Details of the Drug-Related molecule(s) Interaction Atlas

General Information of Drug (ID: DMN8M5P)

Drug Name
PD-168393 Drug Info
Synonyms
PD168393; 194423-15-9; pd 168393; PD-168393; UNII-3R996Y9T0I; 4-[(3-Bromophenyl)amino]-6-acrylamidoquinazoline; n-{4-[(3-bromophenyl)amino]quinazolin-6-yl}prop-2-enamide; N-[4-(3-bromoanilino)quinazolin-6-yl]prop-2-enamide; CHEMBL285063; 3R996Y9T0I; C17H13BrN4O; N-[4-(3-Bromo-phenylamino)-quinazolin-6-yl]-acrylamide; 2-Propenamide, N-(4-((3-bromophenyl)amino)-6-quinazolinyl)-; 2-Propenamide, N-[4-[(3-bromophenyl)amino]-6-quinazolinyl]-; nchembio866-comp2; N-(4-((3-bromophenyl)amino)quinazolin-6-yl)acrylamide
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Cross-matching ID
PubChem CID
4708
ChEBI ID
CHEBI:131504
CAS Number
CAS 194423-15-9
TTD Drug ID
DMN8M5P

Molecule-Related Drug Atlas

Molecule-Related Drug Atlas
Molecule Type:
DTT
DOT
Drug Status:
Approved Drug(s)
Clinical Trial Drug(s)
Investigative Drug(s)
Download the Complete Related Drug List
Drug(s) Targeting Epidermal growth factor receptor (EGFR)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Sorafenib DMS8IFC Adenocarcinoma 2D40 Approved [5]
Lapatinib DM3BH1Y Breast cancer 2C60-2C65 Approved [6]
Gefitinib DM15F0X Colon adenocarcinoma Approved [7]
Erlotinib DMCMBHA Adrenal gland neoplasm Approved [8]
Vandetanib DMRICNP Solid tumour/cancer 2A00-2F9Z Approved [9]
Dacomitinib DMOH8VY Non-small-cell lung cancer 2C25.Y Approved [10]
BIBW 2992 DMTKD7Q Non-small-cell lung cancer 2C25.Y Approved [11]
SKI-758 DMQ8E9R Ischemia 8B10-8B11 Approved [12]
Epidermal growth factor DMVONE6 Vulnerary ND56.Z Approved [10]
Merimepodib DM0HS92 Breast cancer 2C60-2C65 Approved [13]
BIBW 2992 DMTKD7Q Non-small-cell lung cancer 2C25.Y Approved [21]
Gefitinib DM15F0X Colon adenocarcinoma Approved [22]
Erlotinib DMCMBHA Adrenal gland neoplasm Approved [23]
Lapatinib DM3BH1Y Breast cancer 2C60-2C65 Approved [24]
Gemcitabine DMSE3I7 Anterior urethra cancer Approved [25]
Cisplatin DMRHGI9 Adenocarcinoma 2D40 Approved [26]
Sertraline DM0FB1J Coronary heart disease BA80.Z Approved [27]
Hydrogen peroxide DM1NG5W Infectious disease 1A00-CA43.1 Approved [28]
Selenium DM25CGV N. A. N. A. Approved [29]
Deoxycholic acid DM3GYAL Subcutaneous fat disorder EF02 Approved [30]
⏷ Show the Full List of 20 Drug(s)
Drug(s) Targeting ERBB2 messenger RNA (HER2 mRNA)
Drug Name Drug ID Indication ICD 11 Highest Status REF
HKI-272 DM6QOVN Breast cancer 2C60-2C65 Phase 3 [14]
BMS-690514 DMX302C Chronic pain MG30 Phase 2 [15]
3,4-di-(4-methoxyphenyl)-1H-pyrrole-2,5-dione DMDO175 Discovery agent N.A. Investigative [16]
3,4-diphenyl-1H-pyrrole-2,5-dione DMPK6YT Discovery agent N.A. Investigative [16]
3-(4-methoxyphenyl)-4-phenyl-1H-pyrrole-2,5-dione DMGC7RY Discovery agent N.A. Investigative [16]
BMS-536924 DMXJB4N Discovery agent N.A. Investigative [17]
3-(indole-3-yl)-4-phenyl-1H-pyrrole-2,5-dione DM3EV9N Discovery agent N.A. Investigative [16]
PMID24915291C38 DMBXT9J Discovery agent N.A. Investigative [18]
Geldanamycin-estradiol hybrid DMUSJ96 Discovery agent N.A. Investigative [19]
CL-387785 DMLKFZC Discovery agent N.A. Investigative [20]
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Drug(s) Affected By C-X-C motif chemokine 10 (CXCL10)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Nitric Oxide DM1RBYG Hypertension BA00-BA04 Approved [31]
Quercetin DM3NC4M Obesity 5B81 Approved [32]
Troglitazone DM3VFPD Diabetic complication 5A2Y Approved [33]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [34]
Isotretinoin DM4QTBN Acne vulgaris ED80 Approved [35]
Isoniazid DM5JVS3 Latent tuberculosis infection Approved [36]
Arsenic trioxide DM61TA4 Acute lymphoblastic leukaemia 2A85 Approved [37]
Ciclosporin DMAZJFX Graft-versus-host disease 4B24 Approved [38]
Tofacitinib DMBS370 Rheumatoid arthritis FA20 Approved [39]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [40]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By C-C motif chemokine 2 (CCL2)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Indinavir DM0T3YH Human immunodeficiency virus infection 1C62 Approved [41]
Fulvestrant DM0YZC6 Breast cancer 2C60-2C65 Approved [42]
Gefitinib DM15F0X Colon adenocarcinoma Approved [43]
Hydrogen peroxide DM1NG5W Infectious disease 1A00-CA43.1 Approved [44]
Imiquimod DM1TMA3 Alopecia areata ED70.2 Approved [45]
Methimazole DM25FL8 Hyperthyroidism 5A02 Approved [46]
TECFIDERA DM2OVDT Multiple sclerosis 8A40 Approved [47]
Methotrexate DM2TEOL Anterior urethra cancer Approved [48]
Simvastatin DM30SGU Arteriosclerosis BD40 Approved [49]
Quercetin DM3NC4M Obesity 5B81 Approved [32]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Mitogen-activated protein kinase 3 (MAPK3)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Cisplatin DMRHGI9 Adenocarcinoma 2D40 Approved [50]
Progesterone DMUY35B Amenorrhea GA20.0 Approved [51]
Cannabidiol DM0659E Dravet syndrome 8A61.11 Approved [52]
Sertraline DM0FB1J Coronary heart disease BA80.Z Approved [53]
Beta-carotene DM0RXBT Vitamin deficiency 5B55-5B71 Approved [54]
Fulvestrant DM0YZC6 Breast cancer 2C60-2C65 Approved [55]
Secobarbital DM14RF5 Epilepsy 8A60-8A68 Approved [56]
Gefitinib DM15F0X Colon adenocarcinoma Approved [57]
Fexofenadine DM17ONX Allergic rhinitis CA08.0 Approved [58]
Hydrogen peroxide DM1NG5W Infectious disease 1A00-CA43.1 Approved [59]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Mitogen-activated protein kinase 1 (MAPK1)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Ethanol DMDRQZU Chronic pain MG30 Approved [60]
Progesterone DMUY35B Amenorrhea GA20.0 Approved [51]
Carvedilol DMHTEAO Chronic heart failure BD1Z Approved [61]
Paclitaxel DMLB81S Breast carcinoma Approved [62]
Etoposide DMNH3PG Acute myelogenous leukaemia 2A41 Approved [63]
Cisplatin DMRHGI9 Adenocarcinoma 2D40 Approved [50]
Urokinase DM0GOUD Myocardial infarction BA41-BA43 Approved [64]
Cannabidiol DM0659E Dravet syndrome 8A61.11 Approved [65]
Sertraline DM0FB1J Coronary heart disease BA80.Z Approved [53]
Beta-carotene DM0RXBT Vitamin deficiency 5B55-5B71 Approved [54]
⏷ Show the Full List of 10 Drug(s)

Molecular Interaction Atlas of This Drug

Molecular Interaction Atlas
Download the Complete Interaction Atlas for Visualization in Cytoscape

Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Epidermal growth factor receptor (EGFR) TTGKNB4 EGFR_HUMAN Inhibitor [2]
ERBB2 messenger RNA (HER2 mRNA) TTR5TV4 ERBB2_HUMAN Inhibitor [1]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
C-C motif chemokine 2 (CCL2) OTAD2HEL CCL2_HUMAN Gene/Protein Processing [3]
C-X-C motif chemokine 10 (CXCL10) OTTLQ6S0 CXL10_HUMAN Gene/Protein Processing [3]
Epidermal growth factor receptor (EGFR) OTAPLO1S EGFR_HUMAN Post-Translational Modifications [3]
Mitogen-activated protein kinase 1 (MAPK1) OTH85PI5 MK01_HUMAN Post-Translational Modifications [4]
Mitogen-activated protein kinase 3 (MAPK3) OTCYKGKO MK03_HUMAN Post-Translational Modifications [4]

References

1 Tyrosine kinase inhibitors. 15. 4-(Phenylamino)quinazoline and 4-(phenylamino)pyrido[d]pyrimidine acrylamides as irreversible inhibitors of the ATP... J Med Chem. 1999 May 20;42(10):1803-15.
2 Structure-guided development of affinity probes for tyrosine kinases using chemical genetics. Nat Chem Biol. 2007 Apr;3(4):229-38.
3 Plant polyphenols regulate chemokine expression and tissue repair in human keratinocytes through interaction with cytoplasmic and nuclear components of epidermal growth factor receptor system. Antioxid Redox Signal. 2012 Feb 15;16(4):314-28. doi: 10.1089/ars.2011.4053. Epub 2011 Dec 1.
4 Resveratrol induces long-lasting IL-8 expression and peculiar EGFR activation/distribution in human keratinocytes: mechanisms and implications for skin administration. PLoS One. 2013;8(3):e59632. doi: 10.1371/journal.pone.0059632. Epub 2013 Mar 18.
5 Nasopharyngeal carcinoma: Current treatment options and future directions. J Nasopharyng Carcinoma, 2014, 1(16): e16.
6 Triple negative breast cancer--current status and prospective targeted treatment based on HER1 (EGFR), TOP2A and C-MYC gene assessment. Biomed Pap Med Fac Univ Palacky Olomouc Czech Repub. 2009 Mar;153(1):13-7.
7 Gefitinib ('Iressa', ZD1839) and new epidermal growth factor receptor inhibitors. Br J Cancer. 2004 Feb 9;90(3):566-72.
8 Quantitative prediction of fold resistance for inhibitors of EGFR. Biochemistry. 2009 Sep 8;48(35):8435-48.
9 A comparison of physicochemical property profiles of marketed oral drugs and orally bioavailable anti-cancer protein kinase inhibitors in clinical development. Curr Top Med Chem. 2007;7(14):1408-22.
10 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Target id: 1797).
11 Boehringer Ingelheim. Product Development Pipeline. June 2 2009.
12 Synthesis and Src kinase inhibitory activity of a series of 4-[(2,4-dichloro-5-methoxyphenyl)amino]-7-furyl-3-quinolinecarbonitriles. J Med Chem. 2006 Dec 28;49(26):7868-76.
13 Clinical pipeline report, company report or official report of GlaxoSmithKline (2009).
14 Identification of genotype-correlated sensitivity to selective kinase inhibitors by using high-throughput tumor cell line profiling. Proc Natl Acad Sci U S A. 2007 Dec 11;104(50):19936-41.
15 Preclinical pharmacokinetics and in vitro metabolism of BMS-690514, a potent inhibitor of EGFR and VEGFR2. J Pharm Sci. 2010 Aug;99(8):3579-93.
16 Design, synthesis, and biological evaluation of 3,4-diarylmaleimides as angiogenesis inhibitors. J Med Chem. 2006 Feb 23;49(4):1271-81.
17 Discovery of a (1H-benzoimidazol-2-yl)-1H-pyridin-2-one (BMS-536924) inhibitor of insulin-like growth factor I receptor kinase with in vivo antitum... J Med Chem. 2005 Sep 8;48(18):5639-43.
18 Discovery of a series of 2,5-diaminopyrimidine covalent irreversible inhibitors of Bruton's tyrosine kinase with in vivo antitumor activity. J Med Chem. 2014 Jun 26;57(12):5112-28.
19 Synthesis and evaluation of geldanamycin-estradiol hybrids. Bioorg Med Chem Lett. 1999 May 3;9(9):1233-8.
20 Tyrosine kinase inhibitors. 19. 6-Alkynamides of 4-anilinoquinazolines and 4-anilinopyrido[3,4-d]pyrimidines as irreversible inhibitors of the erbB... J Med Chem. 2006 Feb 23;49(4):1475-85.
21 Cysteine mapping in conformationally distinct kinase nucleotide binding sites: application to the design of selective covalent inhibitors. J Med Chem. 2011 Mar 10;54(5):1347-55. doi: 10.1021/jm101396q. Epub 2011 Feb 15.
22 Dasatinib (BMS-354825) selectively induces apoptosis in lung cancer cells dependent on epidermal growth factor receptor signaling for survival. Cancer Res. 2006 Jun 1;66(11):5542-8. doi: 10.1158/0008-5472.CAN-05-4620.
23 Activating mutations in the epidermal growth factor receptor underlying responsiveness of non-small-cell lung cancer to gefitinib. N Engl J Med. 2004 May 20;350(21):2129-39. doi: 10.1056/NEJMoa040938. Epub 2004 Apr 29.
24 The dual ErbB1/ErbB2 inhibitor, lapatinib (GW572016), cooperates with tamoxifen to inhibit both cell proliferation- and estrogen-dependent gene expression in antiestrogen-resistant breast cancer. Cancer Res. 2005 Jan 1;65(1):18-25.
25 A fine-needle aspirate-based vulnerability assay identifies polo-like kinase 1 as a mediator of gemcitabine resistance in pancreatic cancer. Mol Cancer Ther. 2010 Feb;9(2):311-8. doi: 10.1158/1535-7163.MCT-09-0693. Epub 2010 Jan 26.
26 Prediction of chemosensitivity using multigene analysis in head and neck squamous cell carcinoma. Oncology. 2007;73(1-2):104-11. doi: 10.1159/000120998. Epub 2008 Mar 13.
27 Sertraline induces endoplasmic reticulum stress in hepatic cells. Toxicology. 2014 Aug 1;322:78-88. doi: 10.1016/j.tox.2014.05.007. Epub 2014 May 24.
28 Minimal peroxide exposure of neuronal cells induces multifaceted adaptive responses. PLoS One. 2010 Dec 17;5(12):e14352. doi: 10.1371/journal.pone.0014352.
29 Inhibition of invasion and induction of apoptosis by selenium in human malignant brain tumour cells in vitro. Int J Oncol. 2007 May;30(5):1263-71.
30 Ligand-dependent activation of the epidermal growth factor receptor by secondary bile acids in polarizing colon cancer cells. Surgery. 2005 Sep;138(3):415-21. doi: 10.1016/j.surg.2005.06.030.
31 Regulatory role of nitric oxide on monocyte-derived dendritic cell functions. J Interferon Cytokine Res. 2003 Aug;23(8):423-31. doi: 10.1089/107999003322277838.
32 Plant polyphenols differentially modulate inflammatory responses of human keratinocytes by interfering with activation of transcription factors NFB and AhR and EGFR-ERK pathway. Toxicol Appl Pharmacol. 2011 Sep 1;255(2):138-49.
33 Increased sensitivity for troglitazone-induced cytotoxicity using a human in vitro co-culture model. Toxicol In Vitro. 2009 Oct;23(7):1387-95.
34 Transcriptional and Metabolic Dissection of ATRA-Induced Granulocytic Differentiation in NB4 Acute Promyelocytic Leukemia Cells. Cells. 2020 Nov 5;9(11):2423. doi: 10.3390/cells9112423.
35 13-cis retinoic acid inhibits development and progression of chronic allograft nephropathy. Am J Pathol. 2005 Jul;167(1):285-98. doi: 10.1016/S0002-9440(10)62973-2.
36 Characterization of drug-specific signaling between primary human hepatocytes and immune cells. Toxicol Sci. 2017 Jul 1;158(1):76-89.
37 Gene expression profile induced by arsenic trioxide in chronic lymphocytic leukemia cells reveals a central role for heme oxygenase-1 in apoptosis and regulation of matrix metalloproteinase-9. Oncotarget. 2016 Dec 13;7(50):83359-83377.
38 Comparison of HepG2 and HepaRG by whole-genome gene expression analysis for the purpose of chemical hazard identification. Toxicol Sci. 2010 May;115(1):66-79.
39 Regulation of inflammatory responses in tumor necrosis factor-activated and rheumatoid arthritis synovial macrophages by JAK inhibitors. Arthritis Rheum. 2012 Dec;64(12):3856-66. doi: 10.1002/art.37691.
40 Integrative omics data analyses of repeated dose toxicity of valproic acid in vitro reveal new mechanisms of steatosis induction. Toxicology. 2018 Jan 15;393:160-170.
41 Some HIV antiretrovirals increase oxidative stress and alter chemokine, cytokine or adiponectin production in human adipocytes and macrophages. Antivir Ther. 2007;12(4):489-500.
42 Arsenite and cadmium promote the development of mammary tumors. Carcinogenesis. 2020 Jul 14;41(7):1005-1014. doi: 10.1093/carcin/bgz176.
43 Crosstalk between alveolar macrophages and alveolar epithelial cells/fibroblasts contributes to the pulmonary toxicity of gefitinib. Toxicol Lett. 2021 Mar 1;338:1-9. doi: 10.1016/j.toxlet.2020.11.011. Epub 2020 Nov 25.
44 Oxidative Stress Alters miRNA and Gene Expression Profiles in Villous First Trimester Trophoblasts. Biomed Res Int. 2015;2015:257090. doi: 10.1155/2015/257090. Epub 2015 Aug 3.
45 Cannabidiol selectively modulates interleukin (IL)-1 and IL-6 production in toll-like receptor activated human peripheral blood monocytes. Toxicology. 2021 Dec;464:153016. doi: 10.1016/j.tox.2021.153016. Epub 2021 Nov 2.
46 Monitoring of deiodinase deficiency based on transcriptomic responses in SH-SY5Y cells. Arch Toxicol. 2013 Jun;87(6):1103-13. doi: 10.1007/s00204-013-1018-4. Epub 2013 Feb 10.
47 Dimethyl Fumarate Inhibits the Nuclear Factor B Pathway in Breast Cancer Cells by Covalent Modification of p65 Protein. J Biol Chem. 2016 Feb 12;291(7):3639-47. doi: 10.1074/jbc.M115.679704. Epub 2015 Dec 18.
48 The contribution of methotrexate exposure and host factors on transcriptional variance in human liver. Toxicol Sci. 2007 Jun;97(2):582-94.
49 Simvastatin reduces expression of cytokines interleukin-6, interleukin-8, and monocyte chemoattractant protein-1 in circulating monocytes from hypercholesterolemic patients. Arterioscler Thromb Vasc Biol. 2002 Jul 1;22(7):1194-9. doi: 10.1161/01.atv.0000022694.16328.cc.
50 Treatment with anticancer agents induces dysregulation of specific Wnt signaling pathways in human ovarian luteinized granulosa cells in vitro. Toxicol Sci. 2013 Nov;136(1):183-92. doi: 10.1093/toxsci/kft175. Epub 2013 Aug 16.
51 Progesterone increases csk homologous kinase in HMC-1560 human mast cells and reduces cell proliferation. J Cell Biochem. 2007 Dec 1;102(5):1271-80. doi: 10.1002/jcb.21357.
52 Cannabidiol upregulates melanogenesis through CB1 dependent pathway by activating p38 MAPK and p42/44 MAPK. Chem Biol Interact. 2017 Aug 1;273:107-114. doi: 10.1016/j.cbi.2017.06.005. Epub 2017 Jun 7.
53 Sertraline, an antidepressant, induces apoptosis in hepatic cells through the mitogen-activated protein kinase pathway. Toxicol Sci. 2014 Feb;137(2):404-15. doi: 10.1093/toxsci/kft254. Epub 2013 Nov 5.
54 Growth stimulation of human pulmonary adenocarcinoma cells and small airway epithelial cells by beta-carotene via activation of cAMP, PKA, CREB and ERK1/2. Int J Cancer. 2006 Mar 15;118(6):1370-80. doi: 10.1002/ijc.21537.
55 Estrogen and pure antiestrogen fulvestrant (ICI 182 780) augment cell-matrigel adhesion of MCF-7 breast cancer cells through a novel G protein coupled estrogen receptor (GPR30)-to-calpain signaling axis. Toxicol Appl Pharmacol. 2014 Mar 1;275(2):176-81. doi: 10.1016/j.taap.2014.01.005. Epub 2014 Jan 17.
56 Inhibition of activator protein 1 by barbiturates is mediated by differential effects on mitogen-activated protein kinases and the small G proteins ras and rac-1. J Pharmacol Exp Ther. 2004 Dec;311(3):1232-40. doi: 10.1124/jpet.104.071332. Epub 2004 Jul 19.
57 Growth of hormone-dependent MCF-7 breast cancer cells is promoted by constitutive caveolin-1 whose expression is lost in an EGF-R-mediated manner during development of tamoxifen resistance. Breast Cancer Res Treat. 2010 Feb;119(3):575-91. doi: 10.1007/s10549-009-0355-8. Epub 2009 Mar 15.
58 Effect of histamine H1 receptor antagonists on TARC/CCL17 and MDC/CCL22 production from CD14+ cells induced by antigenic stimulation in vitro. Int Arch Allergy Immunol. 2011;155(1):38-51. doi: 10.1159/000318720. Epub 2010 Nov 25.
59 SIRT3 Mediates the Antioxidant Effect of Hydrogen Sulfide in Endothelial Cells. Antioxid Redox Signal. 2016 Feb 20;24(6):329-43. doi: 10.1089/ars.2015.6331. Epub 2015 Nov 10.
60 Downregulation of mitogen-activated protein kinases (MAPKs) in chronic ethanol-induced fatty liver. Toxicol Mech Methods. 2020 Jul;30(6):407-416. doi: 10.1080/15376516.2020.1747126. Epub 2020 Apr 1.
61 A unique mechanism of beta-blocker action: carvedilol stimulates beta-arrestin signaling. Proc Natl Acad Sci U S A. 2007 Oct 16;104(42):16657-62. doi: 10.1073/pnas.0707936104. Epub 2007 Oct 9.
62 The stent-eluting drugs sirolimus and paclitaxel suppress healing of the endothelium by induction of autophagy. Am J Pathol. 2009 Nov;175(5):2226-34.
63 Modulation of apoptosis in HaCaT keratinocytes via differential regulation of ERK signaling pathway by flavonoids. J Biol Chem. 2005 Sep 9;280(36):31498-507. doi: 10.1074/jbc.M505537200. Epub 2005 Jul 13.
64 ADReCS-Target: target profiles for aiding drug safety research and application. Nucleic Acids Res. 2018 Jan 4;46(D1):D911-D917. doi: 10.1093/nar/gkx899.
65 Cannabidiol Modulates the Immunophenotype and Inhibits the Activation of the Inflammasome in Human Gingival Mesenchymal Stem Cells. Front Physiol. 2016 Nov 24;7:559. doi: 10.3389/fphys.2016.00559. eCollection 2016.