General Information of Drug (ID: DMEQH6J)

Drug Name
Flavone Drug Info
Synonyms
Flavone; FLAVONE; 525-82-6; 2-Phenylchromone; 2-Phenyl-4H-chromen-4-one; 2-Phenyl-4-chromone; Asmacoril; 2-Phenyl-4H-1-benzopyran-4-one; 2-Phenyl-4-benzopyron; 4H-1-Benzopyran-4-one, 2-phenyl-; Chromocor; Cromaril; 2-phenylchromen-4-one; Phenylchromone; 2-Phenyl-chromen-4-one; 2-Phenyl-gamma-benzopyrone; 2-Phenylbenzopyran-4-one; Cromarile; 2-Phenyl-4H-benzopyran-4-one; Flavon; 2-Phenylchrome; UNII-S2V45N7G3B; NSC 19028; 2-Phenyl-4H-chromen-4-on; CCRIS 4288; NSC19028; EINECS 208-383-8; NSC-19028; BRN 0157598
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1] , [2]
Cross-matching ID
PubChem CID
10680
ChEBI ID
CHEBI:42491
CAS Number
CAS 525-82-6
TTD Drug ID
DMEQH6J
INTEDE Drug ID
DR2144

Molecule-Related Drug Atlas

Molecule-Related Drug Atlas
Molecule Type:
DTT
DME
Drug Status:
Approved Drug(s)
Clinical Trial Drug(s)
Investigative Drug(s)
Discontinued Drug(s)
Preclinical Drug(s)
Patented Agent(s)
Drug(s) Metabolized By Cytochrome P450 2A6 (CYP2A6)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Fluorouracil DMUM7HZ Solid tumour/cancer 2A00-2F9Z Approved [10]
Progesterone DMUY35B Premature labour JB00 Approved [11]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [12]
Acetaminophen DMUIE76 Pain MG30-MG3Z Approved [13]
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [11]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [14]
Metronidazole DMTIVEN Amoebiasis 1A36 Approved [15]
Propofol DMB4OLE Anaesthesia 9A78.6 Approved [16]
Nicotine DMWX5CO Nicotine dependence 6C4A.2 Approved [17]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [11]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Metabolized By Biphenyl dioxygenase (bphC)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Isoflavone DM7U58J Asthma CA23 Phase 4 [9]
AUS-131 DMUXO3Z Benign prostatic hyperplasia GA90 Phase 2 [9]
Flavanone DMNWIYM Discovery agent N.A. Investigative [9]
Drug(s) Metabolized By Naphthalene dioxygenase (doxB)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Isoflavone DM7U58J Asthma CA23 Phase 4 [9]
Drug(s) Targeting Aromatase (CYP19A1)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Anastrozole DMNP60F Breast cancer 2C60-2C65 Approved [18]
Letrozole DMH07Y3 Hormonally-responsive breast cancer 2C60-2C65 Approved [19]
Exemestane DM9HPW3 Hormonally-responsive breast cancer 2C60-2C65 Approved [19]
Aminoglutethimide DMWFHMZ Cushing disease 5A70 Approved [20]
FADROZOLE DM3C5GZ Breast cancer 2C60-2C65 Approved [21]
Testolactone DMVY4GN Breast cancer 2C60-2C65 Approved [22]
Atamestane + Toremifene DM3QLK2 Breast cancer 2C60-2C65 Phase 3 [23]
LIAROZOLE DM4OYXE Dermatological disease DA24.Y Phase 2/3 [6]
Coumate DMVKW0N Breast cancer 2C60-2C65 Phase 2 [24]
Dextromethorphan+quinidine DMFI5J4 Diabetic neuropathy 8C0Z Phase 2 [25]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
IB-MECA DM9G5XD Psoriasis vulgaris EA90 Phase 3 [26]
Tonapofylline DMBH316 Acute and chronic heart failure BD1Z Phase 2 [27]
NITD609 DMQHBSX Malaria 1F40-1F45 Phase 2 [28]
CF102 DMP56WJ Hepatocellular carcinoma 2C12.02 Phase 2 [29]
SCH-442416 DMQ2K1V N. A. N. A. Phase 1 [30]
BEMESETRON DMSPJX9 N. A. N. A. Discontinued in Phase 3 [31]
BAY 60-6583 DMTEJV1 Myocardial ischemia BA6Z Preclinical [32]
CF602 DM0ULO2 Inflammation 1A00-CA43.1 Preclinical [29]
CF502 DMQSJ20 Inflammation 1A00-CA43.1 Preclinical [29]
Methylthioadenosine DMC8J6F Multiple sclerosis 8A40 Terminated [33]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Dihydrotestosterone DM3S8XC Prostate hyperplasia GA90 Phase 4 [34]
BAY 86-5044 DMRZLU4 Breast cancer 2C60-2C65 Phase 2 [35]
TRC-253 DMXI8CD Prostate cancer 2C82.0 Phase 1/2 [36]
ISIS-AR DM8P3N5 Prostate cancer 2C82.0 Phase 1 [37]
EZN-4176 DMNPS59 Prostate cancer 2C82.0 Phase 1 [38]
Eugenol DM7US1H Discovery agent N.A. Patented [39]
RU-58841 DMMEAZ2 Acne vulgaris ED80 Discontinued in Phase 1 [40]
Apigenin DMI3491 Discovery agent N.A. Investigative [5]
Kaempferol DMHEMUB Discovery agent N.A. Investigative [5]
LGD-5552 DM67KWM Discovery agent N.A. Investigative [41]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Ethanol DMDRQZU Chronic pain MG30 Approved [42]
Zolpidem DMWOSKJ Insomnia 7A00-7A0Z Approved [43]
Methoxyflurane DML0RAE Anaesthesia 9A78.6 Approved [42]
Nitrazepam DMEGIQ6 Epilepsy 8A60-8A68 Approved [42]
Allopregnanolone DMNLHAC Depression 6A70-6A7Z Approved [44]
Clobazam - Lundbeck DMW1OQ0 Anxiety disorder 6B00-6B0Z Approved [42]
Hexobarbital DMQ314B Anaesthesia 9A78.6 Approved [42]
THIOCOLCHICOSIDE DMEPWYA Muscle spasm MB47.3 Approved [45]
Meprobamate DMHM93Y Anxiety disorder 6B00-6B0Z Approved [42]
Zaleplon DMGFWSM Insomnia 7A00-7A0Z Approved [46]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Phenobarbital DMXZOCG Seizure disorder 8A6Z Approved [42]
Allopregnanolone DMNLHAC Depression 6A70-6A7Z Approved [47]
THIOCOLCHICOSIDE DMEPWYA Muscle spasm MB47.3 Approved [45]
Clonazepam DMTO13J Epilepsy 8A60-8A68 Approved [48]
Piperazine DMTY9LU Ascariasis 1F62 Approved [49]
Alpidem DMN7Y9K Anxiety disorder 6B00-6B0Z Approved [50]
Moxidectin DMYGHX5 Onchocerciasis 1F6A Approved [51]
DP-VPA DMGOXPQ Bipolar disorder 6A60 Approved [52]
Androsterone DMITJAK N. A. N. A. Phase 3 [47]
ZK-93423 DMFWMKZ Epileptic seizures 8A61-8A6Z Phase 3 [53]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Adenosine DMM2NSK Paroxysmal supraventricular tachycardia BC81.Z Approved [46]
Vidarabine DM0N85H Herpes simplex virus infection 1F00 Approved [46]
Tonapofylline DMBH316 Acute and chronic heart failure BD1Z Phase 2 [27]
YT-146 DM3YVKQ Hypertension BA00-BA04 Phase 2 [54]
AB928 DMDOXMN Metastatic colorectal cancer 2B91 Phase 1/2 [36]
KF-17837 DMQ6DLZ Parkinson disease 8A00.0 Phase 1 [55]
Xanthine DMFBOQ7 Apnea MD11.0 Phase 1 [56]
CVT-6883 DMY84TW Asthma CA23 Phase 1 [57]
PBF-1129 DMOPGXM Non-small-cell lung cancer 2C25.Y Phase 1 [36]
PF-1913539 DMXEU14 Alzheimer disease 8A20 Discontinued in Phase 3 [58]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Caffeine DMKBJWP Orthostatic hypotension BA21 Approved [59]
Rolofylline DMSZPR3 Heart failure BD10-BD13 Phase 3 [60]
Tonapofylline DMBH316 Acute and chronic heart failure BD1Z Phase 2 [27]
AMP-579 DMJ4GPR Hyperlipidaemia 5C80 Phase 2 [61]
SELODENOSON DMQM3IX Cardiac arrhythmias BC9Z Phase 2 [62]
Apaxifylline DMQMV9F Cognitive impairment 6D71 Phase 2 [63]
SLV320 DM867BJ Heart failure BD10-BD13 Phase 2 [64]
DTI-0009 DMV84OK Atrial fibrillation BC81.3 Phase 2 [62]
Capadenoson DMYWO62 Atrial fibrillation BC81.3 Phase 2 [65]
BAY 1067197 DM4JGNH Heart failure BD10-BD13 Phase 2 [66]
⏷ 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
Adenosine A1 receptor (ADORA1) TTK25J1 AA1R_HUMAN Antagonist [3]
Adenosine A2b receptor (ADORA2B) TTNE7KG AA2BR_HUMAN Antagonist [3]
Adenosine A3 receptor (ADORA3) TTJFY5U AA3R_HUMAN Antagonist [3] , [4]
Androgen receptor messenger RNA (AR mRNA) TTKPW01 ANDR_HUMAN Inhibitor [5]
Aromatase (CYP19A1) TTSZLWK CP19A_HUMAN Inhibitor [6]
GABA(A) receptor alpha-1 (GABRA1) TT1MPAY GBRA1_HUMAN Inhibitor [7]
Gamma-aminobutyric acid receptor (GAR) TTNJYV2 NOUNIPROTAC Inhibitor [2]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 2A6 (CYP2A6) DEJVYAZ CP2A6_HUMAN Substrate [8]
Naphthalene dioxygenase (doxB) DEE76YZ NDOB_PSEU8 Substrate [9]
Biphenyl dioxygenase (bphC) DEUX61H BPHC_PSEFK Substrate [9]

References

1 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. (Ligand id: 409).
2 Refinement and evaluation of a pharmacophore model for flavone derivatives binding to the benzodiazepine site of the GABA(A) receptor. J Med Chem. 2002 Sep 12;45(19):4188-201.
3 Synthesis and biological activities of flavonoid derivatives as A3 adenosine receptor antagonists. J Med Chem. 1996 Jun 7;39(12):2293-301.
4 Interactions of flavonoids and other phytochemicals with adenosine receptors. J Med Chem. 1996 Feb 2;39(3):781-8.
5 Effect of flavonoids on androgen and glucocorticoid receptors based on in vitro reporter gene assay. Bioorg Med Chem Lett. 2009 Aug 15;19(16):4706-10.
6 Pharmacophore modeling strategies for the development of novel nonsteroidal inhibitors of human aromatase (CYP19). Bioorg Med Chem Lett. 2010 May 15;20(10):3050-64.
7 Synthesis of halogenated/nitrated flavone derivatives and evaluation of their affinity for the central benzodiazepine receptor, Bioorg. Med. Chem. Lett. 7(15):2003-2008 (1997).
8 Site-specific oxidation of flavanone and flavone by cytochrome P450 2A6 in human liver microsomes. Xenobiotica. 2019 Jul;49(7):791-802.
9 Flavonoids biotransformation by bacterial non-heme dioxygenases, biphenyl and naphthalene dioxygenase. Appl Microbiol Biotechnol. 2011 Jul;91(2):219-28.
10 Roles of cytochromes P450 1A2, 2A6, and 2C8 in 5-fluorouracil formation from tegafur, an anticancer prodrug, in human liver microsomes. Drug Metab Dispos. 2000 Dec;28(12):1457-63.
11 Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.
12 Genotoxicity of tamoxifen, tamoxifen epoxide and toremifene in human lymphoblastoid cells containing human cytochrome P450s. Carcinogenesis. 1994 Jan;15(1):5-9.
13 Metabolic interactions between acetaminophen (paracetamol) and two flavonoids, luteolin and quercetin, through in-vitro inhibition studies. J Pharm Pharmacol. 2017 Dec;69(12):1762-1772.
14 Psychotropic drug interactions with valproate. Clin Neuropharmacol. 2005 Mar-Apr;28(2):96-101.
15 The role of human cytochrome P450 enzymes in the formation of 2-hydroxymetronidazole: CYP2A6 is the high affinity (low Km) catalyst. Drug Metab Dispos. 2013 Sep;41(9):1686-94.
16 Possible involvement of multiple human cytochrome P450 isoforms in the liver metabolism of propofol. Br J Anaesth. 1998 Jun;80(6):788-95.
17 CYP2A6- and CYP2A13-catalyzed metabolism of the nicotine delta-5'(1')iminium ion. J Pharmacol Exp Ther. 2012 Nov;343(2):307-15.
18 Effective aromatase inhibition by anastrozole in a patient with gonadotropin-independent precocious puberty in McCune-Albright syndrome. J Pediatr Endocrinol Metab. 2002;15 Suppl 3:945-8.
19 Aromatase inhibitors--theoretical concept and present experiences in the treatment of endometriosis. Zentralbl Gynakol. 2003 Jul-Aug;125(7-8):247-51.
20 Aminoglutethimide-induced protein free radical formation on myeloperoxidase: a potential mechanism of agranulocytosis. Chem Res Toxicol. 2007 Jul;20(7):1038-45.
21 Enantioselective nonsteroidal aromatase inhibitors identified through a multidisciplinary medicinal chemistry approach. J Med Chem. 2005 Nov 17;48(23):7282-9.
22 Aromatase inhibitors for male infertility. J Urol. 2002 Feb;167(2 Pt 1):624-9.
23 Toremifene-atamestane; alone or in combination: predictions from the preclinical intratumoral aromatase model. J Steroid Biochem Mol Biol. 2008 Jan;108(1-2):1-7.
24 Highly potent first examples of dual aromatase-steroid sulfatase inhibitors based on a biphenyl template. J Med Chem. 2010 Mar 11;53(5):2155-70.
25 Emerging drugs in neuropathic pain. Expert Opin Emerg Drugs. 2007 Mar;12(1):113-26.
26 A role for central A3-adenosine receptors. Mediation of behavioral depressant effects. FEBS Lett. 1993 Dec 20;336(1):57-60.
27 2-Amino-5-benzoyl-4-phenylthiazoles: Development of potent and selective adenosine A1 receptor antagonists. Bioorg Med Chem. 2010 Mar 15;18(6):2195-2203.
28 Spiroindolones, a potent compound class for the treatment of malaria. Science. 2010 Sep 3;329(5996):1175-80.
29 2011 Pipeline of Can-Fite BioPharm.
30 Synthesis and evaluation of 1,2,4-triazolo[1,5-c]pyrimidine derivatives as A2A receptor-selective antagonists. Bioorg Med Chem Lett. 2010 Oct 1;20(19):5690-4.
31 2-n-Butyl-9-methyl-8-[1,2,3]triazol-2-yl-9H-purin-6-ylamine and analogues as A2A adenosine receptor antagonists. Design, synthesis, and pharmacolog... J Med Chem. 2005 Nov 3;48(22):6887-96.
32 Protein kinase C protects preconditioned rabbit hearts by increasing sensitivity of adenosine A2b-dependent signaling during early reperfusion. J Mol Cell Cardiol. 2007 Sep;43(3):262-71.
33 Novel amino acid derived natural products from the ascidian Atriolum robustum: identification and pharmacological characterization of a unique aden... J Med Chem. 2004 Apr 22;47(9):2243-55.
34 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: 628).
35 Synthesis and biological activity of a novel, highly potent progesterone receptor antagonist. J Med Chem. 2000 Dec 28;43(26):5010-6.
36 Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
37 Clinical pipeline report, company report or official report of ISIS Pharmaceuticals.
38 2011 Pipeline of Santaris Pharma.
39 Effect of essential oils, such as raspberry ketone and its derivatives, on antiandrogenic activity based on in vitro reporter gene assay. Bioorg Med Chem Lett. 2010 Apr 1;20(7):2111-4.
40 Rational design and synthesis of 4-((1R,2R)-2-hydroxycyclohexyl)-2(trifluoromethyl)benzonitrile (PF-998425), a novel, nonsteroidal androgen recepto... J Med Chem. 2008 Nov 13;51(21):7010-4.
41 Antiinflammatory glucocorticoid receptor ligand with reduced side effects exhibits an altered protein-protein interaction profile. Proc Natl Acad Sci U S A. 2007 Dec 4;104(49):19244-9.
42 DrugBank: a knowledgebase for drugs, drug actions and drug targets. Nucleic Acids Res. 2008 Jan;36(Database issue):D901-6.
43 Zolpidem, a selective GABA(A) receptor alpha1 subunit agonist, induces comparable Fos expression in oxytocinergic neurons of the hypothalamic paraventricular and accessory but not supraoptic nuclei in the rat.Brain Res Bull.2006 Dec 11;71(1-3):200-7.
44 Neurosteroid analogues. 10. The effect of methyl group substitution at the C-6 and C-7 positions on the GABA modulatory and anesthetic actions of (... J Med Chem. 2005 Apr 21;48(8):3051-9.
45 3-demethoxy-3-glycosylaminothiocolchicines: Synthesis of a new class of putative muscle relaxant compounds. J Med Chem. 2006 Sep 7;49(18):5571-7.
46 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
47 Neurosteroid analogues. 11. Alternative ring system scaffolds: gamma-aminobutyric acid receptor modulation and anesthetic actions of benz[f]indenes. J Med Chem. 2006 Jul 27;49(15):4595-605.
48 Glutamate- and GABA-based CNS therapeutics. Curr Opin Pharmacol. 2006 Feb;6(1):7-17.
49 Cyclooctadepsipeptides--an anthelmintically active class of compounds exhibiting a novel mode of action. Int J Antimicrob Agents. 2003 Sep;22(3):318-31.
50 Synthesis and binding affinity of 2-phenylimidazo[1,2-alpha]pyridine derivatives for both central and peripheral benzodiazepine receptors. A new se... J Med Chem. 1997 Sep 12;40(19):3109-18.
51 2018 FDA drug approvals.Nat Rev Drug Discov. 2019 Feb;18(2):85-89.
52 DP-VPA D-Pharm. Curr Opin Investig Drugs. 2002 Jun;3(6):921-3.
53 Structural requirements for agonist actions at the benzodiazepine receptor: studies with analogues of 6-(benzyloxy)-4-(methoxymethyl)-beta-carbolin... J Med Chem. 1990 Mar;33(3):1062-9.
54 Identification of adenosine A2 receptor-cAMP system in human aortic endothelial cells. Biochem Biophys Res Commun. 1994 Mar 15;199(2):905-10.
55 Photoisomerization of a potent and selective adenosine A2 antagonist, (E)-1,3-Dipropyl-8-(3,4-dimethoxystyryl)-7-methylxanthine. J Med Chem. 1993 Nov 12;36(23):3731-3.
56 Role of adenosine in asthma. Drug Dev Res. 1996;39:333-6.
57 GS-6201, a selective blocker of the A2B adenosine receptor, attenuates cardiac remodeling after acute myocardial infarction in the mouse. J Pharmacol Exp Ther. 2012 Dec;343(3):587-95.
58 Differences in the order of potency for agonists but not antagonists at human and rat adenosine A2A receptors. Biochem Pharmacol. 1999 Jan 1;57(1):65-75.
59 Caffeine as a psychomotor stimulant: mechanism of action. Cell Mol Life Sci. 2004 Apr;61(7-8):857-72.
60 Association between the PDE4D gene and ischaemic stroke in the Chinese Han population. Clin Sci (Lond). 2009 Aug 17;117(7):265-72.
61 Adenosine A1/A2a receptor agonist AMP-579 induces acute and delayed preconditioning against in vivo myocardial stunning. Am J Physiol Heart Circ Physiol. 2004 Dec;287(6):H2746-53.
62 Recent developments in adenosine receptor ligands and their potential as novel drugs. Biochim Biophys Acta. 2011 May;1808(5):1290-308.
63 Trusted, scientifically sound profiles of drug programs, clinical trials, safety reports, and company deals, written by scientists. Springer. 2015. Adis Insight (drug id 800004779)
64 Role of matrix metalloproteinases and their tissue inhibitors as potential biomarkers of left ventricular remodelling in the athlete's heart. Clin Sci (Lond). 2009 Jul 16;117(4):157-64.
65 A1 adenosine receptor agonists and their potential therapeutic applications. Expert Opin Investig Drugs. 2008 Dec;17(12):1901-10.
66 Separation of on-target efficacy from adverse effects through rational design of a bitopic adenosine receptor agonist. Current Issue vol. 111 no. 12 Celine Valant, 4614-4619.