Details of the Drug

General Information of Drug (ID: DMJ03UM)

Drug Name
ROLIPRAM
Synonyms
61413-54-5; ZK 62711; Rolipramum; Rolipramum [Latin]; 4-[3-(Cyclopentyloxy)-4-methoxyphenyl]-2-pyrrolidinone; Adeo; Rolipram [USAN:INN]; 4-[3-(cyclopentyloxy)-4-methoxyphenyl]pyrrolidin-2-one; 4-(3-(cyclopentyloxy)-4-methoxyphenyl)pyrrolidin-2-one; 4-(3-(Cyclopentyloxy)-4-methoxyphenyl)-2-pyrrolidinone; (R,S)-rolipram; ZK-62711; CHEMBL63; EINECS 262-771-1; BRN 1588548; MLS000069691; CHEBI:104872; HJORMJIFDVBMOB-UHFFFAOYSA-N; 4-(3-Cyclopentyloxy-4-methoxyphenyl)-2-pyrrolidone; [3H]rolipram
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 275.34
Logarithm of the Partition Coefficient (xlogp) 2.2
Rotatable Bond Count (rotbonds) 4
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 3
Chemical Identifiers
Formula
C16H21NO3
IUPAC Name
4-(3-cyclopentyloxy-4-methoxyphenyl)pyrrolidin-2-one
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
Cross-matching ID
PubChem CID
5092
ChEBI ID
CHEBI:104872
CAS Number
61413-54-5
UNII
K676NL63N7
DrugBank ID
DB01954
TTD ID
D0T5PO

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Phosphodiesterase 4A (PDE4A) TTZ97H5 PDE4A_HUMAN Inhibitor [2]
Phosphodiesterase 4B (PDE4B) TTVIAT9 PDE4B_HUMAN Inhibitor [3]
Phosphodiesterase 4D (PDE4D) TTSKMI8 PDE4D_HUMAN Inhibitor [4]
Phosphodiesterase 5A (PDE5A) TTJ0IQB PDE5A_HUMAN Inhibitor [5]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Amphiregulin (AREG) OTJFOR67 AREG_HUMAN Gene/Protein Processing [6]
C-X-C motif chemokine 10 (CXCL10) OTTLQ6S0 CXL10_HUMAN Protein Interaction/Cellular Processes [7]
Cadherin-1 (CDH1) OTFJMXPM CADH1_HUMAN Gene/Protein Processing [8]
Cystic fibrosis transmembrane conductance regulator (CFTR) OT6B22QH CFTR_HUMAN Gene/Protein Processing [9]
Interleukin-10 (IL10) OTIRFRXC IL10_HUMAN Protein Interaction/Cellular Processes [10]
Interleukin-13 (IL13) OTI4YS3Y IL13_HUMAN Gene/Protein Processing [11]
Leukotriene C4 synthase (LTC4S) OT3XNFJZ LTC4S_HUMAN Protein Interaction/Cellular Processes [11]
Matrix metalloproteinase-9 (MMP9) OTB2QDAV MMP9_HUMAN Gene/Protein Processing [8]
Metalloproteinase inhibitor 1 (TIMP1) OTOXC51H TIMP1_HUMAN Gene/Protein Processing [8]
Mothers against decapentaplegic homolog 1 (SMAD1) OTQSHR25 SMAD1_HUMAN Gene/Protein Processing [8]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Discovery agent
ICD Disease Classification N.A.
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Phosphodiesterase 4A (PDE4A) DTT PDE4A 9.26E-01 -3.01E-03 -0.01
Phosphodiesterase 4B (PDE4B) DTT PDE4B 2.75E-01 -0.13 -0.3
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 5313).
2 Discovery of micromolar PDE IV inhibitors that exhibit much reduced affinity for the [3H]rolipram binding site: 3-norbornyloxy-4-methoxyphenylmethylene oxindoles, Bioorg. Med. Chem. Lett. 5(17):1965-1968 (1995).
3 Novel heterocyclic-fused pyridazinones as potent and selective phosphodiesterase IV inhibitors. J Med Chem. 1997 May 9;40(10):1417-21.
4 In silico search for multi-target anti-inflammatories in Chinese herbs and formulas. Bioorg Med Chem. 2010 Mar 15;18(6):2204-2218.
5 Cyclic GMP phosphodiesterase inhibitors. 2. Requirement of 6-substitution of quinazoline derivatives for potent and selective inhibitory activity. J Med Chem. 1994 Jun 24;37(13):2106-11.
6 The epidermal growth factor-like growth factor amphiregulin is strongly induced by the adenosine 3',5'-monophosphate pathway in various cell types. Endocrinology. 2004 Nov;145(11):5177-84. doi: 10.1210/en.2004-0232. Epub 2004 Jul 29.
7 The role of IFN-gamma in regulation of IFN-gamma-inducible protein 10 (IP-10) expression in lung epithelial cell and peripheral blood mononuclear cell co-cultures. Respir Res. 2007 Nov 8;8(1):80. doi: 10.1186/1465-9921-8-80.
8 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.
9 Phosphodiesterase 4D forms a cAMP diffusion barrier at the apical membrane of the airway epithelium. J Biol Chem. 2005 Mar 4;280(9):7997-8003. doi: 10.1074/jbc.M407521200. Epub 2004 Dec 15.
10 Phosphodiesterase type 4 inhibitors, but not glucocorticoids, are more potent in suppression of cytokine secretion by mononuclear cells from atopic than nonatopic donors. J Allergy Clin Immunol. 1998 Nov;102(5):797-804. doi: 10.1016/s0091-6749(98)70020-x.
11 Global expression profiling of theophylline response genes in macrophages: evidence of airway anti-inflammatory regulation. Respir Res. 2005 Aug 8;6(1):89. doi: 10.1186/1465-9921-6-89.