General Information of Drug (ID: DMHAZLM)

Drug Name
Naringenin Drug Info
Synonyms
naringenin; 5,7-Dihydroxy-2-(4-hydroxyphenyl)chroman-4-one; 67604-48-2; 4',5,7-Trihydroxyflavanone; Naringenine; (+/-)-Naringenin; naringetol; 480-41-1; salipurpol; (-)-Naringenin; NARIGENIN; Salipurol; 5,7,4'-Trihydroxyflavanone; 93602-28-9; (S)-Naringenin; BE-14348A; NSC 34875; ( inverted exclamation markA)-Naringenin; CHEMBL32571; MLS000738094; MLS000028739; CHEBI:50202; Flavanone, 4',5,7-trihydroxy-; FTVWIRXFELQLPI-UHFFFAOYSA-N; NSC34875; NSC11855; MFCD00006844; SMR000059039; AK122638; NSC 11855; 4',7-Trihydroxyflavanone
Cross-matching ID
PubChem CID
932
ChEBI ID
CHEBI:50202
CAS Number
CAS 67604-48-2
TTD Drug ID
DMHAZLM
VARIDT Drug ID
DR00833
INTEDE Drug ID
DR2246

Molecule-Related Drug Atlas

Molecule-Related Drug Atlas
Molecule Type:
DTT
DTP
DME
Drug Status:
Approved Drug(s)
Discontinued Drug(s)
Investigative Drug(s)
Clinical Trial Drug(s)
Drug(s) Metabolized By Cytochrome P450 105D7 (cyp105)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Diclofenac DMPIHLS Osteoarthritis FA00-FA05 Approved [7]
Mevastatin DM1LGKP N. A. N. A. Terminated [7]
Q-27137207 DML5KMT Discovery agent N.A. Investigative [7] , [8]
Drug(s) Transported By P-glycoprotein 1 (ABCB1)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Amoxicillin DMUYNEI Bacterial infection 1A00-1C4Z Approved [9]
Doxorubicin DMVP5YE Solid tumour/cancer 2A00-2F9Z Approved [10]
Methotrexate DM2TEOL leukaemia 2A60-2B33 Approved [11]
Folic acid DMEMBJC Folate-deficiency anemia 3A02.Y Approved [12]
Fluorouracil DMUM7HZ Solid tumour/cancer 2A00-2F9Z Approved [11]
Cisplatin DMRHGI9 Solid tumour/cancer 2A00-2F9Z Approved [11]
Progesterone DMUY35B Premature labour JB00 Approved [13]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [11]
Estradiol DMUNTE3 Breast cancer 2C60-2C65 Approved [14]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [15]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Targeting Aromatase (CYP19A1)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Anastrozole DMNP60F Breast cancer 2C60-2C65 Approved [16]
Letrozole DMH07Y3 Hormonally-responsive breast cancer 2C60-2C65 Approved [17]
Exemestane DM9HPW3 Hormonally-responsive breast cancer 2C60-2C65 Approved [17]
Aminoglutethimide DMWFHMZ Cushing disease 5A70 Approved [18]
FADROZOLE DM3C5GZ Breast cancer 2C60-2C65 Approved [19]
Testolactone DMVY4GN Breast cancer 2C60-2C65 Approved [20]
Atamestane + Toremifene DM3QLK2 Breast cancer 2C60-2C65 Phase 3 [21]
LIAROZOLE DM4OYXE Dermatological disease DA24.Y Phase 2/3 [1]
Coumate DMVKW0N Breast cancer 2C60-2C65 Phase 2 [22]
Dextromethorphan+quinidine DMFI5J4 Diabetic neuropathy 8C0Z Phase 2 [23]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Nicotinamide-Adenine-Dinucleotide DM9LRKB N. A. N. A. Investigative [24]
2'-Monophosphoadenosine 5'-Diphosphoribose DME9S8M Discovery agent N.A. Investigative [24]
Apigenin DMI3491 Discovery agent N.A. Investigative [3]
Kaempferol DMHEMUB Discovery agent N.A. Investigative [3]
4-ANDROSTENE-3-17-DIONE DMSE8NU Discovery agent N.A. Investigative [24]
6-(3-Hydroxy-phenyl)-naphthalen-2-ol DMH8WA2 Discovery agent N.A. Investigative [25]
7-(3-Hydroxy-phenyl)-naphthalen-2-ol DM2I91C Discovery agent N.A. Investigative [26]
NSC-94258 DM6VY3P Discovery agent N.A. Investigative [3]
4-[5-(3-Hydroxyphenyl)-3-thienyl]-2-methylphenol DM7ERYJ Discovery agent N.A. Investigative [27]
6-(4-Hydroxy-phenyl)-naphthalen-1-ol DM2V9XI Discovery agent N.A. Investigative [26]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Conjugated estrogens DMLT0E1 Menopause symptom GA30.0 Approved [28]
Trilostane DMQZ9GF Cushing disease 5A70 Approved [29]
ARZOXIFENE DMOKCVI Breast cancer 2C60-2C65 Approved [30]
Estrogen DMGY0UT Menopause symptom GA30.0 Approved [31]
Premarin/Pravachol DMLSOB7 Hyperlipidaemia 5C80 Phase 3 [32]
MF-101 DM8Z0I3 Hepatitis virus infection 1E50-1E51 Phase 3 [33]
Genistein DM0JETC Menopause symptom GA30.0 Phase 2/3 [34]
AUS-131 DMZMSQJ Hot flushes GA30 Phase 2 [35]
ERB-041 DMCEPUA Inflammatory bowel disease DD72 Phase 2 [36]
Erteberel DMU1XZD Prostate hyperplasia GA90 Phase 2 [37]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
BAICALEIN DM4C7E6 Influenza virus infection 1E30-1E32 Phase 2 [5]
2-Sulfhydryl-Ethanol DMJBO3D Discovery agent N.A. Investigative [38]
Kaempferol DMHEMUB Discovery agent N.A. Investigative [5]
S-(N-butyl-N-hydroxycarbamoyl)glutathione DMU7EQV Discovery agent N.A. Investigative [39]
S-(N-heptyl-N-hydroxycarbamoyl)glutathione DMV6T1Q Discovery agent N.A. Investigative [39]
S-(N-propyl-N-hydroxycarbamoyl)glutathione DMRFKZ6 Discovery agent N.A. Investigative [39]
S-(N-Hydroxy-N-Iodophenylcarbamoyl)Glutathione DM1AHIW Discovery agent N.A. Investigative [38]
S-(N-pentyl-N-hydroxycarbamoyl)glutathione DM4E9J2 Discovery agent N.A. Investigative [39]
S-(N-methyl-N-hydroxycarbamoyl)glutathione DM1C9W3 Discovery agent N.A. Investigative [39]
S-(N-4bromophenyl-N-hydroxycarbamoyl)glutathione DM3FXPV Discovery agent N.A. Investigative [39]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
PINOCEMBRIN DM96VWD N. A. N. A. Phase 2 [2]
Chrysin DM7V2LG Discovery agent N.A. Investigative [2]
Apigenin DMI3491 Discovery agent N.A. Investigative [2]
Kaempferol DMHEMUB Discovery agent N.A. Investigative [2]
ISORHAMNETIN DMQ4Z6E Discovery agent N.A. Investigative [2]
Acacetin DMQOB0X Discovery agent N.A. Investigative [2]
TRISMETHOXYRESVERATROL DM6USPC Discovery agent N.A. Investigative [40]
Galangin DM5TQ2O Discovery agent N.A. Investigative [2]
CHRYSOERIOL DM96ECL Discovery agent N.A. Investigative [2]
DIOSMETIN DM4KXIM Discovery agent N.A. Investigative [2]
⏷ 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
Aromatase (CYP19A1) TTSZLWK CP19A_HUMAN Inhibitor [1]
Cytochrome P450 1B1 (CYP1B1) TTI84H7 CP1B1_HUMAN Inhibitor [2]
Estradiol 17 beta-dehydrogenase 1 (17-beta-HSD1) TTIWB6L DHB1_HUMAN Inhibitor [3]
Estrogen receptor beta (ESR2) TTOM3J0 ESR2_HUMAN Inhibitor [4]
Lactoylglutathione lyase (GLO1) TTV9A7R LGUL_HUMAN Inhibitor [5]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
P-glycoprotein 1 (ABCB1) DTUGYRD MDR1_HUMAN Substrate [6]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 105D7 (cyp105) Main DME DECV2ME CYP28_STRAW Substrate [7] , [8]

References

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2 Selective inhibition of methoxyflavonoids on human CYP1B1 activity. Bioorg Med Chem. 2010 Sep 1;18(17):6310-5.
3 Discovery of nonsteroidal 17beta-hydroxysteroid dehydrogenase 1 inhibitors by pharmacophore-based screening of virtual compound libraries. J Med Chem. 2008 Jul 24;51(14):4188-99.
4 Subtle side-chain modifications of the hop phytoestrogen 8-prenylnaringenin result in distinct agonist/antagonist activity profiles for estrogen re... J Med Chem. 2006 Dec 14;49(25):7357-65.
5 Structure-activity relationship of human GLO I inhibitory natural flavonoids and their growth inhibitory effects. Bioorg Med Chem. 2008 Apr 1;16(7):3969-75.
6 Flavonoid permeability across an in situ model of the blood-brain barrier. Free Radic Biol Med. 2004 Mar 1;36(5):592-604.
7 The metagenome of Caracolus marginella gut microbiome using culture independent approaches and shotgun sequencing. Data Brief. 2017 Nov 22;16:501-505.
8 Hydroxylation of Compactin (ML-236B) by CYP105D7 (SAV_7469) from Streptomyces avermitilis. J Microbiol Biotechnol. 2017 May 28;27(5):956-964.
9 Human intestinal transporter database: QSAR modeling and virtual profiling of drug uptake, efflux and interactions. Pharm Res. 2013 Apr;30(4):996-1007.
10 MDR1 (ABCB1) G1199A (Ser400Asn) polymorphism alters transepithelial permeability and sensitivity to anticancer agents. Cancer Chemother Pharmacol. 2009 Jun;64(1):183-8.
11 Mammalian drug efflux transporters of the ATP binding cassette (ABC) family in multidrug resistance: A review of the past decade. Cancer Lett. 2016 Jan 1;370(1):153-64.
12 Folate transporter expression decreases in the human placenta throughout pregnancy and in pre-eclampsia. Pregnancy Hypertens. 2012 Apr;2(2):123-31.
13 Comparative studies on in vitro methods for evaluating in vivo function of MDR1 P-glycoprotein. Pharm Res. 2001 Dec;18(12):1660-8.
14 Antiestrogens and steroid hormones: substrates of the human P-glycoprotein. Biochem Pharmacol. 1994 Jul 19;48(2):287-92.
15 Association of genetic polymorphisms in the influx transporter SLCO1B3 and the efflux transporter ABCB1 with imatinib pharmacokinetics in patients with chronic myeloid leukemia. Ther Drug Monit. 2011 Apr;33(2):244-50.
16 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.
17 Aromatase inhibitors--theoretical concept and present experiences in the treatment of endometriosis. Zentralbl Gynakol. 2003 Jul-Aug;125(7-8):247-51.
18 Aminoglutethimide-induced protein free radical formation on myeloperoxidase: a potential mechanism of agranulocytosis. Chem Res Toxicol. 2007 Jul;20(7):1038-45.
19 Enantioselective nonsteroidal aromatase inhibitors identified through a multidisciplinary medicinal chemistry approach. J Med Chem. 2005 Nov 17;48(23):7282-9.
20 Aromatase inhibitors for male infertility. J Urol. 2002 Feb;167(2 Pt 1):624-9.
21 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.
22 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.
23 Emerging drugs in neuropathic pain. Expert Opin Emerg Drugs. 2007 Mar;12(1):113-26.
24 How many drug targets are there Nat Rev Drug Discov. 2006 Dec;5(12):993-6.
25 Substituted 6-phenyl-2-naphthols. Potent and selective nonsteroidal inhibitors of 17beta-hydroxysteroid dehydrogenase type 1 (17beta-HSD1): design,... J Med Chem. 2008 Aug 14;51(15):4685-98.
26 Design, synthesis, and biological evaluation of (hydroxyphenyl)naphthalene and -quinoline derivatives: potent and selective nonsteroidal inhibitors... J Med Chem. 2008 Apr 10;51(7):2158-69.
27 New insights into the SAR and binding modes of bis(hydroxyphenyl)thiophenes and -benzenes: influence of additional substituents on 17beta-hydroxyst... J Med Chem. 2009 Nov 12;52(21):6724-43.
28 Differential biochemical and cellular actions of Premarin estrogens: distinct pharmacology of bazedoxifene-conjugated estrogens combination. Mol Endocrinol. 2009 Jan;23(1):74-85.
29 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
30 Benzothiophene selective estrogen receptor modulators with modulated oxidative activity and receptor affinity. J Med Chem. 2007 May 31;50(11):2682-92.
31 Estrogen inhibits the vascular injury response in estrogen receptor beta-deficient female mice. Proc Natl Acad Sci U S A. 1999 Dec 21;96(26):15133-6.
32 Lovastatin and beyond: the history of the HMG-CoA reductase inhibitors. Nat Rev Drug Discov. 2003 Jul;2(7):517-26.
33 MF101, a selective estrogen receptor beta modulator for the treatment of menopausal hot flushes: a phase II clinical trial. Menopause. 2009 May-Jun;16(3):458-65.
34 Company report (Axcentua)
35 S-equol, a potent ligand for estrogen receptor beta, is the exclusive enantiomeric form of the soy isoflavone metabolite produced by human intestinal bacterial flora. Am J Clin Nutr. 2005 May;81(5):1072-9.
36 Erb-041, an estrogen receptor-beta agonist, inhibits skin photocarcinogenesis in SKH-1 hairless mice by downregulating the WNT signaling pathway. Cancer Prev Res (Phila). 2014 Feb;7(2):186-98.
37 Trusted, scientifically sound profiles of drug programs, clinical trials, safety reports, and company deals, written by scientists. Springer. 2015. Adis Insight (drug id 800031986)
38 DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Nucleic Acids Res. 2011 Jan;39(Database issue):D1035-41.
39 Role of hydrophobic interactions in binding S-(N-aryl/alkyl-N-hydroxycarbamoyl)glutathiones to the active site of the antitumor target enzyme glyoxalase I. J Med Chem. 2000 Oct 19;43(21):3981-6.
40 Design, synthesis, and discovery of novel trans-stilbene analogues as potent and selective human cytochrome P450 1B1 inhibitors. J Med Chem. 2002 Jan 3;45(1):160-4.