apratastat: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
| ID Source | ID |
|---|---|
| PubMed CID | 11452716 |
| CHEMBL ID | 206815 |
| CHEBI ID | 177520 |
| SCHEMBL ID | 2834310 |
| MeSH ID | M0465174 |
| Synonym |
|---|
| tmi 005 |
| apratastat |
| (3s)-n-hydroxy-4-[4-(4-hydroxybut-2-ynoxy)phenyl]sulonyl-2,2-dimethylthiomorpholine-3-carboxamide |
| CHEBI:177520 |
| 287405-51-0 |
| D08859 |
| apratastat (usan/inn) |
| CHEMBL206815 , |
| tmi-05 |
| tmi-005 |
| (s)-n-hydroxy-4-(4-(4-hydroxybut-2-ynyloxy)phenylsulfonyl)-2,2-dimethylthiomorpholine-3-carboxamide |
| bdbm50181008 |
| apratastat [usan:inn] |
| unii-c6bz5263bj |
| 4-((4-(2-butynyloxy)phenyl)sulfonyl)-n-hydroxy-2,2-dimethyl-(3s)thiomorpholinecarboxamide |
| c6bz5263bj , |
| (3s)-n-hydroxy-4-((4-((4-hydroxybut-2-ynyl)oxy)phenyl)sulfonyl)-2,2-dimethylthiomorpholine-3-carboxamide |
| BCPP000041 |
| apratastat [usan] |
| 3-thiomorpholinecarboxamide, n-hydroxy-4-((4-((4-hydroxy-2-butynyl)oxy)phenyl)sulfonyl)-2,2-dimethyl, (3s)- |
| (3s)-n-hydroxy-4-[[4-[(4-hydroxybut-2-ynyl)oxy]phenyl]sulfonyl]-2,2-dimethylthiomorpholine-3-carboxamide |
| apratastat [inn] |
| (3s)-n-hydroxy-4-[4-(4-hydroxybut-2-ynoxy)phenyl]sulfonyl-2,2-dimethylthiomorpholine-3-carboxamide |
| gtpl6482 |
| compound 5h [pmid: 16426848] |
| tmi005 |
| MLS006010301 |
| smr004701369 |
| SCHEMBL2834310 |
| (s)-4-[4-(4-hydroxy-but-2-ynyloxy)-benzenesulfonyl]-2,2-dimethyl-thiomorpholine-3-carboxylic acid hydroxyamide |
| apratastat, >=98% (hplc) |
| DB13020 |
| HY-119307 |
| Q27074484 |
| CS-0066985 |
| (s)-n-hydroxy-4-((4-((4-hydroxybut-2-yn-1-yl)oxy)phenyl)sulfonyl)-2,2-dimethylthiomorpholine-3-carboxamide |
| A937207 |
| MS-27179 |
| DTXSID10870312 |
| E98872 |
| AKOS040741161 |
Apratastat is an orally active, potent, and reversible dual inhibitor of tumor necrosis factor-α converting enzyme (TACE) and matrix metalloproteinases (MMPs)
| Excerpt | Reference | Relevance |
|---|---|---|
| "Apratastat is an orally active, potent, and reversible dual inhibitor of tumor necrosis factor-α converting enzyme (TACE) and matrix metalloproteinases (MMPs). " | ( Pharmacokinetic-pharmacodynamic modeling of apratastat: a population-based approach. Afsharvand, M; Duan, L; Noveck, R; Raible, D; Shu, C; Zhang, H; Zhou, H, 2011) | 2.07 |
| Excerpt | Reference | Relevance |
|---|---|---|
| "Apratastat can potently inhibit the release of TNF-α in vitro, ex vivo, and in vivo." | ( Pharmacokinetic-pharmacodynamic modeling of apratastat: a population-based approach. Afsharvand, M; Duan, L; Noveck, R; Raible, D; Shu, C; Zhang, H; Zhou, H, 2011) | 1.35 |
| Excerpt | Reference | Relevance |
|---|---|---|
| " This study characterizes the pharmacodynamic (PD) effect of apratastat following oral administration on tumor necrosis factor-alpha (TNF-α) release." | ( Pharmacokinetic-pharmacodynamic modeling of apratastat: a population-based approach. Afsharvand, M; Duan, L; Noveck, R; Raible, D; Shu, C; Zhang, H; Zhou, H, 2011) | 0.87 |
| Excerpt | Reference | Relevance |
|---|---|---|
| " In summary, TMI-1, a dual TACE/MMP inhibitor, represents a unique class of orally bioavailable small molecule TNF inhibitors that may be effective and beneficial for treating RA." | ( Identification and characterization of 4-[[4-(2-butynyloxy)phenyl]sulfonyl]-N-hydroxy-2,2-dimethyl-(3S)thiomorpholinecarboxamide (TMI-1), a novel dual tumor necrosis factor-alpha-converting enzyme/matrix metalloprotease inhibitor for the treatment of rheu Barone, D; Black, R; Brennan, F; Clarke, D; Cummons, T; Feldmann, M; Frost, P; Gibbons, J; Hegen, M; Larsen, G; Levin, J; Li, G; Lin, LL; Mohler, K; Nickerson-Nutter, C; Robertshaw, H; Skotnicki, J; Vansell, N; Xu, J; Zhang, Y, 2004) | 0.32 |
| " Since the discovery of anti-TNF-alpha biologicals, much efforts have gone into developing an orally bioavailable small size TNF-alpha antagonist." | ( Current perspective of TACE inhibitors: a review. DasGupta, S; Giridhar, R; Murumkar, PR; Yadav, MR, 2009) | 0.35 |
| Excerpt | Relevance | Reference |
|---|---|---|
| " Even though the dosage provided adequate exposure to inhibit TNF-α release, apratastat was not efficacious in rheumatoid arthritis (RA)." | ( Pharmacokinetic-pharmacodynamic modeling of apratastat: a population-based approach. Afsharvand, M; Duan, L; Noveck, R; Raible, D; Shu, C; Zhang, H; Zhou, H, 2011) | 0.86 |
| Class | Description |
|---|---|
| sulfonamide | An amide of a sulfonic acid RS(=O)2NR'2. |
| [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) |
|---|---|---|---|---|---|---|---|
| Interstitial collagenase | Homo sapiens (human) | IC50 (µMol) | 0.0330 | 0.0002 | 0.8502 | 10.0000 | AID261911 |
| Collagenase 3 | Homo sapiens (human) | IC50 (µMol) | 0.0080 | 0.0000 | 0.7675 | 10.0000 | AID261912 |
| Disintegrin and metalloproteinase domain-containing protein 17 | Homo sapiens (human) | IC50 (µMol) | 0.1441 | 0.0002 | 1.0140 | 10.0000 | AID1443172; AID1443180; AID1443187; AID261910; AID261914; AID347023 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID1347411 | qHTS to identify inhibitors of the type 1 interferon - major histocompatibility complex class I in skeletal muscle: primary screen against the NCATS Mechanism Interrogation Plate v5.0 (MIPE) Libary | 2020 | ACS chemical biology, 07-17, Volume: 15, Issue:7 | High-Throughput Screening to Identify Inhibitors of the Type I Interferon-Major Histocompatibility Complex Class I Pathway in Skeletal Muscle. |
| AID261919 | Bioavailability in mouse at 10 mg/kg | 2006 | Bioorganic & medicinal chemistry letters, Mar-15, Volume: 16, Issue:6 | Acetylenic TACE inhibitors. Part 3: Thiomorpholine sulfonamide hydroxamates. |
| AID1443180 | Inhibition of TACE in NHEK assessed as reduction in LPS/TPA-stimulated TNFalpha production preincubated for 1 hr followed by LPS/TPA stimulation for 24 hrs by HTRF assay | 2017 | Bioorganic & medicinal chemistry letters, 04-15, Volume: 27, Issue:8 | Identification of novel TACE inhibitors compatible with topical application. |
| AID261911 | Inhibition of MMP1 | 2006 | Bioorganic & medicinal chemistry letters, Mar-15, Volume: 16, Issue:6 | Acetylenic TACE inhibitors. Part 3: Thiomorpholine sulfonamide hydroxamates. |
| AID261920 | Bioavailability in rat at 10 mg/kg | 2006 | Bioorganic & medicinal chemistry letters, Mar-15, Volume: 16, Issue:6 | Acetylenic TACE inhibitors. Part 3: Thiomorpholine sulfonamide hydroxamates. |
| AID347023 | Inhibition of TACE | 2009 | Bioorganic & medicinal chemistry, Jan-15, Volume: 17, Issue:2 | Current perspective of TACE inhibitors: a review. |
| AID261910 | Inhibition of TACE | 2006 | Bioorganic & medicinal chemistry letters, Mar-15, Volume: 16, Issue:6 | Acetylenic TACE inhibitors. Part 3: Thiomorpholine sulfonamide hydroxamates. |
| AID261917 | Permeability across Caco-2 cell membrane | 2006 | Bioorganic & medicinal chemistry letters, Mar-15, Volume: 16, Issue:6 | Acetylenic TACE inhibitors. Part 3: Thiomorpholine sulfonamide hydroxamates. |
| AID261915 | Inhibition of LPS-stimulated TNFalpha production in mouse at 50 mg/kg, po | 2006 | Bioorganic & medicinal chemistry letters, Mar-15, Volume: 16, Issue:6 | Acetylenic TACE inhibitors. Part 3: Thiomorpholine sulfonamide hydroxamates. |
| AID1443187 | Inhibition of TACE in human PBMC assessed as inhibition of TNFalpha production | 2017 | Bioorganic & medicinal chemistry letters, 04-15, Volume: 27, Issue:8 | Identification of novel TACE inhibitors compatible with topical application. |
| AID261912 | Inhibition of MMP13 | 2006 | Bioorganic & medicinal chemistry letters, Mar-15, Volume: 16, Issue:6 | Acetylenic TACE inhibitors. Part 3: Thiomorpholine sulfonamide hydroxamates. |
| AID261913 | Inhibition of LPS-stimulated TNF production in THP cells at 3 uM | 2006 | Bioorganic & medicinal chemistry letters, Mar-15, Volume: 16, Issue:6 | Acetylenic TACE inhibitors. Part 3: Thiomorpholine sulfonamide hydroxamates. |
| AID261914 | Inhibition of LPS-stimulated TNF production in THP cells at 1 uM | 2006 | Bioorganic & medicinal chemistry letters, Mar-15, Volume: 16, Issue:6 | Acetylenic TACE inhibitors. Part 3: Thiomorpholine sulfonamide hydroxamates. |
| AID261916 | Inhibition of LPS-stimulated TNF production in human whole blood | 2006 | Bioorganic & medicinal chemistry letters, Mar-15, Volume: 16, Issue:6 | Acetylenic TACE inhibitors. Part 3: Thiomorpholine sulfonamide hydroxamates. |
| AID261918 | Inhibition of LPS-stimulated TNFalpha production in mouse | 2006 | Bioorganic & medicinal chemistry letters, Mar-15, Volume: 16, Issue:6 | Acetylenic TACE inhibitors. Part 3: Thiomorpholine sulfonamide hydroxamates. |
| AID1443184 | Aqueous solubility of the compound | 2017 | Bioorganic & medicinal chemistry letters, 04-15, Volume: 27, Issue:8 | Identification of novel TACE inhibitors compatible with topical application. |
| AID1443172 | Inhibition of recombinant human TACE catalytic domain using Mca-Pro-Leu-Ala-Gln-Ala-Val-Dpa-Arg-Ser-Ser-Ser-Arg-NH2 as substrate after 2 hrs by fluorescence assay | 2017 | Bioorganic & medicinal chemistry letters, 04-15, Volume: 27, Issue:8 | Identification of novel TACE inhibitors compatible with topical application. |
| AID261921 | Bioavailability in dog at 10 mg/kg | 2006 | Bioorganic & medicinal chemistry letters, Mar-15, Volume: 16, Issue:6 | Acetylenic TACE inhibitors. Part 3: Thiomorpholine sulfonamide hydroxamates. |
| AID1345458 | Human ADAM17 (M12: Astacin/Adamalysin) | 2006 | Bioorganic & medicinal chemistry letters, Mar-15, Volume: 16, Issue:6 | Acetylenic TACE inhibitors. Part 3: Thiomorpholine sulfonamide hydroxamates. |
| AID1345409 | Human MMP13 (M10: Matrix metallopeptidase) | 2006 | Bioorganic & medicinal chemistry letters, Mar-15, Volume: 16, Issue:6 | Acetylenic TACE inhibitors. Part 3: Thiomorpholine sulfonamide hydroxamates. |
| AID1345698 | Human MMP1 (M10: Matrix metallopeptidase) | 2006 | Bioorganic & medicinal chemistry letters, Mar-15, Volume: 16, Issue:6 | Acetylenic TACE inhibitors. Part 3: Thiomorpholine sulfonamide hydroxamates. |
| [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 (54.55) | 29.6817 |
| 2010's | 4 (36.36) | 24.3611 |
| 2020's | 1 (9.09) | 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 moderate demand-to-supply ratio for research on this compound.
| This Compound (21.20) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 1 (9.09%) | 5.53% |
| Reviews | 1 (9.09%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 9 (81.82%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||