Page last updated: 2024-12-08
cgs 27023a
Description
Research Excerpts
Clinical Trials
Roles
Classes
Pathways
Study Profile
Bioassays
Related Drugs
Related Conditions
Protein Interactions
Research Growth
Market Indicators
Description
CGS 27023A: a matrix metalloproteinase inhibitor [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
Cross-References
| ID Source | ID |
|---|---|
| PubMed CID | 446504 |
| CHEMBL ID | 514138 |
| CHEMBL ID | 267178 |
| SCHEMBL ID | 3468445 |
| MeSH ID | M0256695 |
Synonyms (45)
| Synonym |
|---|
| cgs 27023a |
| cgs 27023 |
| chembl514138 , |
| (2r)-n-hydroxy-2-[(4-methoxybenzene)(pyridin-3-ylmethyl)sulfonamido]-3-methylbutanamide |
| bmcl16311 compound 1a |
| bdbm8465 |
| n-hydroxy-2(r)-[[(4-methoxyphenyl)sulfonyl](3-picolyl)amino]-3-methylbutanamide hydrochloride |
| CGS , |
| 1BM6 |
| 1EUB |
| cgs-27023a |
| (2r)-n-hydroxy-2-[(4-methoxyphenyl)sulfonyl-(pyridin-3-ylmethyl)amino]-3-methylbutanamide |
| DB07556 |
| cgs-27023 |
| CHEMBL267178 |
| (s)-n-hydroxy-2-[(4-methoxy-benzenesulfonyl)-pyridin-3-ylmethyl-amino]-3-methyl-butyramide |
| (r)-n-hydroxy-2-[(4-methoxy-benzenesulfonyl)-pyridin-3-ylmethyl-amino]-3-methyl-butyramide; hydrochloride |
| 2-[benzyl-(4-methoxy-benzenesulfonyl)-amino]-n-hydroxy-3-methyl-butyramide(cgs-27023a) |
| (s)-n-hydroxy-2-(4-methoxy-n-(pyridin-3-ylmethyl)phenylsulfonamido)-3-methylbutanamide |
| (r)-n-hydroxy-2-[(4-methoxy-benzenesulfonyl)-pyridin-3-ylmethyl-amino]-3-methyl-butyramide |
| bdbm50066658 |
| n-hydroxy-2(r)-[[(4-methoxyphenyl)sulfonyl](3-picolyl)-amino]-3-methyl-butanamide |
| n-hydroxy-2-[(4-methoxy-benzenesulfonyl)-pyridin-3-ylmethyl-amino]-3-methyl-butyramide |
| (r)-n-(1-(hydroxyamino)-2-methylpropyl)-4-methoxy-n-(pyridin-3-ylmethyl)benzenesulfonamide hydrochloride |
| (r)-n-hydroxy-2-(4-methoxy-n-(pyridin-3-ylmethyl)phenylsulfonamido)-3-methylbutanamide |
| 3-[((r)-1-hydroxycarbamoyl-2-methyl-propylamino)-methyl]-pyridine-4-sulfonic acid methyl ester |
| cgs27023a |
| gtpl8846 |
| 2W0D |
| SCHEMBL3468445 |
| mmi270 |
| n-hydroxy-2(r)-[[4-methoxybenzenesulfonyl](3-picolyl)amino]3-methylbutanamide |
| BSIZUMJRKYHEBR-QGZVFWFLSA-N |
| n-hydroxy-2(r)-[[4-methoxybenzenesulfonyl](3-picolyl)amino]-3-methylbutanamide |
| n-hydroxy-n~2~-[(4-methoxyphenyl)sulfonyl]-n~2~-(pyridin-3-ylmethyl)-d-valinamide |
| cgs 27023a free |
| unii-80axy59it2 |
| Q27075945 |
| 161314-70-1 |
| cgs-27023a free base |
| mmi270b free base |
| 80AXY59IT2 , |
| butanamide, n-hydroxy-2-(((4-methoxyphenyl)sulfonyl)(3-pyridinylmethyl)amino)-3-methyl-, (2r)- |
| mmi-270b free base |
| cgs27023afree |
Research Excerpts
Treatment
Pharmacokinetics
| Excerpt | Reference | Relevance |
|---|---|---|
| " Mean Cmax was significantly decreased after food intake." | ( Effect of food on the pharmacokinetics of oral MMI270B (CGS 27023A), a novel matrix metalloproteinase inhibitor. Choi, L; Eskens, FA; Harris, AL; Levitt, NC; Mather, R; Sparreboom, A; Verweij, J, 2000) | 0.55 |
| " We assessed the feasibility and pharmacokinetic interactions of combining MMI270 with 5-fluorouracil (5-FU) and folinic acid (FA)." | ( A dose-finding and pharmacokinetic study of the matrix metalloproteinase inhibitor MMI270 (previously termed CGS27023A) with 5-FU and folinic acid. Blackey, R; Cassidy, J; Choi, L; Devlin, M; Eatock, M; Johnson, J; Morrison, R; Owen, S; Twelves, C, 2005) | 0.33 |
Bioavailability
Dosage Studied
| Excerpt | Relevance | Reference |
|---|---|---|
| " There was a dose-response increase of MMP-2 and TIMP-1 with MMI270." | ( Phase I and pharmacological study of the oral matrix metalloproteinase inhibitor, MMI270 (CGS27023A), in patients with advanced solid cancer. Choi, L; Denis, LJ; Eskens, FA; Foekens, JA; Harris, AL; Levitt, NC; Nakajima, M; O'Byrne, KJ; Owen, SJ; Propper, DJ; Steward, WP; Talbot, DC; Verweij, J; Wilner, S; Wood, JM, 2001) | 0.31 |
| " The chromatographic conditions resolved isobaric interference peaks observed in samples from patients dosed with MMI270B." | ( Rapid analysis of MMI270B, an inhibitor of matrix metalloproteases in human plasma by liquid chromatography-tandem mass spectrometry: matrix interference in patient samples. Majumdar, TK; Tse, FL; Vedananda, S, 2004) | 0.32 |
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
Protein Targets (10)
Inhibition Measurements
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Chain A, STROMELYSIN-1 | Homo sapiens (human) | Ki | 0.0130 | 0.0130 | 0.0130 | 0.0130 | AID977610 |
| Chain A, COLLAGENASE 3 | Homo sapiens (human) | Ki | 0.0019 | 0.0019 | 0.0019 | 0.0019 | AID977610 |
| Interstitial collagenase | Homo sapiens (human) | IC50 (µMol) | 0.0310 | 0.0002 | 0.8502 | 10.0000 | AID1574099; AID1799084 |
| Interstitial collagenase | Homo sapiens (human) | Ki | 0.0211 | 0.0003 | 0.4948 | 7.0000 | AID1796992; AID1799084 |
| 72 kDa type IV collagenase | Homo sapiens (human) | IC50 (µMol) | 0.0297 | 0.0000 | 1.2848 | 10.0000 | AID1381208; AID1574100; AID1594560 |
| 72 kDa type IV collagenase | Homo sapiens (human) | Ki | 0.0260 | 0.0000 | 0.3466 | 3.0000 | AID1796992 |
| Stromelysin-1 | Homo sapiens (human) | IC50 (µMol) | 0.0256 | 0.0000 | 1.1484 | 10.0000 | AID1378663; AID1381214; AID1799084 |
| Stromelysin-1 | Homo sapiens (human) | Ki | 0.0211 | 0.0003 | 0.5425 | 8.0000 | AID1796992; AID1799084 |
| Matrix metalloproteinase-9 | Homo sapiens (human) | IC50 (µMol) | 0.0191 | 0.0000 | 0.7053 | 10.0000 | AID1378665; AID1381215; AID1574101; AID1594562; AID1799084 |
| Matrix metalloproteinase-9 | Homo sapiens (human) | Ki | 0.0211 | 0.0002 | 0.1281 | 0.8000 | AID1796992; AID1799084 |
| Lethal factor | Bacillus anthracis | IC50 (µMol) | 1.2000 | 0.0970 | 2.8597 | 6.0000 | AID1796193 |
| Neutrophil collagenase | Homo sapiens (human) | IC50 (µMol) | 0.0105 | 0.0000 | 0.9272 | 10.0000 | AID1378664; AID1594561 |
| Collagenase 3 | Homo sapiens (human) | IC50 (µMol) | 0.0209 | 0.0000 | 0.7675 | 10.0000 | AID1594563; AID1799084 |
| Collagenase 3 | Homo sapiens (human) | Ki | 0.0013 | 0.0000 | 0.4759 | 3.8000 | AID1799084 |
| Matrix metalloproteinase-14 | Homo sapiens (human) | IC50 (µMol) | 0.0230 | 0.0003 | 0.7182 | 10.0000 | AID1574102 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
Biological Processes (102)
Molecular Functions (14)
Ceullar Components (20)
Bioassays (31)
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID1796193 | Fluorescence Resonance Energy Transfer Assay (FRET) from Article 10.1016/j.bmcl.2005.10.088: \\The discovery of a potent and selective lethal factor inhibitor for adjunct therapy of anthrax infection.\\ | 2006 | Bioorganic & medicinal chemistry letters, Feb-15, Volume: 16, Issue:4 | The discovery of a potent and selective lethal factor inhibitor for adjunct therapy of anthrax infection. |
| AID1796992 | Enzyme Inhibition Assay from Article 10.1021/jm960871c: \\Discovery of CGS 27023A, a non-peptidic, potent, and orally active stromelysin inhibitor that blocks cartilage degradation in rabbits.\\ | 1997 | Journal of medicinal chemistry, Aug-01, Volume: 40, Issue:16 | Discovery of CGS 27023A, a non-peptidic, potent, and orally active stromelysin inhibitor that blocks cartilage degradation in rabbits. |
| AID1799084 | Determination of MMP-13 Activity from Article 10.1021/jm801394m: \\Discovery of potent, selective, and orally active carboxylic acid based inhibitors of matrix metalloproteinase-13.\\ | 2009 | Journal of medicinal chemistry, Jun-11, Volume: 52, Issue:11 | Discovery of potent, selective, and orally active carboxylic acid based inhibitors of matrix metalloproteinase-13. |
| AID1345461 | Human MMP8 (M10: Matrix metallopeptidase) | 2011 | European journal of medicinal chemistry, Jul, Volume: 46, Issue:7 | Synthesis and biological evaluation in U87MG glioma cells of (ethynylthiophene)sulfonamido-based hydroxamates as matrix metalloproteinase inhibitors. |
| AID1345449 | Human MMP25 (M10: Matrix metallopeptidase) | 2011 | European journal of medicinal chemistry, Jul, Volume: 46, Issue:7 | Synthesis and biological evaluation in U87MG glioma cells of (ethynylthiophene)sulfonamido-based hydroxamates as matrix metalloproteinase inhibitors. |
| AID1345698 | Human MMP1 (M10: Matrix metallopeptidase) | 2011 | European journal of medicinal chemistry, Jul, Volume: 46, Issue:7 | Synthesis and biological evaluation in U87MG glioma cells of (ethynylthiophene)sulfonamido-based hydroxamates as matrix metalloproteinase inhibitors. |
| AID1345417 | Human MMP2 (M10: Matrix metallopeptidase) | 2011 | European journal of medicinal chemistry, Jul, Volume: 46, Issue:7 | Synthesis and biological evaluation in U87MG glioma cells of (ethynylthiophene)sulfonamido-based hydroxamates as matrix metalloproteinase inhibitors. |
| AID1345460 | Human MMP3 (M10: Matrix metallopeptidase) | 2011 | European journal of medicinal chemistry, Jul, Volume: 46, Issue:7 | Synthesis and biological evaluation in U87MG glioma cells of (ethynylthiophene)sulfonamido-based hydroxamates as matrix metalloproteinase inhibitors. |
| AID1345436 | Human MMP14 (M10: Matrix metallopeptidase) | 2011 | European journal of medicinal chemistry, Jul, Volume: 46, Issue:7 | Synthesis and biological evaluation in U87MG glioma cells of (ethynylthiophene)sulfonamido-based hydroxamates as matrix metalloproteinase inhibitors. |
| AID1345442 | Human MMP9 (M10: Matrix metallopeptidase) | 2011 | European journal of medicinal chemistry, Jul, Volume: 46, Issue:7 | Synthesis and biological evaluation in U87MG glioma cells of (ethynylthiophene)sulfonamido-based hydroxamates as matrix metalloproteinase inhibitors. |
| AID1339600 | Inhibition of MMP-9 homodimerization in human T98G cells assessed as reduction in cell invasion at 25 nM measured after 24 hrs by p-formaldehyde/crystal violet staining based matrigel basement membrane transwell assay | 2017 | ACS medicinal chemistry letters, Mar-09, Volume: 8, Issue:3 | Bifunctional Inhibitors as a New Tool To Reduce Cancer Cell Invasion by Impairing MMP-9 Homodimerization. |
| AID1339598 | Inhibition of MMP-9 homodimerization in human U87MG cells assessed as reduction in cell invasion at 25 nM measured after 24 hrs by p-formaldehyde/crystal violet staining based matrigel basement membrane transwell assay | 2017 | ACS medicinal chemistry letters, Mar-09, Volume: 8, Issue:3 | Bifunctional Inhibitors as a New Tool To Reduce Cancer Cell Invasion by Impairing MMP-9 Homodimerization. |
| AID1381214 | Inhibition of recombinant human MMP3 preincubated for 30 mins followed by McaPro-Leu-Gly-Leu-Dpa-Ala-Arg-NH2 substrate addition measured by fluorescence assay | 2018 | Bioorganic & medicinal chemistry letters, 08-01, Volume: 28, Issue:14 | Lung cancer and matrix metalloproteinases inhibitors of polyphenols from Selaginella tamariscina with suppression activity of migration. |
| AID1594563 | Inhibition of human MMP13 using (7-methoxycoumarin-4-yl)acetyl-Pro-Leu-Gly-Leu-(3-(2,4-dinitrophenyl)-L-2,3-diamino-propionyl)Ala-Arg-NH2 as substrate preincubated for 30 mins followed by substrate addition and measured by fluorescence assay | 2019 | Bioorganic & medicinal chemistry, 05-15, Volume: 27, Issue:10 | Proline-based hydroxamates targeting the zinc-dependent deacetylase LpxC: Synthesis, antibacterial properties, and docking studies. |
| AID1378665 | Inhibition of recombinant human MMP9 (Ala20 to Asp707 residues) expressed in CHO cells using Mca-Pro-LeuGly-Leu-Dpa-Ala-Arg-NH2 as substrate preincubated for 30 mins followed by substrate addition by fluorescence assay | 2017 | European journal of medicinal chemistry, Sep-29, Volume: 138 | Discovery of dehydroabietic acid sulfonamide based derivatives as selective matrix metalloproteinases inactivators that inhibit cell migration and proliferation. |
| AID1594561 | Inhibition of human MMP8 using (7-methoxycoumarin-4-yl)acetyl-Pro-Leu-Gly-Leu-(3-(2,4-dinitrophenyl)-L-2,3-diamino-propionyl)Ala-Arg-NH2 as substrate preincubated for 30 mins followed by substrate addition and measured by fluorescence assay | 2019 | Bioorganic & medicinal chemistry, 05-15, Volume: 27, Issue:10 | Proline-based hydroxamates targeting the zinc-dependent deacetylase LpxC: Synthesis, antibacterial properties, and docking studies. |
| AID1594560 | Inhibition of human MMP2 using (7-methoxycoumarin-4-yl)acetyl-Pro-Leu-Gly-Leu-(3-(2,4-dinitrophenyl)-L-2,3-diamino-propionyl)Ala-Arg-NH2 as substrate preincubated for 30 mins followed by substrate addition and measured by fluorescence assay | 2019 | Bioorganic & medicinal chemistry, 05-15, Volume: 27, Issue:10 | Proline-based hydroxamates targeting the zinc-dependent deacetylase LpxC: Synthesis, antibacterial properties, and docking studies. |
| AID1381215 | Inhibition of recombinant human MMP9 preincubated for 30 mins followed by McaPro-Leu-Gly-Leu-Dpa-Ala-Arg-NH2 substrate addition measured by fluorescence assay | 2018 | Bioorganic & medicinal chemistry letters, 08-01, Volume: 28, Issue:14 | Lung cancer and matrix metalloproteinases inhibitors of polyphenols from Selaginella tamariscina with suppression activity of migration. |
| AID1574099 | Inhibition of recombinant human pro-MMP1 using Mca-Lys-Pro-Leu-Gly-Leu-Dap(Dnp)-Ala-Arg-NH2 as substrate preincubated for 3 hrs followed by substrate addition and measured every 10 secs for 15 mins in presence of APMA by fluorometric assay | 2019 | Bioorganic & medicinal chemistry, 01-01, Volume: 27, Issue:1 | Design, synthesis and biological evaluation of bifunctional inhibitors of membrane type 1 matrix metalloproteinase (MT1-MMP). |
| AID1378663 | Inhibition of recombinant human MMP3 (Tyr18 to Cys477 residues) expressed in mouse myeloma cells using Mca-Pro-LeuGly-Leu-Dpa-Ala-Arg-NH2 as substrate preincubated for 30 mins followed by substrate addition by fluorescence assay | 2017 | European journal of medicinal chemistry, Sep-29, Volume: 138 | Discovery of dehydroabietic acid sulfonamide based derivatives as selective matrix metalloproteinases inactivators that inhibit cell migration and proliferation. |
| AID1378664 | Inhibition of recombinant human MMP8 (Phe21 to Gly467 residues) expressed in mouse myeloma cells using Mca-Pro-LeuGly-Leu-Dpa-Ala-Arg-NH2 as substrate preincubated for 30 mins followed by substrate addition by fluorescence assay | 2017 | European journal of medicinal chemistry, Sep-29, Volume: 138 | Discovery of dehydroabietic acid sulfonamide based derivatives as selective matrix metalloproteinases inactivators that inhibit cell migration and proliferation. |
| AID1339599 | Inhibition of MMP-9 homodimerization in human U343MG cells assessed as reduction in cell invasion at 25 nM measured after 24 hrs by p-formaldehyde/crystal violet staining based matrigel basement membrane transwell assay | 2017 | ACS medicinal chemistry letters, Mar-09, Volume: 8, Issue:3 | Bifunctional Inhibitors as a New Tool To Reduce Cancer Cell Invasion by Impairing MMP-9 Homodimerization. |
| AID1594562 | Inhibition of human MMP9 using (7-methoxycoumarin-4-yl)acetyl-Pro-Leu-Gly-Leu-(3-(2,4-dinitrophenyl)-L-2,3-diamino-propionyl)Ala-Arg-NH2 as substrate preincubated for 30 mins followed by substrate addition and measured by fluorescence assay | 2019 | Bioorganic & medicinal chemistry, 05-15, Volume: 27, Issue:10 | Proline-based hydroxamates targeting the zinc-dependent deacetylase LpxC: Synthesis, antibacterial properties, and docking studies. |
| AID1381208 | Inhibition of recombinant human MMP2 preincubated for 30 mins followed by McaPro-Leu-Gly-Leu-Dpa-Ala-Arg-NH2 substrate addition measured by fluorescence assay | 2018 | Bioorganic & medicinal chemistry letters, 08-01, Volume: 28, Issue:14 | Lung cancer and matrix metalloproteinases inhibitors of polyphenols from Selaginella tamariscina with suppression activity of migration. |
| AID1574102 | Inhibition of recombinant human MT1-MMP catalytic domain using Mca-Lys-Pro-Leu-Gly-Leu-Dap(Dnp)-Ala-Arg-NH2 as substrate preincubated for 3 hrs followed by substrate addition and measured every 10 secs for 15 min by fluorometric assay | 2019 | Bioorganic & medicinal chemistry, 01-01, Volume: 27, Issue:1 | Design, synthesis and biological evaluation of bifunctional inhibitors of membrane type 1 matrix metalloproteinase (MT1-MMP). |
| AID1574100 | Inhibition of recombinant human proMMP2 using Mca-Lys-Pro-Leu-Gly-Leu-Dap(Dnp)-Ala-Arg-NH2 as substrate preincubated for 3 hrs followed by substrate addition and measured every 10 secs for 15 mins in presence of APMA by fluorometric assay | 2019 | Bioorganic & medicinal chemistry, 01-01, Volume: 27, Issue:1 | Design, synthesis and biological evaluation of bifunctional inhibitors of membrane type 1 matrix metalloproteinase (MT1-MMP). |
| AID1574101 | Inhibition of recombinant human proMMP9 using Mca-Lys-Pro-Leu-Gly-Leu-Dap(Dnp)-Ala-Arg-NH2 as substrate preincubated for 3 hrs followed by substrate addition and measured every 10 secs for 15 mins in presence of APMA by fluorometric assay | 2019 | Bioorganic & medicinal chemistry, 01-01, Volume: 27, Issue:1 | Design, synthesis and biological evaluation of bifunctional inhibitors of membrane type 1 matrix metalloproteinase (MT1-MMP). |
| AID1811 | Experimentally measured binding affinity data derived from PDB | 1998 | Biochemistry, Oct-06, Volume: 37, Issue:40 | Solution structure of the catalytic domain of human stromelysin-1 complexed to a potent, nonpeptidic inhibitor. |
| AID977610 | Experimentally measured binding affinity data (Ki) for protein-ligand complexes derived from PDB | 1998 | Biochemistry, Oct-06, Volume: 37, Issue:40 | Solution structure of the catalytic domain of human stromelysin-1 complexed to a potent, nonpeptidic inhibitor. |
| AID1811 | Experimentally measured binding affinity data derived from PDB | 2000 | Journal of molecular biology, Aug-11, Volume: 301, Issue:2 | Solution structure of the catalytic domain of human collagenase-3 (MMP-13) complexed to a potent non-peptidic sulfonamide inhibitor: binding comparison with stromelysin-1 and collagenase-1. |
| AID977610 | Experimentally measured binding affinity data (Ki) for protein-ligand complexes derived from PDB | 2000 | Journal of molecular biology, Aug-11, Volume: 301, Issue:2 | Solution structure of the catalytic domain of human collagenase-3 (MMP-13) complexed to a potent non-peptidic sulfonamide inhibitor: binding comparison with stromelysin-1 and collagenase-1. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
Research
Studies (71)
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 0 (0.00) | 18.7374 |
| 1990's | 15 (21.13) | 18.2507 |
| 2000's | 44 (61.97) | 29.6817 |
| 2010's | 12 (16.90) | 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] | ||
Market Indicators
Research Demand Index: 10.12
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 (10.12) All Compounds (24.57) |
Study Types
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 3 (4.17%) | 5.53% |
| Reviews | 1 (1.39%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 68 (94.44%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||