General Information of Drug (ID: DMY64HE)

Drug Name
alpha-linolenic acid Drug Info
Synonyms
Linolenic acid; linolenic acid; alpha-Linolenic acid; 463-40-1; linolenate; (9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid; a-Linolenic acid; cis,cis,cis-9,12,15-Octadecatrienoic acid; all-cis-9,12,15-Octadecatrienoic acid; alpha-Linolenate; 9-cis,12-cis,15-cis-Octadecatrienoic acid; (Z,Z,Z)-9,12,15-Octadecatrienoic acid; Linolenic acid (8CI); 9,12,15-Octadecatrienoic acid, (Z,Z,Z)-; (9,12,15)-linolenic acid; alpha-Lnn; 9Z,12Z,15Z-Octadecatrienoic acid; Industrene 120; CCRIS 656; UNII-0RBV727H71; (9Z,12Z,15Z)-Octadecatrienoic acid; linolenate; alpha-LA; C18:3; LINOLENIC ACID
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Cross-matching ID
PubChem CID
5280934
ChEBI ID
CHEBI:27432
CAS Number
CAS 463-40-1
TTD Drug ID
DMY64HE
INTEDE Drug ID
DR1988

Molecule-Related Drug Atlas

Molecule-Related Drug Atlas
Molecule Type:
DTT
DME
DOT
Drug Status:
Clinical Trial Drug(s)
Investigative Drug(s)
Approved Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
TAK-875 DMIM5AP Type-2 diabetes 5A11 Phase 3 [13]
Fasiglifam hemihydrate DMTGYSO Type-2 diabetes 5A11 Phase 3 [14]
PBI-4050 DMPXK27 Idiopathic pulmonary fibrosis CB03.4 Phase 2 [15]
P-1736 DMEYQPN Diabetic complication 5A2Y Phase 2 [16]
JTT-851 DMED5J6 Type-2 diabetes 5A11 Phase 2 [17]
SHR0534 DMGFTAI Type 2 diabetes 5A11 Phase 1 [18]
LY-2881835 DM5EXJV Type-2 diabetes 5A11 Phase 1 [17]
P11187 DMXZOI0 Type-2 diabetes 5A11 Phase 1 [17]
CPL207-280CA DMFMGZR Type 2 diabetes 5A11 Phase 1 [18]
LY2922470 DMGLTE2 Type 2 diabetes 5A11 Phase 1 [19]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
GW9508 DMVKZ5I Discovery agent N.A. Investigative [20]
PMID24997608CA DML0PFU Discovery agent N.A. Investigative [21]
grifolic acid DMGTRZE Discovery agent N.A. Investigative [22]
TUG-891 DMJRGZT Discovery agent N.A. Investigative [23]
NCG21 DMMRWJG Discovery agent N.A. Investigative [24]
Drug Name Drug ID Indication ICD 11 Highest Status REF
Ibuprofen DM8VCBE Dysmenorrhea GA34.3 Approved [25]
Naproxen DMZ5RGV Bursitis Approved [26]
Etodolac DM6WJO9 Osteoarthritis FA00-FA05 Approved [27]
Indomethacin DMSC4A7 Bursitis Approved [28]
Celecoxib DM6LOQU Dysmenorrhea GA34.3 Approved [29]
Nabumetone DMAT2XH Osteoarthritis FA00-FA05 Approved [30]
Rofecoxib DM3P5DA Osteoarthritis FA00-FA05 Approved [31]
Flurbiprofen DMGN4BY Osteoarthritis FA00-FA05 Approved [32]
Eicosapentaenoic acid/docosa-hexaenoic acid DMMUCG4 Hypertriglyceridemia 5C80.1 Approved [4]
Aminosalicylic Acid DMENSL5 Crohn disease DD70 Approved [28]
Etoposide DMNH3PG Acute myelogenous leukaemia 2A41 Approved [34]
Dapsone DM4LT8A Acne vulgaris ED80 Approved [33]
Eicosapentaenoic acid/docosa-hexaenoic acid DMMUCG4 Hypertriglyceridemia 5C80.1 Approved [5]
Epanova DMHEAGL Hypertriglyceridemia 5C80.1 Approved [35]
Gamma-Homolinolenic acid DMSXKYG Malnutrition 5B50-5B71 Approved [5]
Gamolenic acid DMQN30Z Allergy 4A80-4A85 Approved [5]
Omega-6-FA DMBWY8V N. A. N. A. Phase 3 [36]
Arachidonic Acid DMUOQZD Discovery agent N.A. Investigative [37]
Eicosadienoic acid DMVJK9W N. A. N. A. Investigative [5]
Icosapentum DMF1CM7 N. A. N. A. Investigative [5]
⏷ Show the Full List of 20 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [33]
Etoposide DMNH3PG Acute myelogenous leukaemia 2A41 Approved [34]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [33]
Diazepam DM08E9O Alcohol withdrawal Approved [33]
Dapsone DM4LT8A Acne vulgaris ED80 Approved [33]
Ifosfamide DMCT3I8 Adult central nervous system germ cell tumor Approved [33]
Nateglinide DMLK2QH Diabetic complication 5A2Y Approved [33]
Thalidomide DM70BU5 Adult T-cell leukemia/lymphoma Approved [33]
Ketobemidone DMM3L6Z Pain MG30-MG3Z Approved [33]
Irbesartan DMTP1DC Diabetic kidney disease GB61.Z Approved [33]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Eicosapentaenoic acid/docosa-hexaenoic acid DMMUCG4 Hypertriglyceridemia 5C80.1 Approved [38]
Etoposide DMNH3PG Acute myelogenous leukaemia 2A41 Approved [39]
Gamolenic acid DMQN30Z Allergy 4A80-4A85 Approved [12]
Cannabidiol DM0659E Dravet syndrome 8A61.11 Approved [40]
Flupentixol DM0DJ9O Schizophrenia 6A20 Approved [41]
Sertraline DM0FB1J Coronary heart disease BA80.Z Approved [42]
Ibandronate DM0QZBN Hypercalcaemia 5B91.0 Approved [43]
Fulvestrant DM0YZC6 Breast cancer 2C60-2C65 Approved [44]
Fexofenadine DM17ONX Allergic rhinitis CA08.0 Approved [45]
Hydrogen peroxide DM1NG5W Infectious disease 1A00-CA43.1 Approved [46]
⏷ 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 [47]
Rofecoxib DM3P5DA Osteoarthritis FA00-FA05 Approved [47]
Etoricoxib DM6A4NW Rheumatoid arthritis FA20 Approved [47]
Capsaicin DMGMF6V Back pain ME84.Z Approved [48]
Hesperetin DMKER83 High blood cholesterol level 5C80.00 Approved [49]
Stiripentol DMMSDOY Dravet syndrome 8A61.11 Approved [50]
Nifedipine DMSVOZT Angina pectoris BA40 Approved [51]
Zileuton DMVRIC2 Allergic asthma CA23.0 Approved [52]
Nicotine DMWX5CO Lung cancer 2C25.0 Approved [53]
Clonidine DM6RZ9Q Attention deficit hyperactivity disorder 6A05.Z Approved [54]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Cytochrome P450 2E1 (CYP2E1)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Fomepizole DM6VOWQ Athylene glycol or methanol poisoning NE61 Approved [55]
Ademetionine DMYQDBO Hepatic fibrosis DB93.0 Approved [56]
Theophylline DMRJFN9 Bronchitis CA20 Approved [54]
Rifampicin DM5DSFZ Non-insulin dependent diabetes 5A11 Approved [57]
Ethanol DMDRQZU Chronic pain MG30 Approved [58]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [59]
Phenobarbital DMXZOCG Cluster headache 8A81.0 Approved [60]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [61]
Didanosine DMI2QPE Human immunodeficiency virus infection 1C62 Approved [54]
Thioridazine DM35M8J Schizophrenia 6A20 Approved [62]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Cytochrome P450 3A4 (CYP3A4)
Drug Name Drug ID Indication ICD 11 Highest Status REF
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 [67]
Ivermectin DMDBX5F Intestinal strongyloidiasis due to nematode parasite 1F6B Approved [67]
Loratadine DMF3AN7 Allergy 4A80-4A85 Approved [68]
Nelfinavir mesylate DMFX6G8 N. A. N. A. Approved [69]
Capsaicin DMGMF6V Back pain ME84.Z Approved [70]
Axitinib DMGVH6N Renal cell carcinoma 2C90 Approved [71]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Cytochrome P450 2C9 (CYP2C9)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Cannabidiol DM0659E Dravet syndrome 8A61.11 Approved [64]
Troglitazone DM3VFPD Diabetic complication 5A2Y Approved [72]
Dapsone DM4LT8A Acne vulgaris ED80 Approved [67]
Voriconazole DMAOL2S Aspergillosis 1F20 Approved [66]
Capsaicin DMGMF6V Back pain ME84.Z Approved [48]
Zafirlukast DMHNQOG Asthma CA23 Approved [73]
Niclosamide DMJAGXQ Cestodes infection 1F70-1F76 Approved [67]
Eicosapentaenoic acid/docosa-hexaenoic acid DMMUCG4 Hypertriglyceridemia 5C80.1 Approved [10]
Fluconazole DMOWZ6B Cryptococcal meningitis Approved [66]
Quinine DMSWYF5 Malaria 1F40-1F45 Approved [67]
⏷ 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 [62]
Voriconazole DMAOL2S Aspergillosis 1F20 Approved [66]
Chloramphenicol DMFXEWT Bacterial infection 1A00-1C4Z Approved [74]
Capsaicin DMGMF6V Back pain ME84.Z Approved [48]
Pentamidine DMHZJCG African trypanosomiasis 1F51 Approved [67]
Stiripentol DMMSDOY Dravet syndrome 8A61.11 Approved [50]
Quinine DMSWYF5 Malaria 1F40-1F45 Approved [67]
Desipramine DMT2FDC Attention deficit hyperactivity disorder 6A05.Z Approved [62]
Amitriptyline DMK7F9S Depression 6A70-6A7Z Approved [54]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Heme oxygenase 1 (HMOX1)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Dexamethasone DMMWZET Acute adrenal insufficiency Approved [75]
Cannabidiol DM0659E Dravet syndrome 8A61.11 Approved [76]
Pantothenic acid DM091H2 Vitamin deficiency 5B55-5B71 Approved [77]
Verapamil DMA7PEW Angina pectoris BA40 Approved [78]
Fulvestrant DM0YZC6 Breast cancer 2C60-2C65 Approved [79]
Hydrogen peroxide DM1NG5W Infectious disease 1A00-CA43.1 Approved [80]
Selenium DM25CGV N. A. N. A. Approved [81]
TECFIDERA DM2OVDT Multiple sclerosis 8A40 Approved [82]
Sulindac DM2QHZU Acute myelogenous leukaemia 2A41 Approved [83]
Methotrexate DM2TEOL Anterior urethra cancer Approved [84]
⏷ 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 [85]
Hydrogen peroxide DM1NG5W Infectious disease 1A00-CA43.1 Approved [80]
Methimazole DM25FL8 Hyperthyroidism 5A02 Approved [86]
Clavulanate DM2FGRT Bacteremia 1A73 Approved [87]
Sulindac DM2QHZU Acute myelogenous leukaemia 2A41 Approved [88]
Quercetin DM3NC4M Obesity 5B81 Approved [89]
Troglitazone DM3VFPD Diabetic complication 5A2Y Approved [90]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [91]
Acetic Acid, Glacial DM4SJ5Y infection in the ear canal AA0Y Approved [92]
Arsenic trioxide DM61TA4 Acute lymphoblastic leukaemia 2A85 Approved [93]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Cholinesterase (BCHE)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Cocaine DMSOX7I Anaesthesia 9A78.6 Approved [94]
Tacrine DM51FY6 Alzheimer disease 8A20 Approved [95]
Galantamine DMEO794 Alzheimer disease 8A20 Approved [96]
Rivastigmine DMG629M Alzheimer disease 8A20 Approved [97]
Donepezil DMIYG7Z Advanced cancer 2A00-2F9Z Approved [54]
Succinylcholine DM2ET1M Plasma cell myeloma 2A83.1 Approved [98]
Ethopropazine DM0N3L7 Parkinson disease 8A00.0 Approved [95]
Dimenhydrinate DM264B3 Meniere disease AB31.0 Approved [99]
Cyclophosphamide DM4O2Z7 Advanced cancer 2A00-2F9Z Approved [100]
Chlorpheniramine DM5URA2 Allergic rhinitis CA08.0 Approved [99]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Artemisinin DMOY7W3 Malaria 1F40-1F45 Approved [101]
Progesterone DMUY35B Amenorrhea GA20.0 Approved [102]
Thiotepa DMIZKOP Breast cancer 2C60-2C65 Approved [103]
Phenytoin DMNOKBV Epilepsy 8A60-8A68 Approved [104]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [105]
Ethacrynic acid DM60QMR Edema MG29 Approved [106]
Cisplatin DMRHGI9 Adenocarcinoma 2D40 Approved [107]
Busulfan DMXYJ9C Chronic myelogenous leukaemia 2A20.0 Approved [108]
Hydrogen peroxide DM1NG5W Infectious disease 1A00-CA43.1 Approved [109]
Methotrexate DM2TEOL Anterior urethra cancer Approved [110]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Cytochrome P450 2A6 (CYP2A6)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Tegafur DM31ZQM Solid tumour/cancer 2A00-2F9Z Approved [111]
Methoxsalen DME8FZ9 Cutaneous T-cell lymphoma 2B01 Approved [112]
Fluorouracil DMUM7HZ Adenocarcinoma 2D40 Approved [113]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [114]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [59]
Progesterone DMUY35B Amenorrhea GA20.0 Approved [115]
Ifosfamide DMCT3I8 Adult central nervous system germ cell tumor Approved [116]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [117]
Letrozole DMH07Y3 Estrogen-receptor positive breast cancer Approved [118]
Nicotine DMWX5CO Lung cancer 2C25.0 Approved [119]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Bexarotene DMOBIKY Cutaneous T-cell lymphoma 2B01 Approved [120]
Hydrogen peroxide DM1NG5W Infectious disease 1A00-CA43.1 Approved [109]
Selenium DM25CGV N. A. N. A. Approved [121]
obeticholic acid DM3Q1SM Primary biliary cholangitis DB96.1 Approved [122]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [123]
Isotretinoin DM4QTBN Acne vulgaris ED80 Approved [124]
Arsenic trioxide DM61TA4 Acute lymphoblastic leukaemia 2A85 Approved [125]
Acitretin DM8BKU9 Psoriasis vulgaris EA90 Approved [126]
Ibuprofen DM8VCBE Dysmenorrhea GA34.3 Approved [127]
Calcitriol DM8ZVJ7 Congenital alopecia LC30 Approved [128]
⏷ 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 [40]
Hydrogen peroxide DM1NG5W Infectious disease 1A00-CA43.1 Approved [129]
Quercetin DM3NC4M Obesity 5B81 Approved [130]
Troglitazone DM3VFPD Diabetic complication 5A2Y Approved [131]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [132]
Glucosamine DM4ZLFD Osteoarthritis FA00-FA05 Approved [133]
Isoniazid DM5JVS3 Latent tuberculosis infection Approved [134]
Arsenic trioxide DM61TA4 Acute lymphoblastic leukaemia 2A85 Approved [135]
Aspirin DM672AH Acute coronary syndrome BA41 Approved [136]
Stavudine DM6DEK9 Human immunodeficiency virus infection 1C62 Approved [137]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Methimazole DM25FL8 Hyperthyroidism 5A02 Approved [138]
Quercetin DM3NC4M Obesity 5B81 Approved [139]
Rifampicin DM5DSFZ Non-insulin dependent diabetes 5A11 Approved [140]
Ciclosporin DMAZJFX Graft-versus-host disease 4B24 Approved [141]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [142]
Ergocalciferol DMHO0AR Hypoparathyroidism 5A50 Approved [143]
Alitretinoin DMME8LH Kaposi sarcoma 2B57 Approved [144]
Masoprocol DMMVNZ0 Prostate cancer 2C82.0 Approved [143]
Azathioprine DMMZSXQ Lupus nephritis 4A40.0Y Approved [145]
Amiodarone DMUTEX3 Tachyarrhythmias BC71 Approved [146]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Clofibrate DMPC1J7 Dysbetalipoproteinemia 5C80.2 Approved [147]
Methotrexate DM2TEOL Anterior urethra cancer Approved [148]
Quercetin DM3NC4M Obesity 5B81 Approved [139]
obeticholic acid DM3Q1SM Primary biliary cholangitis DB96.1 Approved [122]
Troglitazone DM3VFPD Diabetic complication 5A2Y Approved [149]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [91]
Arsenic trioxide DM61TA4 Acute lymphoblastic leukaemia 2A85 Approved [150]
Aspirin DM672AH Acute coronary syndrome BA41 Approved [151]
Liothyronine DM6IR3P Congenital hypothyroidism Approved [152]
Marinol DM70IK5 Anorexia nervosa cachexia 6B80 Approved [153]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Thyroxine 5-deiodinase (DIO3)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Tretinoin DM49DUI Acne vulgaris ED80 Approved [154]
Vemurafenib DM62UG5 Melanoma 2C30 Approved [155]
Liothyronine DM6IR3P Congenital hypothyroidism Approved [156]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [61]
Ergocalciferol DMHO0AR Hypoparathyroidism 5A50 Approved [143]
Alitretinoin DMME8LH Kaposi sarcoma 2B57 Approved [154]
Masoprocol DMMVNZ0 Prostate cancer 2C82.0 Approved [143]
Dexamethasone DMMWZET Acute adrenal insufficiency Approved [154]
Decitabine DMQL8XJ Acute myelogenous leukaemia 2A41 Approved [157]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [154]
⏷ 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 [85]
Sulindac DM2QHZU Acute myelogenous leukaemia 2A41 Approved [158]
Methotrexate DM2TEOL Anterior urethra cancer Approved [148]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [159]
Aspirin DM672AH Acute coronary syndrome BA41 Approved [160]
Hydroquinone DM6AVR4 Melasma ED60.1 Approved [161]
Marinol DM70IK5 Anorexia nervosa cachexia 6B80 Approved [162]
Calcitriol DM8ZVJ7 Congenital alopecia LC30 Approved [163]
Ciclosporin DMAZJFX Graft-versus-host disease 4B24 Approved [141]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [117]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Methotrexate DM2TEOL Anterior urethra cancer Approved [148]
Troglitazone DM3VFPD Diabetic complication 5A2Y Approved [164]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [132]
Arsenic trioxide DM61TA4 Acute lymphoblastic leukaemia 2A85 Approved [165]
Aspirin DM672AH Acute coronary syndrome BA41 Approved [136]
Prasterone DM67VKL Chronic obstructive pulmonary disease CA22 Approved [166]
Marinol DM70IK5 Anorexia nervosa cachexia 6B80 Approved [167]
Testosterone DM7HUNW Hot flushes GA30 Approved [168]
Calcitriol DM8ZVJ7 Congenital alopecia LC30 Approved [163]
Ciclosporin DMAZJFX Graft-versus-host disease 4B24 Approved [141]
⏷ 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 [169]
Quercetin DM3NC4M Obesity 5B81 Approved [170]
Troglitazone DM3VFPD Diabetic complication 5A2Y Approved [171]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [144]
Methylprednisolone DM4BDON Acute adrenal insufficiency Approved [172]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [61]
Mifepristone DMGZQEF Cushing disease 5A70 Approved [173]
Ergocalciferol DMHO0AR Hypoparathyroidism 5A50 Approved [143]
Zoledronate DMIXC7G Adenocarcinoma 2D40 Approved [174]
Temozolomide DMKECZD Adenocarcinoma 2D40 Approved [175]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Bile acid receptor (NR1H4)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Hydrogen peroxide DM1NG5W Infectious disease 1A00-CA43.1 Approved [176]
Nitrendipine DM21C09 Hypertension BA00-BA04 Approved [177]
Deoxycholic acid DM3GYAL Subcutaneous fat disorder EF02 Approved [178]
Quercetin DM3NC4M Obesity 5B81 Approved [139]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [179]
Nefazodone DM4ZS8M Major depressive disorder 6A70.3 Approved [180]
Nisoldipine DM7ISKJ Hypertension BA00-BA04 Approved [177]
Cholic Acid DM7OKQV Cholelithiasis DC11 Approved [178]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [181]
Ciclosporin DMAZJFX Graft-versus-host disease 4B24 Approved [141]
⏷ 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
Free fatty acid receptor 1 (GPR40) TTB8FUC FFAR1_HUMAN Agonist [2]
G-protein coupled receptor 120 (GPR120) TT08JVB FFAR4_HUMAN Agonist [3]
Prostaglandin G/H synthase 2 (COX-2) TTVKILB PGH2_HUMAN Inhibitor [4]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Prostaglandin G/H synthase 2 (COX-2) DE492CE PGH2_HUMAN Substrate [5]
Prostaglandin G/H synthase 1 (COX-1) DE073H6 PGH1_HUMAN Substrate [5]
Carboxylic ester hydrolase (CEH) DE30GZN A0A317G4I6_BUTFI Substrate [6] , [7]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Bile acid receptor (NR1H4) OTWZLPTB NR1H4_HUMAN Protein Interaction/Cellular Processes [8]
Carnitine O-palmitoyltransferase 1, liver isoform (CPT1A) OTI862QH CPT1A_HUMAN Gene/Protein Processing [8]
Cholinesterase (BCHE) OTOH3WQ9 CHLE_HUMAN Gene/Protein Processing [9]
Cytochrome P450 1A2 (CYP1A2) OTLLBX48 CP1A2_HUMAN Gene/Protein Processing [10]
Cytochrome P450 2A6 (CYP2A6) OT52TWG3 CP2A6_HUMAN Gene/Protein Processing [11]
Cytochrome P450 2C19 (CYP2C19) OTFMJYYE CP2CJ_HUMAN Gene/Protein Processing [10]
Cytochrome P450 2C9 (CYP2C9) OTGLBN29 CP2C9_HUMAN Gene/Protein Processing [10]
Cytochrome P450 2E1 (CYP2E1) OTHQ17JG CP2E1_HUMAN Gene/Protein Processing [10]
Cytochrome P450 3A4 (CYP3A4) OTQGYY83 CP3A4_HUMAN Gene/Protein Processing [10]
Glutamate--cysteine ligase catalytic subunit (GCLC) OTESDI4D GSH1_HUMAN Gene/Protein Processing [12]

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 1049).
2 Free fatty acids regulate insulin secretion from pancreatic beta cells through GPR40. Nature. 2003 Mar 13;422(6928):173-6.
3 Cloning and characterization of the rat free fatty acid receptor GPR120: in vivo effect of the natural ligand on GLP-1 secretion and proliferation of pancreatic beta cells. Naunyn Schmiedebergs Arch Pharmacol. 2008 Jun;377(4-6):515-22.
4 Cox-2 inhibitory effects of naturally occurring and modified fatty acids. J Nat Prod. 2001 Jun;64(6):745-9.
5 Divergent cyclooxygenase responses to fatty acid structure and peroxide level in fish and mammalian prostaglandin H synthases. FASEB J. 2006 Jun;20(8):1097-108.
6 Immunogenic inhibition of prominent ruminal bacteria as a means to reduce lipolysis and biohydrogenation activity in vitro. Food Chem. 2017 Mar 1;218:372-377.
7 Cell-associated alpha-amylases of butyrate-producing Firmicute bacteria from the human colon. Microbiology. 2006 Nov;152(Pt 11):3281-3290.
8 Polyunsaturated fatty acids are FXR ligands and differentially regulate expression of FXR targets. DNA Cell Biol. 2004 Aug;23(8):519-26. doi: 10.1089/1044549041562267.
9 Butyrylcholinesterase expression is regulated by fatty acids in HepG2 cells. Chem Biol Interact. 2016 Nov 25;259(Pt B):276-281.
10 The inhibitory effect of polyunsaturated fatty acids on human CYP enzymes. Life Sci. 2006 Nov 25;79(26):2432-40.
11 High fat diet-induced hepatic 18-carbon fatty acids accumulation up-regulates CYP2A5/CYP2A6 via NF-E2-related factor 2. Front Pharmacol. 2017 May 15;8:233.
12 Conjugated linoleic acid, unlike other unsaturated fatty acids, strongly induces glutathione synthesis without any lipoperoxidation. Br J Nutr. 2006 Nov;96(5):811-9.
13 Efficacy and safety of fasiglifam (TAK-875), a G protein-coupled receptor 40 agonist, in Japanese patients with type 2 diabetes inadequately controlled by diet and exercise: a randomized, double-blind, placebo-controlled, phase III trial. Diabetes Obes Metab. 2015 Jul;17(7):675-81.
14 A novel antidiabetic drug, fasiglifam/TAK-875, acts as an ago-allosteric modulator of FFAR1. PLoS One. 2013 Oct 10;8(10):e76280.
15 Phase 2 clinical trial of PBI-4050 in patients with idiopathic pulmonary fibrosis. Eur Respir J. 2019 Mar 18;53(3):1800663.
16 Discovery of p1736, a novel antidiabetic compound that improves peripheral insulin sensitivity in mice models. PLoS One. 2013 Oct 23;8(10):e77946.
17 Treatment of Type 2 Diabetes by Free Fatty Acid Receptor Agonists. Front Endocrinol (Lausanne) 2014; 5: 137.
18 Targeting metabolic dysregulation for fibrosis therapy. Nat Rev Drug Discov. 2020 Jan;19(1):57-75.
19 The Discovery, Preclinical, and Early Clinical Development of Potent and Selective GPR40 Agonists for the Treatment of Type 2 Diabetes Mellitus (LY2881835, LY2922083, and LY2922470). J Med Chem. 2016 Dec 22;59(24):10891-10916.
20 Free fatty acid receptors and drug discovery. Biol Pharm Bull. 2008 Oct;31(10):1847-51.
21 A Gpr120-selective agonist improves insulin resistance and chronic inflammation in obese mice. Nat Med. 2014 Aug;20(8):942-7.
22 Novel selective ligands for free fatty acid receptors GPR120 and GPR40. Naunyn Schmiedebergs Arch Pharmacol. 2009 Sep;380(3):247-55.
23 Discovery of a potent and selective GPR120 agonist. J Med Chem. 2012 May 10;55(9):4511-5.
24 Identification of G protein-coupled receptor 120-selective agonists derived from PPARgamma agonists. J Med Chem. 2008 Dec 11;51(23):7640-4.
25 Maternal toxicity of nonsteroidal anti-inflammatory drugs as an important factor affecting prenatal development. Reprod Toxicol. 2009 Sep;28(2):239-44.
26 Comparative inhibitory activity of rofecoxib, meloxicam, diclofenac, ibuprofen, and naproxen on COX-2 versus COX-1 in healthy volunteers. J Clin Pharmacol. 2000 Oct;40(10):1109-20.
27 Membranous nephropathy associated with the relatively selective cyclooxygenase-2 inhibitor, etodolac, in a patient with early rheumatoid arthritis. Intern Med. 2007;46(13):1055-8.
28 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
29 Pfizer. Product Development Pipeline. March 31 2009.
30 Renal effects of nabumetone, a COX-2 antagonist: impairment of function in isolated perfused rat kidneys contrasts with preserved renal function in vivo. Exp Nephrol. 2001;9(6):387-96.
31 Privileged structures: a useful concept for the rational design of new lead drug candidates. Mini Rev Med Chem. 2007 Nov;7(11):1108-19.
32 Flurbiprofen, a cyclooxygenase inhibitor, protects mice from hepatic ischemia/reperfusion injury by inhibiting GSK-3 signaling and mitochondrial permeability transition.Mol Med.2012 Sep 25;18:1128-35.
33 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.
34 Peroxidative free radical formation and O-demethylation of etoposide(VP-16) and teniposide(VM-26). Biochem Biophys Res Commun. 1986 Feb 26;135(1):215-20.
35 Structural basis of fatty acid substrate binding to cyclooxygenase-2. J Biol Chem. 2010 Jul 16;285(29):22152-63.
36 Health implications of high dietary omega-6 polyunsaturated Fatty acids. J Nutr Metab. 2012;2012:539426.
37 PharmGKB summary: very important pharmacogene information for PTGS2. Pharmacogenet Genomics. 2011 Sep;21(9):607-13.
38 Docosahexaenoic acid regulates gene expression in HUVEC cells treated with polycyclic aromatic hydrocarbons. Toxicol Lett. 2015 Jul 16;236(2):75-81.
39 Etoposide induces necrosis through p53-mediated antiapoptosis in human kidney proximal tubule cells. Toxicol Sci. 2015 Nov;148(1):204-19.
40 COX-2 and PPAR-gama confer cannabidiol-induced apoptosis of human lung cancer cells. Mol Cancer Ther. 2013 Jan;12(1):69-82.
41 Mitochondrial involvement in schizophrenia and other functional psychoses. Neurochem Res. 1996 Sep;21(9):995-1004.
42 Immunomodulatory effect of selective serotonin reuptake inhibitors (SSRIs) on human T lymphocyte function and gene expression. Eur Neuropsychopharmacol. 2007 Dec;17(12):774-80.
43 Stimulation of cyclooxygenase-2 expression by bone-derived transforming growth factor-beta enhances bone metastases in breast cancer. Cancer Res. 2006 Feb 15;66(4):2067-73.
44 Arsenite and cadmium promote the development of mammary tumors. Carcinogenesis. 2020 Jul 14;41(7):1005-1014. doi: 10.1093/carcin/bgz176.
45 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.
46 A2E selectively induces cox-2 in ARPE-19 and human neural cells. Curr Eye Res. 2006 Mar;31(3):259-63.
47 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.
48 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.
49 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.
50 Stiripentol. Expert Opin Investig Drugs. 2005 Jul;14(7):905-11.
51 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.
52 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.
53 Predictive three-dimensional quantitative structure-activity relationship of cytochrome P450 1A2 inhibitors. J Med Chem. 2005 Jun 2;48(11):3808-15.
54 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.
55 Chemical inhibitors of cytochrome P450 isoforms in human liver microsomes: a re-evaluation of P450 isoform selectivity. Eur J Drug Metab Pharmacokinet. 2011 Mar;36(1):1-16.
56 Inhibition of CYP2E1 catalytic activity in vitro by S-adenosyl-L-methionine. Biochem Pharmacol. 2005 Apr 1;69(7):1081-93.
57 Characterization of primary human hepatocytes, HepG2 cells, and HepaRG cells at the mRNA level and CYP activity in response to inducers and their predictivity for the detection of human hepatotoxins. Cell Biol Toxicol. 2012 Apr;28(2):69-87.
58 An in vitro model of human acute ethanol exposure that incorporates CXCR3- and CXCR4-dependent recruitment of immune cells. Toxicol Sci. 2013 Mar;132(1):131-41.
59 Multiple microRNAs function as self-protective modules in acetaminophen-induced hepatotoxicity in humans. Arch Toxicol. 2018 Feb;92(2):845-858.
60 Proteomic analysis of hepatic effects of phenobarbital in mice with humanized liver. Arch Toxicol. 2022 Oct;96(10):2739-2754. doi: 10.1007/s00204-022-03338-7. Epub 2022 Jul 26.
61 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.
62 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.
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 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.
68 Cetirizine and loratadine-based antihistamines with 5-lipoxygenase inhibitory activity. Bioorg Med Chem Lett. 2004 Nov 15;14(22):5591-4.
69 Mechanism-based inactivation of CYP3A by HIV protease inhibitors. J Pharmacol Exp Ther. 2005 Feb;312(2):583-91.
70 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.
71 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.
72 Comparative effects of thiazolidinediones on in vitro P450 enzyme induction and inhibition. Drug Metab Dispos. 2003 Apr;31(4):439-46.
73 Potential of pranlukast and zafirlukast in the inhibition of human liver cytochrome P450 enzymes. Xenobiotica. 2004 May;34(5):429-38.
74 Cytochrome P450 inhibition potential of new psychoactive substances of the tryptamine class. Toxicol Lett. 2016 Jan 22;241:82-94.
75 Dexamethasone and the inflammatory response in explants of human omental adipose tissue. Mol Cell Endocrinol. 2010 Feb 5;315(1-2):292-8.
76 Inhibiting Heat Shock Proteins Can Potentiate the Cytotoxic Effect of Cannabidiol in Human Glioma Cells. Anticancer Res. 2015 Nov;35(11):5827-37.
77 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.
78 Protective role of HO-1 for alcohol-dependent liver damage. Dig Dis. 2010;28(6):792-8. doi: 10.1159/000324287. Epub 2011 Apr 27.
79 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.
80 Neuroprotective effects of glucomoringin-isothiocyanate against H(2)O(2)-Induced cytotoxicity in neuroblastoma (SH-SY5Y) cells. Neurotoxicology. 2019 Dec;75:89-104. doi: 10.1016/j.neuro.2019.09.008. Epub 2019 Sep 12.
81 High selenium status in individuals exposed to arsenic through coal-burning in Shaanxi (PR of China) modulates antioxidant enzymes, heme oxygenase-1 and DNA damage. Clin Chim Acta. 2010 Sep 6;411(17-18):1312-8.
82 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.
83 Combination treatment with arsenic trioxide and sulindac enhances apoptotic cell death in lung cancer cells via activation of oxidative stress and mitogen-activated protein kinases. Oncol Rep. 2008 Aug;20(2):379-84.
84 Functional gene expression profile underlying methotrexate-induced senescence in human colon cancer cells. Tumour Biol. 2011 Oct;32(5):965-76.
85 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.
86 Blood cell oxidative stress precedes hemolysis in whole blood-liver slice co-cultures of rat, dog, and human tissues. Toxicol Appl Pharmacol. 2010 May 1;244(3):354-65. doi: 10.1016/j.taap.2010.01.017. Epub 2010 Feb 6.
87 Molecular mechanisms of hepatotoxic cholestasis by clavulanic acid: Role of NRF2 and FXR pathways. Food Chem Toxicol. 2021 Dec;158:112664. doi: 10.1016/j.fct.2021.112664. Epub 2021 Nov 9.
88 Induction of multidrug resistance proteins MRP1 and MRP3 and gamma-glutamylcysteine synthetase gene expression by nonsteroidal anti-inflammatory drugs in human colon cancer cells. Biochem Biophys Res Commun. 2002 Feb 8;290(5):1427-33. doi: 10.1006/bbrc.2002.6367.
89 Flavonoids increase the intracellular glutathione level by transactivation of the gamma-glutamylcysteine synthetase catalytical subunit promoter. Free Radic Biol Med. 2002 Mar 1;32(5):386-93. doi: 10.1016/s0891-5849(01)00812-7.
90 Effects of ciglitazone and troglitazone on the proliferation of human stomach cancer cells. World J Gastroenterol. 2009 Jan 21;15(3):310-20.
91 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.
92 Glycidamide and cis-2-butene-1,4-dial (BDA) as potential carcinogens and promoters of liver cancer - An in vitro study. Food Chem Toxicol. 2022 Aug;166:113251. doi: 10.1016/j.fct.2022.113251. Epub 2022 Jun 21.
93 Darinaparsin induces a unique cellular response and is active in an arsenic trioxide-resistant myeloma cell line. Mol Cancer Ther. 2009 May;8(5):1197-206.
94 Increased organophosphate scavenging in a butyrylcholinesterase mutant. Chem Biol Interact. 2008 Sep 25;175(1-3):376-9. doi: 10.1016/j.cbi.2008.04.012. Epub 2008 Apr 22.
95 Comparative effects of cationic triarylmethane, phenoxazine and phenothiazine dyes on horse serum butyrylcholinesterase. Arch Biochem Biophys. 2008 Oct 15;478(2):201-5.
96 Lichens of parmelioid clade as promising multitarget neuroprotective agents. Chem Res Toxicol. 2019 Jun 17;32(6):1165-1177.
97 Potencies and selectivities of inhibitors of acetylcholinesterase and its molecular forms in normal and Alzheimer's disease brain. Acta Biol Hung. 2003;54(2):183-9. doi: 10.1556/ABiol.54.2003.2.7.
98 Response of the newborn to succinlycholine injection in homozygotic atypical mothers. Anesthesiology. 1975 Jul;43(1):115-6. doi: 10.1097/00000542-197507000-00028.
99 Cholinesterase inhibition by phenothiazine and nonphenothiazine antihistaminics: analysis of its postulated role in synergizing organophosphate toxicity. Toxicol Appl Pharmacol. 1975 Feb;31(2):179-90.
100 Qualitative defects of pseudocholinesterase activity. Anaesthesia. 1967 Jan;22(1):55-68.
101 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.
102 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.
103 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.
104 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.
105 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.
106 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.
107 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.
108 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.
109 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.
110 Global molecular effects of tocilizumab therapy in rheumatoid arthritis synovium. Arthritis Rheumatol. 2014 Jan;66(1):15-23.
111 Cyp2a6 is a principal enzyme involved in hydroxylation of 1,7-dimethylxanthine, a main caffeine metabolite, in humans. Drug Metab Dispos. 2005 Sep;33(9):1361-6. doi: 10.1124/dmd.105.004796. Epub 2005 Jun 24.
112 Mimicking gene defects to treat drug dependence. Ann N Y Acad Sci. 2000;909:233-46. doi: 10.1111/j.1749-6632.2000.tb06685.x.
113 Expression of CYP2A6 in tumor cells augments cellular sensitivity to tegafur. Jpn J Cancer Res. 2001 May;92(5):524-8. doi: 10.1111/j.1349-7006.2001.tb01125.x.
114 CYP1A1/1B1 and CYP2A6/2A13 activity is conserved in cultures of differentiated primary human tracheobronchial epithelial cells. Toxicol In Vitro. 2011 Jun;25(4):922-9.
115 Isoform-specific regulation of cytochromes P450 expression by estradiol and progesterone. Drug Metab Dispos. 2013 Feb;41(2):263-9.
116 Measurement of 4-hydroxylation of ifosfamide in human liver microsomes using the estimation of free and protein-bound acrolein and codetermination of keto- and carboxyifosfamide. J Cancer Res Clin Oncol. 2002 Jul;128(7):385-92.
117 Integrated 'omics analysis reveals new drug-induced mitochondrial perturbations in human hepatocytes. Toxicol Lett. 2018 Jun 1;289:1-13.
118 Deactivation of anti-cancer drug letrozole to a carbinol metabolite by polymorphic cytochrome P450 2A6 in human liver microsomes. Xenobiotica. 2009 Nov;39(11):795-802. doi: 10.3109/00498250903171395.
119 A novel single nucleotide polymorphism altering stability and activity of CYP2a6. Biochem Biophys Res Commun. 2001 Mar 2;281(3):810-4. doi: 10.1006/bbrc.2001.4422.
120 Phthalates efficiently bind to human peroxisome proliferator activated receptor and retinoid X receptor , , subtypes: an in silico approach. J Appl Toxicol. 2014 Jul;34(7):754-65. doi: 10.1002/jat.2902. Epub 2013 Jul 11.
121 Cross-species global and subset gene expression profiling identifies genes involved in prostate cancer response to selenium. BMC Genomics. 2004 Aug 20;5(1):58. doi: 10.1186/1471-2164-5-58.
122 Pharmacotoxicology of clinically-relevant concentrations of obeticholic acid in an organotypic human hepatocyte system. Toxicol In Vitro. 2017 Mar;39:93-103.
123 Identification and characterization of the human retinoid X receptor alpha gene promoter. Gene. 2006 May 10;372:118-27. doi: 10.1016/j.gene.2005.12.027. Epub 2006 Mar 6.
124 Chemical genomics profiling of environmental chemical modulation of human nuclear receptors. Environ Health Perspect. 2011 Aug;119(8):1142-8. doi: 10.1289/ehp.1002952. Epub 2011 May 4.
125 Arsenic trioxide and cisplatin synergism increase cytotoxicity in human ovarian cancer cells: therapeutic potential for ovarian cancer. Cancer Sci. 2009 Dec;100(12):2459-64.
126 Limited Chemical Structural Diversity Found to Modulate Thyroid Hormone Receptor in the Tox21 Chemical Library. Environ Health Perspect. 2019 Sep;127(9):97009. doi: 10.1289/EHP5314. Epub 2019 Sep 30.
127 Transcriptomics hit the target: monitoring of ligand-activated and stress response pathways for chemical testing. Toxicol In Vitro. 2015 Dec 25;30(1 Pt A):7-18.
128 The functional consequences of cross-talk between the vitamin D receptor and ERK signaling pathways are cell-specific. J Biol Chem. 2004 Nov 5;279(45):47298-310. doi: 10.1074/jbc.M404101200. Epub 2004 Aug 25.
129 Protective effects of myricitrin against osteoporosis via reducing reactive oxygen species and bone-resorbing cytokines. Toxicol Appl Pharmacol. 2014 Nov 1;280(3):550-60.
130 The effect of quercetin and kaempferol aglycones and glucuronides on peroxisome proliferator-activated receptor-gamma (PPAR-). Food Funct. 2015 Apr;6(4):1098-107. doi: 10.1039/c5fo00076a.
131 Induction of solid tumor differentiation by the peroxisome proliferator-activated receptor-gamma ligand troglitazone in patients with liposarcoma. Proc Natl Acad Sci U S A. 1999 Mar 30;96(7):3951-6. doi: 10.1073/pnas.96.7.3951.
132 Development of a neural teratogenicity test based on human embryonic stem cells: response to retinoic acid exposure. Toxicol Sci. 2011 Dec;124(2):370-7.
133 Glucosamine sulfate reduces prostaglandin E(2) production in osteoarthritic chondrocytes through inhibition of microsomal PGE synthase-1. J Rheumatol. 2012 Mar;39(3):635-44. doi: 10.3899/jrheum.110621. Epub 2011 Nov 15.
134 Isoniazid suppresses antioxidant response element activities and impairs adipogenesis in mouse and human preadipocytes. Toxicol Appl Pharmacol. 2013 Dec 15;273(3):435-41. doi: 10.1016/j.taap.2013.10.005. Epub 2013 Oct 12.
135 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.
136 Aspirin inhibits MMP-9 mRNA expression and release via the PPARalpha/gamma and COX-2/mPGES-1-mediated pathways in macrophages derived from THP-1 cells. Biomed Pharmacother. 2010 Feb;64(2):118-23. doi: 10.1016/j.biopha.2009.04.033. Epub 2009 Oct 17.
137 Mitochondrial proliferation, DNA depletion and adipocyte differentiation in subcutaneous adipose tissue of HIV-positive HAART recipients. Antivir Ther. 2003 Aug;8(4):323-31.
138 Thyroid organotypic rat and human cultures used to investigate drug effects on thyroid function, hormone synthesis and release pathways. Toxicol Appl Pharmacol. 2012 Apr 1;260(1):81-8. doi: 10.1016/j.taap.2012.01.029. Epub 2012 Feb 8.
139 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.
140 Integrated analysis of rifampicin-induced microRNA and gene expression changes in human hepatocytes. Drug Metab Pharmacokinet. 2014;29(4):333-40.
141 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.
142 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.
143 Screening the ToxCast Phase 1, Phase 2, and e1k Chemical Libraries for Inhibitors of Iodothyronine Deiodinases. Toxicol Sci. 2019 Apr 1;168(2):430-442. doi: 10.1093/toxsci/kfy302.
144 Effects of all-trans and 9-cis retinoic acid on differentiating human neural stem cells in vitro. Toxicology. 2023 Mar 15;487:153461. doi: 10.1016/j.tox.2023.153461. Epub 2023 Feb 16.
145 A transcriptomics-based in vitro assay for predicting chemical genotoxicity in vivo. Carcinogenesis. 2012 Jul;33(7):1421-9.
146 Regulation of type 1 iodothyronine deiodinase in health and disease. Thyroid. 2005 Aug;15(8):835-40. doi: 10.1089/thy.2005.15.835.
147 Positive regulation of hepatic carnitine palmitoyl transferase 1A (CPT1A) activities by soy isoflavones and L-carnitine. Eur J Nutr. 2006 Mar;45(3):159-64. doi: 10.1007/s00394-005-0576-5. Epub 2005 Dec 20.
148 The contribution of methotrexate exposure and host factors on transcriptional variance in human liver. Toxicol Sci. 2007 Jun;97(2):582-94.
149 Species-specific toxicity of diclofenac and troglitazone in primary human and rat hepatocytes. Chem Biol Interact. 2009 Apr 15;179(1):17-24.
150 Chronic occupational exposure to arsenic induces carcinogenic gene signaling networks and neoplastic transformation in human lung epithelial cells. Toxicol Appl Pharmacol. 2012 Jun 1;261(2):204-16.
151 Aspirin regulates hepatocellular lipid metabolism by activating AMPK signaling pathway. J Toxicol Sci. 2015 Feb;40(1):127-36. doi: 10.2131/jts.40.127.
152 Role of sirtuin 1 in the regulation of hepatic gene expression by thyroid hormone. J Biol Chem. 2013 Jan 11;288(2):807-18. doi: 10.1074/jbc.M112.437970. Epub 2012 Dec 3.
153 JunD is involved in the antiproliferative effect of Delta9-tetrahydrocannabinol on human breast cancer cells. Oncogene. 2008 Aug 28;27(37):5033-44.
154 Regulation of type III iodothyronine deiodinase expression in human cell lines. Endocrinology. 2006 Dec;147(12):5845-54. doi: 10.1210/en.2006-0590. Epub 2006 Aug 24.
155 MAPK and SHH pathways modulate type 3 deiodinase expression in papillary thyroid carcinoma. Endocr Relat Cancer. 2016 Mar;23(3):135-46. doi: 10.1530/ERC-15-0162.
156 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.
157 Disturbance of the Dlk1-Dio3 imprinted domain may underlie placental Dio3 suppression and extracellular thyroid hormone disturbance in placenta-derived JEG-3 cells following decabromodiphenyl ether (BDE209) exposure. Toxicology. 2021 Jun 30;458:152837. doi: 10.1016/j.tox.2021.152837. Epub 2021 Jun 21.
158 Functional characterization of peroxisome proliferator-activated receptor-/ expression in colon cancer. Mol Carcinog. 2011 Nov;50(11):884-900. doi: 10.1002/mc.20757. Epub 2011 Mar 11.
159 Phenotypic characterization of retinoic acid differentiated SH-SY5Y cells by transcriptional profiling. PLoS One. 2013 May 28;8(5):e63862.
160 Aspirin-induced apoptosis in jurkat cells is not mediated by peroxisome proliferator-activated receptor delta. Mol Cell Biochem. 2004 Nov;266(1-2):57-63. doi: 10.1023/b:mcbi.0000049138.67699.7b.
161 Keratinocyte-derived IL-36gama plays a role in hydroquinone-induced chemical leukoderma through inhibition of melanogenesis in human epidermal melanocytes. Arch Toxicol. 2019 Aug;93(8):2307-2320.
162 (9)-Tetrahydrocannabinol upregulates fatty acid 2-hydroxylase (FA2H) via PPAR induction: A possible evidence for the cancellation of PPAR/-mediated inhibition of PPAR in MDA-MB-231?cells. Arch Biochem Biophys. 2019 Feb 15;662:219-225. doi: 10.1016/j.abb.2018.12.011. Epub 2018 Dec 13.
163 Cross-talk between vitamin D receptor (VDR)- and peroxisome proliferator-activated receptor (PPAR)-signaling in melanoma cells. Anticancer Res. 2009 Sep;29(9):3647-58.
164 The ligands/activators for peroxisome proliferator-activated receptor alpha (PPARalpha) and PPARgamma increase Cu2+,Zn2+-superoxide dismutase and decrease p22phox message expressions in primary endothelial cells. Metabolism. 2001 Jan;50(1):3-11.
165 Arsenic trioxide promotes senescence and regulates the balance of adipogenic and osteogenic differentiation in human mesenchymal stem cells. Acta Biochim Biophys Sin (Shanghai). 2011 Mar;43(3):204-9. doi: 10.1093/abbs/gmq130. Epub 2011 Jan 21.
166 Modulation of receptor phosphorylation contributes to activation of peroxisome proliferator activated receptor alpha by dehydroepiandrosterone and other peroxisome proliferators. Mol Pharmacol. 2008 Mar;73(3):968-76. doi: 10.1124/mol.107.036780. Epub 2007 Dec 13.
167 (9)-THC modulation of fatty acid 2-hydroxylase (FA2H) gene expression: possible involvement of induced levels of PPARalpha in MDA-MB-231 breast cancer cells. Toxicology. 2014 Dec 4;326:18-24.
168 Effects of 1alpha,25 dihydroxyvitamin D3 and testosterone on miRNA and mRNA expression in LNCaP cells. Mol Cancer. 2011 May 18;10:58.
169 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.
170 The small polyphenolic molecule kaempferol increases cellular energy expenditure and thyroid hormone activation. Diabetes. 2007 Mar;56(3):767-76. doi: 10.2337/db06-1488.
171 Type 2 deiodinase expression is induced by peroxisomal proliferator-activated receptor-gamma agonists in skeletal myocytes. Endocrinology. 2009 Apr;150(4):1976-83. doi: 10.1210/en.2008-0938. Epub 2008 Nov 26.
172 Antirheumatic drug response signatures in human chondrocytes: potential molecular targets to stimulate cartilage regeneration. Arthritis Res Ther. 2009;11(1):R15.
173 Mifepristone induced progesterone withdrawal reveals novel regulatory pathways in human endometrium. Mol Hum Reprod. 2007 Sep;13(9):641-54.
174 Interleukin-19 as a translational indicator of renal injury. Arch Toxicol. 2015 Jan;89(1):101-6.
175 Temozolomide induces activation of Wnt/-catenin signaling in glioma cells via PI3K/Akt pathway: implications in glioma therapy. Cell Biol Toxicol. 2020 Jun;36(3):273-278. doi: 10.1007/s10565-019-09502-7. Epub 2019 Nov 22.
176 Time series analysis of oxidative stress response patterns in HepG2: a toxicogenomics approach. Toxicology. 2013 Apr 5;306:24-34.
177 Quantitative high-throughput profiling of environmental chemicals and drugs that modulate farnesoid X receptor. Sci Rep. 2014 Sep 26;4:6437. doi: 10.1038/srep06437.
178 Potency of individual bile acids to regulate bile acid synthesis and transport genes in primary human hepatocyte cultures. Toxicol Sci. 2014 Oct;141(2):538-46. doi: 10.1093/toxsci/kfu151. Epub 2014 Jul 23.
179 The farnesoid X receptor FXRalpha/NR1H4 acquired ligand specificity for bile salts late in vertebrate evolution. Am J Physiol Regul Integr Comp Physiol. 2007 Sep;293(3):R1400-9. doi: 10.1152/ajpregu.00781.2006. Epub 2007 Jun 13.
180 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.
181 Investigation of imatinib and other approved drugs as starting points for antidiabetic drug discovery with FXR modulating activity. Biochem Pharmacol. 2012 Jun 15;83(12):1674-81. doi: 10.1016/j.bcp.2012.02.027. Epub 2012 Mar 7.