SCH 351591: a phosphodiesterase 4 inhibitor; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
SCH-351591 : An aromatic amide resulting from the formal condensation of the carboxy group of 8-methoxy-2-(trifluoromethyl)quinoline-5-carboxylic acid with the primary amino group of 3,5-dichloropyridin-4-amine 1-oxide. It is a potent inhibitor of phosphodiesterase IV (PDE4). [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 | 9802841 |
| CHEMBL ID | 250546 |
| CHEBI ID | 77774 |
| SCHEMBL ID | 157018 |
| MeSH ID | M0430389 |
| Synonym |
|---|
| sch-351591 |
| n-(3,5-dichloro-1-oxidopyridin-4-yl)-8-methoxy-2-(trifluoromethyl)quinoline-5-carboxamide |
| CHEMBL250546 , |
| chebi:77774 , |
| 3,5-dichloro-4-[(8-methoxy-2-trifluoromethyl-quinoline-5-carbonyl)-amino]-1-oxo-1,2-dihydro-pyridinium |
| bdbm50219270 |
| 3,5-dichloro-4-[(8-methoxy-2-trifluoromethyl-quinoline-5-carbonyl)-amino]-pyridin-1-ol anion |
| 8-methoxy-2-trifluoromethyl-quinoline-5-carboxylic acid (3,5-dichloro-1-oxy-pyridin-4-yl)-amide |
| n-(3,5-dichloro-1-oxido-4-pyridinyl)-8-methoxy-2-(trifluoromethyl)-5-quinolinecarboxamide |
| sch351591 |
| 444659-43-2 |
| sch 351591 |
| unii-g6ef7v146s |
| n-(3,5-dichloro-1-oxido-4-pyridinyl)-8-methoxy-2-(trifluoromethyl)-5-quinoline carboxamide |
| g6ef7v146s , |
| d 4396 |
| 5-quinolinecarboxamide, n-(3,5-dichloro-1-oxido-4-pyridinyl)-8-methoxy-2- (trifluoromethyl)- |
| SCHEMBL157018 |
| 8-methoxy-2-trifluoromethylquinoline-5-carboxylic acid (3,5-dichloro-1-oxypyridin-4-yl)amide |
| DTXSID8044125 |
| 266995-28-2 |
| n-(3,5-dichloro-1-oxo-4-pyridyl)-8-methoxy-2-(trifluoromethyl)quinoline-5-carboxamide |
| d-4396 |
| 5-quinolinecarboxamide, n-(3,5-dichloro-1-oxido-4-pyridinyl)-8-methoxy-2-(trifluoromethyl)- |
| npgrearfjmftdf-uhfffaoysa-n |
| Q27147371 |
| n-(3,5-dichloro-1-hydroxypyridin-4-ylidene)-8-methoxy-2-(trifluoromethyl)quinoline-5-carboxamide |
| ruogjykoqbfjig-uhfffaoysa-n |
| Excerpt | Reference | Relevance |
|---|---|---|
| "This report describes the findings of preclinical testing of SCH 351591, a selective phosphodiesterase 4 inhibitor, in CD-1 mice over a wide range of doses, in which the heart and reproductive organs of both sexes demonstrated toxic effects." | ( Myocardial and reproductive system toxicity of SCH 351591, a selective phosphodiesterase-4 inhibitor, in CD-1 mice. Kaminska-McNamara, GZ; Klein, MF; Losco, PE; Poulet, FM, 2010) | 0.86 |
| Excerpt | Relevance | Reference |
|---|---|---|
| " Early mortality, involving monkeys dosed with 12 or 24 mg/kg, was attributed to sepsis (2 monkeys) or colon inflammation (3 monkeys)." | ( The toxicity of SCH 351591, a novel phosphodiesterase-4 inhibitor, in Cynomolgus monkeys. Anthes, JC; Barat, SA; Blackshear, PE; Bober, LA; Cuss, FM; Evans, EW; Fine, JS; Losco, PE; Mirro, EJ; Reyderman, L, ) | 0.48 |
| " Previous research has suggested early events might be occurring well in advance of the full lesions that appear forty-eight to seventy-two hours after dosing with SCH 351591, a PDE IV inhibitor." | ( Early events in vascular injury in the rat induced by the phosphodiesterase IV inhibitor SCH 351591. Espandiari, P; Gu, YZ; Knapton, A; Miller, T; Smith, R; Snyder, RD; Weaver, JL; Zhang, J, 2010) | 0.78 |
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| cAMP-specific 3',5'-cyclic phosphodiesterase 4D | Rattus norvegicus (Norway rat) | IC50 (µMol) | 0.1500 | 0.0003 | 2.7232 | 10.0000 | AID160106 |
| cAMP-specific 3',5'-cyclic phosphodiesterase 4C | Rattus norvegicus (Norway rat) | IC50 (µMol) | 0.1500 | 0.0003 | 2.7232 | 10.0000 | AID160106 |
| cAMP-specific 3',5'-cyclic phosphodiesterase 4B | Rattus norvegicus (Norway rat) | IC50 (µMol) | 0.1500 | 0.0003 | 2.6638 | 10.0000 | AID160106 |
| cAMP-specific 3',5'-cyclic phosphodiesterase 4A | Homo sapiens (human) | IC50 (µMol) | 0.0600 | 0.0000 | 1.0680 | 10.0000 | AID159797; AID159798 |
| cAMP-specific 3',5'-cyclic phosphodiesterase 4A | Rattus norvegicus (Norway rat) | IC50 (µMol) | 0.1500 | 0.0003 | 2.7232 | 10.0000 | AID160106 |
| cAMP-specific 3',5'-cyclic phosphodiesterase 4B | Homo sapiens (human) | IC50 (µMol) | 0.0600 | 0.0000 | 1.1040 | 10.0000 | AID159797; AID159798; AID309103 |
| cAMP-specific 3',5'-cyclic phosphodiesterase 4C | Homo sapiens (human) | IC50 (µMol) | 0.0600 | 0.0000 | 1.4651 | 10.0000 | AID159797; AID159798 |
| cAMP-specific 3',5'-cyclic phosphodiesterase 4D | Homo sapiens (human) | IC50 (µMol) | 0.0600 | 0.0000 | 1.1463 | 10.0000 | AID159797; AID159798 |
| Dual 3',5'-cyclic-AMP and -GMP phosphodiesterase 11A | Homo sapiens (human) | IC50 (µMol) | 10.0000 | 0.0000 | 1.9700 | 9.2000 | AID309106 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Homo sapiens (human) | IC50 (µMol) | 10.0000 | 0.0000 | 1.4904 | 9.2000 | AID309105 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID13118 | AUC in rat after 3mg/kg oral dose | 2002 | Bioorganic & medicinal chemistry letters, Jun-17, Volume: 12, Issue:12 | Synthesis and profile of SCH351591, a novel PDE4 inhibitor. |
| AID159797 | Inhibition of Phosphodiesterase 4 | 2002 | Bioorganic & medicinal chemistry letters, Jun-17, Volume: 12, Issue:12 | Synthesis and profile of SCH351591, a novel PDE4 inhibitor. |
| AID309103 | Inhibition of PDE4B | 2007 | Bioorganic & medicinal chemistry letters, Sep-15, Volume: 17, Issue:18 | Discovery of a highly potent series of oxazole-based phosphodiesterase 4 inhibitors. |
| AID158276 | Inhibition of Phosphodiesterase 7 from human T-lymphocyte cell line | 2002 | Bioorganic & medicinal chemistry letters, Jun-17, Volume: 12, Issue:12 | Synthesis and profile of SCH351591, a novel PDE4 inhibitor. |
| AID11999 | Cmax in rat after 3mg/kg oral dose | 2002 | Bioorganic & medicinal chemistry letters, Jun-17, Volume: 12, Issue:12 | Synthesis and profile of SCH351591, a novel PDE4 inhibitor. |
| AID159362 | Inhibition of Phosphodiesterase 3 from human platelets | 2002 | Bioorganic & medicinal chemistry letters, Jun-17, Volume: 12, Issue:12 | Synthesis and profile of SCH351591, a novel PDE4 inhibitor. |
| AID160106 | Inhibition of rolipram binding to PDE4 of rat brain | 2002 | Bioorganic & medicinal chemistry letters, Jun-17, Volume: 12, Issue:12 | Synthesis and profile of SCH351591, a novel PDE4 inhibitor. |
| AID363081 | Inhibition of PDE4 | 2008 | Journal of medicinal chemistry, Sep-25, Volume: 51, Issue:18 | Recent advances on phosphodiesterase 4 inhibitors for the treatment of asthma and chronic obstructive pulmonary disease. |
| AID157764 | Relative inhibition of phosphodiesterase 4 and rolipram binding | 2002 | Bioorganic & medicinal chemistry letters, Jun-17, Volume: 12, Issue:12 | Synthesis and profile of SCH351591, a novel PDE4 inhibitor. |
| AID309105 | Inhibition of PDE10 | 2007 | Bioorganic & medicinal chemistry letters, Sep-15, Volume: 17, Issue:18 | Discovery of a highly potent series of oxazole-based phosphodiesterase 4 inhibitors. |
| AID158916 | Inhibition of recombinant Phosphodiesterase 1 | 2002 | Bioorganic & medicinal chemistry letters, Jun-17, Volume: 12, Issue:12 | Synthesis and profile of SCH351591, a novel PDE4 inhibitor. |
| AID7390 | AUC in guinea pig after 3mg/kg oral dose | 2002 | Bioorganic & medicinal chemistry letters, Jun-17, Volume: 12, Issue:12 | Synthesis and profile of SCH351591, a novel PDE4 inhibitor. |
| AID363103 | Displacement of [3H]rolipram from PDE4 by RBA | 2008 | Journal of medicinal chemistry, Sep-25, Volume: 51, Issue:18 | Recent advances on phosphodiesterase 4 inhibitors for the treatment of asthma and chronic obstructive pulmonary disease. |
| AID7397 | Cmax in guinea pig after 3mg/kg oral dose | 2002 | Bioorganic & medicinal chemistry letters, Jun-17, Volume: 12, Issue:12 | Synthesis and profile of SCH351591, a novel PDE4 inhibitor. |
| AID309106 | Inhibition of PDE11 | 2007 | Bioorganic & medicinal chemistry letters, Sep-15, Volume: 17, Issue:18 | Discovery of a highly potent series of oxazole-based phosphodiesterase 4 inhibitors. |
| AID159798 | Inhibition of Phosphodiesterase 4 from human U937 cells | 2002 | Bioorganic & medicinal chemistry letters, Jun-17, Volume: 12, Issue:12 | Synthesis and profile of SCH351591, a novel PDE4 inhibitor. |
| AID158098 | Inhibition of Phosphodiesterase 5 from human platelets | 2002 | Bioorganic & medicinal chemistry letters, Jun-17, Volume: 12, Issue:12 | Synthesis and profile of SCH351591, a novel PDE4 inhibitor. |
| AID159066 | Inhibition of Phosphodiesterase 2 | 2002 | Bioorganic & medicinal chemistry letters, Jun-17, Volume: 12, Issue:12 | Synthesis and profile of SCH351591, a novel PDE4 inhibitor. |
| [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 | 0 (0.00) | 18.2507 |
| 2000's | 6 (66.67) | 29.6817 |
| 2010's | 3 (33.33) | 24.3611 |
| 2020's | 0 (0.00) | 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 (11.77) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 1 (10.00%) | 5.53% |
| Reviews | 1 (10.00%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 8 (80.00%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||