General Information of Drug (ID: DM2NUH3)

Drug Name
Imipramine Drug Info
Synonyms
Antideprin; Berkomine; Censtim; Censtin; Declomipramine; Dimipressin; Dpid; Dynaprin; Eupramin; Imavate; Imidobenzyle; Imipramin; Imipramina; Imipraminum; Imiprin; Imizin; Imizinum; Impramine; Intalpram; Iramil; Irmin; Janimine; Melipramin; Melipramine; Nelipramin; Norchlorimipramine; Norfranil; Pramine; Prazepine; Promiben;Psychoforin; Surplix; Timolet; Tofranil; Imipramina [Italian]; Tofraniln A; Antideprin (TN); Deprimin (TN); Deprinol (TN); Depsonil (TN); Dyna-zina; Dynaprin (TN); Eupramin (TN); G-22355; Imipramil (TN); Imipramina [INN-Spanish]; Imipramine (INN); Imipramine [INN:BAN]; Imipraminum [INN-Latin]; Irmin (TN); Janimine (TN); Janimine (hydrochloride); Melipramin (TN); SK-Pramine; Surplix (TN); Tofranil(TN); Tofranil (free base); Tofranil (hydrochloride); Tofranil, base; N-(gamma-Dimethylaminopropyl)iminodibenzyl; N-(gamma.-Dimethylaminopropyl)iminodibenzyl; N-(3-Dimethylaminopropyl)-o-iminodibenzyl; 1-(3-Dimethylaminopropyl)-4,5-dihydro-2,3,6,7-dibenzazepine; 10,11-Dihydro-5-(3-(dimethylamino)propyl)-5H-dibenz[b,f]azepine; 10,11-Dihydro-N,N-dimethyl-5H-dibenz[b,f]azepine-5-propanamine; 2,2'-(3-Dimethylaminopropylimino)bibenzyl; 2,2'-(3-Dimethylaminopropylimino)dibenzyl; 3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-N,N-dimethylpropan-1-amine; 3-(5,6-dihydrobenzo[b][1]benzazepin-11-yl)-N,N-dimethylpropan-1-amine; 5,6-Dihydro-N-(3-(dimethylamino)propyl)-11H-dibenz(b,e)azepine; 5,6-Dihydro-N-[3-(dimethylamino)propyl]-11H-dibenz[b,e]azepine; 5-(3-(Dimethylamino)propyl)-10,11-dihydro-5H-dibenz(b,f)azepine; 5-(3-Dimethylaminopropyl)-10,11-dihydro-5H-dibenzo(b,f)azepine; 5H-Dibenz(b,f)azepine,5-[3-(dimethylamino)propyl]-10,11-dihydro-mixed with ethyl alcohol; 5H-Dibenz(b,f)azepine-5-propanamine, 10,11-dihydro-N,N-dimethyl-(9CI)
Indication
Disease Entry ICD 11 Status REF
Depression 6A70-6A7Z Approved [1]
Nocturia MF55 Approved [2]
Therapeutic Class
Antidepressants
Cross-matching ID
PubChem CID
3696
ChEBI ID
CHEMBL11
CAS Number
CAS 50-49-7
TTD Drug ID
DM2NUH3
VARIDT Drug ID
DR00552
INTEDE Drug ID
DR0861
ACDINA Drug ID
D00325

Molecule-Related Drug Atlas

Molecule-Related Drug Atlas
Molecule Type:
DTT
DTP
DME
DOT
Drug Status:
Approved Drug(s)
Investigative Drug(s)
Clinical Trial Drug(s)
Patented Agent(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [19]
Amitriptyline DMK7F9S Depression 6A70-6A7Z Approved [20]
Desipramine DMT2FDC Attention deficit hyperactivity disorder 6A05.Z Approved [19]
Cocaine DMSOX7I Anaesthesia 9A78.6 Approved [21]
Bupropion DM5PCS7 Depression 6A70-6A7Z Approved [22]
Tapentadol hydrochloride DMXLSH3 Acute pain MG31 Approved [23]
Venlafaxine DMR6QH0 Anxiety disorder 6B00-6B0Z Approved [22]
Trimipramine DM1SC8M Major depressive disorder 6A70.3 Approved [24]
Duloxetine DM9BI7M Depression 6A70-6A7Z Approved [25]
Levomilnacipran DMV26S8 Fibromyalgia MG30.01 Approved [26]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Transported By P-glycoprotein 1 (ABCB1)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Amoxicillin DMUYNEI Acute otitis media AB00 Approved [27]
Doxorubicin DMVP5YE Acute myelogenous leukaemia 2A41 Approved [28]
Methotrexate DM2TEOL Anterior urethra cancer Approved [29]
Folic Acid DMEMBJC Colorectal carcinoma Approved [30]
Fluorouracil DMUM7HZ Adenocarcinoma 2D40 Approved [29]
Cisplatin DMRHGI9 Adenocarcinoma 2D40 Approved [29]
Progesterone DMUY35B Amenorrhea GA20.0 Approved [31]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [29]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [32]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [33]
⏷ Show the Full List of 10 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 [34]
Progesterone DMUY35B Amenorrhea GA20.0 Approved [35]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [36]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [37]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [38]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [39]
Etoposide DMNH3PG Acute myelogenous leukaemia 2A41 Approved [40]
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [41]
Prasterone DM67VKL Chronic obstructive pulmonary disease CA22 Approved [35]
Verapamil DMA7PEW Angina pectoris BA40 Approved [42]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Metabolized By Cytochrome P450 1A2 (CYP1A2)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Fluorouracil DMUM7HZ Adenocarcinoma 2D40 Approved [43]
Dinoprostone DMTYOPD Medical abortion JA00.1Z Approved [44]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [45]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [46]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [47]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [48]
Etoposide DMNH3PG Acute myelogenous leukaemia 2A41 Approved [40]
Oxaliplatin DMQNWRD Adenocarcinoma 2D40 Approved [49]
Verapamil DMA7PEW Angina pectoris BA40 Approved [50]
Diclofenac DMPIHLS Chronic renal failure GB61.Z Approved [51]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [52]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [53]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [54]
Etoposide DMNH3PG Acute myelogenous leukaemia 2A41 Approved [55]
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [56]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [57]
Mycophenolate mofetil DMPQAGE Hepatosplenic T-cell lymphoma Approved [58]
Metronidazole DMTIVEN Abscess Approved [59]
Propofol DMB4OLE Anaesthesia 9A78.6 Approved [60]
Ethanol DMDRQZU Chronic pain MG30 Approved [61]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Metabolized By Cytochrome P450 2D6 (CYP2D6)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Doxorubicin DMVP5YE Acute myelogenous leukaemia 2A41 Approved [62]
Progesterone DMUY35B Amenorrhea GA20.0 Approved [63]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [64]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [38]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [42]
Quinine DMSWYF5 Malaria 1F40-1F45 Approved [65]
Propofol DMB4OLE Anaesthesia 9A78.6 Approved [66]
Dopamine DMPGUCF Acromegaly 5A60.0 Approved [67]
Nicotine DMWX5CO Lung cancer 2C25.0 Approved [68]
Propranolol DM79NTF Angina pectoris BA40 Approved [69]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Metabolized By Cytochrome P450 3A7 (CYP3A7)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Progesterone DMUY35B Amenorrhea GA20.0 Approved [70]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [71]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [71]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [71]
Prasterone DM67VKL Chronic obstructive pulmonary disease CA22 Approved [72]
Verapamil DMA7PEW Angina pectoris BA40 Approved [73]
Sorafenib DMS8IFC Adenocarcinoma 2D40 Approved [71]
Quinine DMSWYF5 Malaria 1F40-1F45 Approved [71]
Irinotecan DMP6SC2 Adenocarcinoma 2D40 Approved [71]
Metronidazole DMTIVEN Abscess Approved [74]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Metabolized By Cytochrome P450 2C18 (CYP2C18)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Verapamil DMA7PEW Angina pectoris BA40 Approved [72]
Diclofenac DMPIHLS Chronic renal failure GB61.Z Approved [75]
Propofol DMB4OLE Anaesthesia 9A78.6 Approved [76]
Phenytoin DMNOKBV Epilepsy 8A60-8A68 Approved [72]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [77]
Diazepam DM08E9O Alcohol withdrawal Approved [78]
Methadone DMTW6IU Advanced cancer 2A00-2F9Z Approved [79]
Dapsone DM4LT8A Acne vulgaris ED80 Approved [80]
Lidocaine DML4ZOT Anaesthesia 9A78.6 Approved [72]
Phenobarbital DMXZOCG Cluster headache 8A81.0 Approved [81]
⏷ 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 [82]
Verapamil DMA7PEW Angina pectoris BA40 Approved [72]
Diclofenac DMPIHLS Chronic renal failure GB61.Z Approved [83]
Estrone DM5T6US Acne vulgaris ED80 Approved [84]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [85]
Irinotecan DMP6SC2 Adenocarcinoma 2D40 Approved [86]
Propofol DMB4OLE Anaesthesia 9A78.6 Approved [87]
Nicotine DMWX5CO Lung cancer 2C25.0 Approved [88]
Phenytoin DMNOKBV Epilepsy 8A60-8A68 Approved [89]
Amitriptyline DMK7F9S Depression 6A70-6A7Z Approved [90]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Metabolized By Mephenytoin 4-hydroxylase (CYP2C19)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Amoxicillin DMUYNEI Acute otitis media AB00 Approved [91]
Progesterone DMUY35B Amenorrhea GA20.0 Approved [92]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [93]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [94]
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [72]
Verapamil DMA7PEW Angina pectoris BA40 Approved [95]
Diclofenac DMPIHLS Chronic renal failure GB61.Z Approved [75]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [96]
Quinine DMSWYF5 Malaria 1F40-1F45 Approved [97]
Propofol DMB4OLE Anaesthesia 9A78.6 Approved [76]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Erythromycin DM4K7GQ Acne vulgaris ED80 Approved [11]
Chlorpromazine DMBGZI3 Acute intermittent hepatic porphyria 5C58.11 Approved [11]
Benzphetamine DMIJATC Obesity 5B81 Approved [11]
Ethylmorphine DM0YROF Discovery agent N.A. Investigative [11]
Drug(s) Affected By Nuclear protein 1 (NUPR1)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Cannabidiol DM0659E Dravet syndrome 8A61.11 Approved [98]
Sertraline DM0FB1J Coronary heart disease BA80.Z Approved [12]
Ofloxacin DM0VQN3 Acute gonococcal cervicitis Approved [99]
Citalopram DM2G9AE Acute coronary syndrome BA41 Approved [100]
Thioridazine DM35M8J Schizophrenia 6A20 Approved [12]
Quercetin DM3NC4M Obesity 5B81 Approved [101]
Fluoxetine DM3PD2C Bipolar depression Approved [12]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [102]
Erythromycin DM4K7GQ Acne vulgaris ED80 Approved [99]
Isoniazid DM5JVS3 Latent tuberculosis infection Approved [99]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Sertraline DM0FB1J Coronary heart disease BA80.Z Approved [12]
Hydrogen peroxide DM1NG5W Infectious disease 1A00-CA43.1 Approved [103]
Citalopram DM2G9AE Acute coronary syndrome BA41 Approved [100]
Thioridazine DM35M8J Schizophrenia 6A20 Approved [12]
Rofecoxib DM3P5DA Osteoarthritis FA00-FA05 Approved [104]
Fluoxetine DM3PD2C Bipolar depression Approved [12]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [105]
Isotretinoin DM4QTBN Acne vulgaris ED80 Approved [105]
Chlorpromazine DMBGZI3 Acute intermittent hepatic porphyria 5C58.11 Approved [12]
Aspirin DM672AH Acute coronary syndrome BA41 Approved [106]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
2-deoxyglucose DMIAHVU Solid tumour/cancer 2A00-2F9Z Approved [107]
Cannabidiol DM0659E Dravet syndrome 8A61.11 Approved [108]
Sertraline DM0FB1J Coronary heart disease BA80.Z Approved [12]
Citalopram DM2G9AE Acute coronary syndrome BA41 Approved [100]
Methotrexate DM2TEOL Anterior urethra cancer Approved [109]
Thioridazine DM35M8J Schizophrenia 6A20 Approved [12]
Quercetin DM3NC4M Obesity 5B81 Approved [101]
Fluoxetine DM3PD2C Bipolar depression Approved [12]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [110]
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [111]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Inhibin beta E chain (INHBE)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Sertraline DM0FB1J Coronary heart disease BA80.Z Approved [12]
Citalopram DM2G9AE Acute coronary syndrome BA41 Approved [100]
Thioridazine DM35M8J Schizophrenia 6A20 Approved [12]
Quercetin DM3NC4M Obesity 5B81 Approved [101]
Fluoxetine DM3PD2C Bipolar depression Approved [12]
Troglitazone DM3VFPD Diabetic complication 5A2Y Approved [112]
Erythromycin DM4K7GQ Acne vulgaris ED80 Approved [99]
Clarithromycin DM4M1SG Acute maxillary sinusitis Approved [12]
Panobinostat DM58WKG Chronic graft versus host disease Approved [113]
Isoniazid DM5JVS3 Latent tuberculosis infection Approved [99]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Acid ceramidase (ASAH1)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Sertraline DM0FB1J Coronary heart disease BA80.Z Approved [12]
Beta-carotene DM0RXBT Vitamin deficiency 5B55-5B71 Approved [114]
Ofloxacin DM0VQN3 Acute gonococcal cervicitis Approved [99]
Hydrogen peroxide DM1NG5W Infectious disease 1A00-CA43.1 Approved [115]
Thioridazine DM35M8J Schizophrenia 6A20 Approved [99]
Quercetin DM3NC4M Obesity 5B81 Approved [101]
Fluoxetine DM3PD2C Bipolar depression Approved [12]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [116]
Erythromycin DM4K7GQ Acne vulgaris ED80 Approved [99]
Clarithromycin DM4M1SG Acute maxillary sinusitis Approved [12]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Calcipotriol DM03CP7 Psoriasis EA90 Approved [117]
Sertraline DM0FB1J Coronary heart disease BA80.Z Approved [12]
Fulvestrant DM0YZC6 Breast cancer 2C60-2C65 Approved [118]
Hydrogen peroxide DM1NG5W Infectious disease 1A00-CA43.1 Approved [119]
Clavulanate DM2FGRT Bacteremia 1A73 Approved [120]
Thioridazine DM35M8J Schizophrenia 6A20 Approved [99]
Deoxycholic acid DM3GYAL Subcutaneous fat disorder EF02 Approved [121]
Quercetin DM3NC4M Obesity 5B81 Approved [101]
Fluoxetine DM3PD2C Bipolar depression Approved [12]
obeticholic acid DM3Q1SM Primary biliary cholangitis DB96.1 Approved [122]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Sertraline DM0FB1J Coronary heart disease BA80.Z Approved [12]
Citalopram DM2G9AE Acute coronary syndrome BA41 Approved [100]
Thioridazine DM35M8J Schizophrenia 6A20 Approved [99]
Fluoxetine DM3PD2C Bipolar depression Approved [99]
Chlorpromazine DMBGZI3 Acute intermittent hepatic porphyria 5C58.11 Approved [12]
Hydroquinone DM6AVR4 Melasma ED60.1 Approved [123]
Testosterone DM7HUNW Hot flushes GA30 Approved [124]
Calcitriol DM8ZVJ7 Congenital alopecia LC30 Approved [124]
Haloperidol DM96SE0 Delirium Approved [99]
Ciclosporin DMAZJFX Graft-versus-host disease 4B24 Approved [125]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Sertraline DM0FB1J Coronary heart disease BA80.Z Approved [12]
Thioridazine DM35M8J Schizophrenia 6A20 Approved [12]
Fluoxetine DM3PD2C Bipolar depression Approved [12]
Erythromycin DM4K7GQ Acne vulgaris ED80 Approved [99]
Chlorpromazine DMBGZI3 Acute intermittent hepatic porphyria 5C58.11 Approved [12]
Haloperidol DM96SE0 Delirium Approved [99]
Ciclosporin DMAZJFX Graft-versus-host disease 4B24 Approved [126]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [127]
Clozapine DMFC71L Schizophrenia 6A20 Approved [12]
Pentamidine DMHZJCG African trypanosomiasis 1F51 Approved [12]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Protein DEPP1 (DEPP1)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Sertraline DM0FB1J Coronary heart disease BA80.Z Approved [12]
Ofloxacin DM0VQN3 Acute gonococcal cervicitis Approved [99]
Fulvestrant DM0YZC6 Breast cancer 2C60-2C65 Approved [128]
Thioridazine DM35M8J Schizophrenia 6A20 Approved [12]
Quercetin DM3NC4M Obesity 5B81 Approved [101]
Fluoxetine DM3PD2C Bipolar depression Approved [12]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [129]
Erythromycin DM4K7GQ Acne vulgaris ED80 Approved [99]
Isoniazid DM5JVS3 Latent tuberculosis infection Approved [99]
Chlorpromazine DMBGZI3 Acute intermittent hepatic porphyria 5C58.11 Approved [12]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Stearoyl-CoA desaturase (SCD)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Clavulanate DM2FGRT Bacteremia 1A73 Approved [120]
Citalopram DM2G9AE Acute coronary syndrome BA41 Approved [18]
Methotrexate DM2TEOL Anterior urethra cancer Approved [130]
Quercetin DM3NC4M Obesity 5B81 Approved [101]
Rofecoxib DM3P5DA Osteoarthritis FA00-FA05 Approved [104]
Fluoxetine DM3PD2C Bipolar depression Approved [18]
Fructose DM43AN2 Vomiting MD90 Approved [131]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [132]
Bupropion DM5PCS7 Depression 6A70-6A7Z Approved [18]
Calcitriol DM8ZVJ7 Congenital alopecia LC30 Approved [133]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Albumin (ALB)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [134]
Sulfamethoxazole DMB08GE Acute otitis media AB00 Approved [135]
Tolbutamide DM02AWV Advanced cancer 2A00-2F9Z Approved [136]
Diazepam DM08E9O Alcohol withdrawal Approved [137]
Sertraline DM0FB1J Coronary heart disease BA80.Z Approved [138]
Methimazole DM25FL8 Hyperthyroidism 5A02 Approved [139]
Colchicine DM2POTE Acute gout flare FA25.0 Approved [140]
Methotrexate DM2TEOL Anterior urethra cancer Approved [141]
Quercetin DM3NC4M Obesity 5B81 Approved [142]
obeticholic acid DM3Q1SM Primary biliary cholangitis DB96.1 Approved [143]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Salmeterol DMIEU69 Allergic asthma CA23.0 Approved [144]
Bambuterol DMKLSHF Asthma CA23 Approved [145]
Terbutaline DMD4381 Asthma CA23 Approved [146]
Salbutamol DMN9CWF Acute asthma CA23 Approved [147]
Methotrexate DM2TEOL Anterior urethra cancer Approved [109]
Epinephrine DM3KJBC Acute asthma CA23 Approved [148]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [129]
Liothyronine DM6IR3P Congenital hypothyroidism Approved [149]
Ergotidine DM78IME Osteoarthritis FA00-FA05 Approved [150]
Propranolol DM79NTF Angina pectoris BA40 Approved [151]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Poly polymerase 1 (PARP1)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Cannabidiol DM0659E Dravet syndrome 8A61.11 Approved [98]
Gefitinib DM15F0X Colon adenocarcinoma Approved [152]
Hydrogen peroxide DM1NG5W Infectious disease 1A00-CA43.1 Approved [153]
Nitric Oxide DM1RBYG Hypertension BA00-BA04 Approved [154]
Citalopram DM2G9AE Acute coronary syndrome BA41 Approved [155]
Ciprofloxacin XR DM2NLS9 Acute gonococcal cervicitis Approved [156]
Colchicine DM2POTE Acute gout flare FA25.0 Approved [157]
Sulindac DM2QHZU Acute myelogenous leukaemia 2A41 Approved [158]
Methotrexate DM2TEOL Anterior urethra cancer Approved [159]
Simvastatin DM30SGU Arteriosclerosis BD40 Approved [160]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Quercetin DM3NC4M Obesity 5B81 Approved [101]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [161]
Panobinostat DM58WKG Chronic graft versus host disease Approved [113]
Disopyramide DM5SYZP Long QT syndrome BC65.0 Approved [14]
Chlorpromazine DMBGZI3 Acute intermittent hepatic porphyria 5C58.11 Approved [14]
Testosterone DM7HUNW Hot flushes GA30 Approved [124]
Calcitriol DM8ZVJ7 Congenital alopecia LC30 Approved [124]
Ciclosporin DMAZJFX Graft-versus-host disease 4B24 Approved [126]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [127]
Ursodeoxycholic acid DMCUT21 Cholelithiasis DC11 Approved [162]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Hydrogen peroxide DM1NG5W Infectious disease 1A00-CA43.1 Approved [163]
SPI-1005 DM6XFHS Reperfusion injury ND56.Z Approved [17]
Sulindac DM2QHZU Acute myelogenous leukaemia 2A41 Approved [164]
Simvastatin DM30SGU Arteriosclerosis BD40 Approved [165]
Ceftazidime DM41GRA Bacteremia 1A73 Approved [17]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [161]
Chlorpheniramine DM5URA2 Allergic rhinitis CA08.0 Approved [17]
Ethacrynic acid DM60QMR Edema MG29 Approved [17]
Arsenic trioxide DM61TA4 Acute lymphoblastic leukaemia 2A85 Approved [17]
Aspirin DM672AH Acute coronary syndrome BA41 Approved [164]
⏷ 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 [166]
Fulvestrant DM0YZC6 Breast cancer 2C60-2C65 Approved [167]
Hydrogen peroxide DM1NG5W Infectious disease 1A00-CA43.1 Approved [168]
Citalopram DM2G9AE Acute coronary syndrome BA41 Approved [18]
Quercetin DM3NC4M Obesity 5B81 Approved [169]
Fluoxetine DM3PD2C Bipolar depression Approved [18]
obeticholic acid DM3Q1SM Primary biliary cholangitis DB96.1 Approved [143]
Troglitazone DM3VFPD Diabetic complication 5A2Y Approved [112]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [132]
Crizotinib DM4F29C Non-small-cell lung cancer 2C25.Y Approved [170]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Pyrimethamine DM5X7VY Malaria 1F40-1F45 Approved [171]
Cimetidine DMH61ZB Acid-reflux disorder DA22 Approved [172]
Verapamil DMA7PEW Angina pectoris BA40 Approved [173]
Methotrexate DM2TEOL Anterior urethra cancer Approved [130]
Rifampicin DM5DSFZ Non-insulin dependent diabetes 5A11 Approved [174]
Ciclosporin DMAZJFX Graft-versus-host disease 4B24 Approved [126]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [175]
Zoledronate DMIXC7G Adenocarcinoma 2D40 Approved [176]
Quinidine DMLPICK N. A. N. A. Approved [172]
Mebendazole DMO14SG Ascariasis 1F62 Approved [177]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Sertraline DM0FB1J Coronary heart disease BA80.Z Approved [16]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [178]
Diclofenac DMPIHLS Chronic renal failure GB61.Z Approved [179]
Arsenic DMTL2Y1 N. A. N. A. Approved [180]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [181]
Doxorubicin DMVP5YE Acute myelogenous leukaemia 2A41 Approved [182]
Carbamazepine DMZOLBI Epilepsy 8A60-8A68 Approved [179]
Benzo(a)pyrene DMN7J43 N. A. N. A. Phase 1 [183]
PMID28870136-Compound-52 DMFDERP N. A. N. A. Patented [184]
COUMARIN DM0N8ZM Discovery agent N.A. Investigative [184]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Hydrogen peroxide DM1NG5W Infectious disease 1A00-CA43.1 Approved [168]
Selenium DM25CGV N. A. N. A. Approved [185]
Colchicine DM2POTE Acute gout flare FA25.0 Approved [186]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [116]
Gabapentin DM6T924 Complex partial seizure 8A68.0 Approved [186]
Ciclosporin DMAZJFX Graft-versus-host disease 4B24 Approved [126]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [127]
Melphalan DMOLNHF Hematologic disease 3C0Z Approved [187]
Cupric Sulfate DMP0NFQ Fungal infection 1F29-1F2F Approved [188]
Cisplatin DMRHGI9 Adenocarcinoma 2D40 Approved [189]
⏷ 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
Norepinephrine transporter (NET) TTAWNKZ SC6A2_HUMAN Inhibitor [3]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
P-glycoprotein 1 (ABCB1) DTUGYRD MDR1_HUMAN Substrate [4]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4) Main DME DE4LYSA CP3A4_HUMAN Substrate [5]
Cytochrome P450 2D6 (CYP2D6) DECB0K3 CP2D6_HUMAN Substrate [6]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DEYGVN4 UD11_HUMAN Substrate [7]
Mephenytoin 4-hydroxylase (CYP2C19) Main DME DEGTFWK CP2CJ_HUMAN Substrate [8]
Cytochrome P450 1A2 (CYP1A2) Main DME DEJGDUW CP1A2_HUMAN Substrate [9]
Cytochrome P450 2B6 (CYP2B6) DEPKLMQ CP2B6_HUMAN Substrate [9]
Cytochrome P450 3A7 (CYP3A7) DERD86B CP3A7_HUMAN Substrate [10]
Cytochrome P450 2C18 (CYP2C18) DEZMWRE CP2CI_HUMAN Substrate [9]
Docosahexaenoic acid omega-hydroxylase (CYP4F11) DEIZLTN CP4FB_HUMAN Substrate [11]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Acid ceramidase (ASAH1) OT1DNGXL ASAH1_HUMAN Gene/Protein Processing [12]
Albumin (ALB) OTVMM513 ALBU_HUMAN Protein Interaction/Cellular Processes [13]
Alpha-1-acid glycoprotein 2 (ORM2) OTRJGZP8 A1AG2_HUMAN Protein Interaction/Cellular Processes [14]
Alpha-1-antichymotrypsin (SERPINA3) OT9BP2S0 AACT_HUMAN Gene/Protein Processing [12]
Beta-2 adrenergic receptor (ADRB2) OTSDOX4Q ADRB2_HUMAN Gene/Protein Processing [15]
DnaJ homolog subfamily C member 5 (DNAJC5) OTCZDXAL DNJC5_HUMAN Gene/Protein Processing [16]
Fibronectin type III domain-containing protein 4 (FNDC4) OTOQK0WK FNDC4_HUMAN Gene/Protein Processing [12]
Heat shock factor protein 1 (HSF1) OTYNJ4KP HSF1_HUMAN Gene/Protein Processing [17]
Hydroxymethylglutaryl-CoA synthase, cytoplasmic (HMGCS1) OTCO26FV HMCS1_HUMAN Gene/Protein Processing [18]
Inhibin beta E chain (INHBE) OTOI2NYG INHBE_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: 357).
2 Imipramine FDA Label
3 Invivo antioxidant status: a putative target of antidepressant action. Prog Neuropsychopharmacol Biol Psychiatry. 2009 Mar 17;33(2):220-8.
4 Caco-2 permeability, P-glycoprotein transport ratios and brain penetration of heterocyclic drugs. Int J Pharm. 2003 Sep 16;263(1-2):113-22.
5 Variability in metabolism of imipramine and desipramine using urinary excretion data. J Anal Toxicol. 2014 Jul-Aug;38(6):368-74.
6 QTc prolongation associated with combination therapy of levofloxacin, imipramine, and fluoxetine. Ann Pharmacother. 2005 Mar;39(3):543-6.
7 Liquid chromatography-tandem mass spectrometry method for measurement of nicotine N-glucuronide: a marker for human UGT2B10 inhibition. J Pharm Biomed Anal. 2011 Jul 15;55(5):964-71.
8 Inhibitory effects of tricyclic antidepressants (TCAs) on human cytochrome P450 enzymes in vitro: mechanism of drug interaction between TCAs and phenytoin. Drug Metab Dispos. 2002 Oct;30(10):1102-7.
9 Reappraisal of human CYP isoforms involved in imipramine N-demethylation and 2-hydroxylation: a study using microsomes obtained from putative extensive and poor metabolizers of S-mephenytoin and eleven recombinant human CYPs. J Pharmacol Exp Ther. 1997 Jun;281(3):1199-210.
10 Catalysis of drug oxidation during embryogenesis in human hepatic tissues using imipramine as a model substrate. Drug Metab Dispos. 1999 Nov;27(11):1306-8.
11 Expression and characterization of human cytochrome P450 4F11: putative role in the metabolism of therapeutic drugs and eicosanoids. Toxicol Appl Pharmacol. 2004 Sep 15;199(3):295-304.
12 A toxicogenomic approach to drug-induced phospholipidosis: analysis of its induction mechanism and establishment of a novel in vitro screening system. Toxicol Sci. 2005 Feb;83(2):282-92.
13 Use of peak decay analysis and affinity microcolumns containing silica monoliths for rapid determination of drug-protein dissociation rates. J Chromatogr A. 2011 Apr 15;1218(15):2072-8. doi: 10.1016/j.chroma.2010.09.070. Epub 2010 Oct 16.
14 Binding of disopyramide, methadone, dipyridamole, chlorpromazine, lignocaine and progesterone to the two main genetic variants of human alpha 1-acid glycoprotein: evidence for drug-binding differences between the variants and for the presence of two separate drug-binding sites on alpha 1-acid glycoprotein. Pharmacogenetics. 1996 Oct;6(5):403-15. doi: 10.1097/00008571-199610000-00004.
15 Neutrophil beta(2)-adrenoceptor function in major depression: G(s) coupling, effects of imipramine and relationship to treatment outcome. Eur J Pharmacol. 1999 Dec 15;386(2-3):135-44. doi: 10.1016/s0014-2999(99)00749-9.
16 Induction of cysteine string protein after chronic antidepressant treatment in rat frontal cortex. Neurosci Lett. 2001 Apr 6;301(3):183-6. doi: 10.1016/s0304-3940(01)01638-x.
17 A Gene Expression Biomarker Predicts Heat Shock Factor 1 Activation in a Gene Expression Compendium. Chem Res Toxicol. 2021 Jul 19;34(7):1721-1737. doi: 10.1021/acs.chemrestox.0c00510. Epub 2021 Jun 25.
18 Antidepressant drugs activate SREBP and up-regulate cholesterol and fatty acid biosynthesis in human glial cells. Neurosci Lett. 2006 Mar 13;395(3):185-90. doi: 10.1016/j.neulet.2005.10.096. Epub 2005 Dec 1.
19 Augmentation effect of combination therapy of aripiprazole and antidepressants on forced swimming test in mice. Psychopharmacology (Berl). 2009 Sep;206(1):97-107.
20 Treatment of comorbid pain with serotonin norepinephrine reuptake inhibitors. CNS Spectr. 2008 Jul;13(7 Suppl 11):22-6.
21 Differential involvement of the norepinephrine, serotonin and dopamine reuptake transporter proteins in cocaine-induced taste aversion. Pharmacol Biochem Behav. 2009 Jul;93(1):75-81.
22 Clinically relevant drug interactions with new generation antidepressants and antipsychotics. Ther Umsch. 2009 Jun;66(6):485-92.
23 2008 FDA drug approvals. Nat Rev Drug Discov. 2009 Feb;8(2):93-6.
24 Antidepressants suppress production of the Th1 cytokine interferon-gamma, independent of monoamine transporter blockade. Eur Neuropsychopharmacol. 2006 Oct;16(7):481-90.
25 Multi-target therapeutics: when the whole is greater than the sum of the parts. Drug Discov Today. 2007 Jan;12(1-2):34-42.
26 Hughes B: 2009 FDA drug approvals. Nat Rev Drug Discov. 2010 Feb;9(2):89-92.
27 Human intestinal transporter database: QSAR modeling and virtual profiling of drug uptake, efflux and interactions. Pharm Res. 2013 Apr;30(4):996-1007.
28 MDR1 (ABCB1) G1199A (Ser400Asn) polymorphism alters transepithelial permeability and sensitivity to anticancer agents. Cancer Chemother Pharmacol. 2009 Jun;64(1):183-8.
29 Mammalian drug efflux transporters of the ATP binding cassette (ABC) family in multidrug resistance: A review of the past decade. Cancer Lett. 2016 Jan 1;370(1):153-64.
30 Folate transporter expression decreases in the human placenta throughout pregnancy and in pre-eclampsia. Pregnancy Hypertens. 2012 Apr;2(2):123-31.
31 Comparative studies on in vitro methods for evaluating in vivo function of MDR1 P-glycoprotein. Pharm Res. 2001 Dec;18(12):1660-8.
32 Antiestrogens and steroid hormones: substrates of the human P-glycoprotein. Biochem Pharmacol. 1994 Jul 19;48(2):287-92.
33 Association of genetic polymorphisms in the influx transporter SLCO1B3 and the efflux transporter ABCB1 with imatinib pharmacokinetics in patients with chronic myeloid leukemia. Ther Drug Monit. 2011 Apr;33(2):244-50.
34 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.
35 Contribution of human hepatic cytochrome P450 isoforms to regioselective hydroxylation of steroid hormones. Xenobiotica. 1998 Jun;28(6):539-47.
36 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.
37 Isoform-specific regulation of cytochromes P450 expression by estradiol and progesterone. Drug Metab Dispos. 2013 Feb;41(2):263-9.
38 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.
39 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.
40 Effects of morin on the pharmacokinetics of etoposide in rats. Biopharm Drug Dispos. 2007 Apr;28(3):151-6.
41 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.
42 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.
43 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.
44 Effects of polyunsaturated fatty acids on prostaglandin synthesis and cyclooxygenase-mediated DNA adduct formation by heterocyclic aromatic amines in human adenocarcinoma colon cells. Mol Carcinog. 2004 Jul;40(3):180-8.
45 Endoxifen and other metabolites of tamoxifen inhibit human hydroxysteroid sulfotransferase 2A1 (hSULT2A1). Drug Metab Dispos. 2014 Nov;42(11):1843-50.
46 Cytochrome P450 1A2 (CYP1A2) activity and risk factors for breast cancer: a cross-sectional study. Breast Cancer Res. 2004;6(4):R352-65.
47 PharmGKB summary: pathways of acetaminophen metabolism at the therapeutic versus toxic doses. Pharmacogenet Genomics. 2015 Aug;25(8):416-26.
48 The effect of apigenin on pharmacokinetics of imatinib and its metabolite N-desmethyl imatinib in rats. Biomed Res Int. 2013;2013:789184.
49 The influence of metabolic gene polymorphisms on urinary 1-hydroxypyrene concentrations in Chinese coke oven workers. Sci Total Environ. 2007 Aug 1;381(1-3):38-46.
50 Identification of P450 enzymes involved in metabolism of verapamil in humans. Naunyn Schmiedebergs Arch Pharmacol. 1993 Sep;348(3):332-7.
51 Metabolism and metabolic inhibition of xanthotoxol in human liver microsomes. Evid Based Complement Alternat Med. 2016;2016:5416509.
52 Functional significance of UDP-glucuronosyltransferase variants in the metabolism of active tamoxifen metabolites. Cancer Res. 2009 Mar 1;69(5):1892-900.
53 Functional characterization of human and cynomolgus monkey UDP-glucuronosyltransferase 1A1 enzymes. Life Sci. 2010 Aug 14;87(7-8):261-8.
54 Effect of UDP-glucuronosyltransferase (UGT) 1A polymorphism (rs8330 and rs10929303) on glucuronidation status of acetaminophen. Dose Response. 2017 Sep 11;15(3):1559325817723731.
55 UDP-glucuronosyltransferase 1A1 is the principal enzyme responsible for etoposide glucuronidation in human liver and intestinal microsomes: structural characterization of phenolic and alcoholic glucuronides of etoposide and estimation of enzyme kinetics. Drug Metab Dispos. 2007 Mar;35(3):371-80.
56 Interindividual variability in pharmacokinetics of generic nucleoside reverse transcriptase inhibitors in TB/HIV-coinfected Ghanaian patients: UGT2B7*1c is associated with faster zidovudine clearance and glucuronidation. J Clin Pharmacol. 2009 Sep;49(9):1079-90.
57 Effect of aging on glucuronidation of valproic acid in human liver microsomes and the role of UDP-glucuronosyltransferase UGT1A4, UGT1A8, and UGT1A10. Drug Metab Dispos. 2009 Jan;37(1):229-36.
58 Characterization of rat intestinal microsomal UDP-glucuronosyltransferase activity toward mycophenolic acid. Drug Metab Dispos. 2006 Sep;34(9):1632-9.
59 Drug-drug interactions for UDP-glucuronosyltransferase substrates: a pharmacokinetic explanation for typically observed low exposure (AUCi/AUC) ratios. Drug Metab Dispos. 2004 Nov;32(11):1201-8.
60 Substrate-dependent modulation of UDP-glucuronosyltransferase 1A1 (UGT1A1) by propofol in recombinant human UGT1A1 and human liver microsomes. Basic Clin Pharmacol Toxicol. 2007 Sep;101(3):211-4.
61 Identification and preliminary characterization of UDP-glucuronosyltransferases catalyzing formation of ethyl glucuronide. Anal Bioanal Chem. 2014 Apr;406(9-10):2325-32.
62 Inhibitory effects of anticancer drugs on dextromethorphan-O-demethylase activity in human liver microsomes. Cancer Chemother Pharmacol. 1993;32(6):491-5.
63 Effect of genetic polymorphism on the metabolism of endogenous neuroactive substances, progesterone and p-tyramine, catalyzed by CYP2D6. Brain Res Mol Brain Res. 2004 Oct 22;129(1-2):117-23.
64 CYP2D6 polymorphisms and tamoxifen metabolism: clinical relevance. Curr Oncol Rep. 2010 Jan;12(1):7-15.
65 Inhibition of cytochrome P450 2D6: structure-activity studies using a series of quinidine and quinine analogues. Chem Res Toxicol. 2003 Apr;16(4):450-9.
66 Effects of propofol on human hepatic microsomal cytochrome P450 activities. Xenobiotica. 1998 Sep;28(9):845-53.
67 Pharmacogenetics of schizophrenia. Am J Med Genet. 2000 Spring;97(1):98-106.
68 Roles of CYP2A6 and CYP2B6 in nicotine C-oxidation by human liver microsomes. Arch Toxicol. 1999 Mar;73(2):65-70.
69 Structure-activity relationship for human cytochrome P450 substrates and inhibitors. Drug Metab Rev. 2002 Feb-May;34(1-2):69-82.
70 The role of cytochrome P450 3A (CYP3A) isoform(s) in oxidative metabolism of testosterone and benzphetamine in human adult and fetal liver. J Steroid Biochem Mol Biol. 1993 Jan;44(1):61-7.
71 Drug Interactions Flockhart Table
72 Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.
73 Prediction of cytochrome P450 3A inhibition by verapamil enantiomers and their metabolites. Drug Metab Dispos. 2004 Feb;32(2):259-66.
74 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.
75 Diclofenac and its derivatives as tools for studying human cytochromes P450 active sites: particular efficiency and regioselectivity of P450 2Cs. Biochemistry. 1999 Oct 26;38(43):14264-70.
76 Possible involvement of multiple human cytochrome P450 isoforms in the liver metabolism of propofol. Br J Anaesth. 1998 Jun;80(6):788-95.
77 Identification of human cytochrome P450s involved in the formation of all-trans-retinoic acid principal metabolites. Mol Pharmacol. 2000 Dec;58(6):1341-8.
78 Targeted antipeptide antibodies to cytochrome P450 2C18 based on epitope mapping of an inhibitory monoclonal antibody to P450 2C51. Arch Biochem Biophys. 1997 Feb 15;338(2):157-64.
79 Involvement of cytochrome P450 3A4 enzyme in the N-demethylation of methadone in human liver microsomes. Chem Res Toxicol. 1996 Mar;9(2):365-73.
80 CYP2C8/9 mediate dapsone N-hydroxylation at clinical concentrations of dapsone. Drug Metab Dispos. 2000 Aug;28(8):865-8.
81 Induction of CYP2C genes in human hepatocytes in primary culture. Drug Metab Dispos. 2001 Mar;29(3):242-51.
82 Effect of tamoxifen on the enzymatic activity of human cytochrome CYP2B6. J Pharmacol Exp Ther. 2002 Jun;301(3):945-52.
83 Hepatic metabolism of diclofenac: role of human CYP in the minor oxidative pathways. Biochem Pharmacol. 1999 Sep 1;58(5):787-96.
84 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.
85 Insights into CYP2B6-mediated drug-drug interactions. Acta Pharm Sin B. 2016 Sep;6(5):413-425.
86 Drugs that may have potential CYP2B6 interactions.
87 Involvement of human cytochrome P450 2B6 in the omega- and 4-hydroxylation of the anesthetic agent propofol. Xenobiotica. 2007 Jul;37(7):717-24.
88 Nicotine and 4-(methylnitrosamino)-1-(3-pyridyl)-butanone metabolism by cytochrome P450 2B6. Drug Metab Dispos. 2005 Dec;33(12):1760-4.
89 PharmGKB summary: phenytoin pathway. Pharmacogenet Genomics. 2012 Jun;22(6):466-70.
90 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.
91 High-dose rabeprazole/amoxicillin therapy as the second-line regimen after failure to eradicate H. pylori by triple therapy with the usual doses of a proton pump inhibitor, clarithromycin and amoxicillin. Hepatogastroenterology. 2003 Nov-Dec;50(54):2274-8.
92 Progesterone and testosterone hydroxylation by cytochromes P450 2C19, 2C9, and 3A4 in human liver microsomes. Arch Biochem Biophys. 1997 Oct 1;346(1):161-9.
93 Cytochrome P450 pharmacogenetics and cancer. Oncogene. 2006 Mar 13;25(11):1679-91.
94 CYP2C19*17 is associated with decreased breast cancer risk. Breast Cancer Res Treat. 2009 May;115(2):391-6.
95 Cytochromes of the P450 2C subfamily are the major enzymes involved in the O-demethylation of verapamil in humans. Naunyn Schmiedebergs Arch Pharmacol. 1995 Dec;353(1):116-21.
96 A mechanistic approach to antiepileptic drug interactions. Ann Pharmacother. 1998 May;32(5):554-63.
97 Organic anion-transporting polypeptide B (OATP-B) and its functional comparison with three other OATPs of human liver. Gastroenterology. 2001 Feb;120(2):525-33.
98 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.
99 Determination of phospholipidosis potential based on gene expression analysis in HepG2 cells. Toxicol Sci. 2007 Mar;96(1):101-14.
100 In vitro detection of drug-induced phospholipidosis using gene expression and fluorescent phospholipid based methodologies. Toxicol Sci. 2007 Sep;99(1):162-73.
101 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.
102 Effect of retinoic acid on gene expression in human conjunctival epithelium: secretory phospholipase A2 mediates retinoic acid induction of MUC16. Invest Ophthalmol Vis Sci. 2005 Nov;46(11):4050-61.
103 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.
104 Rofecoxib modulates multiple gene expression pathways in a clinical model of acute inflammatory pain. Pain. 2007 Mar;128(1-2):136-47.
105 Retinoic acid and its 4-oxo metabolites are functionally active in human skin cells in vitro. J Invest Dermatol. 2005 Jul;125(1):143-53.
106 Effects of aspirin on metastasis-associated gene expression detected by cDNA microarray. Acta Pharmacol Sin. 2004 Oct;25(10):1327-33.
107 Kinetic analysis of the liver-type (GLUT2) and brain-type (GLUT3) glucose transporters in Xenopus oocytes: substrate specificities and effects of transport inhibitors. Biochem J. 1993 Mar 15;290 ( Pt 3)(Pt 3):701-6. doi: 10.1042/bj2900701.
108 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.
109 Global molecular effects of tocilizumab therapy in rheumatoid arthritis synovium. Arthritis Rheumatol. 2014 Jan;66(1):15-23.
110 Retinoic acid represses a cassette of candidate pluripotency chromosome 12p genes during induced loss of human embryonal carcinoma tumorigenicity. Biochim Biophys Acta. 2005 Oct 15;1731(1):48-56. doi: 10.1016/j.bbaexp.2005.08.006. Epub 2005 Sep 1.
111 Differential gene expression in human hepatocyte cell lines exposed to the antiretroviral agent zidovudine. Arch Toxicol. 2014 Mar;88(3):609-23. doi: 10.1007/s00204-013-1169-3. Epub 2013 Nov 30.
112 Transcriptomic analysis of untreated and drug-treated differentiated HepaRG cells over a 2-week period. Toxicol In Vitro. 2015 Dec 25;30(1 Pt A):27-35.
113 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.
114 Beta-carotene and apocarotenals promote retinoid signaling in BEAS-2B human bronchioepithelial cells. Arch Biochem Biophys. 2006 Nov 1;455(1):48-60.
115 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.
116 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.
117 Adaptive homeostasis of the vitamin D-vitamin D nuclear receptor axis in 8-methoxypsoralen-induced hepatotoxicity. Toxicol Appl Pharmacol. 2019 Jan 1;362:150-158. doi: 10.1016/j.taap.2018.11.002. Epub 2018 Nov 10.
118 Arsenite and cadmium promote the development of mammary tumors. Carcinogenesis. 2020 Jul 14;41(7):1005-1014. doi: 10.1093/carcin/bgz176.
119 Time series analysis of oxidative stress response patterns in HepG2: a toxicogenomics approach. Toxicology. 2013 Apr 5;306:24-34.
120 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.
121 Farnesoid X receptor induces murine scavenger receptor Class B type I via intron binding. PLoS One. 2012;7(4):e35895. doi: 10.1371/journal.pone.0035895. Epub 2012 Apr 23.
122 The methyl transferase PRMT1 functions as co-activator of farnesoid X receptor (FXR)/9-cis retinoid X receptor and regulates transcription of FXR responsive genes. Mol Pharmacol. 2005 Aug;68(2):551-8. doi: 10.1124/mol.105.012104. Epub 2005 May 23.
123 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.
124 Effects of 1alpha,25 dihydroxyvitamin D3 and testosterone on miRNA and mRNA expression in LNCaP cells. Mol Cancer. 2011 May 18;10:58.
125 Integrating multiple omics to unravel mechanisms of Cyclosporin A induced hepatotoxicity in vitro. Toxicol In Vitro. 2015 Apr;29(3):489-501.
126 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.
127 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.
128 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.
129 Phenotypic characterization of retinoic acid differentiated SH-SY5Y cells by transcriptional profiling. PLoS One. 2013 May 28;8(5):e63862.
130 The contribution of methotrexate exposure and host factors on transcriptional variance in human liver. Toxicol Sci. 2007 Jun;97(2):582-94.
131 Effects of four-week high-fructose diet on gene expression in skeletal muscle of healthy men. Diabetes Metab. 2008 Feb;34(1):82-5. doi: 10.1016/j.diabet.2007.08.004. Epub 2007 Dec 11.
132 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.
133 Inhibition of fatty acid synthase expression by 1alpha,25-dihydroxyvitamin D3 in prostate cancer cells. J Steroid Biochem Mol Biol. 2003 May;85(1):1-8. doi: 10.1016/s0960-0760(03)00142-0.
134 Gene expression analysis of precision-cut human liver slices indicates stable expression of ADME-Tox related genes. Toxicol Appl Pharmacol. 2011 May 15;253(1):57-69.
135 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.
136 A protein-coated magnetic beads as a tool for the rapid drug-protein binding study. J Pharm Biomed Anal. 2010 Jul 8;52(3):420-4. doi: 10.1016/j.jpba.2009.06.023. Epub 2009 Jun 18.
137 The three recombinant domains of human serum albumin. Structural characterization and ligand binding properties. J Biol Chem. 1999 Oct 8;274(41):29303-10. doi: 10.1074/jbc.274.41.29303.
138 Exploring binding properties of sertraline with human serum albumin: Combination of spectroscopic and molecular modeling studies. Chem Biol Interact. 2015 Dec 5;242:235-46. doi: 10.1016/j.cbi.2015.10.006. Epub 2015 Oct 22.
139 Low-expressional IGF1 mediated methimazole-induced liver developmental toxicity in fetal mice. Toxicology. 2018 Sep 1;408:70-79. doi: 10.1016/j.tox.2018.07.004. Epub 2018 Jul 7.
140 [Colchicine in chronic liver disease of alcoholic etiology. Double-blind, randomized study of its effects on blood levels of plasma proteins and clinical course in patients]. Rev Assoc Med Bras (1992). 1995 May-Jun;41(3):207-12.
141 Editor's Highlight: Modeling Compound-Induced Fibrogenesis In Vitro Using Three-Dimensional Bioprinted Human Liver Tissues. Toxicol Sci. 2016 Dec;154(2):354-367. doi: 10.1093/toxsci/kfw169. Epub 2016 Sep 7.
142 Covalent binding of the flavonoid quercetin to human serum albumin. J Agric Food Chem. 2005 May 18;53(10):4194-7. doi: 10.1021/jf050061m.
143 Pharmacotoxicology of clinically-relevant concentrations of obeticholic acid in an organotypic human hepatocyte system. Toxicol In Vitro. 2017 Mar;39:93-103.
144 Pleiotropic beta-agonist-promoted receptor conformations and signals independent of intrinsic activity. Am J Respir Cell Mol Biol. 2007 Feb;36(2):236-43. doi: 10.1165/rcmb.2006-0257OC. Epub 2006 Sep 15.
145 Development of 3D-QSAR models for predicting the activities of chemicals to stimulate muscle growth via (2)-adrenoceptor. Toxicol In Vitro. 2021 Dec;77:105251. doi: 10.1016/j.tiv.2021.105251. Epub 2021 Sep 30.
146 Beta2-adrenergic receptor polymorphisms in African American children with status asthmaticus. Pediatr Crit Care Med. 2006 Jan;7(1):15-8. doi: 10.1097/01.pcc.0000194010.63115.a2.
147 beta2-adrenergic receptor polymorphisms and salbutamol-stimulated energy expenditure. J Clin Endocrinol Metab. 2005 Apr;90(4):2301-7. doi: 10.1210/jc.2004-1356. Epub 2005 Feb 1.
148 Myocardial ischaemia and ventricular arrhthymias precipitated by physiological concentrations of adrenaline in patients with coronary artery disease. Br Heart J. 1992 May;67(5):419-20. doi: 10.1136/hrt.67.5.419-b.
149 Hormonal regulation of beta2-adrenergic receptor level in prostate cancer. Prostate. 2008 Jul 1;68(10):1133-42. doi: 10.1002/pros.20778.
150 Histamine augments beta2-adrenoceptor-induced cyclic AMP accumulation in human prostate cancer cells DU-145 independently of known histamine receptors. Biochem Pharmacol. 2007 Mar 15;73(6):814-23. doi: 10.1016/j.bcp.2006.11.022. Epub 2006 Dec 1.
151 Expression of inwardly rectifying potassium channels (GIRKs) and beta-adrenergic regulation of breast cancer cell lines. BMC Cancer. 2004 Dec 16;4:93. doi: 10.1186/1471-2407-4-93.
152 Evidence of securin-mediated resistance to gefitinib-induced apoptosis in human cancer cells. Chem Biol Interact. 2013 Apr 25;203(2):412-22. doi: 10.1016/j.cbi.2013.03.011. Epub 2013 Mar 22.
153 Cigarette smoke and asbestos activate poly-ADP-ribose polymerase in alveolar epithelial cells. J Investig Med. 2001 Jan;49(1):68-76. doi: 10.2310/6650.2001.34092.
154 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.
155 The antidepressants imipramine, clomipramine, and citalopram induce apoptosis in human acute myeloid leukemia HL-60 cells via caspase-3 activation. J Biochem Mol Toxicol. 1999;13(6):338-47. doi: 10.1002/(sici)1099-0461(1999)13:6<338::aid-jbt8>3.0.co;2-7.
156 Ciprofloxacin mediated cell growth inhibition, S/G2-M cell cycle arrest, and apoptosis in a human transitional cell carcinoma of the bladder cell line. Clin Cancer Res. 2000 Mar;6(3):891-900.
157 Investigation of molecular mechanisms underlying the antiproliferative effects of colchicine against PC3 prostate cancer cells. Toxicol In Vitro. 2021 Jun;73:105138. doi: 10.1016/j.tiv.2021.105138. Epub 2021 Mar 6.
158 Sulindac enhances adenoviral vector expressing mda-7/IL-24-mediated apoptosis in human lung cancer. Mol Cancer Ther. 2005 Feb;4(2):291-304.
159 Methotrexate induces poly(ADP-ribose) polymerase-dependent, caspase 3-independent apoptosis in subsets of proliferating CD4+ T cells. Clin Exp Immunol. 2007 May;148(2):288-95. doi: 10.1111/j.1365-2249.2007.03335.x. Epub 2007 Feb 7.
160 Statin-triggered cell death in primary human lung mesenchymal cells involves p53-PUMA and release of Smac and Omi but not cytochrome c. Biochim Biophys Acta. 2010 Apr;1803(4):452-67. doi: 10.1016/j.bbamcr.2009.12.005. Epub 2010 Jan 4.
161 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.
162 Gene expression profiling of early primary biliary cirrhosis: possible insights into the mechanism of action of ursodeoxycholic acid. Liver Int. 2008 Aug;28(7):997-1010. doi: 10.1111/j.1478-3231.2008.01744.x. Epub 2008 Apr 15.
163 NRF2 transcriptionally activates the heat shock factor 1 promoter under oxidative stress and affects survival and migration potential of MCF7 cells. J Biol Chem. 2018 Dec 14;293(50):19303-19316. doi: 10.1074/jbc.RA118.003376. Epub 2018 Oct 11.
164 Non-steroidal anti-inflammatory drugs inhibit the expression of cytokines and induce HSP70 in human monocytes. Cytokine. 1999 May;11(5):347-58. doi: 10.1006/cyto.1998.0437.
165 Simvastatin induces heat shock factor 1 in vascular endothelial cells. Atherosclerosis. 2006 Oct;188(2):265-73. doi: 10.1016/j.atherosclerosis.2005.10.045. Epub 2005 Dec 20.
166 Cannabidiol Displays Proteomic Similarities to Antipsychotics in Cuprizone-Exposed Human Oligodendrocytic Cell Line MO3.13. Front Mol Neurosci. 2021 May 28;14:673144. doi: 10.3389/fnmol.2021.673144. eCollection 2021.
167 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.
168 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.
169 Hypoxia-inducible factor-1 (HIF-1) pathway activation by quercetin in human lens epithelial cells. Exp Eye Res. 2009 Dec;89(6):995-1002. doi: 10.1016/j.exer.2009.08.011. Epub 2009 Sep 1.
170 Multi-parameter in vitro toxicity testing of crizotinib, sunitinib, erlotinib, and nilotinib in human cardiomyocytes. Toxicol Appl Pharmacol. 2013 Oct 1;272(1):245-55.
171 Interactions between Oroxylin A with the solute carrier transporters and ATP-binding cassette transporters: Drug transporters profile for this flavonoid. Chem Biol Interact. 2020 Jun 1;324:109097. doi: 10.1016/j.cbi.2020.109097. Epub 2020 Apr 16.
172 Molecular identification and functional characterization of rat multidrug and toxin extrusion type transporter 1 as an organic cation/H+ antiporter in the kidney. Drug Metab Dispos. 2006 Nov;34(11):1868-74. doi: 10.1124/dmd.106.010876. Epub 2006 Aug 23.
173 Neonicotinoid pesticides poorly interact with human drug transporters. J Biochem Mol Toxicol. 2019 Oct;33(10):e22379. doi: 10.1002/jbt.22379. Epub 2019 Jul 31.
174 Rifampin Regulation of Drug Transporters Gene Expression and the Association of MicroRNAs in Human Hepatocytes. Front Pharmacol. 2016 Apr 26;7:111.
175 Stem cell transcriptome responses and corresponding biomarkers that indicate the transition from adaptive responses to cytotoxicity. Chem Res Toxicol. 2017 Apr 17;30(4):905-922.
176 Interleukin-19 as a translational indicator of renal injury. Arch Toxicol. 2015 Jan;89(1):101-6.
177 Mebendazole, an antiparasitic drug, inhibits drug transporters expression in preclinical model of gastric peritoneal carcinomatosis. Toxicol In Vitro. 2017 Sep;43:87-91. doi: 10.1016/j.tiv.2017.06.007. Epub 2017 Jun 9.
178 Human embryonic stem cell-derived test systems for developmental neurotoxicity: a transcriptomics approach. Arch Toxicol. 2013 Jan;87(1):123-43.
179 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.
180 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.
181 Genistein and bisphenol A exposure cause estrogen receptor 1 to bind thousands of sites in a cell type-specific manner. Genome Res. 2012 Nov;22(11):2153-62.
182 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.
183 Exome-wide mutation profile in benzo[a]pyrene-derived post-stasis and immortal human mammary epithelial cells. Mutat Res Genet Toxicol Environ Mutagen. 2014 Dec;775-776:48-54. doi: 10.1016/j.mrgentox.2014.10.011. Epub 2014 Nov 4.
184 Quantitative phosphoproteomics reveal cellular responses from caffeine, coumarin and quercetin in treated HepG2 cells. Toxicol Appl Pharmacol. 2022 Aug 15;449:116110. doi: 10.1016/j.taap.2022.116110. Epub 2022 Jun 7.
185 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.
186 Establishment of a 13 genes-based molecular prediction score model to discriminate the neurotoxic potential of food relevant-chemicals. Toxicol Lett. 2022 Feb 1;355:1-18. doi: 10.1016/j.toxlet.2021.10.013. Epub 2021 Nov 5.
187 Bone marrow osteoblast damage by chemotherapeutic agents. PLoS One. 2012;7(2):e30758. doi: 10.1371/journal.pone.0030758. Epub 2012 Feb 17.
188 Physiological and toxicological transcriptome changes in HepG2 cells exposed to copper. Physiol Genomics. 2009 Aug 7;38(3):386-401.
189 Activation of AIFM2 enhances apoptosis of human lung cancer cells undergoing toxicological stress. Toxicol Lett. 2016 Sep 6;258:227-236.