P450, family III, P450C3, PDE 21, PDE IVB, PDE32, PDE4, PDE43, PDE46, PDE4A11, PDE4A_HUMAN, PDE4B5, PDE4B_HUMAN, PDE4C_HUMAN, PDE4DN2, PDE4D_HUMAN, Phosphodiesterase 4A, Phosphodiesterase 4A, cAMP-specific (dunce, Phosphodiesterase 4B, Phosphodiesterase 4B cAMP specific, Phosphodiesterase 4B, cAMP specific (phosphodiesterase E4 dunce homolog, Drosophila), Phosphodiesterase 4C, Phosphodiesterase 4C cAMP specific, Phosphodiesterase 4C, cAMP specific (phosphodiesterase E1 dunce homolog, Drosophila), Phosphodiesterase 4D cAMP specific (dunce (Drosophila) homolog phosphodiesterase E3), Phosphodiesterase 4D cAMP specific (phosphodiesterase E3 dunce homolog Drosophila), Phosphodiesterase 4D cAMP-specific, Phosphodiesterase 4D, cAMP specific (dunce), Phosphodiesterase E1 dunce homolog, Phosphodiesterase E1 dunce homolog Drosophila, Phosphodiesterase E2 dunce homolog, Drosophila, Phosphodiesterase type 4C, Quinine 3-monooxygenase, RSTS, RTS, Rubinstein Taybi syndrome, STRK1, Taurochenodeoxycholate 6-alpha-hydroxylase, cAMP specific 3' 5' cyclic phosphodiesterase 4C, cAMP specific 3',5' cyclic phosphodiesterase 4D, cAMP specific phosphodiesterase, cAMP specific phosphodiesterase 4D, cAMP specific phosphodiesterase PDE4D6, cAMP-specific 3'', cAMP-specific 3',5'-cyclic phosphodiesterase 4A, cAMP-specific 3',5'-cyclic phosphodiesterase 4B, cAMP-specific phosphodiesterase-4 B isoform, cytochrome P450, subfamily IIIA (niphedipine oxidase), polypeptide 3, cytochrome P450, subfamily IIIA (niphedipine oxidase), polypeptide 4, dunce like phosphodiesterase E2, dunce-like phosphodiesterase E4, phosphodiesterase 4A cAMP specific, phosphodiesterase E2 dunce homolog, phosphodiesterase isozyme 4, phosphodiesterase type 4A11
Recommended products
MW 275.34 Da, Purity >98%. Selective PDE4 inhibitor (IC50 = 0.22 μM). More active enantiomer: 2-10-fold more potent that the (S)-(+)-enantiomer (ab120030).
Key facts
- CAS number
- 85416-75-7
- Purity
- > 98%
- Form
- Solid
- Molecular weight
- 275.34 Da
- Molecular formula
- C16H21NO3
- PubChem identifier
- 448055
- Nature
- Synthetic
- Solubility
Soluble in DMSO to 100 mM.
- Biochemical name
- (R)-(-)-Rolipram
- Biological description
Selective PDE4 inhibitor (IC50 = 0.22 μM). More active enantiomer: 2-10-fold more potent that the (S)-(+)-enantiomer (ab120030).
- Canonical SMILES
- COC1=C(C=C(C=C1)C2CC(=O)NC2)OC3CCCC3
- Isomeric SMILES
- COC1=C(C=C(C=C1)[C@H]2CC(=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)/t12-/m0/s1
- InChIKey
- HJORMJIFDVBMOB-LBPRGKRZSA-N
- IUPAC name
- (4R)-4-(3-cyclopentyloxy-4-methoxyphenyl)pyrrolidin-2-one
Storage
- Shipped at conditions
- Ambient - Can Ship with Ice
- Appropriate short-term storage conditions
- +4°C
- Appropriate long-term storage conditions
- +4°C
- Storage information
- Store under desiccating conditions, The product can be stored for up to 12 months
Supplementary info
- This supplementary information is collated from multiple sources and compiled automatically.
- Activity summary
CREBBP also called CREB-binding protein and Cytochrome P450 3A4 (CYP3A4) are important proteins in human biology. CREBBP has a mass of approximately 265 kDa and is widely expressed across different tissues. It functions as a transcriptional co-activator with intrinsic acetyltransferase activity. CYP3A4 an important enzyme in the cytochrome P450 superfamily weighs about 57 kDa and is mainly found in the liver and intestines where it plays a significant role in drug metabolism. The PDE4 family including isoforms PDE4A PDE4B PDE4C and PDE4D are cAMP-specific phosphodiesterases with isoform-specific roles in degrading cyclic AMP an essential second messenger molecule in cells.
- Biological function summary
CREBBP interacts with many transcription factors and co-regulates gene expressions essential for cell growth differentiation and apoptosis. It is part of large protein complexes including the transcription machinery. CYP3A4 metabolizes a vast array of xenobiotics and endogenous compounds influencing drug clearance and metabolic activation. The PDE4 family consisting of PDE4A PDE4B PDE4C and PDE4D regulates cellular cAMP levels affecting various signaling pathways linked to inflammation and immune response.
- Pathways
CREBBP participates in the chromatin remodeling and gene transcription pathways relating to proteins like p300. CYP3A4 is integral to the drug metabolism pathway closely interacting with proteins such as CYP2C9. PDE4 isoforms contribute to the cAMP signaling pathway affecting downstream proteins involved in immune and inflammatory responses. In these pathways they modulate signaling cascades important for physiological responses.
- Associated diseases and disorders
Mutations or dysregulation of CREBBP associate with Rubinstein-Taybi syndrome and certain cancers. CREBBP interacts with p300 which also links to these conditions. CYP3A4 dysfunction can influence the progression of liver diseases and drug-induced hepatotoxicity. PDE4 inhibitors like those targeting PDE4D and PDE4B show therapeutic potential in treating inflammatory diseases such as asthma and chronic obstructive pulmonary disease (COPD) with connections to immune-modulating proteins.
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Chemical Structure - (R)-(-)-Rolipram, Selective PDE4 inhibitor (ab120031)
2D chemical structure image of ab120031, (R)-(-)-Rolipram, Selective PDE4 inhibitor
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