General Information of Drug (ID: DM3C5GZ)

Drug Name
FADROZOLE Drug Info
Synonyms
102676-47-1; CGS-16949A; Fadrozole [INN]; Fadrozolum [INN-Latin]; Fadrozol [INN-Spanish]; CHEMBL9298; Fadrozole (INN); 5-p-cyanophenyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyridine; Benzonitrile, 4-(5,6,7,8-tetrahydroimidazo(1,5-a)pyridin-5-yl)-; Fadrozolum; Fadrozol; 4-{5H,6H,7H,8H-imidazo[1,5-a]pyridin-5-yl}benzonitrile; Benzonitrile, 4-(5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-5-yl)-
Indication
Disease Entry ICD 11 Status REF
Breast cancer 2C60-2C65 Approved [1]
Cross-matching ID
PubChem CID
59693
ChEBI ID
CHEBI:94355
CAS Number
CAS 102676-47-1
TTD Drug ID
DM3C5GZ

Molecule-Related Drug Atlas

Molecule-Related Drug Atlas
Molecule Type:
DTT
DOT
Drug Status:
Approved Drug(s)
Clinical Trial Drug(s)
Discontinued Drug(s)
Investigative Drug(s)
Drug(s) Targeting Aromatase (CYP19A1)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Anastrozole DMNP60F Breast cancer 2C60-2C65 Approved [7]
Letrozole DMH07Y3 Estrogen-receptor positive breast cancer Approved [8]
Exemestane DM9HPW3 Hormonally-responsive breast cancer 2C60-2C65 Approved [8]
Aminoglutethimide DMWFHMZ Cushing disease 5A70 Approved [9]
Testolactone DMVY4GN Breast cancer 2C60-2C65 Approved [10]
LIAROZOLE DM4OYXE Dermatological disease DA24.Y Phase 2/3 [11]
Coumate DMVKW0N Breast cancer 2C60-2C65 Phase 2 [12]
BGS-649 DMO4MNQ Endometriosis GA10 Phase 2 [13]
NARINGENIN DMHAZLM N. A. N. A. Phase 1 [11]
FORMESTANE DMWIDJK Breast cancer 2C60-2C65 Withdrawn from market [14]
Letrozole DMH07Y3 Estrogen-receptor positive breast cancer Approved [27]
Cannabidiol DM0659E Dravet syndrome 8A61.11 Approved [28]
Sertraline DM0FB1J Coronary heart disease BA80.Z Approved [29]
Fulvestrant DM0YZC6 Breast cancer 2C60-2C65 Approved [30]
Citalopram DM2G9AE Acute coronary syndrome BA41 Approved [29]
Methotrexate DM2TEOL Anterior urethra cancer Approved [31]
Bifonazole DM3KN7V Fungal infection 1F29-1F2F Approved [32]
Quercetin DM3NC4M Obesity 5B81 Approved [33]
Fluoxetine DM3PD2C Bipolar depression Approved [29]
obeticholic acid DM3Q1SM Primary biliary cholangitis DB96.1 Approved [34]
⏷ Show the Full List of 20 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Osilodrostat DMIJC9X Cushing disease 5A70 Approved [15]
Metyrapone DMI7FVQ Cushing disease 5A70 Approved [16]
4'-(Pyridin-4-ylmethyl)biphenyl-3,4-diol DM6Z5EK Discovery agent N.A. Investigative [17]
4-Indan-(1Z)-ylidenemethyl-pyridine DM25DR7 Discovery agent N.A. Investigative [18]
4-[(4'-Hydroxybiphenyl-4-yl)methyl]pyridine DMIEMWA Discovery agent N.A. Investigative [17]
4-[5-Fluoro-indan-(1E)-ylidenemethyl]-pyridine DMY08FE Discovery agent N.A. Investigative [18]
5-[5-Fluoro-indan-(1E)-ylidenemethyl]-pyrimidine DM2RIHT Discovery agent N.A. Investigative [18]
4-((1H-imidazol-1-yl)methyl)benzonitrile DMFUBRC Discovery agent N.A. Investigative [3]
4-[5-Fluoro-indan-(1Z)-ylidenemethyl]-pyridine DMHDZUO Discovery agent N.A. Investigative [18]
4-[5-Bromo-indan-(1Z)-ylidenemethyl]-pyridine DMQKHXN Discovery agent N.A. Investigative [18]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Etretinate DM2CZFA Keratosis ED56 Approved [19]
Troglitazone DM3VFPD Diabetic complication 5A2Y Approved [20]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [21]
Prasterone DM67VKL Chronic obstructive pulmonary disease CA22 Approved [22]
Testosterone DM7HUNW Hot flushes GA30 Approved [22]
Pyruvic acid DM7Q41G Malnutrition 5B50-5B71 Approved [23]
Topiramate DM82Z30 Alcohol dependence 6C40.2 Approved [24]
Lamotrigine DM8SXYG Bipolar disorder 6A60 Approved [24]
ABIRATERONE DM8V75C Prostate cancer 2C82.0 Approved [25]
Duloxetine DM9BI7M Depression 6A70-6A7Z Approved [26]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Hydrocortisone DMGEMB7 Acne vulgaris ED80 Approved [35]
Quercetin DM3NC4M Obesity 5B81 Approved [36]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [37]
Ethanol DMDRQZU Chronic pain MG30 Approved [38]
Potassium Chloride DMMTAJC Hypokalemia 5C77 Approved [39]
Mitotane DMU1GX0 Adrenocortical carcinoma 2D11.Z Approved [40]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [41]
Dalcetrapib DMKNCVM Acute coronary syndrome BA41 Phase 3 [42]
Anacetrapib DMP2BFG Arteriosclerosis BD40 Phase 3 [42]
Benzo(a)pyrene DMN7J43 N. A. N. A. Phase 1 [43]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Aldosterone DM9S2JW Hypertension BA00-BA04 Approved [44]
Erythromycin DM4K7GQ Acne vulgaris ED80 Approved [45]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [37]
Potassium Chloride DMMTAJC Hypokalemia 5C77 Approved [39]
Dutasteride DMQ4TJK Benign prostatic hyperplasia GA90 Approved [46]
Mitotane DMU1GX0 Adrenocortical carcinoma 2D11.Z Approved [47]
Amoxicillin DMUYNEI Acute otitis media AB00 Approved [45]
Carbamazepine DMZOLBI Epilepsy 8A60-8A68 Approved [48]
Irbesartan DMTP1DC Diabetic kidney disease GB61.Z Approved [49]
Testosterone DM7HUNW Hot flushes GA30 Approved [44]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Hydrogen peroxide DM1NG5W Infectious disease 1A00-CA43.1 Approved [50]
Bifonazole DM3KN7V Fungal infection 1F29-1F2F Approved [6]
Quercetin DM3NC4M Obesity 5B81 Approved [51]
obeticholic acid DM3Q1SM Primary biliary cholangitis DB96.1 Approved [34]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [52]
Isotretinoin DM4QTBN Acne vulgaris ED80 Approved [53]
Marinol DM70IK5 Anorexia nervosa cachexia 6B80 Approved [54]
Testosterone DM7HUNW Hot flushes GA30 Approved [55]
Leflunomide DMR8ONJ Arthritis FA20 Approved [56]
Ciclosporin DMAZJFX Graft-versus-host disease 4B24 Approved [57]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Cytochrome P450 2A6 (CYP2A6)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Tegafur DM31ZQM Solid tumour/cancer 2A00-2F9Z Approved [58]
Methoxsalen DME8FZ9 Cutaneous T-cell lymphoma 2B01 Approved [59]
Fluorouracil DMUM7HZ Adenocarcinoma 2D40 Approved [60]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [61]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [62]
Progesterone DMUY35B Amenorrhea GA20.0 Approved [63]
Ifosfamide DMCT3I8 Adult central nervous system germ cell tumor Approved [64]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [65]
Letrozole DMH07Y3 Estrogen-receptor positive breast cancer Approved [66]
Nicotine DMWX5CO Lung cancer 2C25.0 Approved [67]
⏷ 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 [2]
Steroid 11-beta-hydroxylase (CYP11B1) TTIQUX7 C11B1_HUMAN Inhibitor [3]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Aromatase (CYP19A1) OTZ6XF74 CP19A_HUMAN Gene/Protein Processing [4]
Cytochrome P450 11B1, mitochondrial (CYP11B1) OTKKL894 C11B1_HUMAN Gene/Protein Processing [4]
Cytochrome P450 11B2, mitochondrial (CYP11B2) OTIOLWYN C11B2_HUMAN Gene/Protein Processing [4]
Cytochrome P450 2A6 (CYP2A6) OT52TWG3 CP2A6_HUMAN Regulation of Drug Effects [5]
Lanosterol 14-alpha demethylase (CYP51A1) OTAYHG9C CP51A_HUMAN Gene/Protein Processing [6]
Steroid 17-alpha-hydroxylase/17,20 lyase (CYP17A1) OTZKVLVJ CP17A_HUMAN Gene/Protein Processing [4]

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: 8311).
2 Enantioselective nonsteroidal aromatase inhibitors identified through a multidisciplinary medicinal chemistry approach. J Med Chem. 2005 Nov 17;48(23):7282-9.
3 Synthesis, biological evaluation, and molecular modeling of 1-benzyl-1H-imidazoles as selective inhibitors of aldosterone synthase (CYP11B2). J Med Chem. 2010 Feb 25;53(4):1712-25.
4 Synthesis and evaluation of (pyridylmethylene)tetrahydronaphthalenes/-indanes and structurally modified derivatives: potent and selective inhibitors of aldosterone synthase. J Med Chem. 2005 Mar 10;48(5):1563-75.
5 Essential requirements for substrate binding affinity and selectivity toward human CYP2 family enzymes. Arch Biochem Biophys. 2003 Jan 1;409(1):32-44.
6 Comparison of lanosterol-14 alpha-demethylase (CYP51) of human and Candida albicans for inhibition by different antifungal azoles. Toxicology. 2006 Nov 10;228(1):24-32. doi: 10.1016/j.tox.2006.08.007. Epub 2006 Aug 12.
7 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.
8 Aromatase inhibitors--theoretical concept and present experiences in the treatment of endometriosis. Zentralbl Gynakol. 2003 Jul-Aug;125(7-8):247-51.
9 Aminoglutethimide-induced protein free radical formation on myeloperoxidase: a potential mechanism of agranulocytosis. Chem Res Toxicol. 2007 Jul;20(7):1038-45.
10 Aromatase inhibitors for male infertility. J Urol. 2002 Feb;167(2 Pt 1):624-9.
11 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.
12 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.
13 Trusted, scientifically sound profiles of drug programs, clinical trials, safety reports, and company deals, written by scientists. Springer. 2015. Adis Insight (drug id 800032111)
14 The taiwaniaquinoids: a review. J Nat Prod. 2010 Feb 26;73(2):284-98.
15 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health Human Services. 2020
16 Effects of 3-MeSO2-DDE and some CYP inhibitors on glucocorticoid steroidogenesis in the H295R human adrenocortical carcinoma cell line. Toxicol In Vitro. 2002 Apr;16(2):113-21.
17 Replacement of imidazolyl by pyridyl in biphenylmethylenes results in selective CYP17 and dual CYP17/CYP11B1 inhibitors for the treatment of prosta... J Med Chem. 2010 Aug 12;53(15):5749-58.
18 Synthesis and evaluation of (pyridylmethylene)tetrahydronaphthalenes/-indanes and structurally modified derivatives: potent and selective inhibitor... J Med Chem. 2005 Mar 10;48(5):1563-75.
19 Retinoids and retinol differentially regulate steroid biosynthesis in ovarian theca cells isolated from normal cycling women and women with polycystic ovary syndrome. J Clin Endocrinol Metab. 2005 Aug;90(8):4858-65. doi: 10.1210/jc.2005-0330. Epub 2005 May 24.
20 Cinnamic acid based thiazolidinediones inhibit human P450c17 and 3beta-hydroxysteroid dehydrogenase and improve insulin sensitivity independent of PPARgamma agonist activity. J Mol Endocrinol. 2004 Apr;32(2):425-36.
21 Use of organ culture to study the human fetal testis development: effect of retinoic acid. J Clin Endocrinol Metab. 2006 Jul;91(7):2696-703.
22 Inhibition of CYP17 expression by adrenal androgens and transforming growth factor beta in adrenocortical cells. Acta Biochim Pol. 2004;51(4):907-17.
23 Phosphorylation of CtBP1 by cAMP-dependent protein kinase modulates induction of CYP17 by stimulating partnering of CtBP1 and 2. J Biol Chem. 2008 Mar 14;283(11):6925-34. doi: 10.1074/jbc.M708432200. Epub 2008 Jan 9.
24 Effects of anticonvulsants on human p450c17 (17alpha-hydroxylase/17,20 lyase) and 3beta-hydroxysteroid dehydrogenase type 2. Epilepsia. 2005 Mar;46(3):444-8.
25 A fission yeast-based test system for the determination of IC50 values of anti-prostate tumor drugs acting on CYP21. J Enzyme Inhib Med Chem. 2006 Oct;21(5):547-56.
26 Steroidogenic disruptive effects of the serotonin-noradrenaline reuptake inhibitors duloxetine, venlafaxine and tramadol in the H295R cell assay and in a recombinant CYP17 assay. Toxicol In Vitro. 2018 Mar;47:63-71.
27 Aromatase inhibition: translation into a successful therapeutic approach. Clin Cancer Res. 2005 Apr 15;11(8):2809-21. doi: 10.1158/1078-0432.CCR-04-2187.
28 Cannabidiol (CBD) but not tetrahydrocannabinol (THC) dysregulate in vitro decidualization of human endometrial stromal cells by disruption of estrogen signaling. Reprod Toxicol. 2020 Apr;93:75-82. doi: 10.1016/j.reprotox.2020.01.003. Epub 2020 Jan 14.
29 Effects of selective serotonin reuptake inhibitors on three sex steroids in two versions of the aromatase enzyme inhibition assay and in the H295R cell assay. Toxicol In Vitro. 2015 Oct;29(7):1729-35.
30 Arsenite and cadmium promote the development of mammary tumors. Carcinogenesis. 2020 Jul 14;41(7):1005-1014. doi: 10.1093/carcin/bgz176.
31 The contribution of methotrexate exposure and host factors on transcriptional variance in human liver. Toxicol Sci. 2007 Jun;97(2):582-94.
32 Comparative assessment of the inhibition of recombinant human CYP19 (aromatase) by azoles used in agriculture and as drugs for humans. Endocr Res. 2004 Aug;30(3):387-94.
33 Estrogen synthesis in human colon cancer epithelial cells. J Steroid Biochem Mol Biol. 1999 Dec 31;71(5-6):223-30.
34 Pharmacotoxicology of clinically-relevant concentrations of obeticholic acid in an organotypic human hepatocyte system. Toxicol In Vitro. 2017 Mar;39:93-103.
35 Steroid signalling in the ovarian surface epithelium. Trends Endocrinol Metab. 2005 Sep;16(7):327-33.
36 Flavonoids exhibit diverse effects on CYP11B1 expression and cortisol synthesis. Toxicol Appl Pharmacol. 2012 Feb 1;258(3):343-50.
37 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.
38 Autophagy as a compensation mechanism participates in ethanol-induced fetal adrenal dysfunction in female rats. Toxicol Appl Pharmacol. 2018 Apr 15;345:36-47.
39 Blockade of T-type voltage-dependent Ca2+ channels by benidipine, a dihydropyridine calcium channel blocker, inhibits aldosterone production in human adrenocortical cell line NCI-H295R. Eur J Pharmacol. 2008 Apr 28;584(2-3):424-34. doi: 10.1016/j.ejphar.2008.02.001. Epub 2008 Feb 12.
40 Biphasic hormonal responses to the adrenocorticolytic DDT metabolite 3-methylsulfonyl-DDE in human cells. Toxicol Appl Pharmacol. 2010 Feb 1;242(3):281-9.
41 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.
42 Cholesteryl ester-transfer protein inhibitors stimulate aldosterone biosynthesis in adipocytes through Nox-dependent processes. J Pharmacol Exp Ther. 2015 Apr;353(1):27-34.
43 Air pollution and DNA methylation alterations in lung cancer: A systematic and comparative study. Oncotarget. 2017 Jan 3;8(1):1369-1391. doi: 10.18632/oncotarget.13622.
44 [Association study between a polymorphism of aldosterone synthetase gene and the pathogenesis of polycystic ovary syndrome]. Zhonghua Fu Chan Ke Za Zhi. 2003 Feb;38(2):94-7.
45 Modulation of steroidogenic gene expression and hormone production of H295R cells by pharmaceuticals and other environmentally active compounds. Toxicol Appl Pharmacol. 2007 Dec 1;225(2):142-53.
46 Effects of dutasteride on the expression of genes related to androgen metabolism and related pathway in human prostate cancer cell lines. Invest New Drugs. 2007 Oct;25(5):491-7.
47 Mitotane alters mitochondrial respiratory chain activity by inducing cytochrome c oxidase defect in human adrenocortical cells. Endocr Relat Cancer. 2013 May 21;20(3):371-81.
48 Differential effects of antiepileptic drugs on steroidogenesis in a human in vitro cell model. Acta Neurol Scand Suppl. 2009;(189):14-21.
49 Aldosterone synthase (CYP11B2) -344 C/T polymorphism is related to antihypertensive response: result from the Swedish Irbesartan Left Ventricular Hypertrophy Investigation versus Atenolol (SILVHIA) trial. Am J Hypertens. 2002 May;15(5):389-93. doi: 10.1016/s0895-7061(02)02256-2.
50 Minimal peroxide exposure of neuronal cells induces multifaceted adaptive responses. PLoS One. 2010 Dec 17;5(12):e14352. doi: 10.1371/journal.pone.0014352.
51 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.
52 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.
53 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.
54 JunD is involved in the antiproliferative effect of Delta9-tetrahydrocannabinol on human breast cancer cells. Oncogene. 2008 Aug 28;27(37):5033-44.
55 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.
56 Endoplasmic reticulum stress and MAPK signaling pathway activation underlie leflunomide-induced toxicity in HepG2 Cells. Toxicology. 2017 Dec 1;392:11-21.
57 Integrating multiple omics to unravel mechanisms of Cyclosporin A induced hepatotoxicity in vitro. Toxicol In Vitro. 2015 Apr;29(3):489-501.
58 Cyp2a6 is a principal enzyme involved in hydroxylation of 1,7-dimethylxanthine, a main caffeine metabolite, in humans. Drug Metab Dispos. 2005 Sep;33(9):1361-6. doi: 10.1124/dmd.105.004796. Epub 2005 Jun 24.
59 Mimicking gene defects to treat drug dependence. Ann N Y Acad Sci. 2000;909:233-46. doi: 10.1111/j.1749-6632.2000.tb06685.x.
60 Expression of CYP2A6 in tumor cells augments cellular sensitivity to tegafur. Jpn J Cancer Res. 2001 May;92(5):524-8. doi: 10.1111/j.1349-7006.2001.tb01125.x.
61 CYP1A1/1B1 and CYP2A6/2A13 activity is conserved in cultures of differentiated primary human tracheobronchial epithelial cells. Toxicol In Vitro. 2011 Jun;25(4):922-9.
62 Multiple microRNAs function as self-protective modules in acetaminophen-induced hepatotoxicity in humans. Arch Toxicol. 2018 Feb;92(2):845-858.
63 Isoform-specific regulation of cytochromes P450 expression by estradiol and progesterone. Drug Metab Dispos. 2013 Feb;41(2):263-9.
64 Measurement of 4-hydroxylation of ifosfamide in human liver microsomes using the estimation of free and protein-bound acrolein and codetermination of keto- and carboxyifosfamide. J Cancer Res Clin Oncol. 2002 Jul;128(7):385-92.
65 Integrated 'omics analysis reveals new drug-induced mitochondrial perturbations in human hepatocytes. Toxicol Lett. 2018 Jun 1;289:1-13.
66 Deactivation of anti-cancer drug letrozole to a carbinol metabolite by polymorphic cytochrome P450 2A6 in human liver microsomes. Xenobiotica. 2009 Nov;39(11):795-802. doi: 10.3109/00498250903171395.
67 A novel single nucleotide polymorphism altering stability and activity of CYP2a6. Biochem Biophys Res Commun. 2001 Mar 2;281(3):810-4. doi: 10.1006/bbrc.2001.4422.