General Information of Drug (ID: DM04SWY)

Drug Name
1-Phenyl-propane-1,2-dione Drug Info
Synonyms
1-PHENYL-1,2-PROPANEDIONE; 1-Phenylpropane-1,2-dione; 579-07-7; Acetylbenzoyl; Acetyl benzoyl; Benzoylacetyl; 1,2-Propanedione, 1-phenyl-; Methylphenylglyoxal; Pyruvophenone; Phenylmethyldiketone; Benzoyl methyl ketone; Methyl phenyl diketone; 3-Phenyl-2,3-propanedione; Methyl phenyl glyoxal; Phenyl methyl diketone; UNII-ZB5XA3GD0I; 1-phenyl-1,2-propandione; 1-Phenyl-propane-1,2-dione; FEMA No. 3226; CCRIS 6297; NSC 7643; EINECS 209-435-2; ZB5XA3GD0I; AI3-23868; CHEBI:63552; BVQVLAIMHVDZEL-UHFFFAOYSA-N; 1-Phenyl-1,2-propanedione, 98
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Cross-matching ID
PubChem CID
11363
ChEBI ID
CHEBI:63552
CAS Number
CAS 579-07-7
TTD Drug ID
DM04SWY
INTEDE Drug ID
DR2715

Molecule-Related Drug Atlas

Molecule-Related Drug Atlas
Molecule Type:
DTT
DOT
Drug Status:
Approved Drug(s)
Clinical Trial Drug(s)
Discontinued Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Cholic Acid DM7OKQV Cholelithiasis DC11 Approved [4]
PACTIMIBE DM0NZDT Arteriosclerosis BD40 Phase 2/3 [5]
K-604 DMQVN6P Arteriosclerosis BD40 Phase 2 [6]
Eldacimibe DML7WP0 Hyperlipidaemia 5C80 Phase 2 [7]
GR148672X DM7W6YN Acute lymphoblastic leukaemia 2A85 Clinical trial [8]
Avasimibe DMFG4OM Peripheral vascular disease BD4Z Discontinued in Phase 3 [9]
E-5324 DM562BM Hyperlipidaemia 5C80 Discontinued in Phase 2 [10]
RP-64477 DMTQ3BS Hyperlipidaemia 5C80 Discontinued in Phase 2 [11]
CI-976 DMBO28J Hyperlipidaemia 5C80 Discontinued in Phase 2 [12]
CL-283796 DM7LIDT Hyperlipidaemia 5C80 Discontinued in Phase 2 [13]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Cytochrome P450 1A1 (CYP1A1)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Amodiaquine DME4RA8 Malaria 1F40-1F45 Approved [14]
Riluzole DMECBWN Amyotrophic lateral sclerosis 8B60.0 Approved [15]
Flutamide DMK0O7U Prostate cancer 2C82.0 Approved [16]
Menadione DMSJDTY Vitamin K deficiency 5B59 Approved [17]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [18]
Troglitazone DM3VFPD Diabetic complication 5A2Y Approved [19]
Ethacrynic acid DM60QMR Edema MG29 Approved [20]
Marinol DM70IK5 Anorexia nervosa cachexia 6B80 Approved [21]
Ethinyl Estradiol DMODJ40 Acne vulgaris ED80 Approved [22]
Clofibrate DMPC1J7 Dysbetalipoproteinemia 5C80.2 Approved [23]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Heme oxygenase 1 (HMOX1)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Dexamethasone DMMWZET Acute adrenal insufficiency Approved [24]
Cannabidiol DM0659E Dravet syndrome 8A61.11 Approved [25]
Pantothenic acid DM091H2 Vitamin deficiency 5B55-5B71 Approved [26]
Verapamil DMA7PEW Angina pectoris BA40 Approved [27]
Fulvestrant DM0YZC6 Breast cancer 2C60-2C65 Approved [28]
Hydrogen peroxide DM1NG5W Infectious disease 1A00-CA43.1 Approved [29]
Selenium DM25CGV N. A. N. A. Approved [30]
TECFIDERA DM2OVDT Multiple sclerosis 8A40 Approved [31]
Sulindac DM2QHZU Acute myelogenous leukaemia 2A41 Approved [32]
Methotrexate DM2TEOL Anterior urethra cancer Approved [33]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Meclofenamic acid DM05FXR Ankylosing spondylitis FA92.0 Approved [34]
Diazepam DM08E9O Alcohol withdrawal Approved [35]
Hydrogen peroxide DM1NG5W Infectious disease 1A00-CA43.1 Approved [36]
Salicyclic acid DM2F8XZ Acne vulgaris ED80 Approved [2]
Sulindac DM2QHZU Acute myelogenous leukaemia 2A41 Approved [34]
Quercetin DM3NC4M Obesity 5B81 Approved [37]
Arsenic trioxide DM61TA4 Acute lymphoblastic leukaemia 2A85 Approved [38]
Aspirin DM672AH Acute coronary syndrome BA41 Approved [34]
Liothyronine DM6IR3P Congenital hypothyroidism Approved [39]
Testosterone DM7HUNW Hot flushes GA30 Approved [40]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Cannabidiol DM0659E Dravet syndrome 8A61.11 Approved [41]
Fulvestrant DM0YZC6 Breast cancer 2C60-2C65 Approved [42]
Hydrogen peroxide DM1NG5W Infectious disease 1A00-CA43.1 Approved [43]
Salicyclic acid DM2F8XZ Acne vulgaris ED80 Approved [2]
Quercetin DM3NC4M Obesity 5B81 Approved [37]
obeticholic acid DM3Q1SM Primary biliary cholangitis DB96.1 Approved [44]
Troglitazone DM3VFPD Diabetic complication 5A2Y Approved [45]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [46]
Isotretinoin DM4QTBN Acne vulgaris ED80 Approved [47]
Nefazodone DM4ZS8M Major depressive disorder 6A70.3 Approved [48]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Sulindac DM2QHZU Acute myelogenous leukaemia 2A41 Approved [3]
Quercetin DM3NC4M Obesity 5B81 Approved [3]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [49]
Isotretinoin DM4QTBN Acne vulgaris ED80 Approved [47]
Ciclosporin DMAZJFX Graft-versus-host disease 4B24 Approved [50]
Flufenamic Acid DMC8VNH Dysmenorrhea GA34.3 Approved [3]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [51]
Demecolcine DMCZQGK Solid tumour/cancer 2A00-2F9Z Approved [52]
Zoledronate DMIXC7G Adenocarcinoma 2D40 Approved [53]
Temozolomide DMKECZD Adenocarcinoma 2D40 Approved [54]
⏷ Show the Full List of 10 Drug(s)

Molecular Interaction Atlas of This Drug

Molecular Interaction Atlas

Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Liver carboxylesterase (CES1) TTMF541 EST1_HUMAN Inhibitor [1]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Aldo-keto reductase family 1 member C2 (AKR1C2) OTQ2XMO3 AK1C2_HUMAN Gene/Protein Processing [2]
Cytochrome P450 1A1 (CYP1A1) OTE4EFH8 CP1A1_HUMAN Gene/Protein Processing [2]
Dehydrogenase/reductase SDR family member 11 (DHRS11) OTU3J0ZL DHR11_HUMAN Biotransformations [3]
Heme oxygenase 1 (HMOX1) OTC1W6UX HMOX1_HUMAN Gene/Protein Processing [2]
Transcription factor MafF (MAFF) OT9B7MX0 MAFF_HUMAN Gene/Protein Processing [2]

References

1 Identification and characterization of novel benzil (diphenylethane-1,2-dione) analogues as inhibitors of mammalian carboxylesterases. J Med Chem. 2005 Apr 21;48(8):2906-15.
2 A new in vitro method for identifying chemical sensitizers combining peptide binding with ARE/EpRE-mediated gene expression in human skin cells. Cutan Ocul Toxicol. 2010 Sep;29(3):171-92.
3 Rabbit dehydrogenase/reductase SDR family member 11 (DHRS11): Its identity with acetohexamide reductase with broad substrate specificity and inhibitor sensitivity, different from human DHRS11. Chem Biol Interact. 2019 May 25;305:12-20. doi: 10.1016/j.cbi.2019.03.026. Epub 2019 Mar 26.
4 How many drug targets are there Nat Rev Drug Discov. 2006 Dec;5(12):993-6.
5 Novel indoline-based acyl-CoA:cholesterol acyltransferase inhibitor with antiperoxidative activity: improvement of physicochemical properties and b... J Med Chem. 2008 Aug 14;51(15):4823-33.
6 A selective ACAT-1 inhibitor, K-604, suppresses fatty streak lesions in fat-fed hamsters without affecting plasma cholesterol levels. Atherosclerosis. 2007 Apr;191(2):290-7.
7 Prospects for drug therapy for hyperlipoproteinaemia. Diabete Metab. 1995 Apr;21(2):139-46.
8 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: 2592).
9 New advances in lipid-modifying therapies for reducing cardiovascular risk. Cardiology. 2002;97(2):59-66.
10 Effect of the acyl-CoA:cholesterol acyltransferase inhibitor, E5324, on experimental atherosclerosis in rabbits. Atherosclerosis. 1994 Jun;107(2):187-201.
11 RP 64477: a potent inhibitor of acyl-coenzyme A:cholesterol O-acyltransferase with low systemic bioavailability. Biochem Pharmacol. 1996 Feb 23;51(4):413-21.
12 Acyl-coenzyme A:cholesterol-acyltransferase (ACAT) inhibitors modulate monocyte adhesion to aortic endothelial cells. Atherosclerosis. 1995 Jan 6;112(1):7-17.
13 ACAT inhibitors CL 283,546 and CL 283,796 reduce LDL cholesterol without affecting cholesterol absorption in African green monkeys. J Lipid Res. 1995 Jun;36(6):1199-210.
14 Cytochrome P450 1A1/2 induction by antiparasitic drugs: dose-dependent increase in ethoxyresorufin O-deethylase activity and mRNA caused by quinine, primaquine and albendazole in HepG2 cells. Eur J Clin Pharmacol. 2002 Nov;58(8):537-42.
15 Association of CYP1A1 and CYP1B1 inhibition in in vitro assays with drug-induced liver injury. J Toxicol Sci. 2021;46(4):167-176. doi: 10.2131/jts.46.167.
16 Anti-androgenic effect of 6-formylindolo[3,2-b]carbazole (FICZ) in LNCaP cells is mediated by the aryl hydrocarbon-androgen receptors cross-talk. Steroids. 2020 Jan;153:108508. doi: 10.1016/j.steroids.2019.108508. Epub 2019 Oct 3.
17 Pharmacologic profiling of human and rat cytochrome P450 1A1 and 1A2 induction and competition. Arch Toxicol. 2008 Dec;82(12):909-21.
18 Effect of CYP1A1 gene polymorphisms on estrogen metabolism and bone density. J Bone Miner Res. 2005 Feb;20(2):232-9. doi: 10.1359/JBMR.041110. Epub 2004 Nov 16.
19 Increased sensitivity for troglitazone-induced cytotoxicity using a human in vitro co-culture model. Toxicol In Vitro. 2009 Oct;23(7):1387-95.
20 Isoform-specific induction of a human aldo-keto reductase by polycyclic aromatic hydrocarbons (PAHs), electrophiles, and oxidative stress: implications for the alternative pathway of PAH activation catalyzed by human dihydrodiol dehydrogenase. Cancer Res. 1999 Feb 1;59(3):607-14.
21 Gene expression changes in human small airway epithelial cells exposed to Delta9-tetrahydrocannabinol. Toxicol Lett. 2005 Aug 14;158(2):95-107.
22 The metallohormone cadmium modulates AhR-associated gene expression in the small intestine of rats similar to ethinyl-estradiol. Arch Toxicol. 2013 Apr;87(4):633-43.
23 Evidence for a new human CYP1A1 regulation pathway involving PPAR-alpha and 2 PPRE sites. Gastroenterology. 2004 Nov;127(5):1436-45.
24 Dexamethasone and the inflammatory response in explants of human omental adipose tissue. Mol Cell Endocrinol. 2010 Feb 5;315(1-2):292-8.
25 Inhibiting Heat Shock Proteins Can Potentiate the Cytotoxic Effect of Cannabidiol in Human Glioma Cells. Anticancer Res. 2015 Nov;35(11):5827-37.
26 Calcium pantothenate modulates gene expression in proliferating human dermal fibroblasts. Exp Dermatol. 2009 Nov;18(11):969-78. doi: 10.1111/j.1600-0625.2009.00884.x. Epub 2009 Apr 8.
27 Protective role of HO-1 for alcohol-dependent liver damage. Dig Dis. 2010;28(6):792-8. doi: 10.1159/000324287. Epub 2011 Apr 27.
28 ERE-independent ERalpha target genes differentially expressed in human breast tumors. Mol Cell Endocrinol. 2005 Dec 21;245(1-2):53-9. doi: 10.1016/j.mce.2005.10.003. Epub 2005 Nov 17.
29 Neuroprotective effects of glucomoringin-isothiocyanate against H(2)O(2)-Induced cytotoxicity in neuroblastoma (SH-SY5Y) cells. Neurotoxicology. 2019 Dec;75:89-104. doi: 10.1016/j.neuro.2019.09.008. Epub 2019 Sep 12.
30 High selenium status in individuals exposed to arsenic through coal-burning in Shaanxi (PR of China) modulates antioxidant enzymes, heme oxygenase-1 and DNA damage. Clin Chim Acta. 2010 Sep 6;411(17-18):1312-8.
31 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.
32 Combination treatment with arsenic trioxide and sulindac enhances apoptotic cell death in lung cancer cells via activation of oxidative stress and mitogen-activated protein kinases. Oncol Rep. 2008 Aug;20(2):379-84.
33 Functional gene expression profile underlying methotrexate-induced senescence in human colon cancer cells. Tumour Biol. 2011 Oct;32(5):965-76.
34 Type 5 17beta-hydroxysteroid dehydrogenase/prostaglandin F synthase (AKR1C3): role in breast cancer and inhibition by non-steroidal anti-inflammatory drug analogs. Chem Biol Interact. 2009 Mar 16;178(1-3):221-7.
35 Substrate specificity of human 3(20)alpha-hydroxysteroid dehydrogenase for neurosteroids and its inhibition by benzodiazepines. Biol Pharm Bull. 2002 Apr;25(4):441-5.
36 Gene expression after treatment with hydrogen peroxide, menadione, or t-butyl hydroperoxide in breast cancer cells. Cancer Res. 2002 Nov 1;62(21):6246-54.
37 Comparison of phenotypic and transcriptomic effects of false-positive genotoxins, true genotoxins and non-genotoxins using HepG2 cells. Mutagenesis. 2011 Sep;26(5):593-604.
38 Aberrantly expressed genes in HaCaT keratinocytes chronically exposed to arsenic trioxide. Biomark Insights. 2011 Feb 8;6:7-16.
39 Thyroid hormone responsive genes in cultured human fibroblasts. J Clin Endocrinol Metab. 2005 Feb;90(2):936-43.
40 The exosome-like vesicles derived from androgen exposed-prostate stromal cells promote epithelial cells proliferation and epithelial-mesenchymal transition. Toxicol Appl Pharmacol. 2021 Jan 15;411:115384. doi: 10.1016/j.taap.2020.115384. Epub 2020 Dec 25.
41 Cannabidiol induces antioxidant pathways in keratinocytes by targeting BACH1. Redox Biol. 2020 Jan;28:101321. doi: 10.1016/j.redox.2019.101321. Epub 2019 Sep 5.
42 Arsenite and cadmium promote the development of mammary tumors. Carcinogenesis. 2020 Jul 14;41(7):1005-1014. doi: 10.1093/carcin/bgz176.
43 Global gene expression analysis reveals differences in cellular responses to hydroxyl- and superoxide anion radical-induced oxidative stress in caco-2 cells. Toxicol Sci. 2010 Apr;114(2):193-203. doi: 10.1093/toxsci/kfp309. Epub 2009 Dec 31.
44 Pharmacotoxicology of clinically-relevant concentrations of obeticholic acid in an organotypic human hepatocyte system. Toxicol In Vitro. 2017 Mar;39:93-103.
45 Effects of ciglitazone and troglitazone on the proliferation of human stomach cancer cells. World J Gastroenterol. 2009 Jan 21;15(3):310-20.
46 Development of a neural teratogenicity test based on human embryonic stem cells: response to retinoic acid exposure. Toxicol Sci. 2011 Dec;124(2):370-7.
47 Temporal changes in gene expression in the skin of patients treated with isotretinoin provide insight into its mechanism of action. Dermatoendocrinol. 2009 May;1(3):177-87.
48 Robustness testing and optimization of an adverse outcome pathway on cholestatic liver injury. Arch Toxicol. 2020 Apr;94(4):1151-1172. doi: 10.1007/s00204-020-02691-9. Epub 2020 Mar 10.
49 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.
50 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.
51 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.
52 Characterization of formaldehyde's genotoxic mode of action by gene expression analysis in TK6 cells. Arch Toxicol. 2013 Nov;87(11):1999-2012.
53 Interleukin-19 as a translational indicator of renal injury. Arch Toxicol. 2015 Jan;89(1):101-6.
54 Temozolomide induces activation of Wnt/-catenin signaling in glioma cells via PI3K/Akt pathway: implications in glioma therapy. Cell Biol Toxicol. 2020 Jun;36(3):273-278. doi: 10.1007/s10565-019-09502-7. Epub 2019 Nov 22.