N-(4-chlorophenyl)-N-(2-fluoro-4-(2-oxopyridin-1(2H)-yl)phenyl)-4-methoxypyrrolidiine-1,2-dicarboxamide: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
eribaxaban : A member of the class of pyrrolidines that is (2R,4R)-N(1)-(p-chlorophenyl)-4-methoxypyrrolidine-1,2-dicarboxamide in which the nitrogen of the 2-carbamoyl group has been substituted by a 2-fluoro-4-(2-oxopyridin-1(2H)-yl)phenyl group. It is a synthetic organic anticoagulant compound that targets activated factor Xa in the coagulation cascade. [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 | 11634458 |
| CHEMBL ID | 476186 |
| CHEBI ID | 140420 |
| SCHEMBL ID | 76436 |
| MeSH ID | M0515176 |
| Synonym |
|---|
| (2r,4r)-n~1~-(4-chlorophenyl)-n~2~-[2-fluoro-4-(2-oxopyridin-1(2h)-yl)phenyl]-4-methoxypyrrolidine-1,2-dicarboxamide |
| (2r,4r)-n(1)-(4-chlorophenyl)-n(2)-[2-fluoro-4-(2-oxopyridin-1(2h)-yl)phenyl]-4-methoxypyrrolidine-1,2-dicarboxamide |
| eribaxabanum |
| pd 348,292 |
| pd 0348292 |
| pd-0348292 |
| eribaxaban |
| CHEBI:140420 |
| pd 348292 |
| pd0348292 |
| 2PHB , |
| DB06920 |
| 536748-46-6 |
| D08913 |
| eribaxaban (usan) |
| bdbm50266770 |
| CHEMBL476186 , |
| pd 348 |
| pd-348 |
| pd-348292 |
| 1,2-pyrrolidinedicarboxamide, n1-(4-chlorophenyl)-n2-(2-fluoro-4-(2-oxo-1(2h)- pyridinyl)phenyl)-4-methoxy-, (2r,4r)- |
| (2r,4r)-n1-(4-chlorophenyl)-n2-(2-fluoro-4-(2-oxopyridin-1(2h)-yl)phenyl)-4-methoxypyrrolidine-1,2-dicarboxamide |
| unii-5fch6ydy7z |
| 5fch6ydy7z , |
| eribaxaban [usan:inn] |
| n-(4-chlorophenyl)-n-(2-fluoro-4-(2-oxopyridin-1(2h)-yl)phenyl)-4-methoxypyrrolidiine-1,2-dicarboxamide |
| (2r,4r)-1-n-(4-chlorophenyl)-2-n-[2-fluoro-4-(2-oxopyridin-1-yl)phenyl]-4-methoxypyrrolidine-1,2-dicarboxamide |
| gtpl7408 |
| (2r,4r)-n-(4-chlorophenyl)-n'-[2-fluoro-4-(2-oxopyridin-1-yl)phenyl]-4-methoxypyrrolidine-1,2-dicarboxamide |
| eribaxaban [usan] |
| eribaxaban [inn] |
| eribaxaban [who-dd] |
| SCHEMBL76436 |
| DTXSID60201915 |
| Q27077218 |
| AKOS040751714 |
| 1,2-pyrrolidinedicarboxamide, n1-(4-chlorophenyl)-n2-[2-fluoro-4-(2-oxo-1(2h)-pyridinyl)phenyl]-4-methoxy-, (2r,4r)- |
PD 0348292 is an oral, selective, direct and reversible factor Xa inhibitor.
| Excerpt | Reference | Relevance |
|---|---|---|
| "PD 0348292 is an oral, selective, direct and reversible factor Xa inhibitor. " | ( An adaptive-design dose-ranging study of PD 0348292, an oral factor Xa inhibitor, for thromboprophylaxis after total knee replacement surgery. Boyd, RA; Cohen, AT; Dicarlo, L; Mandema, JW; Pak, R, 2013) | 2.1 |
| Excerpt | Reference | Relevance |
|---|---|---|
| " Minor bleeding-related adverse events were observed following multiple doses of PD 0348292." | ( Safety, pharmacokinetics, and pharmacodynamics of PD 0348292, an oral, direct factor Xa inhibitor, after single and multiple dosings in healthy subjects. Boyd, RA; DiCarlo, L; McBride, S; Porcari, A; Wastall, P; Xuan, D, 2016) | 0.91 |
The PD 0348292 dose-response relationship for VTE was statistically significant (P < 0.0). Extensive dose- response modeling and trial simulations were used to select the dose range for the Phase 2 study.
| Role | Description |
|---|---|
| anticoagulant | An agent that prevents blood clotting. |
| EC 3.4.21.6 (coagulation factor Xa) inhibitor | An EC 3.4.21.* (serine endopeptidase) inhibitor that interferes with the action of coagulation factor Xa (EC 3.4.21.6). |
| serine protease inhibitor | Any protease inhibitor that restricts the action of a serine protease. |
| [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 |
|---|---|
| pyridone | |
| secondary carboxamide | A carboxamide resulting from the formal condensation of a carboxylic acid with a primary amine; formula RC(=O)NHR(1). |
| ureas | |
| monochlorobenzenes | Any member of the class of chlorobenzenes containing a mono- or poly-substituted benzene ring in which only one substituent is chlorine. |
| pyrrolidines | Any of a class of heterocyclic amines having a saturated five-membered ring. |
| monofluorobenzenes | Any member of the class of fluorobenzenes containing a mono- or poly-substituted benzene ring carrying a single fluorine substitutent. |
| [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 | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Coagulation factor X | Homo sapiens (human) | IC50 (µMol) | 0.0004 | 0.0003 | 0.5937 | 10.0000 | AID415956; AID527394 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Chain A, Coagulation factor X, heavy chain | Homo sapiens (human) | Kd | 0.0003 | 0.0003 | 0.0003 | 0.0003 | AID977611 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Process | via Protein(s) | Taxonomy |
|---|---|---|
| proteolysis | Coagulation factor X | Homo sapiens (human) |
| blood coagulation | Coagulation factor X | Homo sapiens (human) |
| positive regulation of cell migration | Coagulation factor X | Homo sapiens (human) |
| positive regulation of TOR signaling | Coagulation factor X | Homo sapiens (human) |
| [Information is prepared from geneontology information from the June-17-2024 release] | ||
| Process | via Protein(s) | Taxonomy |
|---|---|---|
| serine-type endopeptidase activity | Coagulation factor X | Homo sapiens (human) |
| calcium ion binding | Coagulation factor X | Homo sapiens (human) |
| protein binding | Coagulation factor X | Homo sapiens (human) |
| phospholipid binding | Coagulation factor X | Homo sapiens (human) |
| [Information is prepared from geneontology information from the June-17-2024 release] | ||
| Process | via Protein(s) | Taxonomy |
|---|---|---|
| extracellular region | Coagulation factor X | Homo sapiens (human) |
| endoplasmic reticulum lumen | Coagulation factor X | Homo sapiens (human) |
| Golgi lumen | Coagulation factor X | Homo sapiens (human) |
| plasma membrane | Coagulation factor X | Homo sapiens (human) |
| external side of plasma membrane | Coagulation factor X | Homo sapiens (human) |
| extracellular space | Coagulation factor X | Homo sapiens (human) |
| [Information is prepared from geneontology information from the June-17-2024 release] | ||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID415957 | Half life in iv dosed rat by cassette studies | 2009 | Bioorganic & medicinal chemistry, Mar-15, Volume: 17, Issue:6 | Exploration of 4,4-disubstituted pyrrolidine-1,2-dicarboxamides as potent, orally active Factor Xa inhibitors with extended duration of action. |
| AID415958 | Half life in iv dosed rat by singleton studies | 2009 | Bioorganic & medicinal chemistry, Mar-15, Volume: 17, Issue:6 | Exploration of 4,4-disubstituted pyrrolidine-1,2-dicarboxamides as potent, orally active Factor Xa inhibitors with extended duration of action. |
| AID527408 | Half life in dog | 2010 | Journal of medicinal chemistry, Sep-09, Volume: 53, Issue:17 | Factor Xa inhibitors: next-generation antithrombotic agents. |
| AID415956 | Inhibition of human Factor-10a | 2009 | Bioorganic & medicinal chemistry, Mar-15, Volume: 17, Issue:6 | Exploration of 4,4-disubstituted pyrrolidine-1,2-dicarboxamides as potent, orally active Factor Xa inhibitors with extended duration of action. |
| AID527410 | Volume of distribution at steady state in dog | 2010 | Journal of medicinal chemistry, Sep-09, Volume: 53, Issue:17 | Factor Xa inhibitors: next-generation antithrombotic agents. |
| AID415961 | Half life in iv dosed dog by singleton studies | 2009 | Bioorganic & medicinal chemistry, Mar-15, Volume: 17, Issue:6 | Exploration of 4,4-disubstituted pyrrolidine-1,2-dicarboxamides as potent, orally active Factor Xa inhibitors with extended duration of action. |
| AID415965 | Volume of distribution at steady state in iv dosed rat by singleton studies | 2009 | Bioorganic & medicinal chemistry, Mar-15, Volume: 17, Issue:6 | Exploration of 4,4-disubstituted pyrrolidine-1,2-dicarboxamides as potent, orally active Factor Xa inhibitors with extended duration of action. |
| AID527409 | Clearance in dog | 2010 | Journal of medicinal chemistry, Sep-09, Volume: 53, Issue:17 | Factor Xa inhibitors: next-generation antithrombotic agents. |
| AID527399 | Anticoagulant activity in human platelet assessed as concentration required to double prothrombin time | 2010 | Journal of medicinal chemistry, Sep-09, Volume: 53, Issue:17 | Factor Xa inhibitors: next-generation antithrombotic agents. |
| AID527428 | Antithrombotic activity in rabbit arteriovenous-shunt thrombosis model measured per hr | 2010 | Journal of medicinal chemistry, Sep-09, Volume: 53, Issue:17 | Factor Xa inhibitors: next-generation antithrombotic agents. |
| AID527412 | Oral bioavailability in rat | 2010 | Journal of medicinal chemistry, Sep-09, Volume: 53, Issue:17 | Factor Xa inhibitors: next-generation antithrombotic agents. |
| AID527407 | Oral bioavailability in dog | 2010 | Journal of medicinal chemistry, Sep-09, Volume: 53, Issue:17 | Factor Xa inhibitors: next-generation antithrombotic agents. |
| AID415959 | Anticoagulant activity in human plasma assessed as concentration required to double the prothrombin time | 2009 | Bioorganic & medicinal chemistry, Mar-15, Volume: 17, Issue:6 | Exploration of 4,4-disubstituted pyrrolidine-1,2-dicarboxamides as potent, orally active Factor Xa inhibitors with extended duration of action. |
| AID415963 | Clearance in iv dosed rat by singleton studies | 2009 | Bioorganic & medicinal chemistry, Mar-15, Volume: 17, Issue:6 | Exploration of 4,4-disubstituted pyrrolidine-1,2-dicarboxamides as potent, orally active Factor Xa inhibitors with extended duration of action. |
| AID527394 | Inhibition of factor 10a | 2010 | Journal of medicinal chemistry, Sep-09, Volume: 53, Issue:17 | Factor Xa inhibitors: next-generation antithrombotic agents. |
| AID527406 | Antithrombotic activity in iv dosed rabbit assessed as reduction in thrombus weight measured per hr | 2010 | Journal of medicinal chemistry, Sep-09, Volume: 53, Issue:17 | Factor Xa inhibitors: next-generation antithrombotic agents. |
| AID977611 | Experimentally measured binding affinity data (Kd) for protein-ligand complexes derived from PDB | 2007 | Chemical biology & drug design, Aug, Volume: 70, Issue:2 | The discovery of (2R,4R)-N-(4-chlorophenyl)-N- (2-fluoro-4-(2-oxopyridin-1(2H)-yl)phenyl)-4-methoxypyrrolidine-1,2-dicarboxamide (PD 0348292), an orally efficacious factor Xa inhibitor. |
| AID1345896 | Human coagulation factor X (S1: Chymotrypsin) | 2009 | Bioorganic & medicinal chemistry, Mar-15, Volume: 17, Issue:6 | Exploration of 4,4-disubstituted pyrrolidine-1,2-dicarboxamides as potent, orally active Factor Xa inhibitors with extended duration of action. |
| [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 (11.82) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 2 (22.22%) | 5.53% |
| Reviews | 1 (11.11%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 6 (66.67%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||