piclamilast: an antiasthmatic agent and phosphodiesterase 4 inhibitor; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
piclamilast : A monocarboxylic acid amide resulting from the formal condensation of the carboxy group of 3-(cyclopentyloxy)-4-methoxybenzoic acid with the primary amino group of 3,5-dichloropyridin-4-amine. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]
| ID Source | ID |
|---|---|
| PubMed CID | 154575 |
| CHEMBL ID | 42126 |
| CHEBI ID | 47619 |
| SCHEMBL ID | 26573 |
| MeSH ID | M0244353 |
| Synonym |
|---|
| rp-73401 |
| rpr-73401 |
| 3-(cyclopentyloxy)-n-(3,5-di-chloro-4-pyridyl)-4-methoxy-benzamide |
| rp 73401 |
| rpr 73401 |
| benzamide, 3-(cyclopentyloxy)-n-(3,5-dichloro-4-pyridinyl)-4-methoxy- |
| 3-(cyclopentyloxy)-n-(3,5-dichloro-4-pyridyl)-4-methoxybenzamide |
| 144035-83-6 |
| piclamilast (usan/inn) |
| D05474 |
| PDSP2_001267 |
| PDSP1_001283 |
| piclamilast |
| 3-(cyclopentyloxy)-n-(3,5-dichloropyridin-4-yl)-4-methoxybenzamide |
| DB01791 |
| 1XM4 |
| 3-(cyclopentyloxy)-n-(3,5-dichloro-4-pyridinyl)-4-methoxybenzamide |
| 3-(cyclopentyloxy)-n-(3,5-dichloro-4-pyridyl)-p-anisamide |
| 1XON |
| cpodpmb |
| bdbm14775 |
| 3-cyclopentyloxy-n-(3,5-dichloropyridin-4-yl)-4-methoxy-benzamide |
| chembl42126 , |
| rp-73-401 |
| rp 73-401 |
| rp73401 |
| rp-73041 |
| chebi:47619 , |
| 3-cyclopentyloxy-n-(3,5-dichloropyridin-4-yl)-4-methoxybenzamide |
| wm58d7c3zt , |
| piclamilast [usan:inn] |
| ccris 8304 |
| unii-wm58d7c3zt |
| piclamilast [inn] |
| piclamilast [usan] |
| piclamilast [who-dd] |
| SCHEMBL26573 |
| piclamilastum |
| n-(3,5-dichloropyrid-4yl)-3-cyclopentyloxy-4-methoxybenzamide |
| n-(3,5-dichloropyrid-4-yl)-3-cyclopentyloxy-4-methoxybenzamide |
| n-(3,5-dichloropyrid-4-yl)-3-cyclopentyloxy-4-methoxy-benzamide |
| n-(3,5-dichloro-pyrid-4-yl)-3-cyclopentyloxy-4-methoxybenzamide |
| 3-(cyclopentyloxy)-n-(3,5-dichloro-4-pyridinyl)-4-methoxybenzamide # |
| smr004703311 |
| MLS006011544 |
| AKOS024458202 |
| HMS3604D06 |
| DTXSID3040227 |
| SR-01000945166-2 |
| SR-01000945166-1 |
| sr-01000945166 |
| CS-0012751 |
| HY-12887 |
| NCGC00371037-01 |
| rp 73401; rpr 73401 |
| 3-(cyclopentyloxy)-n-(3,5-dichloro-4-pyridy)-4-methoxybenzamide |
| Q7190965 |
| EN300-133366 |
| MS-26240 |
| gtpl11627 |
RP 73401 is a potent inhibitor of cyclic nucleotide phosphodiesterase type IV. It suppresses eosinophil function suggesting that it may be a useful agent for the treatment of inflammatory diseases such as asthma.
| Excerpt | Reference | Relevance |
|---|---|---|
| "Thus RP 73401 is a very potent and selective PDE IV inhibitor which suppresses eosinophil function suggesting that it may be a useful agent for the treatment of inflammatory diseases such as asthma." | ( Suppression of eosinophil function by RP 73401, a potent and selective inhibitor of cyclic AMP-specific phosphodiesterase: comparison with rolipram. Ashton, MJ; Foster, M; Karlsson, JA; Maslen, C; Palfreyman, MN; Raeburn, D; Souness, JE; Webber, S, 1995) | 1.02 |
| "RP 73401 is a potent inhibitor of cyclic nucleotide phosphodiesterase type IV. " | ( Human liver CYP2B6-catalyzed hydroxylation of RP 73401. Hsu, SH; Martinet, M; Stevens, JC; White, RB, 1997) | 2 |
RP 73401 administered subsequently to a high fat meal showed a 51% reduction in Cmax and a 5-fold prolongation in tmax as compared to the fasted state.
| Excerpt | Reference | Relevance |
|---|---|---|
| "Early exploratory clinical pharmacokinetic studies can provide valuable information for the design and control of subsequent phase 2 studies." | ( Effect of food and gender on the pharmacokinetics of RP 73401, a phosphodiesterase IV inhibitor. Argenti, D; Jensen, BK; Rohatagi, S; Shah, B; Vaccaro, SK, 2000) | 0.56 |
| " Pharmacokinetic parameters were calculated using non-compartmental techniques." | ( Effect of food and gender on the pharmacokinetics of RP 73401, a phosphodiesterase IV inhibitor. Argenti, D; Jensen, BK; Rohatagi, S; Shah, B; Vaccaro, SK, 2000) | 0.56 |
| " Conversely, RP 73401 administered subsequently to a high fat meal showed a 51% reduction in Cmax and a 5-fold prolongation in tmax as compared to the fasted state." | ( Effect of food and gender on the pharmacokinetics of RP 73401, a phosphodiesterase IV inhibitor. Argenti, D; Jensen, BK; Rohatagi, S; Shah, B; Vaccaro, SK, 2000) | 0.93 |
| "These results successfully allowed the uncomplicated inclusion of females in oral and inhalation studies with RP 73401 and indicated the need to address oral drug dosing conditions in order to minimize sources of pharmacokinetic variability in subsequent phase 2 studies." | ( Effect of food and gender on the pharmacokinetics of RP 73401, a phosphodiesterase IV inhibitor. Argenti, D; Jensen, BK; Rohatagi, S; Shah, B; Vaccaro, SK, 2000) | 0.77 |
| Role | Description |
|---|---|
| phosphodiesterase IV inhibitor | An EC 3.1.4.53 (3',5'-cyclic-AMP phosphodiesterase) inhibitor that specifically blocks the action of phosphodiesterase IV. |
| anti-asthmatic drug | A drug used to treat asthma. |
| bronchodilator agent | An agent that causes an increase in the expansion of a bronchus or bronchial tubes. |
| anti-inflammatory agent | Any compound that has anti-inflammatory effects. |
| [role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] | |
| Class | Description |
|---|---|
| monocarboxylic acid amide | A carboxamide derived from a monocarboxylic acid. |
| benzamides | |
| chloropyridine | Compounds containing a pyridine nucleus substituted with one or more chlorine atoms. |
| aromatic ether | Any ether in which the oxygen is attached to at least one aryl substituent. |
| [compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] | |
| Protein | Taxonomy | Measurement | Average (µ) | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| cytochrome P450 family 3 subfamily A polypeptide 4 | Homo sapiens (human) | Potency | 1.5092 | 0.0123 | 7.9835 | 43.2770 | AID1645841 |
| G | Vesicular stomatitis virus | Potency | 6.7412 | 0.0123 | 8.9648 | 39.8107 | AID1645842 |
| Interferon beta | Homo sapiens (human) | Potency | 6.7412 | 0.0033 | 9.1582 | 39.8107 | AID1645842 |
| HLA class I histocompatibility antigen, B alpha chain | Homo sapiens (human) | Potency | 6.7412 | 0.0123 | 8.9648 | 39.8107 | AID1645842 |
| Inositol hexakisphosphate kinase 1 | Homo sapiens (human) | Potency | 6.7412 | 0.0123 | 8.9648 | 39.8107 | AID1645842 |
| cytochrome P450 2C9, partial | Homo sapiens (human) | Potency | 6.7412 | 0.0123 | 8.9648 | 39.8107 | AID1645842 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID1296008 | Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening | 2020 | SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1 | Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening. |
| AID1347160 | Primary screen NINDS Rhodamine qHTS for Zika virus inhibitors | 2020 | Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49 | Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors. |
| AID1347159 | Primary screen GU Rhodamine qHTS for Zika virus inhibitors: Unlinked NS2B-NS3 protease assay | 2020 | Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49 | Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors. |
| AID1346987 | P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen | 2019 | Molecular pharmacology, 11, Volume: 96, Issue:5 | A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. |
| AID1346986 | P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen | 2019 | Molecular pharmacology, 11, Volume: 96, Issue:5 | A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. |
| AID157921 | In vitro inhibitory activity on unpurified recombinant Phosphodiesterase 4D | 1998 | Journal of medicinal chemistry, Jan-29, Volume: 41, Issue:3 | Striking effect of hydroxamic acid substitution on the phosphodiesterase type 4 (PDE4) and TNF alpha inhibitory activity of two series of rolipram analogues: implications for a new active site model of PDE4. |
| AID117194 | Evaluated for antiinflammatory activity in the TPA induced ear inflammation model at a dose 2 mg/kg (50 ug) | 2002 | Bioorganic & medicinal chemistry letters, Feb-25, Volume: 12, Issue:4 | Synthesis and biological evaluation of imidazol-2-one and 2-cyanoiminoimidazole derivatives: novel series of PDE4 inhibitors. |
| AID275703 | Inhibition of human recombinant PDE4C | 2007 | Journal of medicinal chemistry, Jan-25, Volume: 50, Issue:2 | SAR of a series of 5,6-dihydro-(9H)-pyrazolo[3,4-c]-1,2,4-triazolo[4,3-alpha]pyridines as potent inhibitors of human eosinophil phosphodiesterase. |
| AID481742 | Inhibition of human His6-tagged PDE4B (152-487) expressed in Escherichia coli BL21 (DE3) after 1 hr | 2010 | Bioorganic & medicinal chemistry letters, May-01, Volume: 20, Issue:9 | Water-soluble PDE4 inhibitors for the treatment of dry eye. |
| AID58400 | Emetic effect in dogs at 0.6 mg/kg intravenous dose, 4 of 4 animals affected | 1998 | Journal of medicinal chemistry, Oct-22, Volume: 41, Issue:22 | Novel cyclic compounds as potent phosphodiesterase 4 inhibitors. |
| AID159652 | Binding affinity at Phosphodiesterase 4 by measuring displacement of (+/-)-[3H]- Rolipram to guinea pig brain membranes. | 1998 | Journal of medicinal chemistry, Oct-22, Volume: 41, Issue:22 | Novel cyclic compounds as potent phosphodiesterase 4 inhibitors. |
| AID77068 | In vivo bronchodilator effect on histamine-induced bronchospasm in anaesthetized guinea pigs at 10 ug intravenous dose | 1994 | Journal of medicinal chemistry, May-27, Volume: 37, Issue:11 | Selective type IV phosphodiesterase inhibitors as antiasthmatic agents. The syntheses and biological activities of 3-(cyclopentyloxy)-4-methoxybenzamides and analogues. |
| AID275701 | Inhibition of human recombinant PDE4B | 2007 | Journal of medicinal chemistry, Jan-25, Volume: 50, Issue:2 | SAR of a series of 5,6-dihydro-(9H)-pyrazolo[3,4-c]-1,2,4-triazolo[4,3-alpha]pyridines as potent inhibitors of human eosinophil phosphodiesterase. |
| AID90658 | Evaluated in vitro for its inhibitory activity on LPS-induced TNF-Alpha release in human monocyte. | 1998 | Journal of medicinal chemistry, Jan-29, Volume: 41, Issue:3 | Striking effect of hydroxamic acid substitution on the phosphodiesterase type 4 (PDE4) and TNF alpha inhibitory activity of two series of rolipram analogues: implications for a new active site model of PDE4. |
| AID158459 | Binding affinity against PDE4 was determined using [3H]- rolipram in guinea pig brain membrane binding assay | 1998 | Bioorganic & medicinal chemistry letters, Jul-21, Volume: 8, Issue:14 | The synthesis and biological evaluation of a novel series of indole PDE4 inhibitors I. |
| AID157758 | Inhibition of rolipram binding to phosphodiesterase 4 | 2003 | Bioorganic & medicinal chemistry letters, Jul-21, Volume: 13, Issue:14 | Synthesis and biological activities of 1-pyridylisoquinoline and 1-pyridyldihydroisoquinoline derivatives as PDE4 inhibitors. |
| AID214056 | Arbitary maximal response for cAMP elevation from baseline level was evaluated in Human U-937 cells | 1998 | Journal of medicinal chemistry, Jun-18, Volume: 41, Issue:13 | 7-Oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridines as novel inhibitors of human eosinophil phosphodiesterase. |
| AID158465 | Evaluated in vitro for its inhibitory activity on human monocyte cytosol Phosphodiesterase type 4 (PDE4). | 1998 | Journal of medicinal chemistry, Jan-29, Volume: 41, Issue:3 | Striking effect of hydroxamic acid substitution on the phosphodiesterase type 4 (PDE4) and TNF alpha inhibitory activity of two series of rolipram analogues: implications for a new active site model of PDE4. |
| AID159654 | Inhibition of Phosphodiesterase 4 from human neutrophils | 2000 | Bioorganic & medicinal chemistry letters, Oct-02, Volume: 10, Issue:19 | The synthesis and biological evaluation of a novel series of phthalazine PDE4 inhibitors I. |
| AID159932 | Relative inhibition of rolipram binding and Phosphodiesterase 4 activity | 2002 | Bioorganic & medicinal chemistry letters, Jan-07, Volume: 12, Issue:1 | Phthalazine PDE4 inhibitors. Part 3: the synthesis and in vitro evaluation of derivatives with a hydrogen bond acceptor. |
| AID75781 | In vivo bronchodilator effect on histamine-induced bronchospasm in anaesthetized guinea pigs at 20 ug intravenous dose | 1994 | Journal of medicinal chemistry, May-27, Volume: 37, Issue:11 | Selective type IV phosphodiesterase inhibitors as antiasthmatic agents. The syntheses and biological activities of 3-(cyclopentyloxy)-4-methoxybenzamides and analogues. |
| AID157786 | Inhibition of recombinant human Phosphodiesterase 4B | 1998 | Journal of medicinal chemistry, Jan-29, Volume: 41, Issue:3 | Striking effect of hydroxamic acid substitution on the phosphodiesterase type 4 (PDE4) and TNF alpha inhibitory activity of two series of rolipram analogues: implications for a new active site model of PDE4. |
| AID159638 | Concentration to inhibit 50% of Phosphodiesterase 4 (PDE-4) from guinea pig macrophages | 1998 | Journal of medicinal chemistry, Oct-22, Volume: 41, Issue:22 | Novel cyclic compounds as potent phosphodiesterase 4 inhibitors. |
| AID159663 | Inhibition of rolipram binding to PDE4 | 2001 | Bioorganic & medicinal chemistry letters, Jan-08, Volume: 11, Issue:1 | Phthalazine PDE4 inhibitors. Part 2: the synthesis and biological evaluation of 6-methoxy-1,4-disubstituted derivatives. |
| AID1181896 | Solubility of the compound in 20 % hydroxypropyl-beta-cyclodextrin in water after 1 hr at room temperature | 2014 | Journal of medicinal chemistry, Jul-24, Volume: 57, Issue:14 | Discovery and early clinical development of 2-{6-[2-(3,5-dichloro-4-pyridyl)acetyl]-2,3-dimethoxyphenoxy}-N-propylacetamide (LEO 29102), a soft-drug inhibitor of phosphodiesterase 4 for topical treatment of atopic dermatitis. |
| AID92723 | Evaluated in vitro for its inhibitory activity on LPS-induced TNF-Alpha release in human whole blood. | 1998 | Journal of medicinal chemistry, Jan-29, Volume: 41, Issue:3 | Striking effect of hydroxamic acid substitution on the phosphodiesterase type 4 (PDE4) and TNF alpha inhibitory activity of two series of rolipram analogues: implications for a new active site model of PDE4. |
| AID1181897 | Solubility of the compound in medium chain triglyceride | 2014 | Journal of medicinal chemistry, Jul-24, Volume: 57, Issue:14 | Discovery and early clinical development of 2-{6-[2-(3,5-dichloro-4-pyridyl)acetyl]-2,3-dimethoxyphenoxy}-N-propylacetamide (LEO 29102), a soft-drug inhibitor of phosphodiesterase 4 for topical treatment of atopic dermatitis. |
| AID159636 | Inhibition of solubilized eosinophil PDE IV | 1994 | Journal of medicinal chemistry, May-27, Volume: 37, Issue:11 | Selective type IV phosphodiesterase inhibitors as antiasthmatic agents. The syntheses and biological activities of 3-(cyclopentyloxy)-4-methoxybenzamides and analogues. |
| AID158458 | Inhibition of Phosphodiesterase type 4 (PDE4) from guinea-pig macrophage | 1998 | Bioorganic & medicinal chemistry letters, Jul-21, Volume: 8, Issue:14 | The synthesis and biological evaluation of a novel series of indole PDE4 inhibitors I. |
| AID275704 | Inhibition of human recombinant PDE4D | 2007 | Journal of medicinal chemistry, Jan-25, Volume: 50, Issue:2 | SAR of a series of 5,6-dihydro-(9H)-pyrazolo[3,4-c]-1,2,4-triazolo[4,3-alpha]pyridines as potent inhibitors of human eosinophil phosphodiesterase. |
| AID157759 | Inhibition of Rolipram binding to Phosphodiesterase 4 | 1998 | Bioorganic & medicinal chemistry letters, Oct-06, Volume: 8, Issue:19 | 2-Substituted-4-methoxybenzimidazole-based PDE4 inhibitors. |
| AID1625378 | Inhibition of human His-tagged PDE4D catalytic domain expressed in Escherichia coli BL21-CodonPlus(DE3) cells using [3H]cAMP or [3H]cGMP as substrate incubated for 30 mins by scintillation counting method | 2016 | Journal of medicinal chemistry, Aug-11, Volume: 59, Issue:15 | PDEStrIAn: A Phosphodiesterase Structure and Ligand Interaction Annotated Database As a Tool for Structure-Based Drug Design. |
| AID462321 | Inhibition of human PDE4B | 2010 | Bioorganic & medicinal chemistry, Mar-15, Volume: 18, Issue:6 | In silico search for multi-target anti-inflammatories in Chinese herbs and formulas. |
| AID222460 | Inhibition of TNF alpha synthesis in human monocytes | 2000 | Bioorganic & medicinal chemistry letters, Oct-02, Volume: 10, Issue:19 | The synthesis and biological evaluation of a novel series of phthalazine PDE4 inhibitors I. |
| AID181692 | Increased acid secretion in isolated whole rat stomach | 2000 | Bioorganic & medicinal chemistry letters, Oct-02, Volume: 10, Issue:19 | The synthesis and biological evaluation of a novel series of phthalazine PDE4 inhibitors I. |
| AID481743 | Inhibition of PDE4 expressed in HEK293 cells coexpressing cyclic nucleotide gated ion channel mutant assessed as inhibition of NECA-induced cAMP production treated 15 mins before NECA challenge measured after 45 mins by FLIPR assay | 2010 | Bioorganic & medicinal chemistry letters, May-01, Volume: 20, Issue:9 | Water-soluble PDE4 inhibitors for the treatment of dry eye. |
| AID159783 | Inhibition of human Phosphodiesterase 4 | 2002 | Bioorganic & medicinal chemistry letters, Jan-07, Volume: 12, Issue:1 | Phthalazine PDE4 inhibitors. Part 3: the synthesis and in vitro evaluation of derivatives with a hydrogen bond acceptor. |
| AID155464 | In vitro for the inhibition of TNF alpha release by human peripheral blood monocytes (PBMs) | 2000 | Bioorganic & medicinal chemistry letters, Aug-07, Volume: 10, Issue:15 | Solid-phase synthesis of an arylsulfone hydroxamate library. |
| AID157769 | Inhibition of Rolipram binding to PDE4 | 1998 | Bioorganic & medicinal chemistry letters, Oct-06, Volume: 8, Issue:19 | 2-Substituted-4-methoxybenzimidazole-based PDE4 inhibitors. |
| AID159796 | Inhibitory activity on human eosinophil phosphodiesterase 4. | 1998 | Journal of medicinal chemistry, Jun-18, Volume: 41, Issue:13 | 7-Oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridines as novel inhibitors of human eosinophil phosphodiesterase. |
| AID159635 | Inhibition of guinea pig PDE IV | 1994 | Journal of medicinal chemistry, May-27, Volume: 37, Issue:11 | Selective type IV phosphodiesterase inhibitors as antiasthmatic agents. The syntheses and biological activities of 3-(cyclopentyloxy)-4-methoxybenzamides and analogues. |
| AID184448 | Tested in vivo for lowest active dose that induced inhibitory effect on gastric emptying in rats | 2002 | Bioorganic & medicinal chemistry letters, Feb-25, Volume: 12, Issue:4 | Synthesis and biological evaluation of imidazol-2-one and 2-cyanoiminoimidazole derivatives: novel series of PDE4 inhibitors. |
| AID462320 | Inhibition of human PDE4D | 2010 | Bioorganic & medicinal chemistry, Mar-15, Volume: 18, Issue:6 | In silico search for multi-target anti-inflammatories in Chinese herbs and formulas. |
| AID275700 | Inhibition of human eosinophil phosphodiesterase | 2007 | Journal of medicinal chemistry, Jan-25, Volume: 50, Issue:2 | SAR of a series of 5,6-dihydro-(9H)-pyrazolo[3,4-c]-1,2,4-triazolo[4,3-alpha]pyridines as potent inhibitors of human eosinophil phosphodiesterase. |
| AID275702 | Inhibition of human recombinant PDE4A | 2007 | Journal of medicinal chemistry, Jan-25, Volume: 50, Issue:2 | SAR of a series of 5,6-dihydro-(9H)-pyrazolo[3,4-c]-1,2,4-triazolo[4,3-alpha]pyridines as potent inhibitors of human eosinophil phosphodiesterase. |
| AID1720018 | Inhibition of human PDE4B by scintillation counting method | 2020 | Journal of medicinal chemistry, 10-08, Volume: 63, Issue:19 | Advances in the Development of Phosphodiesterase-4 Inhibitors. |
| AID222461 | Inhibition of TNF-alpha synthesis in human monocytes | 2001 | Bioorganic & medicinal chemistry letters, Jan-08, Volume: 11, Issue:1 | Phthalazine PDE4 inhibitors. Part 2: the synthesis and biological evaluation of 6-methoxy-1,4-disubstituted derivatives. |
| AID59481 | Emetic effect in dogs after intravenous dose | 2000 | Bioorganic & medicinal chemistry letters, Oct-02, Volume: 10, Issue:19 | The synthesis and biological evaluation of a novel series of phthalazine PDE4 inhibitors I. |
| AID1181898 | Solubility of the compound in propylene glycol | 2014 | Journal of medicinal chemistry, Jul-24, Volume: 57, Issue:14 | Discovery and early clinical development of 2-{6-[2-(3,5-dichloro-4-pyridyl)acetyl]-2,3-dimethoxyphenoxy}-N-propylacetamide (LEO 29102), a soft-drug inhibitor of phosphodiesterase 4 for topical treatment of atopic dermatitis. |
| AID131172 | In vivo inhibition of LPS induced tumor necrosis factor (TNF-alpha) in mice | 1998 | Bioorganic & medicinal chemistry letters, Nov-03, Volume: 8, Issue:21 | Orally active indole N-oxide PDE4 inhibitors. |
| AID9945 | Bioavailability in mouse | 1998 | Bioorganic & medicinal chemistry letters, Oct-06, Volume: 8, Issue:19 | 2-Substituted-4-methoxybenzimidazole-based PDE4 inhibitors. |
| AID75783 | In vivo bronchodilator effect on histamine-induced bronchospasm in anaesthetized guinea pigs at 50 ug intravenous dose | 1994 | Journal of medicinal chemistry, May-27, Volume: 37, Issue:11 | Selective type IV phosphodiesterase inhibitors as antiasthmatic agents. The syntheses and biological activities of 3-(cyclopentyloxy)-4-methoxybenzamides and analogues. |
| AID632290 | Inhibition of His-tagged catalytic domain Trypanosoma brucei brucei PDEB1 expressed in baculovirus infected insect Sf21 cells | 2011 | Journal of medicinal chemistry, Dec-08, Volume: 54, Issue:23 | Pharmacological validation of Trypanosoma brucei phosphodiesterases B1 and B2 as druggable targets for African sleeping sickness. |
| AID59506 | Emetic effect in dogs on intravenous dose (4/4) | 1998 | Bioorganic & medicinal chemistry letters, Nov-03, Volume: 8, Issue:21 | Orally active indole N-oxide PDE4 inhibitors. |
| AID157917 | Evaluated in vitro for its inhibitory activity on unpurified recombinant Phosphodiesterase 4C | 1998 | Journal of medicinal chemistry, Jan-29, Volume: 41, Issue:3 | Striking effect of hydroxamic acid substitution on the phosphodiesterase type 4 (PDE4) and TNF alpha inhibitory activity of two series of rolipram analogues: implications for a new active site model of PDE4. |
| AID226828 | Ratio of inhibitory activity against PDE4 to that of binding affinity towards rolipram binding site on PDE4 was determined | 2003 | Bioorganic & medicinal chemistry letters, Jul-21, Volume: 13, Issue:14 | Synthesis and biological activities of 1-pyridylisoquinoline and 1-pyridyldihydroisoquinoline derivatives as PDE4 inhibitors. |
| AID159656 | Inhibition of human Phosphodiesterase 4 | 2001 | Bioorganic & medicinal chemistry letters, Jan-08, Volume: 11, Issue:1 | Phthalazine PDE4 inhibitors. Part 2: the synthesis and biological evaluation of 6-methoxy-1,4-disubstituted derivatives. |
| AID159806 | Inhibition of rolipram binding to Phosphodiesterase 4 | 2002 | Bioorganic & medicinal chemistry letters, Jan-07, Volume: 12, Issue:1 | Phthalazine PDE4 inhibitors. Part 3: the synthesis and in vitro evaluation of derivatives with a hydrogen bond acceptor. |
| AID117193 | Evaluated for antiinflammatory activity in the TPA induced ear inflammation model at a dose 1 mg/kg (25 ug) | 2002 | Bioorganic & medicinal chemistry letters, Feb-25, Volume: 12, Issue:4 | Synthesis and biological evaluation of imidazol-2-one and 2-cyanoiminoimidazole derivatives: novel series of PDE4 inhibitors. |
| AID1720019 | Inhibition of human PDE4D by scintillation counting method | 2020 | Journal of medicinal chemistry, 10-08, Volume: 63, Issue:19 | Advances in the Development of Phosphodiesterase-4 Inhibitors. |
| AID159629 | Inhibition of Phosphodiesterase 4 (PDE4) from guinea pig macrophages | 1998 | Bioorganic & medicinal chemistry letters, Oct-06, Volume: 8, Issue:19 | 2-Substituted-4-methoxybenzimidazole-based PDE4 inhibitors. |
| AID225256 | Inhibitory activity against recombinant phosphodiesterase 4B (PDE4B) of human mononuclear lymphocytes | 2002 | Bioorganic & medicinal chemistry letters, Feb-25, Volume: 12, Issue:4 | Synthesis and biological evaluation of imidazol-2-one and 2-cyanoiminoimidazole derivatives: novel series of PDE4 inhibitors. |
| AID77070 | In vivo bronchodilator effect on histamine-induced bronchospasm in anaesthetized guinea pigs at 20 ug intravenous dose | 1994 | Journal of medicinal chemistry, May-27, Volume: 37, Issue:11 | Selective type IV phosphodiesterase inhibitors as antiasthmatic agents. The syntheses and biological activities of 3-(cyclopentyloxy)-4-methoxybenzamides and analogues. |
| AID159950 | Inhibitory potency against pig aortic PDE IV | 1994 | Journal of medicinal chemistry, May-27, Volume: 37, Issue:11 | Selective type IV phosphodiesterase inhibitors as antiasthmatic agents. The syntheses and biological activities of 3-(cyclopentyloxy)-4-methoxybenzamides and analogues. |
| AID160121 | Inhibition of [3H]rolipram binding to Phosphodiesterase 4 of rat forebrain membrane | 2002 | Bioorganic & medicinal chemistry letters, Feb-25, Volume: 12, Issue:4 | Synthesis and biological evaluation of imidazol-2-one and 2-cyanoiminoimidazole derivatives: novel series of PDE4 inhibitors. |
| AID159631 | Inhibition of PDE4 from guinea pig macrophages | 1998 | Bioorganic & medicinal chemistry letters, Oct-06, Volume: 8, Issue:19 | 2-Substituted-4-methoxybenzimidazole-based PDE4 inhibitors. |
| AID110206 | Inhibition of LPS-induced TNF-alpha production in mice after 30 min peroral dose | 2003 | Bioorganic & medicinal chemistry letters, Jul-21, Volume: 13, Issue:14 | Synthesis and biological activities of 1-pyridylisoquinoline and 1-pyridyldihydroisoquinoline derivatives as PDE4 inhibitors. |
| AID632292 | Antitrypanosomal activity against blood stream Trypanosoma brucei brucei 427 after 48 hrs by Alamar blue assay | 2011 | Journal of medicinal chemistry, Dec-08, Volume: 54, Issue:23 | Pharmacological validation of Trypanosoma brucei phosphodiesterases B1 and B2 as druggable targets for African sleeping sickness. |
| AID158469 | Evaluated in vitro for its inhibitory activity on unpurified recombinant Phosphodiesterase type 4A (PDE4A). | 1998 | Journal of medicinal chemistry, Jan-29, Volume: 41, Issue:3 | Striking effect of hydroxamic acid substitution on the phosphodiesterase type 4 (PDE4) and TNF alpha inhibitory activity of two series of rolipram analogues: implications for a new active site model of PDE4. |
| AID632294 | Inhibition of His-tagged catalytic domain Trypanosoma brucei brucei PDEB1 expressed in baculovirus infected insect Sf21 cells at 100 uM | 2011 | Journal of medicinal chemistry, Dec-08, Volume: 54, Issue:23 | Pharmacological validation of Trypanosoma brucei phosphodiesterases B1 and B2 as druggable targets for African sleeping sickness. |
| AID75779 | In vivo bronchodilator effect on histamine-induced bronchospasm in anaesthetized guinea pigs at 100 ug intravenous dose | 1994 | Journal of medicinal chemistry, May-27, Volume: 37, Issue:11 | Selective type IV phosphodiesterase inhibitors as antiasthmatic agents. The syntheses and biological activities of 3-(cyclopentyloxy)-4-methoxybenzamides and analogues. |
| AID225259 | Affinity for rolipram binding site of phosphodiesterase type IV (PDE4) | 1998 | Bioorganic & medicinal chemistry letters, Nov-03, Volume: 8, Issue:21 | Orally active indole N-oxide PDE4 inhibitors. |
| AID1181895 | Solubility of the compound in 0.067 M phosphate buffer at pH 7.4 | 2014 | Journal of medicinal chemistry, Jul-24, Volume: 57, Issue:14 | Discovery and early clinical development of 2-{6-[2-(3,5-dichloro-4-pyridyl)acetyl]-2,3-dimethoxyphenoxy}-N-propylacetamide (LEO 29102), a soft-drug inhibitor of phosphodiesterase 4 for topical treatment of atopic dermatitis. |
| AID225258 | Inhibition of phosphodiesterase type IV (PDE4) activity | 1998 | Bioorganic & medicinal chemistry letters, Nov-03, Volume: 8, Issue:21 | Orally active indole N-oxide PDE4 inhibitors. |
| AID157744 | Inhibition of phosphodiesterase 4 | 2003 | Bioorganic & medicinal chemistry letters, Jul-21, Volume: 13, Issue:14 | Synthesis and biological activities of 1-pyridylisoquinoline and 1-pyridyldihydroisoquinoline derivatives as PDE4 inhibitors. |
| AID632291 | Inhibition of His-tagged catalytic domain Trypanosoma brucei brucei PDEB2 expressed in baculovirus infected insect Sf21 cells | 2011 | Journal of medicinal chemistry, Dec-08, Volume: 54, Issue:23 | Pharmacological validation of Trypanosoma brucei phosphodiesterases B1 and B2 as druggable targets for African sleeping sickness. |
| AID157304 | Inhibition of rolipram binding to PDE4 from human neutrophils | 2000 | Bioorganic & medicinal chemistry letters, Oct-02, Volume: 10, Issue:19 | The synthesis and biological evaluation of a novel series of phthalazine PDE4 inhibitors I. |
| AID77072 | In vivo bronchodilator effect on histamine-induced bronchospasm in anaesthetized guinea pigs at 50 ug intravenous dose | 1994 | Journal of medicinal chemistry, May-27, Volume: 37, Issue:11 | Selective type IV phosphodiesterase inhibitors as antiasthmatic agents. The syntheses and biological activities of 3-(cyclopentyloxy)-4-methoxybenzamides and analogues. |
| AID1625374 | Inhibition of human His-tagged PDE4B catalytic domain expressed in Escherichia coli BL21-CodonPlus(DE3) cells using [3H]cAMP or [3H]cGMP as substrate incubated for 30 mins by scintillation counting method | 2016 | Journal of medicinal chemistry, Aug-11, Volume: 59, Issue:15 | PDEStrIAn: A Phosphodiesterase Structure and Ligand Interaction Annotated Database As a Tool for Structure-Based Drug Design. |
| AID131050 | Inhibition of LPS-induced tumor necrosis factor-alpha (TNF-alpha) production in mice at 50 mg/kg | 1998 | Bioorganic & medicinal chemistry letters, Jul-21, Volume: 8, Issue:14 | The synthesis and biological evaluation of a novel series of indole PDE4 inhibitors I. |
| AID78148 | Inhibition of superoxide O2-generation from guinea pig peritoneal eosinophils | 1994 | Journal of medicinal chemistry, May-27, Volume: 37, Issue:11 | Selective type IV phosphodiesterase inhibitors as antiasthmatic agents. The syntheses and biological activities of 3-(cyclopentyloxy)-4-methoxybenzamides and analogues. |
| AID1797296 | Phosphodiesterase (PDE) Inhibition Assay from Article 10.1016/j.str.2004.10.004: \\Structural basis for the activity of drugs that inhibit phosphodiesterases.\\ | 2004 | Structure (London, England : 1993), Dec, Volume: 12, Issue:12 | Structural basis for the activity of drugs that inhibit phosphodiesterases. |
| AID977608 | Experimentally measured binding affinity data (IC50) for protein-ligand complexes derived from PDB | 2004 | Structure (London, England : 1993), Dec, Volume: 12, Issue:12 | Structural basis for the activity of drugs that inhibit phosphodiesterases. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 0 (0.00) | 18.7374 |
| 1990's | 22 (24.72) | 18.2507 |
| 2000's | 41 (46.07) | 29.6817 |
| 2010's | 18 (20.22) | 24.3611 |
| 2020's | 8 (8.99) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.
| This Compound (9.92) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 3 (3.26%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 89 (96.74%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||