General Information of Drug (ID: DMOY7W3)

Drug Name
Artemisinin Drug Info
Synonyms
Arteannuin; Artemisine; Artemisinina; Artemisinine; Artemisininum; Artesin; Huanghuahaosu; Qinghaosu; Qinghosu; Quinghaosu; Artemisinin [INN]; Artemisinina [Spanish]; Artemisinine [French]; Artemisininum [Latin]; Qing Hau SU; Qing Hau Sau; Qing Hau Sau [Chinese]; Qinghaosu [Chinese]; Quing Hau Sau; Artemisinin (INN); Coartem, Artemisinin; Artemisia annua L., extract; GNF-PF-5671; GNF-Pf-5341; Octahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano(4,3-j)-1,2-benzodioxepin-10(3H)-one; (+)-Arteannuin; (+)-Artemisinin; (3R,5aS,6R,8aS,9R,12S,12aR)-3,6,9-trimethyloctahydro-3,12-epoxypyrano[4,3-j][1,2]benzodioxepin-10(3H)-one; (3R,5aS,6R,8aS,9R,12S,12aR)-Octahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano(4,3-j)-1,2-benzodioxepin-10(3H)-one; (5aS,6R,8aS,9R,12S,12aR)-3,6,9-trimethyloctahydro-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10(3H)-one; 1,5,9-trimethyl-(1R,4S,5R,9R,12S,13R)-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-one; 3,6,9-trimethyloctahydro-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10(3H)-one
Indication
Disease Entry ICD 11 Status REF
Malaria 1F40-1F45 Approved [1]
Cross-matching ID
PubChem CID
68827
ChEBI ID
CHEBI:223316
CAS Number
CAS 63968-64-9
TTD Drug ID
DMOY7W3
VARIDT Drug ID
DR01207
INTEDE Drug ID
DR0141

Molecule-Related Drug Atlas

Molecule-Related Drug Atlas
Molecule Type:
DTT
DME
DOT
Drug Status:
Approved Drug(s)
Clinical Trial Drug(s)
Investigative Drug(s)
Preclinical Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Leflunomide DMR8ONJ Arthritis FA20 Approved [9]
Teriflunomide DMQ2FKJ Hyperlipidaemia 5C80 Approved [10]
Atovaquone DMY4UMW Fungal infection 1F29-1F2F Approved [11]
Avastin+/-Tarceva DMA86FL Non-small-cell lung cancer 2C25.Y Phase 3 [12]
Acetate Ion DMD08RH Discovery agent N.A. Investigative [13]
B-Octylglucoside DMMO75G Discovery agent N.A. Investigative [13]
Orotate DMMB29S Discovery agent N.A. Investigative [14]
Lauryl Dimethylamine-N-Oxide DM3W2OE Discovery agent N.A. Investigative [13]
1,4-Naphthoquinone DMTCMH7 Discovery agent N.A. Investigative [12]
Dihydroorotate DM76BGZ Discovery agent N.A. Investigative [15]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Dihydroartemisinin DMBXVMZ Malaria 1F40-1F45 Approved [1]
Piperaquine DMT70RC Malaria 1F40-1F45 Approved [1]
Artemisinin SP DMFETDK Malaria 1F40-1F45 Approved [1]
Artesunate DMR27C8 Infection of P. falciparum 1F40 Approved [1]
OZ277 DM1YB0R Malaria 1F40-1F45 Approved [1]
Pyronaridine DMUWAM2 Malaria 1F40-1F45 Approved [1]
Vanadate DMQL0KF Psoriatic arthritis FA21 Phase 3 [16]
THAPSIGARGIN DMDMQIE N. A. N. A. Preclinical [17]
Cyclopiazonic acid DMPJ08G Discovery agent N.A. Investigative [16]
⏷ Show the Full List of 9 Drug(s)
Drug(s) Metabolized By Cytochrome P450 3A4 (CYP3A4)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Doxorubicin DMVP5YE Acute myelogenous leukaemia 2A41 Approved [18]
Progesterone DMUY35B Amenorrhea GA20.0 Approved [19]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [20]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [21]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [22]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [23]
Etoposide DMNH3PG Acute myelogenous leukaemia 2A41 Approved [24]
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [25]
Prasterone DM67VKL Chronic obstructive pulmonary disease CA22 Approved [19]
Verapamil DMA7PEW Angina pectoris BA40 Approved [26]
Eplerenone DMF0NQR Heart failure BD10-BD13 Approved [63]
Cannabidiol DM0659E Dravet syndrome 8A61.11 Approved [64]
Isotretinoin DM4QTBN Acne vulgaris ED80 Approved [65]
Voriconazole DMAOL2S Aspergillosis 1F20 Approved [66]
Proguanil DMBL79I Malaria 1F40-1F45 Approved [7]
Ivermectin DMDBX5F Intestinal strongyloidiasis due to nematode parasite 1F6B Approved [7]
Loratadine DMF3AN7 Allergy 4A80-4A85 Approved [67]
Nelfinavir mesylate DMFX6G8 N. A. N. A. Approved [68]
Capsaicin DMGMF6V Back pain ME84.Z Approved [69]
Axitinib DMGVH6N Renal cell carcinoma 2C90 Approved [70]
⏷ Show the Full List of 20 Drug(s)
Drug(s) Metabolized By Cytochrome P450 2A6 (CYP2A6)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Fluorouracil DMUM7HZ Adenocarcinoma 2D40 Approved [27]
Progesterone DMUY35B Amenorrhea GA20.0 Approved [28]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [29]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [22]
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [28]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [30]
Metronidazole DMTIVEN Abscess Approved [31]
Propofol DMB4OLE Anaesthesia 9A78.6 Approved [32]
Nicotine DMWX5CO Lung cancer 2C25.0 Approved [33]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [28]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Cisplatin DMRHGI9 Adenocarcinoma 2D40 Approved [34]
Progesterone DMUY35B Amenorrhea GA20.0 Approved [35]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [36]
Phenytoin DMNOKBV Epilepsy 8A60-8A68 Approved [37]
Clofibrate DMPC1J7 Dysbetalipoproteinemia 5C80.2 Approved [38]
Trabectedin DMG3Y89 Leiomyosarcoma 2B58 Approved [39]
Busulfan DMXYJ9C Chronic myelogenous leukaemia 2A20.0 Approved [40]
Ethacrynic acid DM60QMR Edema MG29 Approved [41]
Tacrine DM51FY6 Alzheimer disease 8A20 Approved [42]
Melphalan DMOLNHF Hematologic disease 3C0Z Approved [43]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Metabolized By Cytochrome P450 2B6 (CYP2B6)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [44]
Verapamil DMA7PEW Angina pectoris BA40 Approved [28]
Diclofenac DMPIHLS Chronic renal failure GB61.Z Approved [45]
Estrone DM5T6US Acne vulgaris ED80 Approved [46]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [47]
Irinotecan DMP6SC2 Adenocarcinoma 2D40 Approved [48]
Propofol DMB4OLE Anaesthesia 9A78.6 Approved [49]
Nicotine DMWX5CO Lung cancer 2C25.0 Approved [50]
Phenytoin DMNOKBV Epilepsy 8A60-8A68 Approved [51]
Amitriptyline DMK7F9S Depression 6A70-6A7Z Approved [52]
Sertraline DM0FB1J Coronary heart disease BA80.Z Approved [71]
Ritonavir DMU764S Human immunodeficiency virus infection 1C62 Approved [72]
Rifampicin DM5DSFZ Non-insulin dependent diabetes 5A11 Approved [73]
Thalidomide DM70BU5 Adult T-cell leukemia/lymphoma Approved [74]
Phenytoin DMNOKBV Epilepsy 8A60-8A68 Approved [75]
Clopidogrel DMOL54H Acute coronary syndrome BA41 Approved [76]
Malathion DMXZ84M Pediculus capitis infestation 1G00.0 Approved [77]
Phenobarbital DMXZOCG Cluster headache 8A81.0 Approved [78]
Permethrin DMZ0Q1G Pediculus capitis infestation 1G00.0 Approved [79]
Carbamazepine DMZOLBI Epilepsy 8A60-8A68 Approved [80]
⏷ Show the Full List of 20 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Progesterone DMUY35B Amenorrhea GA20.0 Approved [53]
Thiotepa DMIZKOP Breast cancer 2C60-2C65 Approved [54]
Phenytoin DMNOKBV Epilepsy 8A60-8A68 Approved [55]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [56]
Ethacrynic acid DM60QMR Edema MG29 Approved [57]
Cisplatin DMRHGI9 Adenocarcinoma 2D40 Approved [58]
Busulfan DMXYJ9C Chronic myelogenous leukaemia 2A20.0 Approved [59]
Hydrogen peroxide DM1NG5W Infectious disease 1A00-CA43.1 Approved [60]
Methotrexate DM2TEOL Anterior urethra cancer Approved [61]
Quercetin DM3NC4M Obesity 5B81 Approved [62]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Cytochrome P450 1A2 (CYP1A2)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Zolmitriptan DM1IB4Q Migraine 8A80 Approved [81]
Rofecoxib DM3P5DA Osteoarthritis FA00-FA05 Approved [81]
Etoricoxib DM6A4NW Rheumatoid arthritis FA20 Approved [81]
Capsaicin DMGMF6V Back pain ME84.Z Approved [82]
Hesperetin DMKER83 High blood cholesterol level 5C80.00 Approved [83]
Stiripentol DMMSDOY Dravet syndrome 8A61.11 Approved [84]
Nifedipine DMSVOZT Angina pectoris BA40 Approved [85]
Zileuton DMVRIC2 Allergic asthma CA23.0 Approved [86]
Nicotine DMWX5CO Lung cancer 2C25.0 Approved [87]
Clonidine DM6RZ9Q Attention deficit hyperactivity disorder 6A05.Z Approved [88]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Cytochrome P450 2C19 (CYP2C19)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Cannabidiol DM0659E Dravet syndrome 8A61.11 Approved [64]
Thioridazine DM35M8J Schizophrenia 6A20 Approved [89]
Voriconazole DMAOL2S Aspergillosis 1F20 Approved [66]
Chloramphenicol DMFXEWT Bacterial infection 1A00-1C4Z Approved [71]
Capsaicin DMGMF6V Back pain ME84.Z Approved [82]
Pentamidine DMHZJCG African trypanosomiasis 1F51 Approved [7]
Stiripentol DMMSDOY Dravet syndrome 8A61.11 Approved [84]
Quinine DMSWYF5 Malaria 1F40-1F45 Approved [7]
Desipramine DMT2FDC Attention deficit hyperactivity disorder 6A05.Z Approved [89]
Amitriptyline DMK7F9S Depression 6A70-6A7Z Approved [88]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Busulfan DMXYJ9C Chronic myelogenous leukaemia 2A20.0 Approved [90]
Cisplatin DMRHGI9 Adenocarcinoma 2D40 Approved [91]
Etoposide DMNH3PG Acute myelogenous leukaemia 2A41 Approved [92]
Chlorambucil DMRKE63 Chronic lymphocytic leukaemia 2A82.0 Approved [92]
Fluorouracil DMUM7HZ Adenocarcinoma 2D40 Approved [93]
Cannabidiol DM0659E Dravet syndrome 8A61.11 Approved [94]
Hydrogen peroxide DM1NG5W Infectious disease 1A00-CA43.1 Approved [95]
Selenium DM25CGV N. A. N. A. Approved [96]
Etretinate DM2CZFA Keratosis ED56 Approved [97]
Imipramine DM2NUH3 Depression 6A70-6A7Z Approved [98]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Flupentixol DM0DJ9O Schizophrenia 6A20 Approved [99]
Sertraline DM0FB1J Coronary heart disease BA80.Z Approved [100]
Crizotinib DM4F29C Non-small-cell lung cancer 2C25.Y Approved [101]
Lamotrigine DM8SXYG Bipolar disorder 6A60 Approved [102]
Cepharanthine DM9Y5JB N. A. N. A. Approved [103]
Itraconazole DMCR1MV Aspergillosis 1F20 Approved [104]
Clozapine DMFC71L Schizophrenia 6A20 Approved [105]
Midostaurin DMI6E0R Acute myeloid leukaemia 2A60 Approved [106]
Trifluoperazine DMKBYWI Anxiety Approved [107]
Olanzapine DMPFN6Y Bipolar depression Approved [105]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Cisplatin DMRHGI9 Adenocarcinoma 2D40 Approved [108]
Methotrexate DM2TEOL Anterior urethra cancer Approved [109]
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [110]
Arsenic trioxide DM61TA4 Acute lymphoblastic leukaemia 2A85 Approved [111]
Cidofovir DMA13GD Cytomegalovirus infection 1D82 Approved [112]
Paclitaxel DMLB81S Breast carcinoma Approved [113]
Floxuridine DM04LR2 Colorectal cancer 2B91.Z Approved [114]
Cannabidiol DM0659E Dravet syndrome 8A61.11 Approved [115]
Mechlorethamine DM0CVXA Chronic myelogenous leukaemia 2A20.0 Approved [116]
Fulvestrant DM0YZC6 Breast cancer 2C60-2C65 Approved [117]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Cannabidiol DM0659E Dravet syndrome 8A61.11 Approved [118]
Hydrogen peroxide DM1NG5W Infectious disease 1A00-CA43.1 Approved [119]
Panobinostat DM58WKG Chronic graft versus host disease Approved [120]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [121]
Ivermectin DMDBX5F Intestinal strongyloidiasis due to nematode parasite 1F6B Approved [122]
Sodium lauryl sulfate DMLJ634 Constipation DD91.1 Approved [123]
Bortezomib DMNO38U Leukemia Approved [6]
Piroxicam DMTK234 Osteoarthritis FA00-FA05 Approved [124]
Arsenic DMTL2Y1 N. A. N. A. Approved [125]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [126]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Simvastatin DM30SGU Arteriosclerosis BD40 Approved [127]
Quercetin DM3NC4M Obesity 5B81 Approved [128]
Troglitazone DM3VFPD Diabetic complication 5A2Y Approved [129]
Artemether DM48QOT Malaria 1F40-1F45 Approved [130]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [131]
Nefazodone DM4ZS8M Major depressive disorder 6A70.3 Approved [132]
Rifampicin DM5DSFZ Non-insulin dependent diabetes 5A11 Approved [133]
Estrone DM5T6US Acne vulgaris ED80 Approved [134]
Leflunomide DMR8ONJ Arthritis FA20 Approved [135]
Ciclosporin DMAZJFX Graft-versus-host disease 4B24 Approved [136]
⏷ 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
Plasmodium Dihydroorotate dehydrogenase (Malaria DHOdehase) TT3PQ2Y PYRD_PLAF7 Inhibitor [1]
Sarcoplasmic/endoplasmic reticulum calcium ATPase (ATP2A) TTZVSJ2 NOUNIPROTAC Inhibitor [1]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4) DE4LYSA CP3A4_HUMAN Substrate [2]
Glutathione S-transferase alpha-1 (GSTA1) DE4ZHS1 GSTA1_HUMAN Substrate [3]
Cytochrome P450 2A6 (CYP2A6) DEJVYAZ CP2A6_HUMAN Substrate [4]
Cytochrome P450 2B6 (CYP2B6) DEPKLMQ CP2B6_HUMAN Substrate [2]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
ATP-dependent translocase ABCB1 (ABCB1) OTEJROBO MDR1_HUMAN Gene/Protein Processing [5]
Cellular tumor antigen p53 (TP53) OTIE1VH3 P53_HUMAN Gene/Protein Processing [6]
Cytochrome P450 1A2 (CYP1A2) OTLLBX48 CP1A2_HUMAN Gene/Protein Processing [7]
Cytochrome P450 2B6 (CYP2B6) OTOYO4S7 CP2B6_HUMAN Gene/Protein Processing [5]
Cytochrome P450 2C19 (CYP2C19) OTFMJYYE CP2CJ_HUMAN Gene/Protein Processing [7]
Cytochrome P450 3A4 (CYP3A4) OTQGYY83 CP3A4_HUMAN Gene/Protein Processing [5]
Glutathione S-transferase A1 (GSTA1) OTA7K5XA GSTA1_HUMAN Gene/Protein Processing [3]
Glutathione S-transferase P (GSTP1) OTLP0A0Y GSTP1_HUMAN Gene/Protein Processing [3]
Isocitrate dehydrogenase subunit alpha, mitochondrial (IDH3A) OT5QQB5L IDH3A_HUMAN Gene/Protein Processing [6]
Nuclear receptor subfamily 1 group I member 3 (NR1I3) OTS3SGH7 NR1I3_HUMAN Gene/Protein Processing [8]

References

1 The fight against drug-resistant malaria: novel plasmodial targets and antimalarial drugs. Curr Med Chem. 2008;15(2):161-71.
2 Antimalarial artemisinin drugs induce cytochrome P450 and MDR1 expression by activation of xenosensors pregnane X receptor and constitutive androstane receptor. Mol Pharmacol. 2005 Jun;67(6):1954-65.
3 Inhibition of glutathione S-transferases by antimalarial drugs possible implications for circumventing anticancer drug resistance. Int J Cancer. 2002 Feb 10;97(5):700-5.
4 Identification of the human cytochrome P450 enzymes involved in the in vitro metabolism of artemisinin. Br J Clin Pharmacol. 1999 Oct;48(4):528-35.
5 Antimalarial artemisinin drugs induce cytochrome P450 and MDR1 expression by activation of xenosensors pregnane X receptor and constitutive androstane receptor. Mol Pharmacol. 2005 Jun;67(6):1954-65.
6 Identification of Compounds That Inhibit Estrogen-Related Receptor Alpha Signaling Using High-Throughput Screening Assays. Molecules. 2019 Feb 27;24(5):841. doi: 10.3390/molecules24050841.
7 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.
8 In vivo and mechanistic evidence of nuclear receptor CAR induction by artemisinin. Eur J Clin Invest. 2006 Sep;36(9):647-53. doi: 10.1111/j.1365-2362.2006.01700.x.
9 Identification and characterization of potential new therapeutic targets in inflammatory and autoimmune diseases. Eur J Biochem. 1999 Dec;266(3):1184-91.
10 Expression and characterization of E. coli-produced soluble, functional human dihydroorotate dehydrogenase: a potential target for immunosuppression. J Mol Microbiol Biotechnol. 1999 Aug;1(1):183-8.
11 Inhibitor binding in a class 2 dihydroorotate dehydrogenase causes variations in the membrane-associated N-terminal domain. Protein Sci. 2004 Apr;13(4):1031-42.
12 Kinetics of inhibition of human and rat dihydroorotate dehydrogenase by atovaquone, lawsone derivatives, brequinar sodium and polyporic acid. Chem Biol Interact. 2000 Jan 3;124(1):61-76.
13 How many drug targets are there Nat Rev Drug Discov. 2006 Dec;5(12):993-6.
14 Antimalarial activity of orotate analogs that inhibit dihydroorotase and dihydroorotate dehydrogenase. Biochem Pharmacol. 1992 Mar 17;43(6):1295-301.
15 Structure-activity relationships of pyrimidines as dihydroorotate dehydrogenase inhibitors. Biochem Pharmacol. 1988 Oct 15;37(20):3807-16.
16 Expression and functional characterization of a Plasmodium falciparum Ca2+-ATPase (PfATP4) belonging to a subclass unique to apicomplexan organisms. J Biol Chem. 2001 Apr 6;276(14):10782-7.
17 Elucidation of the topography of the thapsigargin binding site in the sarco-endoplasmic calcium ATPase. Bioorg Med Chem. 2010 Aug 1;18(15):5634-46.
18 Expression levels and activation of a PXR variant are directly related to drug resistance in osteosarcoma cell lines. Cancer. 2007 Mar 1;109(5):957-65.
19 Contribution of human hepatic cytochrome P450 isoforms to regioselective hydroxylation of steroid hormones. Xenobiotica. 1998 Jun;28(6):539-47.
20 Comprehensive evaluation of tamoxifen sequential biotransformation by the human cytochrome P450 system in vitro: prominent roles for CYP3A and CYP2D6. J Pharmacol Exp Ther. 2004 Sep;310(3):1062-75.
21 Isoform-specific regulation of cytochromes P450 expression by estradiol and progesterone. Drug Metab Dispos. 2013 Feb;41(2):263-9.
22 Metabolic interactions between acetaminophen (paracetamol) and two flavonoids, luteolin and quercetin, through in-vitro inhibition studies. J Pharm Pharmacol. 2017 Dec;69(12):1762-1772.
23 Potent mechanism-based inhibition of CYP3A4 by imatinib explains its liability to interact with CYP3A4 substrates. Br J Pharmacol. 2012 Apr;165(8):2787-98.
24 Effects of morin on the pharmacokinetics of etoposide in rats. Biopharm Drug Dispos. 2007 Apr;28(3):151-6.
25 The metabolism of zidovudine by human liver microsomes in vitro: formation of 3'-amino-3'-deoxythymidine. Biochem Pharmacol. 1994 Jul 19;48(2):267-76.
26 Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675.
27 Roles of cytochromes P450 1A2, 2A6, and 2C8 in 5-fluorouracil formation from tegafur, an anticancer prodrug, in human liver microsomes. Drug Metab Dispos. 2000 Dec;28(12):1457-63.
28 Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.
29 Genotoxicity of tamoxifen, tamoxifen epoxide and toremifene in human lymphoblastoid cells containing human cytochrome P450s. Carcinogenesis. 1994 Jan;15(1):5-9.
30 Psychotropic drug interactions with valproate. Clin Neuropharmacol. 2005 Mar-Apr;28(2):96-101.
31 The role of human cytochrome P450 enzymes in the formation of 2-hydroxymetronidazole: CYP2A6 is the high affinity (low Km) catalyst. Drug Metab Dispos. 2013 Sep;41(9):1686-94.
32 Possible involvement of multiple human cytochrome P450 isoforms in the liver metabolism of propofol. Br J Anaesth. 1998 Jun;80(6):788-95.
33 CYP2A6- and CYP2A13-catalyzed metabolism of the nicotine delta-5'(1')iminium ion. J Pharmacol Exp Ther. 2012 Nov;343(2):307-15.
34 Role of glutathione S-transferase P1-1 in the cellular detoxification of cisplatin. Mol Cancer Ther. 2008 Oct;7(10):3247-55.
35 Human glutathione transferase A3-3, a highly efficient catalyst of double-bond isomerization in the biosynthetic pathway of steroid hormones. J Biol Chem. 2001 Aug 31;276(35):33061-5.
36 Retinoid X receptor alpha regulates the expression of glutathione s-transferase genes and modulates acetaminophen-glutathione conjugation in mouse liver. Mol Pharmacol. 2005 Dec;68(6):1590-6.
37 Comparison of basal glutathione S-transferase activities and of the influence of phenobarbital, butylated hydroxy-anisole or 5,5'-diphenylhydantoin on enzyme activity in male rodents. Comp Biochem Physiol C. 1987;88(1):91-3.
38 Characterization and formation of the glutathione conjugate of clofibric acid. Drug Metab Dispos. 1995 Jan;23(1):119-23.
39 In vitro characterization of the human biotransformation and CYP reaction phenotype of ET-743 (Yondelis, Trabectidin), a novel marine anti-cancer drug. Invest New Drugs. 2006 Jan;24(1):3-14.
40 Glutathione S-transferase M1 polymorphism: a risk factor for hepatic venoocclusive disease in bone marrow transplantation. Blood. 2004 Sep 1;104(5):1574-7.
41 Purification and biochemical properties of glutathione S-transferase from Lactuca sativa. J Biochem Mol Biol. 2005 Mar 31;38(2):232-7.
42 Combined glutathione-S-transferase M1 and T1 genetic polymorphism and tacrine hepatotoxicity. Clin Pharmacol Ther. 2000 Apr;67(4):432-7.
43 Metabolism of melphalan by rat liver microsomal glutathione S-transferase. Chem Biol Interact. 2005 Apr 15;152(2-3):101-6.
44 Effect of tamoxifen on the enzymatic activity of human cytochrome CYP2B6. J Pharmacol Exp Ther. 2002 Jun;301(3):945-52.
45 Hepatic metabolism of diclofenac: role of human CYP in the minor oxidative pathways. Biochem Pharmacol. 1999 Sep 1;58(5):787-96.
46 Characterization of the oxidative metabolites of 17beta-estradiol and estrone formed by 15 selectively expressed human cytochrome p450 isoforms. Endocrinology. 2003 Aug;144(8):3382-98.
47 Insights into CYP2B6-mediated drug-drug interactions. Acta Pharm Sin B. 2016 Sep;6(5):413-425.
48 Drugs that may have potential CYP2B6 interactions.
49 Involvement of human cytochrome P450 2B6 in the omega- and 4-hydroxylation of the anesthetic agent propofol. Xenobiotica. 2007 Jul;37(7):717-24.
50 Nicotine and 4-(methylnitrosamino)-1-(3-pyridyl)-butanone metabolism by cytochrome P450 2B6. Drug Metab Dispos. 2005 Dec;33(12):1760-4.
51 PharmGKB summary: phenytoin pathway. Pharmacogenet Genomics. 2012 Jun;22(6):466-70.
52 Application of the relative activity factor approach in scaling from heterologously expressed cytochromes p450 to human liver microsomes: studies on amitriptyline as a model substrate. J Pharmacol Exp Ther. 2001 Apr;297(1):326-37.
53 Human glutathione S-transferase A (GSTA) family genes are regulated by steroidogenic factor 1 (SF-1) and are involved in steroidogenesis. FASEB J. 2013 Aug;27(8):3198-208. doi: 10.1096/fj.12-222745. Epub 2013 May 6.
54 Polymorphisms of drug-metabolizing enzymes (GST, CYP2B6 and CYP3A) affect the pharmacokinetics of thiotepa and tepa. Br J Clin Pharmacol. 2009 Jan;67(1):50-60. doi: 10.1111/j.1365-2125.2008.03321.x. Epub 2008 Nov 17.
55 Effects of phenytoin on glutathione status and oxidative stress biomarker gene mRNA levels in cultured precision human liver slices. Toxicol Sci. 2001 Jan;59(1):118-26.
56 Acetaminophen-induced hepatocyte injury: C2-ceramide and oltipraz intervention, hepatocyte nuclear factor 1 and glutathione S-transferase A1 changes. J Appl Toxicol. 2019 Dec;39(12):1640-1650. doi: 10.1002/jat.3881. Epub 2019 Aug 6.
57 Antineoplastic drug sensitivity of human MCF-7 breast cancer cells stably transfected with a human alpha class glutathione S-transferase gene. Cancer Res. 1991 Jan 15;51(2):587-94.
58 Establishment of cisplatin-resistant ovarian yolk sac tumor cells and investigation of the mechanism of cisplatin resistance using this cell line. Gynecol Obstet Invest. 2011;71(2):104-11. doi: 10.1159/000320744. Epub 2010 Dec 9.
59 Overexpression of glutathione S-transferase A1-1 in ECV 304 cells protects against busulfan mediated G2-arrest and induces tissue factor expression. Br J Pharmacol. 2002 Dec;137(7):1100-6. doi: 10.1038/sj.bjp.0704972.
60 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.
61 Global molecular effects of tocilizumab therapy in rheumatoid arthritis synovium. Arthritis Rheumatol. 2014 Jan;66(1):15-23.
62 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.
63 The relative role of CYP3A4 and CYP3A5 in eplerenone metabolism. Toxicol Lett. 2019 Oct 15;315:9-13.
64 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.
65 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.
66 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.
67 Cetirizine and loratadine-based antihistamines with 5-lipoxygenase inhibitory activity. Bioorg Med Chem Lett. 2004 Nov 15;14(22):5591-4.
68 Mechanism-based inactivation of CYP3A by HIV protease inhibitors. J Pharmacol Exp Ther. 2005 Feb;312(2):583-91.
69 Studies of the toxicological potential of capsinoids, XIII: inhibitory effects of capsaicin and capsinoids on cytochrome P450 3A4 in human liver microsomes. Int J Toxicol. 2010 Mar;29(2 Suppl):22S-6S.
70 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.
71 Cytochrome P450 inhibition potential of new psychoactive substances of the tryptamine class. Toxicol Lett. 2016 Jan 22;241:82-94.
72 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.
73 Evaluation of gene induction of drug-metabolizing enzymes and transporters in primary culture of human hepatocytes using high-sensitivity real-time reverse transcription PCR. Yakugaku Zasshi. 2002 May;122(5):339-61.
74 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.
75 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.
76 Identification of novel agonists by high-throughput screening and molecular modelling of human constitutive androstane receptor isoform 3. Arch Toxicol. 2019 Aug;93(8):2247-2264. doi: 10.1007/s00204-019-02495-6. Epub 2019 Jul 16.
77 Characterization of human cytochrome P450 induction by pesticides. Toxicology. 2012 Mar 29;294(1):17-26.
78 Species-specific mechanisms for cholesterol 7alpha-hydroxylase (CYP7A1) regulation by drugs and bile acids. Arch Biochem Biophys. 2005 Feb 1;434(1):75-85.
79 Pyrethroids: cytotoxicity and induction of CYP isoforms in human hepatocytes. Drug Metabol Drug Interact. 2008;23(3-4):211-36.
80 Transcriptional profiling of genes induced in the livers of patients treated with carbamazepine. Clin Pharmacol Ther. 2006 Nov;80(5):440-456.
81 In vitro inhibition of CYP1A2 by model inhibitors, anti-inflammatory analgesics and female sex steroids: predictability of in vivo interactions. Basic Clin Pharmacol Toxicol. 2008 Aug;103(2):157-65.
82 Effects of capsaicin and dihydrocapsaicin on human and rat liver microsomal CYP450 enzyme activities in vitro and in vivo. J Asian Nat Prod Res. 2012;14(4):382-95.
83 Drug interaction study of flavonoids toward CYP3A4 and their quantitative structure activity relationship (QSAR) analysis for predicting potential effects. Toxicol Lett. 2018 Sep 15;294:27-36.
84 Stiripentol. Expert Opin Investig Drugs. 2005 Jul;14(7):905-11.
85 Inhibition of human cytochrome P450 enzymes by 1,4-dihydropyridine calcium antagonists: prediction of in vivo drug-drug interactions. Eur J Clin Pharmacol. 2000 Feb-Mar;55(11-12):843-52.
86 Mechanism-based inhibition of human liver microsomal cytochrome P450 1A2 by zileuton, a 5-lipoxygenase inhibitor. Drug Metab Dispos. 2003 Nov;31(11):1352-60.
87 Predictive three-dimensional quantitative structure-activity relationship of cytochrome P450 1A2 inhibitors. J Med Chem. 2005 Jun 2;48(11):3808-15.
88 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.
89 Inhibition of cytochrome P450 enzymes participating in p-nitrophenol hydroxylation by drugs known as CYP2E1 inhibitors. Chem Biol Interact. 2004 Apr 15;147(3):331-40.
90 Influence of glutathione S-transferase A1, P1, M1, T1 polymorphisms on oral busulfan pharmacokinetics in children with congenital hemoglobinopathies undergoing hematopoietic stem cell transplantation. Pediatr Blood Cancer. 2010 Dec 1;55(6):1172-9. doi: 10.1002/pbc.22739.
91 Activation of AIFM2 enhances apoptosis of human lung cancer cells undergoing toxicological stress. Toxicol Lett. 2016 Sep 6;258:227-236.
92 The influence of coordinate overexpression of glutathione phase II detoxification gene products on drug resistance. J Pharmacol Exp Ther. 2000 Aug;294(2):480-7.
93 Cell-type-specific responses to chemotherapeutics in breast cancer. Cancer Res. 2004 Jun 15;64(12):4218-26.
94 Cannabidiol induces antioxidant pathways in keratinocytes by targeting BACH1. Redox Biol. 2020 Jan;28:101321. doi: 10.1016/j.redox.2019.101321. Epub 2019 Sep 5.
95 Microarray analysis of H2O2-, HNE-, or tBH-treated ARPE-19 cells. Free Radic Biol Med. 2002 Nov 15;33(10):1419-32.
96 Selenium and vitamin E: cell type- and intervention-specific tissue effects in prostate cancer. J Natl Cancer Inst. 2009 Mar 4;101(5):306-20.
97 Consequences of the natural retinoid/retinoid X receptor ligands action in human breast cancer MDA-MB-231 cell line: Focus on functional proteomics. Toxicol Lett. 2017 Nov 5;281:26-34. doi: 10.1016/j.toxlet.2017.09.001. Epub 2017 Sep 5.
98 Glutathione S-transferase pi as a target for tricyclic antidepressants in human brain. Acta Biochim Pol. 2004;51(1):207-12.
99 Characteristics of P388/VMDRC.04, a simple, sensitive model for studying P-glycoprotein antagonists. Cancer Res. 1994 Feb 1;54(3):730-7.
100 Michaelis-Menten kinetic analysis of drugs of abuse to estimate their affinity to human P-glycoprotein. Toxicol Lett. 2013 Feb 27;217(2):137-42. doi: 10.1016/j.toxlet.2012.12.012. Epub 2012 Dec 27.
101 Editor's Highlight: PlacentalDisposition and Effects of Crizotinib: An Ex Vivo Study in the Isolated Dual-Side Perfused Human Cotyledon. Toxicol Sci. 2017 Jun 1;157(2):500-509. doi: 10.1093/toxsci/kfx063.
102 Functional evaluation of polymorphisms in the human ABCB1 gene and the impact on clinical responses of antiepileptic drugs. Pharmacogenet Genomics. 2008 May;18(5):390-402. doi: 10.1097/FPC.0b013e3282f85e36.
103 Cepharanthine potently enhances the sensitivity of anticancer agents in K562 cells. Cancer Sci. 2005 Jun;96(6):372-6. doi: 10.1111/j.1349-7006.2005.00057.x.
104 Clinical pharmacokinetic monitoring of itraconazole is warranted in only a subset of patients. Ther Drug Monit. 2005 Jun;27(3):322-33. doi: 10.1097/01.ftd.0000150135.22645.ea.
105 Evaluation of antipsychotic drugs as inhibitors of multidrug resistance transporter P-glycoprotein. Psychopharmacology (Berl). 2006 Sep;187(4):415-23. doi: 10.1007/s00213-006-0437-9. Epub 2006 Jun 30.
106 Actions of the selective protein kinase C inhibitor PKC412 on B-chronic lymphocytic leukemia cells in vitro. Haematologica. 2002 Feb;87(2):167-76.
107 Characterization of the ATPase activity of the Mr 170,000 to 180,000 membrane glycoprotein (P-glycoprotein) associated with multidrug resistance in K562/ADM cells. Cancer Res. 1988 Sep 1;48(17):4926-32.
108 p53-R175H mutant gains new function in regulation of doxorubicin-induced apoptosis. Int J Cancer. 2005 Apr 10;114(3):331-6. doi: 10.1002/ijc.20818.
109 The contribution of methotrexate exposure and host factors on transcriptional variance in human liver. Toxicol Sci. 2007 Jun;97(2):582-94.
110 Azidothymidine and cisplatin increase p14ARF expression in OVCAR-3 ovarian cancer cell line. Toxicol Appl Pharmacol. 2006 Oct 1;216(1):89-97. doi: 10.1016/j.taap.2006.04.015. Epub 2006 May 19.
111 Quantitative analysis of gene expression changes in response to genotoxic compounds. Toxicol In Vitro. 2017 Mar;39:15-28. doi: 10.1016/j.tiv.2016.11.004. Epub 2016 Nov 5.
112 Induction of apoptosis by cidofovir in human papillomavirus (HPV)-positive cells. Oncol Res. 2000;12(9-10):397-408. doi: 10.3727/096504001108747855.
113 Gallic acid potentiates the apoptotic effect of paclitaxel and carboplatin via overexpression of Bax and P53 on the MCF-7 human breast cancer cell line. J Biochem Mol Toxicol. 2021 Feb;35(2):e22638. doi: 10.1002/jbt.22638. Epub 2020 Oct 1.
114 Regulation of human dUTPase gene expression and p53-mediated transcriptional repression in response to oxaliplatin-induced DNA damage. Nucleic Acids Res. 2009 Jan;37(1):78-95. doi: 10.1093/nar/gkn910. Epub 2008 Nov 16.
115 Role of miRNA in the regulation of cannabidiol-mediated apoptosis in neuroblastoma cells. Oncotarget. 2019 Jan 1;10(1):45-59. doi: 10.18632/oncotarget.26534. eCollection 2019 Jan 1.
116 Nitrogen Mustard Alkylates and Cross-Links p53 in Human Keratinocytes. Chem Res Toxicol. 2022 Apr 18;35(4):636-650. doi: 10.1021/acs.chemrestox.1c00420. Epub 2022 Mar 21.
117 Fulvestrant induces resistance by modulating GPER and CDK6 expression: implication of methyltransferases, deacetylases and the hSWI/SNF chromatin remodelling complex. Br J Cancer. 2013 Nov 12;109(10):2751-62. doi: 10.1038/bjc.2013.583. Epub 2013 Oct 29.
118 Gingival Stromal Cells as an In Vitro Model: Cannabidiol Modulates Genes Linked With Amyotrophic Lateral Sclerosis. J Cell Biochem. 2017 Apr;118(4):819-828. doi: 10.1002/jcb.25757. Epub 2016 Nov 28.
119 The role of NAD(+)-dependent isocitrate dehydrogenase 3 subunit in AFB1 induced liver lesion. Toxicol Lett. 2014 Jan 30;224(3):371-9. doi: 10.1016/j.toxlet.2013.10.037. Epub 2013 Nov 5.
120 A transcriptome-based classifier to identify developmental toxicants by stem cell testing: design, validation and optimization for histone deacetylase inhibitors. Arch Toxicol. 2015 Sep;89(9):1599-618.
121 Human embryonic stem cell-derived test systems for developmental neurotoxicity: a transcriptomics approach. Arch Toxicol. 2013 Jan;87(1):123-43.
122 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.
123 Identification of potential biomarkers for predicting acute dermal irritation by proteomic analysis. J Appl Toxicol. 2011 Nov;31(8):762-72.
124 Apoptosis induced by piroxicam plus cisplatin combined treatment is triggered by p21 in mesothelioma. PLoS One. 2011;6(8):e23569.
125 Prenatal arsenic exposure and the epigenome: identifying sites of 5-methylcytosine alterations that predict functional changes in gene expression in newborn cord blood and subsequent birth outcomes. Toxicol Sci. 2015 Jan;143(1):97-106. doi: 10.1093/toxsci/kfu210. Epub 2014 Oct 10.
126 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.
127 Identification of HMG-CoA reductase inhibitors as activators for human, mouse and rat constitutive androstane receptor. Drug Metab Dispos. 2005 Jul;33(7):924-9.
128 Bioactive terpenoids and flavonoids from Ginkgo biloba extract induce the expression of hepatic drug-metabolizing enzymes through pregnane X receptor, constitutive androstane receptor, and aryl hydrocarbon receptor-mediated pathways. Pharm Res. 2009 Apr;26(4):872-82.
129 Species-specific toxicity of diclofenac and troglitazone in primary human and rat hepatocytes. Chem Biol Interact. 2009 Apr 15;179(1):17-24.
130 Fetal bovine serum and human constitutive androstane receptor: evidence for activation of the SV23 splice variant by artemisinin, artemether, and arteether in a serum-free cell culture system. Toxicol Appl Pharmacol. 2014 Jun 1;277(2):221-30. doi: 10.1016/j.taap.2014.03.023. Epub 2014 Apr 12.
131 Constitutive androstane/active receptor is a target of retinoic acid receptor in humans. Biochem Pharmacol. 2010 Jul 1;80(1):129-35. doi: 10.1016/j.bcp.2010.02.023. Epub 2010 Mar 6.
132 Robustness testing and optimization of an adverse outcome pathway on cholestatic liver injury. Arch Toxicol. 2020 Apr;94(4):1151-1172. doi: 10.1007/s00204-020-02691-9. Epub 2020 Mar 10.
133 Expression and inducibility of cytochrome P450s (CYP1A1, 2B6, 2E1, 3A4) in human cord blood CD34(+) stem cell-derived differentiating neuronal cells. Toxicol Sci. 2012 Oct;129(2):392-410.
134 Agonistic effects of diverse xenobiotics on the constitutive androstane receptor as detected in a recombinant yeast-cell assay. Toxicol In Vitro. 2018 Feb;46:335-349. doi: 10.1016/j.tiv.2017.09.014. Epub 2017 Sep 18.
135 Teriflunomide is an indirect human constitutive androstane receptor (CAR) activator interacting with epidermal growth factor (EGF) signaling. Front Pharmacol. 2018 Oct 11;9:993.
136 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.