N-(4-fluorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide: HIV-1 integrase inhibitor; structure in first source [MeSH]
| ID Source | ID |
|---|---|
| PubMed CID | 6483031 |
| CHEMBL ID | 199145 |
| SCHEMBL ID | 4068615 |
| MeSH ID | M0526215 |
| Synonym |
|---|
| 1,6-naphthyridine-7-carboxamide, n-[(4-fluorophenyl)methyl]-8-hydroxy- |
| n-[(4-fluorophenyl)methyl]-8-hydroxy-1,6-naphthyridine-7-carboxamide |
| naphthyridine carboxamide, 21 |
| bdbm28236 |
| chembl199145 , |
| SCHEMBL4068615 |
| n-(4-fluorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide |
| AGPDHYVMIWYSBH-UHFFFAOYSA-N |
| Protein | Taxonomy | Measurement | Average (mM) | Bioassay(s) |
|---|---|---|---|---|
| Gag-Pol polyprotein | HIV-1 M:B_HXB2R | IC50 | 0.0120 | AID1798876 |
| Integrase | Human immunodeficiency virus 1 | IC50 | 0.0288 | AID254667; AID264957; AID305890; AID387540; AID414282 |
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID305893 | Protein binding in human plasma by ultrafiltration method | 2007 | Bioorganic & medicinal chemistry letters, Mar-01, Volume: 17, Issue:5 ISSN: 0960-894X | A potent and orally active HIV-1 integrase inhibitor. |
| AID264960 | Protein binding in human plasma at pH 7.4 | 2006 | Bioorganic & medicinal chemistry letters, Jun-01, Volume: 16, Issue:11 ISSN: 0960-894X | A series of 5-aminosubstituted 4-fluorobenzyl-8-hydroxy-[1,6]naphthyridine-7-carboxamide HIV-1 integrase inhibitors. |
| AID264958 | Inhibition of HIV1 replication in MT4 cells in presence of 10% FBS | 2006 | Bioorganic & medicinal chemistry letters, Jun-01, Volume: 16, Issue:11 ISSN: 0960-894X | A series of 5-aminosubstituted 4-fluorobenzyl-8-hydroxy-[1,6]naphthyridine-7-carboxamide HIV-1 integrase inhibitors. |
| AID264959 | Inhibition of HIV1 replication in MT4 cells in presence of 50% NHS | 2006 | Bioorganic & medicinal chemistry letters, Jun-01, Volume: 16, Issue:11 ISSN: 0960-894X | A series of 5-aminosubstituted 4-fluorobenzyl-8-hydroxy-[1,6]naphthyridine-7-carboxamide HIV-1 integrase inhibitors. |
| AID255223 | Human plasma albumin binding in pH 7.4 at RT | 2005 | Bioorganic & medicinal chemistry letters, Oct-15, Volume: 15, Issue:20 ISSN: 0960-894X | A series of 5-(5,6)-dihydrouracil substituted 8-hydroxy-[1,6]naphthyridine-7-carboxylic acid 4-fluorobenzylamide inhibitors of HIV-1 integrase and viral replication in cells. |
| AID264957 | Inhibition of strand transfer process of HIV1 integrase | 2006 | Bioorganic & medicinal chemistry letters, Jun-01, Volume: 16, Issue:11 ISSN: 0960-894X | A series of 5-aminosubstituted 4-fluorobenzyl-8-hydroxy-[1,6]naphthyridine-7-carboxamide HIV-1 integrase inhibitors. |
| AID387540 | Inhibition of recombinant HIV1 integrase strand transfer activity using immobilized DNA substrate | 2008 | Bioorganic & medicinal chemistry letters, Oct-01, Volume: 18, Issue:19 ISSN: 1464-3405 | Synthesis of 5-(1-H or 1-alkyl-5-oxopyrrolidin-3-yl)-8-hydroxy-[1,6]-naphthyridine-7-carboxamide inhibitors of HIV-1 integrase. |
| AID414282 | Inhibition of HIV1 recombinant integrase strand transfer activity | 2009 | Bioorganic & medicinal chemistry letters, Mar-15, Volume: 19, Issue:6 ISSN: 1464-3405 | The use of oxadiazole and triazole substituted naphthyridines as HIV-1 integrase inhibitors. Part 1: Establishing the pharmacophore. |
| AID256050 | Antiviral activity in presence of 10% FBS against HIV-1 replication in cells | 2005 | Bioorganic & medicinal chemistry letters, Oct-15, Volume: 15, Issue:20 ISSN: 0960-894X | A series of 5-(5,6)-dihydrouracil substituted 8-hydroxy-[1,6]naphthyridine-7-carboxylic acid 4-fluorobenzylamide inhibitors of HIV-1 integrase and viral replication in cells. |
| AID387542 | Antiviral activity against HIV1 3b in human MT4 cells assessed as decrease in HIV1 p24 core antigen in presence of 10% normal human serum | 2008 | Bioorganic & medicinal chemistry letters, Oct-01, Volume: 18, Issue:19 ISSN: 1464-3405 | Synthesis of 5-(1-H or 1-alkyl-5-oxopyrrolidin-3-yl)-8-hydroxy-[1,6]-naphthyridine-7-carboxamide inhibitors of HIV-1 integrase. |
| AID387543 | Protein binding in human plasma at pH 7.4 | 2008 | Bioorganic & medicinal chemistry letters, Oct-01, Volume: 18, Issue:19 ISSN: 1464-3405 | Synthesis of 5-(1-H or 1-alkyl-5-oxopyrrolidin-3-yl)-8-hydroxy-[1,6]-naphthyridine-7-carboxamide inhibitors of HIV-1 integrase. |
| AID256051 | Antiviral activity in presence of 50% NHS against HIV-1 replication in cells | 2005 | Bioorganic & medicinal chemistry letters, Oct-15, Volume: 15, Issue:20 ISSN: 0960-894X | A series of 5-(5,6)-dihydrouracil substituted 8-hydroxy-[1,6]naphthyridine-7-carboxylic acid 4-fluorobenzylamide inhibitors of HIV-1 integrase and viral replication in cells. |
| AID305890 | Inhibition of HIV1 recombinant integrase catalyzed strand transfer activity | 2007 | Bioorganic & medicinal chemistry letters, Mar-01, Volume: 17, Issue:5 ISSN: 0960-894X | A potent and orally active HIV-1 integrase inhibitor. |
| AID305892 | Antiviral activity against HIV1 3B in MT4 cells assessed as decrease in HIV1 p24 core antigen in presence of normal human serum | 2007 | Bioorganic & medicinal chemistry letters, Mar-01, Volume: 17, Issue:5 ISSN: 0960-894X | A potent and orally active HIV-1 integrase inhibitor. |
| AID414283 | Antiviral activity against HIV by pseudo-type HIV assay | 2009 | Bioorganic & medicinal chemistry letters, Mar-15, Volume: 19, Issue:6 ISSN: 1464-3405 | The use of oxadiazole and triazole substituted naphthyridines as HIV-1 integrase inhibitors. Part 1: Establishing the pharmacophore. |
| AID254667 | Inhibition of strand transfer for HIV-1 integrase | 2005 | Bioorganic & medicinal chemistry letters, Oct-15, Volume: 15, Issue:20 ISSN: 0960-894X | A series of 5-(5,6)-dihydrouracil substituted 8-hydroxy-[1,6]naphthyridine-7-carboxylic acid 4-fluorobenzylamide inhibitors of HIV-1 integrase and viral replication in cells. |
| AID387541 | Antiviral activity against HIV1 3b in human MT4 cells assessed as decrease in HIV1 p24 core antigen in presence of 10% fetal bovine serum | 2008 | Bioorganic & medicinal chemistry letters, Oct-01, Volume: 18, Issue:19 ISSN: 1464-3405 | Synthesis of 5-(1-H or 1-alkyl-5-oxopyrrolidin-3-yl)-8-hydroxy-[1,6]-naphthyridine-7-carboxamide inhibitors of HIV-1 integrase. |
| AID264961 | Clearance in rat at 2 mg/kg, iv | 2006 | Bioorganic & medicinal chemistry letters, Jun-01, Volume: 16, Issue:11 ISSN: 0960-894X | A series of 5-aminosubstituted 4-fluorobenzyl-8-hydroxy-[1,6]naphthyridine-7-carboxamide HIV-1 integrase inhibitors. |
| AID305894 | Partition coefficient, log P at pH 7.4 | 2007 | Bioorganic & medicinal chemistry letters, Mar-01, Volume: 17, Issue:5 ISSN: 0960-894X | A potent and orally active HIV-1 integrase inhibitor. |
| AID1798876 | HIV Integrase Strand Transfer Scintillation Proximity Assay (SPA) from Article 10.1016/j.bmcl.2009.01.090: \\The use of oxadiazole and triazole substituted naphthyridines as HIV-1 integrase inhibitors. Part 1: Establishing the pharmacophore.\\ | 2009 | Bioorganic & medicinal chemistry letters, Mar-15, Volume: 19, Issue:6 ISSN: 1464-3405 | The use of oxadiazole and triazole substituted naphthyridines as HIV-1 integrase inhibitors. Part 1: Establishing the pharmacophore. |
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 0 (0.00) | 18.7374 |
| 1990's | 0 (0.00) | 18.2507 |
| 2000's | 5 (100.00) | 29.6817 |
| 2010's | 0 (0.00) | 24.3611 |
| 2020's | 0 (0.00) | 2.80 |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 0 (0.00%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 5 (100.00%) | 84.16% |
| Substance | Studies | Classes | Roles | First Year | Last Year | Average Age | Relationship Strength | Trials | pre-1990 | 1990's | 2000's | 2010's | post-2020 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| 5-(1,1-dioxido-1,2-thiazinan-2-yl)-n-(4-fluorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide | 2007 | 2009 | 16.0 | high | 0 | 0 | 0 | 2 | 0 | 0 |
| Condition | Indicated | Studies | First Year | Last Year | Average Age | Relationship Strength | Trials | pre-1990 | 1990's | 2000's | 2010's | post-2020 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| HIV Coinfection | 0 | 2009 | 2009 | 15.0 | high | 0 | 0 | 0 | 1 | 0 | 0 | |
| HIV Infections | 0 | 2009 | 2009 | 15.0 | high | 0 | 0 | 0 | 1 | 0 | 0 |
| Article | Year |
|---|---|
| A series of 5-aminosubstituted 4-fluorobenzyl-8-hydroxy-[1,6]naphthyridine-7-carboxamide HIV-1 integrase inhibitors. Bioorganic & medicinal chemistry letters, , Jun-01, Volume: 16, Issue:11 | 2006 |
| A series of 5-(5,6)-dihydrouracil substituted 8-hydroxy-[1,6]naphthyridine-7-carboxylic acid 4-fluorobenzylamide inhibitors of HIV-1 integrase and viral replication in cells. Bioorganic & medicinal chemistry letters, , Oct-15, Volume: 15, Issue:20 | 2005 |