Details of the Drug-Related molecule(s) Interaction Atlas

General Information of Drug (ID: DM5XZYB)

Drug Name
Azide Drug Info
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Cross-matching ID
PubChem CID
33558
ChEBI ID
CHEBI:40910
CAS Number
CAS 14343-69-2
TTD Drug ID
DM5XZYB

Molecule-Related Drug Atlas

Molecule-Related Drug Atlas
Molecule Type:
DTT
DOT
Drug Status:
Approved Drug(s)
Clinical Trial Drug(s)
Patented Agent(s)
Download the Complete Related Drug List
Drug(s) Targeting Carbonic anhydrase I (CA-I)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Salicyclic acid DM2F8XZ Acne vulgaris ED80 Approved [4]
Ethoxzolamide DMVO4ED Glaucoma/ocular hypertension 9C61 Approved [5]
Dichlorphenamide DMH7IDQ Chronic glaucoma 9C61.0Z Approved [5]
Methazolamide DM7J2TA Glaucoma/ocular hypertension 9C61 Approved [6]
Acetazolamide DM1AF5U Absence epilepsy Approved [5]
Curcumin DMQPH29 Solid tumour/cancer 2A00-2F9Z Phase 3 [7]
PARABEN DMEW5Z8 N. A. N. A. Phase 3 [8]
CG-100649 DMIKMA9 Arthritis FA20 Phase 3 [9]
PHENOL DM1QSM3 N. A. N. A. Phase 2/3 [7]
Coumate DMVKW0N Breast cancer 2C60-2C65 Phase 2 [10]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Targeting Carbonic anhydrase II (CA-II)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Salicyclic acid DM2F8XZ Acne vulgaris ED80 Approved [4]
Sulfamylon DMIO1K0 Bacterial infection 1A00-1C4Z Approved [11]
Dorzolamide DMA17D0 Ocular hypertension 9C61.01 Approved [12]
Chlorothiazide DMLHESP Chronic heart failure BD1Z Approved [13]
Ethoxzolamide DMVO4ED Glaucoma/ocular hypertension 9C61 Approved [14]
Dichlorphenamide DMH7IDQ Chronic glaucoma 9C61.0Z Approved [14]
Cyclothiazide DMJ4AWC Congestive heart failure BD10 Approved [15]
Ethinamate DMK57GB Insomnia 7A00-7A0Z Approved [16]
Benzthiazide DMQWZ0H High blood pressure BA00 Approved [17]
Curcumin DMQPH29 Solid tumour/cancer 2A00-2F9Z Phase 3 [7]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Targeting Carbonic anhydrase IX (CA-IX)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Curcumin DMQPH29 Solid tumour/cancer 2A00-2F9Z Phase 3 [7]
PARABEN DMEW5Z8 N. A. N. A. Phase 3 [8]
PHENOL DM1QSM3 N. A. N. A. Phase 2/3 [7]
Coumate DMVKW0N Breast cancer 2C60-2C65 Phase 2 [10]
INDISULAM DM9SX6Y Lymphoma 2A80-2A86 Phase 2 [18]
Girentuximab I-124 DMG3O2Z Renal cell carcinoma 2C90 Phase 2 [19]
SULFAMIDE DMMAS3K N. A. N. A. Phase 1 [20]
BAY 79-4620 DM14XQN Solid tumour/cancer 2A00-2F9Z Phase 1 [21]
90Y-cG250 DMJR6TC Solid tumour/cancer 2A00-2F9Z Phase 1 [22]
FERULIC ACID DMJC7NF Discovery agent N.A. Patented [8]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Apoptosis regulator BAX (BAX)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Sevoflurane DMC9O43 Anaesthesia 9A78.6 Approved [23]
Aprepitant DM053KT Depression 6A70-6A7Z Approved [24]
Cannabidiol DM0659E Dravet syndrome 8A61.11 Approved [25]
Verapamil DMA7PEW Angina pectoris BA40 Approved [26]
Beta-carotene DM0RXBT Vitamin deficiency 5B55-5B71 Approved [27]
Leuprorelin acetate DM15HAT Prostate cancer 2C82.0 Approved [28]
Talazoparib DM1KS78 Breast cancer 2C60-2C65 Approved [29]
Hydrogen peroxide DM1NG5W Infectious disease 1A00-CA43.1 Approved [30]
Meloxicam DM2AR7L Arthritis FA20 Approved [31]
Ciprofloxacin XR DM2NLS9 Acute gonococcal cervicitis Approved [32]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Apoptosis regulator Bcl-2 (BCL2)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Sevoflurane DMC9O43 Anaesthesia 9A78.6 Approved [23]
Docetaxel DMDI269 Advanced cancer 2A00-2F9Z Approved [33]
Cisplatin DMRHGI9 Adenocarcinoma 2D40 Approved [34]
Gemcitabine DMSE3I7 Anterior urethra cancer Approved [35]
Etoposide DMNH3PG Acute myelogenous leukaemia 2A41 Approved [36]
Cannabidiol DM0659E Dravet syndrome 8A61.11 Approved [25]
Verapamil DMA7PEW Angina pectoris BA40 Approved [26]
Mechlorethamine DM0CVXA Chronic myelogenous leukaemia 2A20.0 Approved [37]
Sertraline DM0FB1J Coronary heart disease BA80.Z Approved [38]
Beta-carotene DM0RXBT Vitamin deficiency 5B55-5B71 Approved [39]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Mitofusin-1 (MFN1)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Hydrogen peroxide DM1NG5W Infectious disease 1A00-CA43.1 Approved [40]
Quercetin DM3NC4M Obesity 5B81 Approved [41]
Leflunomide DMR8ONJ Arthritis FA20 Approved [42]
Ciclosporin DMAZJFX Graft-versus-host disease 4B24 Approved [43]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [44]
Ethanol DMDRQZU Chronic pain MG30 Approved [45]
Melatonin DMKWFBT Depression 6A70-6A7Z Approved [46]
Diethylstilbestrol DMN3UXQ Gonorrheal vaginitis GA02 Approved [47]
Bortezomib DMNO38U Leukemia Approved [48]
Cupric Sulfate DMP0NFQ Fungal infection 1F29-1F2F Approved [49]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Mitofusin-2 (MFN2)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Tretinoin DM49DUI Acne vulgaris ED80 Approved [50]
Ciclosporin DMAZJFX Graft-versus-host disease 4B24 Approved [51]
Efavirenz DMC0GSJ Human immunodeficiency virus infection 1C62 Approved [52]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [53]
Ivermectin DMDBX5F Intestinal strongyloidiasis due to nematode parasite 1F6B Approved [54]
Melatonin DMKWFBT Depression 6A70-6A7Z Approved [46]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [55]
Fluorouracil DMUM7HZ Adenocarcinoma 2D40 Approved [56]
Doxorubicin DMVP5YE Acute myelogenous leukaemia 2A41 Approved [57]
Resveratrol DM3RWXL Giant cell arteritis 4A44.2 Phase 3 [58]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Dynamin-1-like protein (DNM1L)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Verapamil DMA7PEW Angina pectoris BA40 Approved [59]
Hydrogen peroxide DM1NG5W Infectious disease 1A00-CA43.1 Approved [60]
Simvastatin DM30SGU Arteriosclerosis BD40 Approved [61]
Ciclosporin DMAZJFX Graft-versus-host disease 4B24 Approved [62]
Efavirenz DMC0GSJ Human immunodeficiency virus infection 1C62 Approved [52]
Ivermectin DMDBX5F Intestinal strongyloidiasis due to nematode parasite 1F6B Approved [54]
Ethanol DMDRQZU Chronic pain MG30 Approved [45]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [63]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [59]
Doxorubicin DMVP5YE Acute myelogenous leukaemia 2A41 Approved [64]
⏷ Show the Full List of 10 Drug(s)

Molecular Interaction Atlas of This Drug

Molecular Interaction Atlas
Download the Complete Interaction Atlas for Visualization in Cytoscape

Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Carbonic anhydrase I (CA-I) TTHQPL7 CAH1_HUMAN Inhibitor [1]
Carbonic anhydrase II (CA-II) TTANPDJ CAH2_HUMAN Inhibitor [2]
Carbonic anhydrase IX (CA-IX) TT2LVK8 CAH9_HUMAN Inhibitor [1]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Apoptosis regulator BAX (BAX) OTAW0V4V BAX_HUMAN Gene/Protein Processing [3]
Apoptosis regulator Bcl-2 (BCL2) OT9DVHC0 BCL2_HUMAN Drug Response [3]
Dynamin-1-like protein (DNM1L) OTXK1Q1G DNM1L_HUMAN Drug Response [3]
Mitofusin-1 (MFN1) OTCBXQZF MFN1_HUMAN Drug Response [3]
Mitofusin-2 (MFN2) OTPYN8A3 MFN2_HUMAN Drug Response [3]

References

1 Carbonic anhydrase inhibitors: inhibition of the membrane-bound human isozyme IV with anions. Bioorg Med Chem Lett. 2004 Dec 6;14(23):5769-73.
2 Carbonic anhydrase inhibitors. Inhibition of the newly isolated murine isozyme XIII with anions. Bioorg Med Chem Lett. 2004 Nov 1;14(21):5435-9.
3 Fragmented mitochondria are sensitized to Bax insertion and activation during apoptosis. Am J Physiol Cell Physiol. 2011 Mar;300(3):C447-55. doi: 10.1152/ajpcell.00402.2010. Epub 2010 Dec 15.
4 Carbonic anhydrase inhibitors: inhibition of mammalian isoforms I-XIV with a series of substituted phenols including paracetamol and salicylic acid. Bioorg Med Chem. 2008 Aug 1;16(15):7424-8.
5 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
6 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: 2597).
7 Carbonic anhydrase inhibitors. Antioxidant polyphenols effectively inhibit mammalian isoforms I-XV. Bioorg Med Chem Lett. 2010 Sep 1;20(17):5050-3.
8 Carbonic anhydrase inhibitors. Inhibition of mammalian isoforms I-XIV with a series of natural product polyphenols and phenolic acids. Bioorg Med Chem. 2010 Mar 15;18(6):2159-2164.
9 Understanding the Dual Inhibition of COX-2 and Carbonic Anhydrase-II by Celecoxib and CG100649 Using Density Functional Theory Calculations and other Molecular Modelling Approaches. Protein Pept Lett. 2015;22(10):903-12.
10 Carbonic anhydrase inhibitors. Interaction of the antitumor sulfamate EMD 486019 with twelve mammalian carbonic anhydrase isoforms: Kinetic and X-r... Bioorg Med Chem Lett. 2008 Aug 1;18(15):4282-6.
11 Sulfonamide linked neoglycoconjugates--a new class of inhibitors for cancer-associated carbonic anhydrases. J Med Chem. 2010 Apr 8;53(7):2913-26.
12 Carbonic anhydrase inhibitors. Inhibition studies of a coral secretory isoform by sulfonamides. Bioorg Med Chem. 2009 Jul 15;17(14):5054-8.
13 Localization of diuretic effects along the loop of Henle: an in vivo microperfusion study in rats. Clin Sci (Lond). 2000 Apr;98(4):481-8.
14 The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42.
15 Selective effect of thiazides on the human osteoblast-like cell line MG-63. Kidney Int. 1996 Nov;50(5):1476-82.
16 Inhibition of carbonic anhydrases I and II by N-unsubstituted carbamate esters. J Biol Chem. 1992 Dec 15;267(35):25044-50.
17 Nature of the inhibition of carbonic anhydrase by acetazolamide and benzthiazide. J Pharmacol Exp Ther. 1961 Mar;131:271-4.
18 Carbonic anhydrase inhibitors: E7070, a sulfonamide anticancer agent, potently inhibits cytosolic isozymes I and II, and transmembrane, tumor-assoc... Bioorg Med Chem Lett. 2004 Jan 5;14(1):217-23.
19 Potential role of (124)I-girentuximab in the presurgical diagnosis of clear-cell renal cell cancer. Biologics. 2012;6:395-407.
20 Carbonic anhydrase inhibitors. Inhibition of isozymes I, II, IV, V, and IX with anions isosteric and isoelectronic with sulfate, nitrate, and carbo... Bioorg Med Chem Lett. 2005 Feb 1;15(3):567-71.
21 Therapeutic mechanism and efficacy of the antibody-drug conjugate BAY 79-4620 targeting human carbonic anhydrase 9. Mol Cancer Ther. 2012 Feb;11(2):340-9.
22 Application of monoclonal antibody G250 recognizing carbonic anhydrase IX in renal cell carcinoma. Int J Mol Sci. 2013 May 29;14(6):11402-23.
23 4.8% sevoflurane induces activation of autophagy in human neuroblastoma SH-SY5Y cells by the AMPK/mTOR signaling pathway. Neurotoxicology. 2022 May;90:256-264. doi: 10.1016/j.neuro.2022.04.008. Epub 2022 Apr 23.
24 Neurokinin-1 receptor (NK1R) inhibition sensitizes APL cells to anti-tumor effect of arsenic trioxide via restriction of NF-B axis: Shedding new light on resistance to Aprepitant. Int J Biochem Cell Biol. 2018 Oct;103:105-114. doi: 10.1016/j.biocel.2018.08.010. Epub 2018 Aug 23.
25 Cannabidiol enhances cytotoxicity of anti-cancer drugs in human head and neck squamous cell carcinoma. Sci Rep. 2020 Nov 26;10(1):20622. doi: 10.1038/s41598-020-77674-y.
26 Verapamil potentiates anti-glioblastoma efficacy of temozolomide by modulating apoptotic signaling. Toxicol In Vitro. 2018 Oct;52:306-313. doi: 10.1016/j.tiv.2018.07.001. Epub 2018 Jul 9.
27 Beta-carotene and apocarotenals promote retinoid signaling in BEAS-2B human bronchioepithelial cells. Arch Biochem Biophys. 2006 Nov 1;455(1):48-60.
28 Effects of gonadotrophin-releasing hormone agonists on apoptosis of granulosa cells. Ann N Y Acad Sci. 2005 May;1042:531-7. doi: 10.1196/annals.1338.065.
29 BMN 673 (talazoparib): A potent PARP inhibitor for triple negative breast cancer with different genetic profile. J Biochem Mol Toxicol. 2019 May;33(5):e22286. doi: 10.1002/jbt.22286. Epub 2019 Jan 23.
30 Microarray analysis of H2O2-, HNE-, or tBH-treated ARPE-19 cells. Free Radic Biol Med. 2002 Nov 15;33(10):1419-32.
31 Combining kallistatin gene therapy and meloxicam to treat hepatocellular carcinoma in mice. Cancer Sci. 2009 Nov;100(11):2226-33. doi: 10.1111/j.1349-7006.2009.01306.x. Epub 2009 Aug 4.
32 Ciprofloxacin mediated cell growth inhibition, S/G2-M cell cycle arrest, and apoptosis in a human transitional cell carcinoma of the bladder cell line. Clin Cancer Res. 2000 Mar;6(3):891-900.
33 Enhanced chemotherapeutic efficacy of docetaxel in human lung cancer cell line via GLUT1 inhibitor. J Biochem Mol Toxicol. 2023 Jun;37(6):e23348. doi: 10.1002/jbt.23348. Epub 2023 Mar 31.
34 Breast cancer cells response to the antineoplastic agents cisplatin, carboplatin, and doxorubicin at the mRNA expression levels of distinct apoptosis-related genes, including the new member, BCL2L12. Ann N Y Acad Sci. 2007 Jan;1095:35-44. doi: 10.1196/annals.1397.005.
35 Extracellular signal-regulated kinase activation and Bcl-2 downregulation mediate apoptosis after gemcitabine treatment partly via a p53-independent pathway. Eur J Pharmacol. 2004 Oct 19;502(3):169-83. doi: 10.1016/j.ejphar.2004.09.006.
36 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.
37 Inhibition of caspase-dependent mitochondrial permeability transition protects airway epithelial cells against mustard-induced apoptosis. Apoptosis. 2006 Sep;11(9):1545-59. doi: 10.1007/s10495-006-8764-1.
38 Sertraline, an antidepressant, induces apoptosis in hepatic cells through the mitogen-activated protein kinase pathway. Toxicol Sci. 2014 Feb;137(2):404-15. doi: 10.1093/toxsci/kft254. Epub 2013 Nov 5.
39 -Carotene Induces Apoptosis in Human Esophageal Squamous Cell Carcinoma Cell Lines via the Cav-1/AKT/NF-B Signaling Pathway. J Biochem Mol Toxicol. 2016 Mar;30(3):148-57. doi: 10.1002/jbt.21773. Epub 2016 Jan 6.
40 Tea polyphenols ameliorates neural redox imbalance and mitochondrial dysfunction via mechanisms linking the key circadian regular Bmal1. Food Chem Toxicol. 2017 Dec;110:189-199. doi: 10.1016/j.fct.2017.10.031. Epub 2017 Oct 20.
41 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.
42 Endoplasmic reticulum stress and MAPK signaling pathway activation underlie leflunomide-induced toxicity in HepG2 Cells. Toxicology. 2017 Dec 1;392:11-21.
43 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.
44 Gene Expression Regulation and Pathway Analysis After Valproic Acid and Carbamazepine Exposure in a Human Embryonic Stem Cell-Based Neurodevelopmental Toxicity Assay. Toxicol Sci. 2015 Aug;146(2):311-20. doi: 10.1093/toxsci/kfv094. Epub 2015 May 15.
45 Protective effects of silibinin against ethanol- or acetaldehyde-caused damage in liver cell lines involve the repression of mitochondrial fission. Toxicol In Vitro. 2022 Apr;80:105330. doi: 10.1016/j.tiv.2022.105330. Epub 2022 Feb 11.
46 Melatonin prevents blood-retinal barrier breakdown and mitochondrial dysfunction in high glucose and hypoxia-induced in vitro diabetic macular edema model. Toxicol In Vitro. 2021 Sep;75:105191. doi: 10.1016/j.tiv.2021.105191. Epub 2021 May 5.
47 Identification of biomarkers and outcomes of endocrine disruption in human ovarian cortex using In Vitro Models. Toxicology. 2023 Feb;485:153425. doi: 10.1016/j.tox.2023.153425. Epub 2023 Jan 5.
48 The proapoptotic effect of zoledronic acid is independent of either the bone microenvironment or the intrinsic resistance to bortezomib of myeloma cells and is enhanced by the combination with arsenic trioxide. Exp Hematol. 2011 Jan;39(1):55-65.
49 Physiological and toxicological transcriptome changes in HepG2 cells exposed to copper. Physiol Genomics. 2009 Aug 7;38(3):386-401.
50 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.
51 Integrative "-Omics" analysis in primary human hepatocytes unravels persistent mechanisms of cyclosporine A-induced cholestasis. Chem Res Toxicol. 2016 Dec 19;29(12):2164-2174.
52 Lon protease: a novel mitochondrial matrix protein in the interconnection between drug-induced mitochondrial dysfunction and endoplasmic reticulum stress. Br J Pharmacol. 2017 Dec;174(23):4409-4429. doi: 10.1111/bph.14045. Epub 2017 Nov 7.
53 Integrated 'omics analysis reveals new drug-induced mitochondrial perturbations in human hepatocytes. Toxicol Lett. 2018 Jun 1;289:1-13.
54 Quantitative proteomics reveals a broad-spectrum antiviral property of ivermectin, benefiting for COVID-19 treatment. J Cell Physiol. 2021 Apr;236(4):2959-2975. doi: 10.1002/jcp.30055. Epub 2020 Sep 22.
55 Gene expression analysis of precision-cut human liver slices indicates stable expression of ADME-Tox related genes. Toxicol Appl Pharmacol. 2011 May 15;253(1):57-69.
56 5-Fluorouracil inhibits neural differentiation via Mfn1/2 reduction in human induced pluripotent stem cells. J Toxicol Sci. 2018;43(12):727-734. doi: 10.2131/jts.43.727.
57 Bringing in vitro analysis closer to in vivo: studying doxorubicin toxicity and associated mechanisms in 3D human microtissues with PBPK-based dose modelling. Toxicol Lett. 2018 Sep 15;294:184-192.
58 Gene expression profiling in Ishikawa cells: a fingerprint for estrogen active compounds. Toxicol Appl Pharmacol. 2009 Apr 1;236(1):85-96.
59 Low doses of BPF-induced hypertrophy in cardiomyocytes derived from human embryonic stem cells via disrupting the mitochondrial fission upon the interaction between ER and calcineurin A-DRP1 signaling pathway. Cell Biol Toxicol. 2022 Jun;38(3):409-426. doi: 10.1007/s10565-021-09615-y. Epub 2021 May 22.
60 Tea polyphenols direct Bmal1-driven ameliorating of the redox imbalance and mitochondrial dysfunction in hepatocytes. Food Chem Toxicol. 2018 Dec;122:181-193.
61 Statin-triggered cell death in primary human lung mesenchymal cells involves p53-PUMA and release of Smac and Omi but not cytochrome c. Biochim Biophys Acta. 2010 Apr;1803(4):452-67. doi: 10.1016/j.bbamcr.2009.12.005. Epub 2010 Jan 4.
62 Integrating multiple omics to unravel mechanisms of Cyclosporin A induced hepatotoxicity in vitro. Toxicol In Vitro. 2015 Apr;29(3):489-501.
63 Increased mitochondrial ROS formation by acetaminophen in human hepatic cells is associated with gene expression changes suggesting disruption of the mitochondrial electron transport chain. Toxicol Lett. 2015 Apr 16;234(2):139-50.
64 Doxorubicin-induced mitophagy and mitochondrial damage is associated with dysregulation of the PINK1/parkin pathway. Toxicol In Vitro. 2018 Sep;51:1-10. doi: 10.1016/j.tiv.2018.05.001. Epub 2018 May 3.