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

General Information of Drug (ID: DML0YEK)

Drug Name
CATECHOL Drug Info
Synonyms
pyrocatechol; 1,2-dihydroxybenzene; 120-80-9; 1,2-benzenediol; benzene-1,2-diol; pyrocatechin; 2-hydroxyphenol; o-Benzenediol; Pyrocatechine; o-Dihydroxybenzene; Oxyphenic acid; o-Hydroxyphenol; o-Hydroquinone; o-Dioxybenzene; o-Phenylenediol; Phthalhydroquinone; Fouramine PCH; Durafur developer C; Pelagol Grey C; benzenediol; Catechin (phenol); Fourrine 68; Benzene, o-dihydroxy-; Catechol (phenol); o-Diphenol; ortho-Hydroxyphenol; Pyrokatechol; Pyrokatechin; Katechol; ortho-Dihydroxybenzene; C.I. Oxidation Base 26
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Cross-matching ID
PubChem CID
289
ChEBI ID
CHEMBL280998
CAS Number
CAS 120-80-9
TTD Drug ID
DML0YEK
INTEDE Drug ID
DR2201

Molecule-Related Drug Atlas

Molecule-Related Drug Atlas
Molecule Type:
DTT
DME
DOT
Drug Status:
Approved Drug(s)
Clinical Trial Drug(s)
Patented Agent(s)
Investigative Drug(s)
Download the Complete Related Drug List
Drug(s) Targeting Carbonic anhydrase XII (CA-XII)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Salicyclic acid DM2F8XZ Acne vulgaris ED80 Approved [8]
Sulfamylon DMIO1K0 Bacterial infection 1A00-1C4Z Approved [9]
Curcumin DMQPH29 Solid tumour/cancer 2A00-2F9Z Phase 3 [10]
PARABEN DMEW5Z8 N. A. N. A. Phase 3 [1]
PHENOL DM1QSM3 N. A. N. A. Phase 2/3 [10]
Coumate DMVKW0N Breast cancer 2C60-2C65 Phase 2 [11]
FERULIC ACID DMJC7NF Discovery agent N.A. Patented [1]
ELLAGIC ACID DMX8BS5 Discovery agent N.A. Investigative [1]
COUMARIN DM0N8ZM Discovery agent N.A. Investigative [12]
CATECHIN DMY38SB Discovery agent N.A. Investigative [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 [8]
Sulfamylon DMIO1K0 Bacterial infection 1A00-1C4Z Approved [9]
Dorzolamide DMA17D0 Ocular hypertension 9C61.01 Approved [13]
Chlorothiazide DMLHESP Chronic heart failure BD1Z Approved [14]
Ethoxzolamide DMVO4ED Glaucoma/ocular hypertension 9C61 Approved [15]
Dichlorphenamide DMH7IDQ Chronic glaucoma 9C61.0Z Approved [15]
Cyclothiazide DMJ4AWC Congestive heart failure BD10 Approved [16]
Ethinamate DMK57GB Insomnia 7A00-7A0Z Approved [17]
Benzthiazide DMQWZ0H High blood pressure BA00 Approved [18]
Curcumin DMQPH29 Solid tumour/cancer 2A00-2F9Z Phase 3 [10]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Targeting Carbonic anhydrase (CA)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Salicyclic acid DM2F8XZ Acne vulgaris ED80 Approved [19]
Sulfamylon DMIO1K0 Bacterial infection 1A00-1C4Z Approved [20]
Quinethazone DMWCOSR Hypertension BA00-BA04 Approved [21]
Curcumin DMQPH29 Solid tumour/cancer 2A00-2F9Z Phase 3 [10]
PARABEN DMEW5Z8 N. A. N. A. Phase 3 [1]
PHENOL DM1QSM3 N. A. N. A. Phase 2/3 [10]
Coumate DMVKW0N Breast cancer 2C60-2C65 Phase 2 [11]
SULFAMIDE DMMAS3K N. A. N. A. Phase 1 [22]
FERULIC ACID DMJC7NF Discovery agent N.A. Patented [1]
PMID30074415-Compound-21 DM3NPOU N. A. N. A. Patented [23]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Targeting Carbonic anhydrase IV (CA-IV)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Salicyclic acid DM2F8XZ Acne vulgaris ED80 Approved [8]
Sulfamylon DMIO1K0 Bacterial infection 1A00-1C4Z Approved [24]
Brinzolamide DMBAPFG Ocular hypertension 9C61.01 Approved [25]
Curcumin DMQPH29 Solid tumour/cancer 2A00-2F9Z Phase 3 [10]
PARABEN DMEW5Z8 N. A. N. A. Phase 3 [1]
PHENOL DM1QSM3 N. A. N. A. Phase 2/3 [10]
Coumate DMVKW0N Breast cancer 2C60-2C65 Phase 2 [11]
Sodium pyruvate DMST6A3 Asthma CA23 Phase 1/2 [26]
SULFAMIDE DMMAS3K N. A. N. A. Phase 1 [22]
FERULIC ACID DMJC7NF Discovery agent N.A. Patented [1]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Metabolized By Glucansucrase (gtf106B)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Sucrose DMVWUCF Discovery agent N.A. Investigative [27]
RESORCINOL DMM37C0 Discovery agent N.A. Investigative [28]
ETHYLGALLATE DMJ6PB8 Discovery agent N.A. Investigative [29]
PYROGALLOL DMG5KDY Discovery agent N.A. Investigative [30]
Drug(s) Affected By C-C motif chemokine 3 (CCL3)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Indinavir DM0T3YH Human immunodeficiency virus infection 1C62 Approved [31]
Methotrexate DM2TEOL Anterior urethra cancer Approved [32]
Troglitazone DM3VFPD Diabetic complication 5A2Y Approved [33]
Penicillamine DM40EF6 Cystinuria 5C60.2 Approved [34]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [35]
Arsenic trioxide DM61TA4 Acute lymphoblastic leukaemia 2A85 Approved [36]
Hydroquinone DM6AVR4 Melasma ED60.1 Approved [4]
Betamethasone DMAHJEF Acute adrenal insufficiency Approved [37]
Emetine DMCT2YF Hepatitis virus infection 1E50-1E51 Approved [37]
Nelfinavir mesylate DMFX6G8 N. A. N. A. Approved [31]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By C-C motif chemokine 4 (CCL4)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Troglitazone DM3VFPD Diabetic complication 5A2Y Approved [33]
Penicillamine DM40EF6 Cystinuria 5C60.2 Approved [34]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [38]
Hydroquinone DM6AVR4 Melasma ED60.1 Approved [4]
Marinol DM70IK5 Anorexia nervosa cachexia 6B80 Approved [39]
Betamethasone DMAHJEF Acute adrenal insufficiency Approved [37]
Ciclosporin DMAZJFX Graft-versus-host disease 4B24 Approved [40]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [41]
Emetine DMCT2YF Hepatitis virus infection 1E50-1E51 Approved [37]
Demecolcine DMCZQGK Solid tumour/cancer 2A00-2F9Z Approved [42]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By C-C motif chemokine 2 (CCL2)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Indinavir DM0T3YH Human immunodeficiency virus infection 1C62 Approved [31]
Fulvestrant DM0YZC6 Breast cancer 2C60-2C65 Approved [43]
Gefitinib DM15F0X Colon adenocarcinoma Approved [44]
Hydrogen peroxide DM1NG5W Infectious disease 1A00-CA43.1 Approved [45]
Imiquimod DM1TMA3 Alopecia areata ED70.2 Approved [46]
Methimazole DM25FL8 Hyperthyroidism 5A02 Approved [47]
TECFIDERA DM2OVDT Multiple sclerosis 8A40 Approved [48]
Methotrexate DM2TEOL Anterior urethra cancer Approved [32]
Simvastatin DM30SGU Arteriosclerosis BD40 Approved [49]
Quercetin DM3NC4M Obesity 5B81 Approved [50]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By C-C motif chemokine 5 (CCL5)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Fulvestrant DM0YZC6 Breast cancer 2C60-2C65 Approved [51]
Hydrogen peroxide DM1NG5W Infectious disease 1A00-CA43.1 Approved [52]
Nitric Oxide DM1RBYG Hypertension BA00-BA04 Approved [53]
Methotrexate DM2TEOL Anterior urethra cancer Approved [32]
Simvastatin DM30SGU Arteriosclerosis BD40 Approved [54]
Troglitazone DM3VFPD Diabetic complication 5A2Y Approved [55]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [38]
Isotretinoin DM4QTBN Acne vulgaris ED80 Approved [56]
Hydroquinone DM6AVR4 Melasma ED60.1 Approved [4]
Liothyronine DM6IR3P Congenital hypothyroidism Approved [57]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Eotaxin (CCL11)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Prednisone DM2HG4X Acute asthma CA23 Approved [58]
Methotrexate DM2TEOL Anterior urethra cancer Approved [32]
Troglitazone DM3VFPD Diabetic complication 5A2Y Approved [59]
Hydroquinone DM6AVR4 Melasma ED60.1 Approved [4]
Marinol DM70IK5 Anorexia nervosa cachexia 6B80 Approved [60]
Ethanol DMDRQZU Chronic pain MG30 Approved [61]
Chloroquine DMSI5CB Malaria 1F40-1F45 Approved [62]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [63]
Doxorubicin DMVP5YE Acute myelogenous leukaemia 2A41 Approved [64]
Tacrolimus DMZ7XNQ Graft-versus-host disease 4B24 Approved [65]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Interleukin-8 (CXCL8)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Hydrocortisone DMGEMB7 Acne vulgaris ED80 Approved [66]
Nicotine DMWX5CO Lung cancer 2C25.0 Approved [67]
Cannabidiol DM0659E Dravet syndrome 8A61.11 Approved [68]
Pantothenic acid DM091H2 Vitamin deficiency 5B55-5B71 Approved [69]
Mechlorethamine DM0CVXA Chronic myelogenous leukaemia 2A20.0 Approved [70]
Fulvestrant DM0YZC6 Breast cancer 2C60-2C65 Approved [71]
Fexofenadine DM17ONX Allergic rhinitis CA08.0 Approved [72]
Hydrogen peroxide DM1NG5W Infectious disease 1A00-CA43.1 Approved [73]
Nitric Oxide DM1RBYG Hypertension BA00-BA04 Approved [74]
Lumiracoxib DM1S4AG Chronic renal failure GB61.Z Approved [72]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Erythroid transcription factor (GATA1)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [75]
Arsenic trioxide DM61TA4 Acute lymphoblastic leukaemia 2A85 Approved [76]
Hydroquinone DM6AVR4 Melasma ED60.1 Approved [77]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [41]
Aclarubicin DMLFZHD Acute myeloid leukaemia 2A60 Approved [78]
Pomalidomide DMTGBAX Plasma cell myeloma 2A83.1 Approved [79]
Doxorubicin DMVP5YE Acute myelogenous leukaemia 2A41 Approved [80]
Vorinostat DMWMPD4 Adult acute monocytic leukemia Approved [81]
phorbol 12-myristate 13-acetate DMJWD62 Acute myeloid leukaemia 2A60 Phase 2 [82]
(+)-JQ1 DM1CZSJ Testicular cancer 2C80 Phase 1 [83]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By 5-aminolevulinate synthase, erythroid-specific, mitochondrial (ALAS2)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Arsenic trioxide DM61TA4 Acute lymphoblastic leukaemia 2A85 Approved [84]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [41]
Irinotecan DMP6SC2 Adenocarcinoma 2D40 Approved [85]
Diclofenac DMPIHLS Chronic renal failure GB61.Z Approved [86]
Carbamazepine DMZOLBI Epilepsy 8A60-8A68 Approved [86]
Benzo(a)pyrene DMN7J43 N. A. N. A. Phase 1 [87]
bisphenol A DM2ZLD7 Discovery agent N.A. Investigative [88]
Butanoic Acid DMTAJP7 Discovery agent N.A. Investigative [89]
Protoporphyrin IX DMWYE7A Discovery agent N.A. Investigative [90]
⏷ Show the Full List of 9 Drug(s)
Drug(s) Affected By Tumor necrosis factor receptor superfamily member 6 (FAS)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Beta-carotene DM0RXBT Vitamin deficiency 5B55-5B71 Approved [91]
Hydrogen peroxide DM1NG5W Infectious disease 1A00-CA43.1 Approved [92]
Nitric Oxide DM1RBYG Hypertension BA00-BA04 Approved [93]
Methotrexate DM2TEOL Anterior urethra cancer Approved [94]
Epinephrine DM3KJBC Acute asthma CA23 Approved [95]
Quercetin DM3NC4M Obesity 5B81 Approved [96]
Troglitazone DM3VFPD Diabetic complication 5A2Y Approved [97]
Fructose DM43AN2 Vomiting MD90 Approved [98]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [91]
Cyclophosphamide DM4O2Z7 Advanced cancer 2A00-2F9Z Approved [99]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Tumor necrosis factor ligand superfamily member 6 (FASLG)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Fulvestrant DM0YZC6 Breast cancer 2C60-2C65 Approved [88]
Gefitinib DM15F0X Colon adenocarcinoma Approved [100]
Hydrogen peroxide DM1NG5W Infectious disease 1A00-CA43.1 Approved [101]
Epinephrine DM3KJBC Acute asthma CA23 Approved [95]
Quercetin DM3NC4M Obesity 5B81 Approved [102]
Troglitazone DM3VFPD Diabetic complication 5A2Y Approved [33]
Fructose DM43AN2 Vomiting MD90 Approved [98]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [103]
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [104]
Rifampicin DM5DSFZ Non-insulin dependent diabetes 5A11 Approved [105]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Transcription factor NF-E2 45 kDa subunit (NFE2)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Hydrogen peroxide DM1NG5W Infectious disease 1A00-CA43.1 Approved [106]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [38]
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [75]
Leflunomide DMR8ONJ Arthritis FA20 Approved [107]
Aclarubicin DMLFZHD Acute myeloid leukaemia 2A60 Approved [78]
Cupric Sulfate DMP0NFQ Fungal infection 1F29-1F2F Approved [108]
Decitabine DMQL8XJ Acute myelogenous leukaemia 2A41 Approved [109]
Cisplatin DMRHGI9 Adenocarcinoma 2D40 Approved [109]
Pomalidomide DMTGBAX Plasma cell myeloma 2A83.1 Approved [79]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [110]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Sialidase-3 (NEU3)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Arsenic trioxide DM61TA4 Acute lymphoblastic leukaemia 2A85 Approved [111]
Hydroquinone DM6AVR4 Melasma ED60.1 Approved [6]
Leflunomide DMR8ONJ Arthritis FA20 Approved [107]
Cisplatin DMRHGI9 Adenocarcinoma 2D40 Approved [112]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [113]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [114]
Doxorubicin DMVP5YE Acute myelogenous leukaemia 2A41 Approved [64]
Urethane DM7NSI0 N. A. N. A. Phase 4 [115]
Benzo(a)pyrene DMN7J43 N. A. N. A. Phase 1 [116]
PMID28460551-Compound-2 DM4DOUB N. A. N. A. Patented [117]
⏷ 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 (CA) TTUNARX NOUNIPROTAC Inhibitor [1]
Carbonic anhydrase II (CA-II) TTANPDJ CAH2_HUMAN Inhibitor [1]
Carbonic anhydrase IV (CA-IV) TTZHA0O CAH4_HUMAN Inhibitor [1]
Carbonic anhydrase XII (CA-XII) TTSYM0R CAH12_HUMAN Inhibitor [1]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Glucansucrase (gtf106B) Main DME DEWRN24 Q5SBN3_LACRE Substrate [2]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
5-aminolevulinate synthase, erythroid-specific, mitochondrial (ALAS2) OTJXOUCL HEM0_HUMAN Gene/Protein Processing [3]
C-C motif chemokine 2 (CCL2) OTAD2HEL CCL2_HUMAN Gene/Protein Processing [4]
C-C motif chemokine 3 (CCL3) OTW2H3ND CCL3_HUMAN Gene/Protein Processing [4]
C-C motif chemokine 4 (CCL4) OT6B8P25 CCL4_HUMAN Gene/Protein Processing [4]
C-C motif chemokine 5 (CCL5) OTSCA5CK CCL5_HUMAN Gene/Protein Processing [4]
Eotaxin (CCL11) OT3BIFPK CCL11_HUMAN Gene/Protein Processing [4]
Erythroid transcription factor (GATA1) OTX1R7O1 GATA1_HUMAN Gene/Protein Processing [3]
Interleukin-8 (CXCL8) OTS7T5VH IL8_HUMAN Gene/Protein Processing [5]
Sialidase-3 (NEU3) OTQ5PQOW NEUR3_HUMAN Gene/Protein Processing [6]
Transcription factor NF-E2 45 kDa subunit (NFE2) OTLM94BI NFE2_HUMAN Gene/Protein Processing [7]

References

1 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.
2 Catechol glucosides act as donor/acceptor substrates of glucansucrase enzymes of Lactobacillus reuteri. Appl Microbiol Biotechnol. 2017 Jun;101(11):4495-4505.
3 The role of DNA methylation in catechol-enhanced erythroid differentiation of K562 cells. Toxicol Appl Pharmacol. 2012 Nov 15;265(1):43-50. doi: 10.1016/j.taap.2012.09.018. Epub 2012 Sep 27.
4 Identification of human cell responses to benzene and benzene metabolites. Genomics. 2007 Sep;90(3):324-33.
5 Stimulation of endothelial IL-8 (eIL-8) production and apoptosis by phenolic metabolites of benzene in HL-60 cells and human bone marrow endothelial cells. Chem Biol Interact. 2004 Aug 10;149(1):37-49. doi: 10.1016/j.cbi.2004.06.004.
6 Phenolic metabolites of benzene induced caspase-dependent cytotoxicities to K562 cells accompanied with decrease in cell surface sialic acids. Environ Toxicol. 2014 Dec;29(12):1437-51. doi: 10.1002/tox.21874. Epub 2013 Jun 17.
7 Changes in DNA methylation of erythroid-specific genes in K562 cells exposed to catechol in long term. Toxicol In Vitro. 2017 Sep;43:21-28. doi: 10.1016/j.tiv.2017.05.019. Epub 2017 May 25.
8 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.
9 Sulfonamide linked neoglycoconjugates--a new class of inhibitors for cancer-associated carbonic anhydrases. J Med Chem. 2010 Apr 8;53(7):2913-26.
10 Carbonic anhydrase inhibitors. Antioxidant polyphenols effectively inhibit mammalian isoforms I-XV. Bioorg Med Chem Lett. 2010 Sep 1;20(17):5050-3.
11 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.
12 Deciphering the mechanism of carbonic anhydrase inhibition with coumarins and thiocoumarins. J Med Chem. 2010 Jan 14;53(1):335-44.
13 Carbonic anhydrase inhibitors. Inhibition studies of a coral secretory isoform by sulfonamides. Bioorg Med Chem. 2009 Jul 15;17(14):5054-8.
14 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.
15 The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42.
16 Selective effect of thiazides on the human osteoblast-like cell line MG-63. Kidney Int. 1996 Nov;50(5):1476-82.
17 Inhibition of carbonic anhydrases I and II by N-unsubstituted carbamate esters. J Biol Chem. 1992 Dec 15;267(35):25044-50.
18 Nature of the inhibition of carbonic anhydrase by acetazolamide and benzthiazide. J Pharmacol Exp Ther. 1961 Mar;131:271-4.
19 Carbonic anhydrase inhibitors: Inhibition of the new membrane-associated isoform XV with phenols. Bioorg Med Chem Lett. 2008 Jun 15;18(12):3593-6.
20 Cloning, expression, post-translational modifications and inhibition studies on the latest mammalian carbonic anhydrase isoform, CA XV. J Med Chem. 2009 Feb 12;52(3):646-54.
21 Carbonic anhydrase inhibitors. Interaction of indapamide and related diuretics with 12 mammalian isozymes and X-ray crystallographic studies for th... Bioorg Med Chem Lett. 2008 Apr 15;18(8):2567-73.
22 Carbonic anhydrase inhibitors: crystallographic and solution binding studies for the interaction of a boron-containing aromatic sulfamide with mamm... Bioorg Med Chem Lett. 2010 Jun 15;20(12):3601-5.
23 Carbonic anhydrase inhibitors as antitumor/antimetastatic agents: a patent review (2008-2018).Expert Opin Ther Pat. 2018 Oct;28(10):729-740.
24 Carbonic anhydrase inhibitors. Inhibition of the membrane-bound human and bovine isozymes IV with sulfonamides. Bioorg Med Chem Lett. 2005 Feb 15;15(4):1149-54.
25 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
26 Carbonic anhydrase inhibitors. Interaction of isozymes I, II, IV, V, and IX with carboxylates. Bioorg Med Chem Lett. 2005 Feb 1;15(3):573-8.
27 Biosolids application affects the competitive sorption and lability of cadmium, copper, nickel, lead, and zinc in fluvial and calcareous soils. Environ Geochem Health. 2017 Dec;39(6):1365-1379.
28 Increased infections with beta-blocker use in ischemic stroke, a beta2-receptor mediated process? Neurol Sci. 2017 Jun;38(6):967-974.
29 Exploring the effects of plant odors, from tree species of differing host quality, on the response of Lymantria dispar males to female sex pheromones. J Chem Ecol. 2017 Mar;43(3):243-253.
30 Impact of low-level laser therapy on hyposalivation, salivary pH, and quality of life in head and neck cancer patients post-radiotherapy. Lasers Med Sci. 2017 May;32(4):827-832.
31 Some HIV antiretrovirals increase oxidative stress and alter chemokine, cytokine or adiponectin production in human adipocytes and macrophages. Antivir Ther. 2007;12(4):489-500.
32 The contribution of methotrexate exposure and host factors on transcriptional variance in human liver. Toxicol Sci. 2007 Jun;97(2):582-94.
33 Increased sensitivity for troglitazone-induced cytotoxicity using a human in vitro co-culture model. Toxicol In Vitro. 2009 Oct;23(7):1387-95.
34 D-Penicillamine targets metastatic melanoma cells with induction of the unfolded protein response (UPR) and Noxa (PMAIP1)-dependent mitochondrial apoptosis. Apoptosis. 2012 Oct;17(10):1079-94.
35 Pharmacogenomic analysis of acute promyelocytic leukemia cells highlights CYP26 cytochrome metabolism in differential all-trans retinoic acid sensitivity. Blood. 2007 May 15;109(10):4450-60.
36 Global effects of inorganic arsenic on gene expression profile in human macrophages. Mol Immunol. 2009 Feb;46(4):649-56.
37 Cell-based and cytokine-directed chemical screen to identify potential anti-multiple myeloma agents. Leuk Res. 2010 Jul;34(7):917-24. doi: 10.1016/j.leukres.2009.12.002. Epub 2010 Feb 8.
38 Differential modulation of PI3-kinase/Akt pathway during all-trans retinoic acid- and Am80-induced HL-60 cell differentiation revealed by DNA microarray analysis. Biochem Pharmacol. 2004 Dec 1;68(11):2177-86.
39 Single-cell Transcriptome Mapping Identifies Common and Cell-type Specific Genes Affected by Acute Delta9-tetrahydrocannabinol in Humans. Sci Rep. 2020 Feb 26;10(1):3450. doi: 10.1038/s41598-020-59827-1.
40 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.
41 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.
42 Characterization of formaldehyde's genotoxic mode of action by gene expression analysis in TK6 cells. Arch Toxicol. 2013 Nov;87(11):1999-2012.
43 Arsenite and cadmium promote the development of mammary tumors. Carcinogenesis. 2020 Jul 14;41(7):1005-1014. doi: 10.1093/carcin/bgz176.
44 Crosstalk between alveolar macrophages and alveolar epithelial cells/fibroblasts contributes to the pulmonary toxicity of gefitinib. Toxicol Lett. 2021 Mar 1;338:1-9. doi: 10.1016/j.toxlet.2020.11.011. Epub 2020 Nov 25.
45 Oxidative Stress Alters miRNA and Gene Expression Profiles in Villous First Trimester Trophoblasts. Biomed Res Int. 2015;2015:257090. doi: 10.1155/2015/257090. Epub 2015 Aug 3.
46 Cannabidiol selectively modulates interleukin (IL)-1 and IL-6 production in toll-like receptor activated human peripheral blood monocytes. Toxicology. 2021 Dec;464:153016. doi: 10.1016/j.tox.2021.153016. Epub 2021 Nov 2.
47 Monitoring of deiodinase deficiency based on transcriptomic responses in SH-SY5Y cells. Arch Toxicol. 2013 Jun;87(6):1103-13. doi: 10.1007/s00204-013-1018-4. Epub 2013 Feb 10.
48 Dimethyl Fumarate Inhibits the Nuclear Factor B Pathway in Breast Cancer Cells by Covalent Modification of p65 Protein. J Biol Chem. 2016 Feb 12;291(7):3639-47. doi: 10.1074/jbc.M115.679704. Epub 2015 Dec 18.
49 Simvastatin reduces expression of cytokines interleukin-6, interleukin-8, and monocyte chemoattractant protein-1 in circulating monocytes from hypercholesterolemic patients. Arterioscler Thromb Vasc Biol. 2002 Jul 1;22(7):1194-9. doi: 10.1161/01.atv.0000022694.16328.cc.
50 Plant polyphenols differentially modulate inflammatory responses of human keratinocytes by interfering with activation of transcription factors NFB and AhR and EGFR-ERK pathway. Toxicol Appl Pharmacol. 2011 Sep 1;255(2):138-49.
51 Gene expression profiles with activation of the estrogen receptor alpha-selective estrogen receptor modulator complex in breast cancer cells expressing wild-type estrogen receptor. Cancer Res. 2002 Aug 1;62(15):4419-26.
52 A copper-hydrogen peroxide redox system induces dityrosine cross-links and chemokine oligomerisation. Cytokine. 2011 Dec;56(3):669-75. doi: 10.1016/j.cyto.2011.08.025. Epub 2011 Oct 1.
53 Regulatory role of nitric oxide on monocyte-derived dendritic cell functions. J Interferon Cytokine Res. 2003 Aug;23(8):423-31. doi: 10.1089/107999003322277838.
54 Simvastatin down regulates mRNA expression of RANTES and CCR5 in posttransplant renal recipients with hyperlipidemia. Transplant Proc. 2006 Nov;38(9):2899-904. doi: 10.1016/j.transproceed.2006.08.136.
55 Effects of ciglitazone and troglitazone on the proliferation of human stomach cancer cells. World J Gastroenterol. 2009 Jan 21;15(3):310-20.
56 13-cis retinoic acid inhibits development and progression of chronic allograft nephropathy. Am J Pathol. 2005 Jul;167(1):285-98. doi: 10.1016/S0002-9440(10)62973-2.
57 2,3,7,8-tetrachlorodibenzo-p-dioxin augments the modulation of gene expression mediated by the thyroid hormone receptor. Toxicol Appl Pharmacol. 2004 Feb 1;194(3):201-10. doi: 10.1016/j.taap.2003.09.010.
58 Alterations in eotaxin, monocyte chemoattractant protein-4, interleukin-5, and interleukin-13 after systemic steroid treatment for nasal polyps. Otolaryngol Head Neck Surg. 2004 Nov;131(5):585-9. doi: 10.1016/j.otohns.2004.05.028.
59 Expression of PPARgamma in eosinophils and its functional role in survival and chemotaxis. Immunol Lett. 2003 Apr 3;86(2):183-9. doi: 10.1016/s0165-2478(03)00003-8.
60 THC exposure of human iPSC neurons impacts genes associated with neuropsychiatric disorders. Transl Psychiatry. 2018 Apr 25;8(1):89. doi: 10.1038/s41398-018-0137-3.
61 Alcohol and Cannabinoids Differentially Affect HIV Infection and Function of Human Monocyte-Derived Dendritic Cells (MDDC). Front Microbiol. 2015 Dec 22;6:1452. doi: 10.3389/fmicb.2015.01452. eCollection 2015.
62 Paradoxical Effect of Chloroquine Treatment in Enhancing Chikungunya Virus Infection. Viruses. 2018 May 17;10(5):268. doi: 10.3390/v10050268.
63 Blood transcript immune signatures distinguish a subset of people with elevated serum ALT from others given acetaminophen. Clin Pharmacol Ther. 2016 Apr;99(4):432-41.
64 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.
65 Tacrolimus decreases the expression of eotaxin, CCR3, RANTES and interleukin-5 in atopic dermatitis. Br J Dermatol. 2005 Jun;152(6):1173-81. doi: 10.1111/j.1365-2133.2005.06474.x.
66 Monomeric and oligomeric flavanols maintain the endogenous glucocorticoid response in human macrophages in pro-oxidant conditions in vitro. Chem Biol Interact. 2018 Aug 1;291:237-244.
67 Nicotine up-regulates IL-8 expression in human gingival epithelial cells following stimulation with IL-1 or P. gingivalis lipopolysaccharide via nicotinic acetylcholine receptor signalling. Arch Oral Biol. 2012 May;57(5):483-90. doi: 10.1016/j.archoralbio.2011.10.007. Epub 2011 Nov 25.
68 Ca(2+) Signaling and IL-8 Secretion in Human Testicular Peritubular Cells Involve the Cation Channel TRPV2. Int J Mol Sci. 2018 Sep 19;19(9):2829. doi: 10.3390/ijms19092829.
69 Calcium pantothenate modulates gene expression in proliferating human dermal fibroblasts. Exp Dermatol. 2009 Nov;18(11):969-78. doi: 10.1111/j.1600-0625.2009.00884.x. Epub 2009 Apr 8.
70 Nitrogen mustard prevents transport of Fra-1 into the nucleus to promote c-Fos- and FosB-dependent IL-8 induction in injured mouse epidermis. Toxicol Lett. 2020 Feb 1;319:256-263. doi: 10.1016/j.toxlet.2019.10.006. Epub 2019 Oct 19.
71 ERE-independent ERalpha target genes differentially expressed in human breast tumors. Mol Cell Endocrinol. 2005 Dec 21;245(1-2):53-9. doi: 10.1016/j.mce.2005.10.003. Epub 2005 Nov 17.
72 An in vitro coculture system of human peripheral blood mononuclear cells with hepatocellular carcinoma-derived cells for predicting drug-induced liver injury. Arch Toxicol. 2021 Jan;95(1):149-168. doi: 10.1007/s00204-020-02882-4. Epub 2020 Aug 20.
73 Gypenosides protect retinal pigment epithelium cells from oxidative stress. Food Chem Toxicol. 2018 Feb;112:76-85.
74 Nitric oxide synthase inhibitors attenuate ozone-induced airway inflammation in guinea pigs. Possible role of interleukin-8. Am J Respir Crit Care Med. 2000 Jan;161(1):249-56. doi: 10.1164/ajrccm.161.1.9804096.
75 3'-Azido-3'-deoxythymidine inhibits erythroid-specific transcription factors in human erythroid K562 leukemia cells. Eur J Haematol. 1996 Jan-Feb;56(1-2):62-7. doi: 10.1111/j.1600-0609.1996.tb00296.x.
76 In vitro dual effect of arsenic trioxide on hemopoiesis: inhibition of erythropoiesis and stimulation of megakaryocytic maturation. Blood Cells Mol Dis. 2006 Jan-Feb;36(1):59-76. doi: 10.1016/j.bcmd.2005.10.005. Epub 2005 Dec 15.
77 Phenolic metabolites of benzene inhibited the erythroid differentiation of K562 cells. Toxicol Lett. 2011 Jun 24;203(3):190-9. doi: 10.1016/j.toxlet.2011.03.012. Epub 2011 Mar 23.
78 Oxidative stress involvement in chemically induced differentiation of K562 cells. Free Radic Biol Med. 2000 Jan 1;28(1):18-27.
79 Immunomodulatory derivative of thalidomide (IMiD CC-4047) induces a shift in lineage commitment by suppressing erythropoiesis and promoting myelopoiesis. Blood. 2005 May 15;105(10):3833-40. doi: 10.1182/blood-2004-03-0828. Epub 2004 Aug 3.
80 Accumulation of gamma-globin mRNA and induction of irreversible erythroid differentiation after treatment of CML cell line K562 with new doxorubicin derivatives. Biochem Pharmacol. 2007 Jan 15;73(2):175-84. doi: 10.1016/j.bcp.2006.09.028. Epub 2006 Oct 4.
81 Effects of arsenic disulfide on apoptosis, histone acetylation, toll like receptor 2 activation, and erythropoiesis in bone marrow mononuclear cells of myelodysplastic syndromes patients in vitro. Leuk Res. 2017 Nov;62:4-11. doi: 10.1016/j.leukres.2017.09.010. Epub 2017 Sep 19.
82 Expression of glutathione S-transferase P1-1 in differentiating K562: role of GATA-1. Biochem Biophys Res Commun. 2003 Nov 28;311(4):815-21.
83 The BET bromodomain inhibitor JQ1 suppresses growth of pancreatic ductal adenocarcinoma in patient-derived xenograft models. Oncogene. 2016 Feb 18;35(7):833-45.
84 Essential role of cell cycle regulatory genes p21 and p27 expression in inhibition of breast cancer cells by arsenic trioxide. Med Oncol. 2011 Dec;28(4):1225-54.
85 In vitro and in vivo irinotecan-induced changes in expression profiles of cell cycle and apoptosis-associated genes in acute myeloid leukemia cells. Mol Cancer Ther. 2005 Jun;4(6):885-900.
86 Drug-induced endoplasmic reticulum and oxidative stress responses independently sensitize toward TNF-mediated hepatotoxicity. Toxicol Sci. 2014 Jul;140(1):144-59. doi: 10.1093/toxsci/kfu072. Epub 2014 Apr 20.
87 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.
88 DNA methylome-wide alterations associated with estrogen receptor-dependent effects of bisphenols in breast cancer. Clin Epigenetics. 2019 Oct 10;11(1):138. doi: 10.1186/s13148-019-0725-y.
89 MS4A3-HSP27 target pathway reveals potential for haematopoietic disorder treatment in alimentary toxic aleukia. Cell Biol Toxicol. 2023 Feb;39(1):201-216. doi: 10.1007/s10565-021-09639-4. Epub 2021 Sep 28.
90 Changes in DNA methylation of erythroid-specific genes in K562 cells exposed to phenol and hydroquinone. Toxicology. 2013 Oct 4;312:108-14. doi: 10.1016/j.tox.2013.08.007. Epub 2013 Aug 20.
91 Beta-carotene and apocarotenals promote retinoid signaling in BEAS-2B human bronchioepithelial cells. Arch Biochem Biophys. 2006 Nov 1;455(1):48-60.
92 Gene expression after treatment with hydrogen peroxide, menadione, or t-butyl hydroperoxide in breast cancer cells. Cancer Res. 2002 Nov 1;62(21):6246-54.
93 Apoptotic signaling pathways induced by nitric oxide in human lymphoblastoid cells expressing wild-type or mutant p53. Cancer Res. 2004 May 1;64(9):3022-9. doi: 10.1158/0008-5472.can-03-1880.
94 Topotecan and methotrexate alter expression of the apoptosis-related genes BCL2, FAS and BCL2L12 in leukemic HL-60 cells. Biol Chem. 2006 Dec;387(12):1629-33. doi: 10.1515/BC.2006.203.
95 Carvedilol prevents epinephrine-induced apoptosis in human coronary artery endothelial cells: modulation of Fas/Fas ligand and caspase-3 pathway. Cardiovasc Res. 2000 Feb;45(3):788-94. doi: 10.1016/s0008-6363(99)00369-7.
96 Multifaceted preventive effects of single agent quercetin on a human prostate adenocarcinoma cell line (PC-3): implications for nutritional transcriptomics and multi-target therapy. Med Oncol. 2011 Dec;28(4):1395-404. doi: 10.1007/s12032-010-9603-3. Epub 2010 Jul 2.
97 Regulatory role of KEAP1 and NRF2 in PPAR expression and chemoresistance in human non-small-cell lung carcinoma cells. Free Radic Biol Med. 2012 Aug 15;53(4):758-68. doi: 10.1016/j.freeradbiomed.2012.05.041. Epub 2012 Jun 7.
98 Non-nutritional sweeteners effects on endothelial vascular function. Toxicol In Vitro. 2020 Feb;62:104694. doi: 10.1016/j.tiv.2019.104694. Epub 2019 Oct 23.
99 Transcriptome-based functional classifiers for direct immunotoxicity. Arch Toxicol. 2014 Mar;88(3):673-89.
100 The anti-cancer drug gefitinib accelerates Fas-mediated apoptosis by enhancing caspase-8 activation in cancer cells. J Toxicol Sci. 2019;44(6):435-440. doi: 10.2131/jts.44.435.
101 NF-B potentiates caspase independent hydrogen peroxide induced cell death. PLoS One. 2011 Feb 15;6(2):e16815. doi: 10.1371/journal.pone.0016815.
102 Quercetin induces FasL-related apoptosis, in part, through promotion of histone H3 acetylation in human leukemia HL-60 cells. Oncol Rep. 2011 Feb;25(2):583-91. doi: 10.3892/or.2010.1097. Epub 2010 Dec 10.
103 Influence of antitumor drugs on the expression of Fas system in SW480 colon cancer cells. Eur J Gastroenterol Hepatol. 2006 Oct;18(10):1071-7. doi: 10.1097/01.meg.0000231750.68513.6c.
104 Acrolein enhances epigenetic modifications, FasL expression and hepatocyte toxicity induced by anti-HIV drug Zidovudine. Toxicol In Vitro. 2016 Sep;35:66-76. doi: 10.1016/j.tiv.2016.05.013. Epub 2016 May 26.
105 Rifampicin inhibits CD95-mediated apoptosis of Jurkat T cells via glucocorticoid receptors by modifying the expression of molecules regulating apoptosis. J Clin Immunol. 2002 Jan;22(1):37-47. doi: 10.1023/a:1014256603539.
106 Global gene expression analysis reveals differences in cellular responses to hydroxyl- and superoxide anion radical-induced oxidative stress in caco-2 cells. Toxicol Sci. 2010 Apr;114(2):193-203. doi: 10.1093/toxsci/kfp309. Epub 2009 Dec 31.
107 Endoplasmic reticulum stress and MAPK signaling pathway activation underlie leflunomide-induced toxicity in HepG2 Cells. Toxicology. 2017 Dec 1;392:11-21.
108 Physiological and toxicological transcriptome changes in HepG2 cells exposed to copper. Physiol Genomics. 2009 Aug 7;38(3):386-401.
109 Acute hypersensitivity of pluripotent testicular cancer-derived embryonal carcinoma to low-dose 5-aza deoxycytidine is associated with global DNA Damage-associated p53 activation, anti-pluripotency and DNA demethylation. PLoS One. 2012;7(12):e53003. doi: 10.1371/journal.pone.0053003. Epub 2012 Dec 27.
110 Identification of novel low-dose bisphenol a targets in human foreskin fibroblast cells derived from hypospadias patients. PLoS One. 2012;7(5):e36711. doi: 10.1371/journal.pone.0036711. Epub 2012 May 4.
111 Role of NADPH oxidase in arsenic-induced reactive oxygen species formation and cytotoxicity in myeloid leukemia cells. Proc Natl Acad Sci U S A. 2004 Mar 30;101(13):4578-83.
112 Activation of AIFM2 enhances apoptosis of human lung cancer cells undergoing toxicological stress. Toxicol Lett. 2016 Sep 6;258:227-236.
113 Predictive toxicology using systemic biology and liver microfluidic "on chip" approaches: application to acetaminophen injury. Toxicol Appl Pharmacol. 2012 Mar 15;259(3):270-80.
114 17-Estradiol Activates HSF1 via MAPK Signaling in ER-Positive Breast Cancer Cells. Cancers (Basel). 2019 Oct 11;11(10):1533. doi: 10.3390/cancers11101533.
115 Ethyl carbamate induces cell death through its effects on multiple metabolic pathways. Chem Biol Interact. 2017 Nov 1;277:21-32.
116 Benzo[a]pyrene increases the Nrf2 content by downregulating the Keap1 message. Toxicol Sci. 2010 Aug;116(2):549-61.
117 Cell-based two-dimensional morphological assessment system to predict cancer drug-induced cardiotoxicity using human induced pluripotent stem cell-derived cardiomyocytes. Toxicol Appl Pharmacol. 2019 Nov 15;383:114761. doi: 10.1016/j.taap.2019.114761. Epub 2019 Sep 15.