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

General Information of Drug (ID: DMCE985)

Drug Name
Phenazone Drug Info
Synonyms
antipyrine; Phenazone; 60-80-0; Antipyrin; Phenazon; Analgesine; Anodynine; Fenazone; Anodynin; Azophen; 2,3-Dimethyl-1-phenyl-5-pyrazolone; Antipirin; Phenozone; Methozin; Azophene; Phenylone; Pyrazophyl; Sedatine; Apirelina; Sedatin; Dimethyloxychinizin; Dimethyloxyquinazine; Phenazonum; Antipyrinum; Oxydimethylquinazine; Azophenum; Parodyne; Phenylon; Fenazona; 3-Antipyrine; Fenazon [Czech]; Auralgan; Fenazon; Fenazona [INN-Spanish]; Phenazone (pharmaceutical); 3H-Pyrazol-3-one, 1,2-dihydro-1,5-dimethyl-2-phenyl-; Oxydimethylquinizine
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Cross-matching ID
PubChem CID
2206
ChEBI ID
CHEBI:31225
CAS Number
CAS 60-80-0
TTD Drug ID
DMCE985
VARIDT Drug ID
DR00941
INTEDE Drug ID
DR0120

Molecule-Related Drug Atlas

Molecule-Related Drug Atlas
Molecule Type:
DTT
DME
DOT
Drug Status:
Approved Drug(s)
Download the Complete Related Drug List
Drug(s) Targeting Prostaglandin G/H synthase 1 (COX-1)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Salicyclic acid DM2F8XZ Acne vulgaris ED80 Approved [7]
Naproxen DMZ5RGV Bursitis Approved [8]
Mesalazine DMOL5IU Diverticulitis Approved [9]
Eicosapentaenoic acid/docosa-hexaenoic acid DMMUCG4 Hypertriglyceridemia 5C80.1 Approved [10]
Bromfenac DMKB79O Pain MG30-MG3Z Approved [11]
Aminosalicylic Acid DMENSL5 Crohn disease DD70 Approved [12]
Flufenamic Acid DMC8VNH Dysmenorrhea GA34.3 Approved [13]
Piroxicam DMTK234 Osteoarthritis FA00-FA05 Approved [12]
Suprofen DMKXJZ7 Miosis LA11.62 Approved [14]
Gamma-Homolinolenic acid DMSXKYG Malnutrition 5B50-5B71 Approved [15]
⏷ 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 [16]
Progesterone DMUY35B Amenorrhea GA20.0 Approved [17]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [18]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [19]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [20]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [21]
Etoposide DMNH3PG Acute myelogenous leukaemia 2A41 Approved [22]
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [23]
Prasterone DM67VKL Chronic obstructive pulmonary disease CA22 Approved [17]
Verapamil DMA7PEW Angina pectoris BA40 Approved [2]
⏷ 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 [24]
Dinoprostone DMTYOPD Medical abortion JA00.1Z Approved [25]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [26]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [27]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [28]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [29]
Etoposide DMNH3PG Acute myelogenous leukaemia 2A41 Approved [22]
Oxaliplatin DMQNWRD Adenocarcinoma 2D40 Approved [30]
Verapamil DMA7PEW Angina pectoris BA40 Approved [31]
Diclofenac DMPIHLS Chronic renal failure GB61.Z Approved [32]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Metabolized By Cytochrome P450 2A6 (CYP2A6)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Fluorouracil DMUM7HZ Adenocarcinoma 2D40 Approved [24]
Progesterone DMUY35B Amenorrhea GA20.0 Approved [33]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [34]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [20]
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [33]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [35]
Metronidazole DMTIVEN Abscess Approved [36]
Propofol DMB4OLE Anaesthesia 9A78.6 Approved [37]
Nicotine DMWX5CO Lung cancer 2C25.0 Approved [38]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [33]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Metabolized By RNA cytidine acetyltransferase (hALP)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Folic Acid DMEMBJC Colorectal carcinoma Approved [39]
Caffeine DMKBJWP Allergic rhinitis CA08.0 Approved [40]
Procainamide DMNMXR8 Ventricular arrhythmias BC71 Approved [41]
Sulfamethoxazole DMB08GE Acute otitis media AB00 Approved [42]
Sulfadiazine DMTW3R8 Rheumatic fever 1B40-1B42 Approved [43]
Tobramycin DMUI0CH Bacteremia 1A73 Approved [44]
Mesalazine DMOL5IU Diverticulitis Approved [45]
Allopurinol DMLPAOB Gout FA25 Approved [46]
Netilmicin DMRD1QK Bacterial infection 1A00-1C4Z Approved [47]
Clonazepam DMTO13J Absence epilepsy Approved [48]
⏷ 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 [49]
Progesterone DMUY35B Amenorrhea GA20.0 Approved [50]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [51]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [20]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [2]
Quinine DMSWYF5 Malaria 1F40-1F45 Approved [52]
Propofol DMB4OLE Anaesthesia 9A78.6 Approved [53]
Dopamine DMPGUCF Acromegaly 5A60.0 Approved [54]
Nicotine DMWX5CO Lung cancer 2C25.0 Approved [55]
Propranolol DM79NTF Angina pectoris BA40 Approved [56]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Metabolized By Cytochrome P450 2E1 (CYP2E1)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Folic Acid DMEMBJC Colorectal carcinoma Approved [57]
Cisplatin DMRHGI9 Adenocarcinoma 2D40 Approved [58]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [34]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [59]
Etoposide DMNH3PG Acute myelogenous leukaemia 2A41 Approved [60]
Oxaliplatin DMQNWRD Adenocarcinoma 2D40 Approved [30]
Verapamil DMA7PEW Angina pectoris BA40 Approved [33]
Estrone DM5T6US Acne vulgaris ED80 Approved [61]
Propofol DMB4OLE Anaesthesia 9A78.6 Approved [62]
Ethanol DMDRQZU Chronic pain MG30 Approved [63]
⏷ 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 [33]
Diclofenac DMPIHLS Chronic renal failure GB61.Z Approved [64]
Propofol DMB4OLE Anaesthesia 9A78.6 Approved [37]
Phenytoin DMNOKBV Epilepsy 8A60-8A68 Approved [33]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [65]
Diazepam DM08E9O Alcohol withdrawal Approved [66]
Methadone DMTW6IU Advanced cancer 2A00-2F9Z Approved [67]
Dapsone DM4LT8A Acne vulgaris ED80 Approved [68]
Lidocaine DML4ZOT Anaesthesia 9A78.6 Approved [33]
Phenobarbital DMXZOCG Cluster headache 8A81.0 Approved [69]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Metabolized By Cytochrome P450 2C8 (CYP2C8)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Fluorouracil DMUM7HZ Adenocarcinoma 2D40 Approved [24]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [70]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [70]
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [33]
Verapamil DMA7PEW Angina pectoris BA40 Approved [71]
Diclofenac DMPIHLS Chronic renal failure GB61.Z Approved [72]
Sorafenib DMS8IFC Adenocarcinoma 2D40 Approved [73]
Quinine DMSWYF5 Malaria 1F40-1F45 Approved [70]
Mycophenolate mofetil DMPQAGE Hepatosplenic T-cell lymphoma Approved [74]
Propofol DMB4OLE Anaesthesia 9A78.6 Approved [37]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Metabolized By Cytochrome P450 2C9 (CYP2C9)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Progesterone DMUY35B Amenorrhea GA20.0 Approved [75]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [76]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [77]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [33]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [78]
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [33]
Verapamil DMA7PEW Angina pectoris BA40 Approved [79]
Diclofenac DMPIHLS Chronic renal failure GB61.Z Approved [80]
Estrone DM5T6US Acne vulgaris ED80 Approved [81]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [82]
⏷ 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 [83]
Verapamil DMA7PEW Angina pectoris BA40 Approved [33]
Diclofenac DMPIHLS Chronic renal failure GB61.Z Approved [84]
Estrone DM5T6US Acne vulgaris ED80 Approved [77]
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 [75]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [92]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [93]
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [33]
Verapamil DMA7PEW Angina pectoris BA40 Approved [94]
Diclofenac DMPIHLS Chronic renal failure GB61.Z Approved [64]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [82]
Quinine DMSWYF5 Malaria 1F40-1F45 Approved [95]
Propofol DMB4OLE Anaesthesia 9A78.6 Approved [37]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Prostaglandin G/H synthase 1 (PTGS1)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Rofecoxib DM3P5DA Osteoarthritis FA00-FA05 Approved [96]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [97]
Flupentixol DM0DJ9O Schizophrenia 6A20 Approved [98]
Quercetin DM3NC4M Obesity 5B81 Approved [99]
Troglitazone DM3VFPD Diabetic complication 5A2Y Approved [100]
Penicillamine DM40EF6 Cystinuria 5C60.2 Approved [101]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [102]
Bupivacaine DM4PRFC Anaesthesia 9A78.6 Approved [103]
Isotretinoin DM4QTBN Acne vulgaris ED80 Approved [102]
Panobinostat DM58WKG Chronic graft versus host disease Approved [104]
⏷ Show the Full List of 10 Drug(s)

Molecular Interaction Atlas of This Drug

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

Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Prostaglandin G/H synthase 1 (COX-1) TT8NGED PGH1_HUMAN Inhibitor [1]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4) DE4LYSA CP3A4_HUMAN Substrate [2]
Cytochrome P450 2E1 (CYP2E1) DEVDYN7 CP2E1_HUMAN Substrate [3]
Cytochrome P450 2D6 (CYP2D6) DECB0K3 CP2D6_HUMAN Substrate [3]
Cytochrome P450 2C9 (CYP2C9) DE5IED8 CP2C9_HUMAN Substrate [2]
Mephenytoin 4-hydroxylase (CYP2C19) DEGTFWK CP2CJ_HUMAN Substrate [4]
Cytochrome P450 2A6 (CYP2A6) DEJVYAZ CP2A6_HUMAN Substrate [3]
Cytochrome P450 1A2 (CYP1A2) DEJGDUW CP1A2_HUMAN Substrate [2]
Cytochrome P450 2B6 (CYP2B6) DEPKLMQ CP2B6_HUMAN Substrate [4]
Cytochrome P450 2C8 (CYP2C8) DES5XRU CP2C8_HUMAN Substrate [2]
Cytochrome P450 2C18 (CYP2C18) DEZMWRE CP2CI_HUMAN Substrate [2]
RNA cytidine acetyltransferase (hALP) DEZV4AP NAT10_HUMAN Substrate [5]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Prostaglandin G/H synthase 1 (PTGS1) OTHCRLEC PGH1_HUMAN Gene/Protein Processing [6]

References

1 Pharmacokinetic and pharmacodynamic aspects of the ideal COX-2 inhibitor: a pharmacologist's perspective. Clin Exp Rheumatol. 2001 Nov-Dec;19(6 Suppl 25):S51-7.
2 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.
3 Identification of the human hepatic cytochromes P450 involved in the in vitro oxidation of antipyrine. Drug Metab Dispos. 1996 Apr;24(4):487-94.
4 Orphenadrine and methimazole inhibit multiple cytochrome P450 enzymes in human liver microsomes. Drug Metab Dispos. 1997 Mar;25(3):390-3.
5 Evaluation of the influence of diabetes mellitus on antipyrine metabolism and CYP1A2 and CYP2D6 activity. Pharmacotherapy. 2000 Feb;20(2):182-90.
6 Cloning, expression, and functional characterization of human cyclooxygenase-1 splicing variants: evidence for intron 1 retention. J Pharmacol Exp Ther. 2005 Dec;315(3):1298-305.
7 The C50T polymorphism of the cyclooxygenase-1 gene and the risk of thrombotic events during low-dose therapy with acetyl salicylic acid. Thromb Haemost. 2008 Jul;100(1):70-5.
8 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.
9 How many drug targets are there Nat Rev Drug Discov. 2006 Dec;5(12):993-6.
10 Cox-2 inhibitory effects of naturally occurring and modified fatty acids. J Nat Prod. 2001 Jun;64(6):745-9.
11 Comparison of cyclooxygenase inhibitory activity and ocular anti-inflammatory effects of ketorolac tromethamine and bromfenac sodium. Curr Med Res Opin. 2006 Jun;22(6):1133-40.
12 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
13 Ouellet M, Percival MD: Effect of inhibitor time-dependency on selectivity towards cyclooxygenase isoforms. Biochem J. 1995 Feb 15;306 ( Pt 1):247-51.
14 Differential binding mode of diverse cyclooxygenase inhibitors. J Mol Graph Model. 2002 Mar;20(5):359-71.
15 Differential metabolism of dihomo-gamma-linolenic acid and arachidonic acid by cyclo-oxygenase-1 and cyclo-oxygenase-2: implications for cellular synthesis of prostaglandin E1 and prostaglandin E2. Biochem J. 2002 Jul 15;365(Pt 2):489-96.
16 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.
17 Contribution of human hepatic cytochrome P450 isoforms to regioselective hydroxylation of steroid hormones. Xenobiotica. 1998 Jun;28(6):539-47.
18 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.
19 Isoform-specific regulation of cytochromes P450 expression by estradiol and progesterone. Drug Metab Dispos. 2013 Feb;41(2):263-9.
20 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.
21 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.
22 Effects of morin on the pharmacokinetics of etoposide in rats. Biopharm Drug Dispos. 2007 Apr;28(3):151-6.
23 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.
24 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.
25 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.
26 Endoxifen and other metabolites of tamoxifen inhibit human hydroxysteroid sulfotransferase 2A1 (hSULT2A1). Drug Metab Dispos. 2014 Nov;42(11):1843-50.
27 Cytochrome P450 1A2 (CYP1A2) activity and risk factors for breast cancer: a cross-sectional study. Breast Cancer Res. 2004;6(4):R352-65.
28 PharmGKB summary: pathways of acetaminophen metabolism at the therapeutic versus toxic doses. Pharmacogenet Genomics. 2015 Aug;25(8):416-26.
29 The effect of apigenin on pharmacokinetics of imatinib and its metabolite N-desmethyl imatinib in rats. Biomed Res Int. 2013;2013:789184.
30 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.
31 Identification of P450 enzymes involved in metabolism of verapamil in humans. Naunyn Schmiedebergs Arch Pharmacol. 1993 Sep;348(3):332-7.
32 Metabolism and metabolic inhibition of xanthotoxol in human liver microsomes. Evid Based Complement Alternat Med. 2016;2016:5416509.
33 Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.
34 Genotoxicity of tamoxifen, tamoxifen epoxide and toremifene in human lymphoblastoid cells containing human cytochrome P450s. Carcinogenesis. 1994 Jan;15(1):5-9.
35 Psychotropic drug interactions with valproate. Clin Neuropharmacol. 2005 Mar-Apr;28(2):96-101.
36 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.
37 Possible involvement of multiple human cytochrome P450 isoforms in the liver metabolism of propofol. Br J Anaesth. 1998 Jun;80(6):788-95.
38 CYP2A6- and CYP2A13-catalyzed metabolism of the nicotine delta-5'(1')iminium ion. J Pharmacol Exp Ther. 2012 Nov;343(2):307-15.
39 Arylamine N-acetyltransferase in human red blood cells. Biochem Pharmacol. 1992 Sep 25;44(6):1099-104.
40 A population and family study of N-acetyltransferase using caffeine urinary metabolites. Clin Pharmacol Ther. 1993 Aug;54(2):134-41.
41 Effect of H2-receptor antagonists on rat liver cytosolic acetyl CoA:arylamine N-acetyltransferase activity. Drug Metab Dispos. 1992 Jan-Feb;20(1):74-8.
42 Crystallization and preliminary X-ray characterization of arylamine N-acetyltransferase C (BanatC) from Bacillus anthracis. Acta Crystallogr Sect F Struct Biol Cryst Commun. 2007 Oct 1;63(Pt 10):862-4.
43 Identification of cytochrome P450 and arylamine N-acetyltransferase isoforms involved in sulfadiazine metabolism. Drug Metab Dispos. 2005 Jul;33(7):969-76.
44 Genetic analysis of bacterial acetyltransferases: identification of amino acids determining the specificities of the aminoglycoside 6'-N-acetyltransferase Ib and IIa proteins. J Bacteriol. 1992 May;174(10):3196-203.
45 NAT1 genotypes do not predict response to mesalamine in patients with ulcerative colitis. Z Gastroenterol. 2008 Mar;46(3):259-65.
46 Xanthine oxidase inhibition by allopurinol affects the reliability of urinary caffeine metabolic ratios as markers for N-acetyltransferase 2 and CYP1A2 activities. Eur J Clin Pharmacol. 1999 Jan;54(11):869-76.
47 Aminoglycoside resistance resulting from tight drug binding to an altered aminoglycoside acetyltransferase. Antimicrob Agents Chemother. 2003 May;47(5):1577-83.
48 Effect of common NAT2 variant alleles in the acetylation of the major clonazepam metabolite, 7-aminoclonazepam. Drug Metab Lett. 2007 Jan;1(1):3-5.
49 Inhibitory effects of anticancer drugs on dextromethorphan-O-demethylase activity in human liver microsomes. Cancer Chemother Pharmacol. 1993;32(6):491-5.
50 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.
51 CYP2D6 polymorphisms and tamoxifen metabolism: clinical relevance. Curr Oncol Rep. 2010 Jan;12(1):7-15.
52 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.
53 Effects of propofol on human hepatic microsomal cytochrome P450 activities. Xenobiotica. 1998 Sep;28(9):845-53.
54 Pharmacogenetics of schizophrenia. Am J Med Genet. 2000 Spring;97(1):98-106.
55 Roles of CYP2A6 and CYP2B6 in nicotine C-oxidation by human liver microsomes. Arch Toxicol. 1999 Mar;73(2):65-70.
56 Structure-activity relationship for human cytochrome P450 substrates and inhibitors. Drug Metab Rev. 2002 Feb-May;34(1-2):69-82.
57 Chronic ethanol feeding and folate deficiency activate hepatic endoplasmic reticulum stress pathway in micropigs. Am J Physiol Gastrointest Liver Physiol. 2005 Jul;289(1):G54-63.
58 Cytochrome P450 2E1 null mice provide novel protection against cisplatin-induced nephrotoxicity and apoptosis. Kidney Int. 2003 May;63(5):1687-96.
59 Acetaminophen induced acute liver failure via oxidative stress and JNK activation: protective role of taurine by the suppression of cytochrome P450 2E1. Free Radic Res. 2010 Mar;44(3):340-55.
60 A study on the metabolism of etoposide and possible interactions with antitumor or supporting agents by human liver microsomes. J Pharmacol Exp Ther. 1998 Sep;286(3):1294-300.
61 Novel metabolic pathway of estrone and 17beta-estradiol catalyzed by cytochrome P-450. Drug Metab Dispos. 2000 Feb;28(2):110-2.
62 Inhibition of cytochrome P450 2E1 by propofol in human and porcine liver microsomes. Biochem Pharmacol. 2002 Oct 1;64(7):1151-6.
63 CYP2E1 and clinical features in alcoholics. Neuropsychobiology. 2003;47(2):86-9.
64 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.
65 Identification of human cytochrome P450s involved in the formation of all-trans-retinoic acid principal metabolites. Mol Pharmacol. 2000 Dec;58(6):1341-8.
66 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.
67 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.
68 CYP2C8/9 mediate dapsone N-hydroxylation at clinical concentrations of dapsone. Drug Metab Dispos. 2000 Aug;28(8):865-8.
69 Induction of CYP2C genes in human hepatocytes in primary culture. Drug Metab Dispos. 2001 Mar;29(3):242-51.
70 Role of cytochrome P450 2C8 in drug metabolism and interactions. Pharmacol Rev. 2016 Jan;68(1):168-241.
71 Differential expression and function of CYP2C isoforms in human intestine and liver. Pharmacogenetics. 2003 Sep;13(9):565-75.
72 Analysis of human cytochrome P450 2C8 substrate specificity using a substrate pharmacophore and site-directed mutants. Biochemistry. 2004 Dec 14;43(49):15379-92.
73 Interaction of sorafenib and cytochrome P450 isoenzymes in patients with advanced melanoma: a phase I/II pharmacokinetic interaction study. Cancer Chemother Pharmacol. 2011 Nov;68(5):1111-8.
74 PharmGKB summary: mycophenolic acid pathway. Pharmacogenet Genomics. 2014 Jan;24(1):73-9.
75 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.
76 Tamoxifen inhibits cytochrome P450 2C9 activity in breast cancer patients. J Chemother. 2006 Aug;18(4):421-4.
77 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.
78 Drug-drug interactions with imatinib: an observational study. Medicine (Baltimore). 2016 Oct;95(40):e5076.
79 Drug interactions with calcium channel blockers: possible involvement of metabolite-intermediate complexation with CYP3A. Drug Metab Dispos. 2000 Feb;28(2):125-30.
80 New insights into the structural features and functional relevance of human cytochrome P450 2C9. Part I. Curr Drug Metab. 2009 Dec;10(10):1075-126.
81 A potential role for the estrogen-metabolizing cytochrome P450 enzymes in human breast carcinogenesis. Breast Cancer Res Treat. 2003 Dec;82(3):191-7.
82 A mechanistic approach to antiepileptic drug interactions. Ann Pharmacother. 1998 May;32(5):554-63.
83 Effect of tamoxifen on the enzymatic activity of human cytochrome CYP2B6. J Pharmacol Exp Ther. 2002 Jun;301(3):945-52.
84 Hepatic metabolism of diclofenac: role of human CYP in the minor oxidative pathways. Biochem Pharmacol. 1999 Sep 1;58(5):787-96.
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 Cytochrome P450 pharmacogenetics and cancer. Oncogene. 2006 Mar 13;25(11):1679-91.
93 CYP2C19*17 is associated with decreased breast cancer risk. Breast Cancer Res Treat. 2009 May;115(2):391-6.
94 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.
95 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.
96 Acetaminophen selectively suppresses peripheral prostaglandin E2 release and increases COX-2 gene expression in a clinical model of acute inflammation. Pain. 2007 Jun;129(3):279-86.
97 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.
98 Mitochondrial involvement in schizophrenia and other functional psychoses. Neurochem Res. 1996 Sep;21(9):995-1004.
99 Quercetin reduces oxidative damage induced by paraquat via modulating expression of antioxidant genes in A549 cells. J Appl Toxicol. 2013 Dec;33(12):1460-7. doi: 10.1002/jat.2812. Epub 2012 Sep 20.
100 Increased sensitivity for troglitazone-induced cytotoxicity using a human in vitro co-culture model. Toxicol In Vitro. 2009 Oct;23(7):1387-95.
101 D-Penicillamine targets metastatic melanoma cells with induction of the unfolded protein response (UPR) and Noxa (PMAIP1)-dependent mitochondrial apoptosis. Apoptosis. 2012 Oct;17(10):1079-94.
102 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.
103 The differential effects of bupivacaine and lidocaine on prostaglandin E2 release, cyclooxygenase gene expression and pain in a clinical pain model. Anesth Analg. 2008 Jan;106(1):321-7, table of contents.
104 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.