General Information of Drug (ID: DMNX245)

Drug Name
NSC-26745 Drug Info
Synonyms
5-Hydroxyflavone; 491-78-1; Primuletin; 5-hydroxy-2-phenyl-4H-chromen-4-one; 5-hydroxy-2-phenylchromen-4-one; NSC-26745; 5-Hydroxy-2-phenyl-chromen-4-one; NSC 26745; 5-Hydroxy-2-phenylchromone; UNII-378AE9MHL3; CHEMBL16807; MLS002639146; 378AE9MHL3; IYBLVRRCNVHZQJ-UHFFFAOYSA-N; NSC26745; MFCD00016944; 4H-1-Benzopyran-4-one,5-hydroxy-2-phenyl-; Primuliten; 5-hydroxy-flavone; 5-Hydroxy-2-phenyl-4-benzopyrone; EINECS 207-743-1; 5-hydroxy-2-phenyl-4h-chromen-4-on; AC1Q6AKC; ACMC-209kf5; Oprea1_688541; 5-Hydroxyflavone, >=97%
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Cross-matching ID
PubChem CID
68112
CAS Number
CAS 491-78-1
TTD Drug ID
DMNX245

Molecule-Related Drug Atlas

Molecule-Related Drug Atlas
Molecule Type:
DTT
DOT
Drug Status:
Approved Drug(s)
Clinical Trial Drug(s)
Patented Agent(s)
Discontinued Drug(s)
Investigative Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Dihydrotestosterone DM3S8XC Prostate hyperplasia GA90 Phase 4 [4]
BAY 86-5044 DMRZLU4 Breast cancer 2C60-2C65 Phase 2 [5]
TRC-253 DMXI8CD Prostate cancer 2C82.0 Phase 1/2 [6]
IONIS-AR-2.5Rx DMF2DMS Prostate cancer 2C82.0 Phase 1/2 [7]
ISIS-AR DM8P3N5 Prostate cancer 2C82.0 Phase 1 [8]
EZN-4176 DMNPS59 Prostate cancer 2C82.0 Phase 1 [9]
EUGENOL DM7US1H Discovery agent N.A. Patented [10]
RU-58841 DMMEAZ2 Acne vulgaris ED80 Discontinued in Phase 1 [11]
flavone DMEQH6J Discovery agent N.A. Investigative [1]
APIGENIN DMI3491 Discovery agent N.A. Investigative [1]
⏷ 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 [12]
Riluzole DMECBWN Amyotrophic lateral sclerosis 8B60.0 Approved [13]
Flutamide DMK0O7U Prostate cancer 2C82.0 Approved [14]
Menadione DMSJDTY Vitamin K deficiency 5B59 Approved [15]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [16]
Troglitazone DM3VFPD Diabetic complication 5A2Y Approved [17]
Ethacrynic acid DM60QMR Edema MG29 Approved [18]
Marinol DM70IK5 Anorexia nervosa cachexia 6B80 Approved [19]
Ethinyl Estradiol DMODJ40 Acne vulgaris ED80 Approved [20]
Clofibrate DMPC1J7 Dysbetalipoproteinemia 5C80.2 Approved [21]
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Drug(s) Affected By Cytochrome P450 1A2 (CYP1A2)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Zolmitriptan DM1IB4Q Migraine 8A80 Approved [22]
Rofecoxib DM3P5DA Osteoarthritis FA00-FA05 Approved [22]
Etoricoxib DM6A4NW Rheumatoid arthritis FA20 Approved [22]
Capsaicin DMGMF6V Back pain ME84.Z Approved [23]
Hesperetin DMKER83 High blood cholesterol level 5C80.00 Approved [24]
Stiripentol DMMSDOY Dravet syndrome 8A61.11 Approved [25]
Nifedipine DMSVOZT Angina pectoris BA40 Approved [26]
Zileuton DMVRIC2 Allergic asthma CA23.0 Approved [27]
Nicotine DMWX5CO Lung cancer 2C25.0 Approved [28]
Clonidine DM6RZ9Q Attention deficit hyperactivity disorder 6A05.Z Approved [29]
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Drug(s) Affected By Cytochrome P450 3A4 (CYP3A4)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Eplerenone DMF0NQR Heart failure BD10-BD13 Approved [30]
Cannabidiol DM0659E Dravet syndrome 8A61.11 Approved [31]
Isotretinoin DM4QTBN Acne vulgaris ED80 Approved [32]
Voriconazole DMAOL2S Aspergillosis 1F20 Approved [33]
Proguanil DMBL79I Malaria 1F40-1F45 Approved [34]
Ivermectin DMDBX5F Intestinal strongyloidiasis due to nematode parasite 1F6B Approved [34]
Loratadine DMF3AN7 Allergy 4A80-4A85 Approved [35]
Nelfinavir mesylate DMFX6G8 N. A. N. A. Approved [36]
Capsaicin DMGMF6V Back pain ME84.Z Approved [37]
Axitinib DMGVH6N Renal cell carcinoma 2C90 Approved [38]
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Drug(s) Affected By Cytochrome P450 2B6 (CYP2B6)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Sertraline DM0FB1J Coronary heart disease BA80.Z Approved [39]
Ritonavir DMU764S Human immunodeficiency virus infection 1C62 Approved [40]
Rifampicin DM5DSFZ Non-insulin dependent diabetes 5A11 Approved [41]
Thalidomide DM70BU5 Adult T-cell leukemia/lymphoma Approved [42]
Phenytoin DMNOKBV Epilepsy 8A60-8A68 Approved [43]
Clopidogrel DMOL54H Acute coronary syndrome BA41 Approved [44]
Artemisinin DMOY7W3 Malaria 1F40-1F45 Approved [45]
Malathion DMXZ84M Pediculus capitis infestation 1G00.0 Approved [46]
Phenobarbital DMXZOCG Cluster headache 8A81.0 Approved [47]
Permethrin DMZ0Q1G Pediculus capitis infestation 1G00.0 Approved [48]
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Drug(s) Affected By Cytochrome P450 2A13 (CYP2A13)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Tretinoin DM49DUI Acne vulgaris ED80 Approved [49]
Rifampicin DM5DSFZ Non-insulin dependent diabetes 5A11 Approved [50]
Phenobarbital DMXZOCG Cluster headache 8A81.0 Approved [50]
Amodiaquine DME4RA8 Malaria 1F40-1F45 Approved [51]
Benzo(a)pyrene DMN7J43 N. A. N. A. Phase 1 [52]
HELENALIN DMMCI4H N. A. N. A. Terminated [53]
Acenaphthenol DMT3QYZ N. A. N. A. Investigative [54]
COUMARIN DM0N8ZM Discovery agent N.A. Investigative [55]
BRN-3548355 DM4KXT0 N. A. N. A. Investigative [55]
Chrysin DM7V2LG Discovery agent N.A. Investigative [3]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Cytochrome P450 1B1 (CYP1B1)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Flutamide DMK0O7U Prostate cancer 2C82.0 Approved [13]
Hydrogen peroxide DM1NG5W Infectious disease 1A00-CA43.1 Approved [56]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [57]
Progesterone DMUY35B Amenorrhea GA20.0 Approved [58]
Estrone DM5T6US Acne vulgaris ED80 Approved [59]
Melatonin DMKWFBT Depression 6A70-6A7Z Approved [60]
Vitamin A DMJ2AH4 Night blindness 9D45 Approved [61]
Amodiaquine DME4RA8 Malaria 1F40-1F45 Approved [51]
Daunorubicin DMQUSBT Acute monocytic leukemia Approved [62]
Pantothenic acid DM091H2 Vitamin deficiency 5B55-5B71 Approved [63]
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Molecular Interaction Atlas of This Drug

Molecular Interaction Atlas

Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Androgen receptor messenger RNA (AR mRNA) TTKPW01 ANDR_HUMAN Inhibitor [1]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Cytochrome P450 1A1 (CYP1A1) OTE4EFH8 CP1A1_HUMAN Gene/Protein Processing [2]
Cytochrome P450 1A2 (CYP1A2) OTLLBX48 CP1A2_HUMAN Gene/Protein Processing [2]
Cytochrome P450 1B1 (CYP1B1) OTYXFLSD CP1B1_HUMAN Biotransformations [3]
Cytochrome P450 2A13 (CYP2A13) OTVUDLT3 CP2AD_HUMAN Biotransformations [3]
Cytochrome P450 2B6 (CYP2B6) OTOYO4S7 CP2B6_HUMAN Biotransformations [3]
Cytochrome P450 3A4 (CYP3A4) OTQGYY83 CP3A4_HUMAN Gene/Protein Processing [2]

References

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3 Oxidation of Flavone, 5-Hydroxyflavone, and 5,7-Dihydroxyflavone to Mono-, Di-, and Tri-Hydroxyflavones by Human Cytochrome P450 Enzymes. Chem Res Toxicol. 2019 Jun 17;32(6):1268-1280. doi: 10.1021/acs.chemrestox.9b00078. Epub 2019 Apr 17.
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30 The relative role of CYP3A4 and CYP3A5 in eplerenone metabolism. Toxicol Lett. 2019 Oct 15;315:9-13.
31 Characterization of the structural determinants required for potent mechanism-based inhibition of human cytochrome P450 1A1 by cannabidiol. Chem Biol Interact. 2014 May 25;215:62-8.
32 Retinoids activate the RXR/SXR-mediated pathway and induce the endogenous CYP3A4 activity in Huh7 human hepatoma cells. Toxicol Sci. 2006 Jul;92(1):51-60.
33 The novel azole R126638 is a selective inhibitor of ergosterol synthesis in Candida albicans, Trichophyton spp., and Microsporum canis. Antimicrob Agents Chemother. 2004 Sep;48(9):3272-8.
34 Application of higher throughput screening (HTS) inhibition assays to evaluate the interaction of antiparasitic drugs with cytochrome P450s. Drug Metab Dispos. 2001 Jan;29(1):30-5.
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36 Mechanism-based inactivation of CYP3A by HIV protease inhibitors. J Pharmacol Exp Ther. 2005 Feb;312(2):583-91.
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38 Investigation of the effects of axitinib on the pharmacokinetics of loperamide and its main metabolite N-demethylated loperamide in rats by UPLC-MS/MS. Chem Biol Interact. 2019 Sep 1;310:108744. doi: 10.1016/j.cbi.2019.108744. Epub 2019 Jul 9.
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40 Transcriptional profiling suggests that Nevirapine and Ritonavir cause drug induced liver injury through distinct mechanisms in primary human hepatocytes. Chem Biol Interact. 2016 Aug 5;255:31-44.
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42 Thalidomide increases human hepatic cytochrome P450 3A enzymes by direct activation of the pregnane X receptor. Chem Res Toxicol. 2014 Feb 17;27(2):304-308.
43 Human constitutive androstane receptor mediates induction of CYP2B6 gene expression by phenytoin. J Biol Chem. 2004 Jul 9;279(28):29295-301. doi: 10.1074/jbc.M400580200. Epub 2004 Apr 28.
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48 Pyrethroids: cytotoxicity and induction of CYP isoforms in human hepatocytes. Drug Metabol Drug Interact. 2008;23(3-4):211-36.
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50 Characterization of primary human hepatocytes, HepG2 cells, and HepaRG cells at the mRNA level and CYP activity in response to inducers and their predictivity for the detection of human hepatotoxins. Cell Biol Toxicol. 2012 Apr;28(2):69-87.
51 Apoptosis contributes to the cytotoxicity induced by amodiaquine and its major metabolite N-desethylamodiaquine in hepatic cells. Toxicol In Vitro. 2020 Feb;62:104669. doi: 10.1016/j.tiv.2019.104669. Epub 2019 Oct 16.
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53 In vitro metabolism of helenalin and its inhibitory effect on human cytochrome P450 activity. Arch Toxicol. 2022 Mar;96(3):793-808. doi: 10.1007/s00204-021-03218-6. Epub 2022 Jan 6.
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55 Functional characterization of CYP2A13 polymorphisms. Xenobiotica. 2007 Dec;37(12):1439-49. doi: 10.1080/00498250701666265.
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62 Genetic variants contributing to daunorubicin-induced cytotoxicity. Cancer Res. 2008 May 1;68(9):3161-8. doi: 10.1158/0008-5472.CAN-07-6381.
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