PD 166866: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
PD-166866 : A member of the class of pyridopyrimidines that is pyrido[2,3-d]pyrimidine substituted by an amino group at position 2, 3,5-dimethoxyphenyl group at position 6, and by a (tert-butylcarbamoyl)nitrilo group at position 7. It is a selective ATP competitive inhibitor of the human fibroblast growth factor-1 receptor (FGFR1) tyrosine kinase with an IC50 of 52.4 nM. [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 | 5328127 |
| CHEMBL ID | 299763 |
| CHEBI ID | 156259 |
| SCHEMBL ID | 1248489 |
| MeSH ID | M0292884 |
| Synonym |
|---|
| bdbm3443 |
| pd 166866 |
| 1-[2-amino-6-(3,5-dimethoxyphenyl)pyrido[2,3-d]pyrimidin-7-yl]-3-tert-butylurea |
| chembl299763 , |
| 6-arylpyrido[2,3-d]pyrimidine deriv. 25 |
| pd166866 , |
| PDSP2_000673 |
| PDSP1_000683 |
| 1-(2-amino-6-(3,5-dimethoxy-phenyl)-pyrido(2,3-d)pyrimidin-7-yl)-3-tert-butyl-urea |
| pd-166866 |
| 1-[2-amino-6-(3,5-dimethoxyphenyl)-pyrido[2,3-d]pyrimidin-7-yl]-3-tert-butyl urea |
| CHEBI:156259 |
| n-[2-amino-6-(3,5-dimethoxyphenyl)pyrido[2,3-d]pyrimidin-7-yl]-n'-(1,1-dimethylethyl)-urea |
| 192705-79-6 |
| HMS3263L17 |
| FT-0673538 |
| S8493 |
| NA856793UT , |
| urea, n-(2-amino-6-(3,5-dimethoxyphenyl)pyrido(2,3-d)pyrimidin-7-yl)-n'-(1,1-dimethylethyl)- |
| 1-(2-amino-6-(3,5-dimethoxyphenyl)-pyrido(2,3-d)pyrimidin-7-yl)-3-tert-butyl urea |
| CCG-222482 |
| unii-na856793ut |
| tox21_501178 |
| NCGC00261863-01 |
| SCHEMBL1248489 |
| AKOS025286334 |
| DTXSID20416144 |
| pd-166866 (pd166866) |
| EX-A1324 |
| AS-74459 |
| pd-166866, >=98% (hplc) |
| J-012463 |
| fgf receptor tyrosine kinase inhibitor |
| HY-101296 |
| CS-6407 |
| BCP20054 |
| fgf receptor tyrosine kinase inhibitor - cas 192705-79-6 |
| 1-(2-amino-6-(3,5-dimethoxyphenyl)pyrido[2,3-d]pyrimidin-7-yl)-3-(tert-butyl)urea. |
| mfcd12922514 |
| 1-(2-amino-6-(3,5-dimethoxyphenyl)pyrido[2,3-d]pyrimidin-7-yl)-3-(tert-butyl)urea |
| urea, n-[2-amino-6-(3,5-dimethoxyphenyl)pyrido[2,3-d]pyrimidin-7-yl]-n'-(1,1-dimethylethyl)- |
| Q27284760 |
| C73670 |
| A912621 |
| fgf receptor tyrosine kinase |
| AC-35802 |
| pfe-pkis 3 |
| Excerpt | Reference | Relevance |
|---|---|---|
| "PD 166866 did not inhibit platelet-derived growth factor, epidermal growth factor or insulin-stimulated receptor autophosphorylation in vascular smooth muscle, A431 or NIHIR cells, respectively, further supporting its specificity for the FGFR-1." | ( In vitro biological characterization and antiangiogenic effects of PD 166866, a selective inhibitor of the FGF-1 receptor tyrosine kinase. Batley, BL; Brown, KJ; Connolly, C; Dahring, TK; Hamby, JM; Lu, GH; Panek, RL, 1998) | 1.26 |
| Excerpt | Reference | Relevance |
|---|---|---|
| " Subsequent SAR studies led to the synthesis of new analogs with improved potency, solubility, and bioavailability relative to the initial lead." | ( Structure-activity relationships for a novel series of pyrido[2,3-d]pyrimidine tyrosine kinase inhibitors. Amar, A; Bradford, L; Connolly, CJ; Dahring, T; Doherty, AM; Fry, DW; Hallak, H; Hamby, JM; Keiser, J; Kraker, AJ; Lu, GH; Major, TC; Nelson, JM; Olsewski, B; Panek, RL; Ryan, MJ; Schroeder, MC; Shen, C; Showalter, HD; Slintak, V; Winters, RT, 1997) | 0.3 |
| Role | Description |
|---|---|
| apoptosis inducer | Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms. |
| antineoplastic agent | A substance that inhibits or prevents the proliferation of neoplasms. |
| EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor | An EC 2.7.10.* (protein-tyrosine kinase) inhibitor that interferes with the action of receptor protein-tyrosine kinase (EC 2.7.10.1). |
| angiogenesis inhibitor | An agent and endogenous substances that antagonize or inhibit the development of new blood vessels. |
| [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 |
|---|---|
| dimethoxybenzene | Any methoxybenzene that consists of a benzene skeleton substituted with two methoxy groups and its derivatives. |
| pyridopyrimidine | Any organic heterobicyclic compound consisting of a pyridine ring ortho-fused at any position to a pyrimidine ring. |
| ureas | |
| biaryl | An organic aromatic compound whose structure contains two aromatic rings or ring systems, joined to each other by a single bond. |
| primary arylamine | A primary amine formally derived from ammonia by replacing one hydrogen atom by an aryl group. R-NH2 where R is an aryl group. |
| [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 (µ) | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| estrogen-related nuclear receptor alpha | Homo sapiens (human) | Potency | 21.1401 | 0.0015 | 30.6073 | 15,848.9004 | AID1224819; AID1224820; AID1224821 |
| [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) |
|---|---|---|---|---|---|---|---|
| Proto-oncogene tyrosine-protein kinase Src | Gallus gallus (chicken) | IC50 (µMol) | 50.0000 | 0.0004 | 0.9151 | 5.1000 | AID219507; AID219524 |
| Epidermal growth factor receptor | Homo sapiens (human) | IC50 (µMol) | 50.0000 | 0.0000 | 0.5369 | 10.0000 | AID69417; AID69732 |
| Platelet-derived growth factor receptor beta | Mus musculus (house mouse) | IC50 (µMol) | 50.0000 | 0.0018 | 0.7552 | 9.5000 | AID155203; AID161090; AID161098 |
| Insulin receptor | Homo sapiens (human) | IC50 (µMol) | 50.0000 | 0.0017 | 0.8479 | 10.0000 | AID93076 |
| Platelet-derived growth factor receptor beta | Homo sapiens (human) | IC50 (µMol) | 33.3493 | 0.0006 | 0.8007 | 8.5000 | AID1795526 |
| Fibroblast growth factor receptor 1 | Homo sapiens (human) | IC50 (µMol) | 12.6095 | 0.0002 | 0.9420 | 10.0000 | AID1795526; AID242108; AID73306; AID73312; AID73438; AID73441 |
| Proto-oncogene tyrosine-protein kinase Src | Homo sapiens (human) | IC50 (µMol) | 40.0096 | 0.0002 | 0.5335 | 10.0000 | AID1795526; AID219521; AID219647 |
| Platelet-derived growth factor receptor alpha | Rattus norvegicus (Norway rat) | IC50 (µMol) | 50.0000 | 0.0050 | 0.7741 | 4.0000 | AID161109; AID166382 |
| Fibroblast growth factor receptor 2 | Homo sapiens (human) | IC50 (µMol) | 0.0600 | 0.0004 | 0.3276 | 8.6200 | AID242108; AID73306; AID73312 |
| Fibroblast growth factor receptor 4 | Homo sapiens (human) | IC50 (µMol) | 0.0600 | 0.0008 | 0.6217 | 8.6200 | AID242108; AID73306; AID73312 |
| Fibroblast growth factor receptor 3 | Homo sapiens (human) | IC50 (µMol) | 0.0600 | 0.0004 | 0.2863 | 8.6200 | AID242108; AID73306; AID73312 |
| Platelet-derived growth factor receptor alpha | Mus musculus (house mouse) | IC50 (µMol) | 50.0000 | 0.0018 | 0.8572 | 9.5000 | AID161098 |
| Gastrin/cholecystokinin type B receptor | Rattus norvegicus (Norway rat) | IC50 (µMol) | 50.0000 | 0.0001 | 0.2480 | 1.4000 | AID219521 |
| Platelet-derived growth factor receptor beta | Rattus norvegicus (Norway rat) | IC50 (µMol) | 50.0000 | 0.0050 | 0.7128 | 4.0000 | AID161109; AID166382 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID1347058 | CD47-SIRPalpha protein protein interaction - HTRF assay qHTS validation | 2019 | PloS one, , Volume: 14, Issue:7 | Quantitative high-throughput screening assays for the discovery and development of SIRPα-CD47 interaction inhibitors. |
| AID1347059 | CD47-SIRPalpha protein protein interaction - Alpha assay qHTS validation | 2019 | PloS one, , Volume: 14, Issue:7 | Quantitative high-throughput screening assays for the discovery and development of SIRPα-CD47 interaction inhibitors. |
| AID1347057 | CD47-SIRPalpha protein protein interaction - LANCE assay qHTS validation | 2019 | PloS one, , Volume: 14, Issue:7 | Quantitative high-throughput screening assays for the discovery and development of SIRPα-CD47 interaction inhibitors. |
| AID1347410 | qHTS for inhibitors of adenylyl cyclases using a fission yeast platform: a pilot screen against the NCATS LOPAC library | 2019 | Cellular signalling, 08, Volume: 60 | A fission yeast platform for heterologous expression of mammalian adenylyl cyclases and high throughput screening. |
| AID1347405 | qHTS to identify inhibitors of the type 1 interferon - major histocompatibility complex class I in skeletal muscle: primary screen against the NCATS LOPAC collection | 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. |
| AID1347151 | Optimization of GU AMC qHTS for Zika virus inhibitors: Unlinked NS2B-NS3 protease assay | 2020 | Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49 | Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors. |
| AID1795526 | Kinase Inhibition Assay from Article 10.1021/jm0004291: \\Soluble 2-substituted aminopyrido[2,3-d]pyrimidin-7-yl ureas. Structure-activity relationships against selected tyrosine kinases and exploration of in vitro and in vivo anticancer activity.\\ | 2001 | Journal of medicinal chemistry, Jun-07, Volume: 44, Issue:12 | Soluble 2-substituted aminopyrido[2,3-d]pyrimidin-7-yl ureas. Structure-activity relationships against selected tyrosine kinases and exploration of in vitro and in vivo anticancer activity. |
| AID69417 | Inhibition of human epidermal growth factor receptor | 1998 | Journal of medicinal chemistry, May-21, Volume: 41, Issue:11 | Development of a binding model to protein tyrosine kinases for substituted pyrido[2,3-d]pyrimidine inhibitors. |
| AID85323 | Inhibition of in vitro cell Human umbilical vein endothelial (HUVEC) cell proliferation | 2000 | Journal of medicinal chemistry, Nov-02, Volume: 43, Issue:22 | 3-(3,5-Dimethoxyphenyl)-1,6-naphthyridine-2,7-diamines and related 2-urea derivatives are potent and selective inhibitors of the FGF receptor-1 tyrosine kinase. |
| AID161109 | Inhibition of Platelet-derived growth factor receptor (PDGFr) tyrosine kinase in rat aortic vascular smooth muscle cells (RAVSMCs). | 1997 | Journal of medicinal chemistry, Jul-18, Volume: 40, Issue:15 | Structure-activity relationships for a novel series of pyrido[2,3-d]pyrimidine tyrosine kinase inhibitors. |
| AID219507 | Ability to prevent phosphorylation of avian c-Src TK | 2001 | Journal of medicinal chemistry, Jun-07, Volume: 44, Issue:12 | Soluble 2-substituted aminopyrido[2,3-d]pyrimidin-7-yl ureas. Structure-activity relationships against selected tyrosine kinases and exploration of in vitro and in vivo anticancer activity. |
| AID9453 | Inhibition of human ovarian carcinoma (A90) FGF-R overexpressing cell proliferation | 2000 | Journal of medicinal chemistry, Nov-02, Volume: 43, Issue:22 | 3-(3,5-Dimethoxyphenyl)-1,6-naphthyridine-2,7-diamines and related 2-urea derivatives are potent and selective inhibitors of the FGF receptor-1 tyrosine kinase. |
| AID93076 | Inhibition of insulin receptor (InsR) tyrosine kinase | 1997 | Journal of medicinal chemistry, Jul-18, Volume: 40, Issue:15 | Structure-activity relationships for a novel series of pyrido[2,3-d]pyrimidine tyrosine kinase inhibitors. |
| AID219521 | Inhibition of the phosphorylation of a random glutamate-tyrosine (4:1) copolymer by isolated avian c-Src protein. | 2000 | Journal of medicinal chemistry, Nov-02, Volume: 43, Issue:22 | 3-(3,5-Dimethoxyphenyl)-1,6-naphthyridine-2,7-diamines and related 2-urea derivatives are potent and selective inhibitors of the FGF receptor-1 tyrosine kinase. |
| AID219647 | Inhibition of C-src tyrosine kinase | 1997 | Journal of medicinal chemistry, Jul-18, Volume: 40, Issue:15 | Structure-activity relationships for a novel series of pyrido[2,3-d]pyrimidine tyrosine kinase inhibitors. |
| AID161090 | Inhibition of the phosphorylation of a random glutamate-tyrosine (4:1) copolymer by isolated mouse Platelet-derived growth factor protein. | 2000 | Journal of medicinal chemistry, Nov-02, Volume: 43, Issue:22 | 3-(3,5-Dimethoxyphenyl)-1,6-naphthyridine-2,7-diamines and related 2-urea derivatives are potent and selective inhibitors of the FGF receptor-1 tyrosine kinase. |
| AID166382 | Inhibition of platelet derived growth factor (PDGF) stimulated PDGF-receptor autophosphorylation in rat aortic vascular smooth muscle cells (RAVSMCs) | 1997 | Journal of medicinal chemistry, Jul-18, Volume: 40, Issue:15 | Structure-activity relationships for a novel series of pyrido[2,3-d]pyrimidine tyrosine kinase inhibitors. |
| AID242232 | Inhibition of Platelet-derived growth factor receptor | 2005 | Bioorganic & medicinal chemistry letters, Apr-01, Volume: 15, Issue:7 | Structure-activity relationships for 2-anilino-6-phenylpyrido[2,3-d]pyrimidin-7(8H)-ones as inhibitors of the cellular checkpoint kinase Wee1. |
| AID161098 | Inhibitory concentration of compound against mouse Platelet-derived growth factor receptor | 1998 | Journal of medicinal chemistry, May-21, Volume: 41, Issue:11 | Development of a binding model to protein tyrosine kinases for substituted pyrido[2,3-d]pyrimidine inhibitors. |
| AID219524 | Inhibition of chicken c-Src tyrosine kinase | 1998 | Journal of medicinal chemistry, May-21, Volume: 41, Issue:11 | Development of a binding model to protein tyrosine kinases for substituted pyrido[2,3-d]pyrimidine inhibitors. |
| AID320710 | Inhibition of FGFR | 2008 | Bioorganic & medicinal chemistry, Jan-15, Volume: 16, Issue:2 | 2D Autocorrelation, CoMFA, and CoMSIA modeling of protein tyrosine kinases' inhibition by substituted pyrido[2,3-d]pyrimidine derivatives. |
| AID85327 | Inhibition of microcapillary growth in HUVEC cells | 2000 | Journal of medicinal chemistry, Nov-02, Volume: 43, Issue:22 | 3-(3,5-Dimethoxyphenyl)-1,6-naphthyridine-2,7-diamines and related 2-urea derivatives are potent and selective inhibitors of the FGF receptor-1 tyrosine kinase. |
| AID69732 | Inhibition of Epidermal growth factor receptor (EGFr) tyrosine kinase | 1997 | Journal of medicinal chemistry, Jul-18, Volume: 40, Issue:15 | Structure-activity relationships for a novel series of pyrido[2,3-d]pyrimidine tyrosine kinase inhibitors. |
| AID73441 | Inhibition of the phosphorylation of a random glutamate-tyrosine (4:1) copolymer by isolated Fibroblast growth factor receptor 1. | 2000 | Journal of medicinal chemistry, Nov-02, Volume: 43, Issue:22 | 3-(3,5-Dimethoxyphenyl)-1,6-naphthyridine-2,7-diamines and related 2-urea derivatives are potent and selective inhibitors of the FGF receptor-1 tyrosine kinase. |
| AID155203 | Ability to prevent phosphorylation of isolated mouse PDGF receptor beta | 2001 | Journal of medicinal chemistry, Jun-07, Volume: 44, Issue:12 | Soluble 2-substituted aminopyrido[2,3-d]pyrimidin-7-yl ureas. Structure-activity relationships against selected tyrosine kinases and exploration of in vitro and in vivo anticancer activity. |
| AID320711 | Inhibition of cSrc | 2008 | Bioorganic & medicinal chemistry, Jan-15, Volume: 16, Issue:2 | 2D Autocorrelation, CoMFA, and CoMSIA modeling of protein tyrosine kinases' inhibition by substituted pyrido[2,3-d]pyrimidine derivatives. |
| AID320709 | Inhibition of PDGFR | 2008 | Bioorganic & medicinal chemistry, Jan-15, Volume: 16, Issue:2 | 2D Autocorrelation, CoMFA, and CoMSIA modeling of protein tyrosine kinases' inhibition by substituted pyrido[2,3-d]pyrimidine derivatives. |
| AID85325 | Inhibition of Matrigel invasion assay in HUVEC cells | 2000 | Journal of medicinal chemistry, Nov-02, Volume: 43, Issue:22 | 3-(3,5-Dimethoxyphenyl)-1,6-naphthyridine-2,7-diamines and related 2-urea derivatives are potent and selective inhibitors of the FGF receptor-1 tyrosine kinase. |
| AID44486 | Inhibition of PDGF-dependent rat glioma C6 cell proliferation | 2000 | Journal of medicinal chemistry, Nov-02, Volume: 43, Issue:22 | 3-(3,5-Dimethoxyphenyl)-1,6-naphthyridine-2,7-diamines and related 2-urea derivatives are potent and selective inhibitors of the FGF receptor-1 tyrosine kinase. |
| AID73438 | Ability to prevent phosphorylation of human fibroblast growth factor receptor 1 | 2001 | Journal of medicinal chemistry, Jun-07, Volume: 44, Issue:12 | Soluble 2-substituted aminopyrido[2,3-d]pyrimidin-7-yl ureas. Structure-activity relationships against selected tyrosine kinases and exploration of in vitro and in vivo anticancer activity. |
| AID73306 | Inhibitory concentration of compound against human fibroblast growth factor receptor | 1998 | Journal of medicinal chemistry, May-21, Volume: 41, Issue:11 | Development of a binding model to protein tyrosine kinases for substituted pyrido[2,3-d]pyrimidine inhibitors. |
| AID73312 | Inhibition of Fibroblast growth factor receptor (FGFr) tyrosine kinase | 1997 | Journal of medicinal chemistry, Jul-18, Volume: 40, Issue:15 | Structure-activity relationships for a novel series of pyrido[2,3-d]pyrimidine tyrosine kinase inhibitors. |
| AID242108 | Inhibition of Fibroblast growth factor receptor | 2005 | Bioorganic & medicinal chemistry letters, Apr-01, Volume: 15, Issue:7 | Structure-activity relationships for 2-anilino-6-phenylpyrido[2,3-d]pyrimidin-7(8H)-ones as inhibitors of the cellular checkpoint kinase Wee1. |
| [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 | 3 (15.00) | 18.2507 |
| 2000's | 11 (55.00) | 29.6817 |
| 2010's | 4 (20.00) | 24.3611 |
| 2020's | 2 (10.00) | 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 moderate demand-to-supply ratio for research on this compound.
| This Compound (19.24) All Compounds (24.57) |
| 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 | 20 (100.00%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||