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

General Information of Drug (ID: DM2AOTZ)

Drug Name
Perazine Drug Info
Synonyms
Perazine maleate; Phenothiazine, 10-(3-(4-methyl-1-piperazinyl)propyl)-, maleate; 84-97-9 (Parent); 10H-Phenothiazine, 10-(3-(4-methyl-1-piperazinyl)propyl)-, (Z)-2-butenedioate; SCHEMBL220704; AC1O6123; LS-105593; 10-[3-(4-methylpiperazin-1-yl)propyl]phenothiazine
Indication
Disease Entry ICD 11 Status REF
Psychotic disorder 6A20-6A25 Approved [1]
Cross-matching ID
PubChem CID
4744
ChEBI ID
CHEBI:59118
CAS Number
CAS 84-97-9
TTD Drug ID
DM2AOTZ
VARIDT Drug ID
DR01265
INTEDE Drug ID
DR1258

Molecule-Related Drug Atlas

Molecule-Related Drug Atlas
Molecule Type:
DTT
DTP
DME
DOT
Drug Status:
Approved Drug(s)
Download the Complete Related Drug List
Drug(s) Targeting Dopamine D2 receptor (D2R)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Dopamine DMPGUCF Acromegaly 5A60.0 Approved [8]
Haloperidol DM96SE0 Delirium Approved [9]
Perphenazine DMA4MRX Schizophrenia 6A20 Approved [10]
Domperidone DMBDPY0 Gastrointestinal disease DE2Z Approved [11]
Levodopa DMN3E57 Parkinson disease 8A00.0 Approved [12]
Quetiapine DM1N62C Anorexia nervosa cachexia 6B80 Approved [13]
Pimozide DMW83TP Schizophrenia 6A20 Approved [14]
Chlorpromazine DMBGZI3 Acute intermittent hepatic porphyria 5C58.11 Approved [15]
Iloperidone DM6AUFY Schizophrenia 6A20 Approved [16]
Risperidone DMN6DXL Bipolar I disorder Approved [17]
⏷ 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 [18]
Doxorubicin DMVP5YE Acute myelogenous leukaemia 2A41 Approved [19]
Methotrexate DM2TEOL Anterior urethra cancer Approved [20]
Folic Acid DMEMBJC Colorectal carcinoma Approved [21]
Fluorouracil DMUM7HZ Adenocarcinoma 2D40 Approved [20]
Cisplatin DMRHGI9 Adenocarcinoma 2D40 Approved [20]
Progesterone DMUY35B Amenorrhea GA20.0 Approved [22]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [20]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [23]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [24]
⏷ 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 [25]
Progesterone DMUY35B Amenorrhea GA20.0 Approved [26]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [27]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [28]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [29]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [30]
Etoposide DMNH3PG Acute myelogenous leukaemia 2A41 Approved [31]
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [32]
Prasterone DM67VKL Chronic obstructive pulmonary disease CA22 Approved [26]
Verapamil DMA7PEW Angina pectoris BA40 Approved [33]
Eplerenone DMF0NQR Heart failure BD10-BD13 Approved [86]
Cannabidiol DM0659E Dravet syndrome 8A61.11 Approved [87]
Isotretinoin DM4QTBN Acne vulgaris ED80 Approved [88]
Voriconazole DMAOL2S Aspergillosis 1F20 Approved [89]
Proguanil DMBL79I Malaria 1F40-1F45 Approved [90]
Ivermectin DMDBX5F Intestinal strongyloidiasis due to nematode parasite 1F6B Approved [90]
Loratadine DMF3AN7 Allergy 4A80-4A85 Approved [91]
Nelfinavir mesylate DMFX6G8 N. A. N. A. Approved [92]
Capsaicin DMGMF6V Back pain ME84.Z Approved [93]
Axitinib DMGVH6N Renal cell carcinoma 2C90 Approved [94]
⏷ Show the Full List of 20 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 [34]
Dinoprostone DMTYOPD Medical abortion JA00.1Z 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 [31]
Oxaliplatin DMQNWRD Adenocarcinoma 2D40 Approved [40]
Verapamil DMA7PEW Angina pectoris BA40 Approved [41]
Diclofenac DMPIHLS Chronic renal failure GB61.Z Approved [42]
⏷ 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 [34]
Progesterone DMUY35B Amenorrhea GA20.0 Approved [43]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [44]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [29]
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [43]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [45]
Metronidazole DMTIVEN Abscess Approved [46]
Propofol DMB4OLE Anaesthesia 9A78.6 Approved [47]
Nicotine DMWX5CO Lung cancer 2C25.0 Approved [48]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [43]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Metabolized By Cytochrome P450 1A1 (CYP1A1)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Progesterone DMUY35B Amenorrhea GA20.0 Approved [49]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [50]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [51]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [52]
Oxaliplatin DMQNWRD Adenocarcinoma 2D40 Approved [40]
Diclofenac DMPIHLS Chronic renal failure GB61.Z Approved [53]
Estrone DM5T6US Acne vulgaris ED80 Approved [54]
Erythromycin DM4K7GQ Acne vulgaris ED80 Approved [55]
Riboflavin DM8YMWE Acne vulgaris ED80 Approved [56]
Mercaptopurine DMTM2IK Acute lymphoblastic leukaemia 2A85 Approved [57]
⏷ 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 [58]
Progesterone DMUY35B Amenorrhea GA20.0 Approved [59]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [60]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [29]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [33]
Quinine DMSWYF5 Malaria 1F40-1F45 Approved [61]
Propofol DMB4OLE Anaesthesia 9A78.6 Approved [62]
Dopamine DMPGUCF Acromegaly 5A60.0 Approved [63]
Nicotine DMWX5CO Lung cancer 2C25.0 Approved [64]
Propranolol DM79NTF Angina pectoris BA40 Approved [65]
⏷ 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 [66]
Cisplatin DMRHGI9 Adenocarcinoma 2D40 Approved [67]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [44]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [68]
Etoposide DMNH3PG Acute myelogenous leukaemia 2A41 Approved [69]
Oxaliplatin DMQNWRD Adenocarcinoma 2D40 Approved [40]
Verapamil DMA7PEW Angina pectoris BA40 Approved [43]
Estrone DM5T6US Acne vulgaris ED80 Approved [70]
Propofol DMB4OLE Anaesthesia 9A78.6 Approved [71]
Ethanol DMDRQZU Chronic pain MG30 Approved [72]
⏷ 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 [73]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [74]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [75]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [43]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [76]
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [43]
Verapamil DMA7PEW Angina pectoris BA40 Approved [77]
Diclofenac DMPIHLS Chronic renal failure GB61.Z Approved [78]
Estrone DM5T6US Acne vulgaris ED80 Approved [79]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [80]
Cannabidiol DM0659E Dravet syndrome 8A61.11 Approved [87]
Troglitazone DM3VFPD Diabetic complication 5A2Y Approved [95]
Dapsone DM4LT8A Acne vulgaris ED80 Approved [90]
Voriconazole DMAOL2S Aspergillosis 1F20 Approved [89]
Capsaicin DMGMF6V Back pain ME84.Z Approved [96]
Zafirlukast DMHNQOG Asthma CA23 Approved [97]
Niclosamide DMJAGXQ Cestodes infection 1F70-1F76 Approved [90]
Eicosapentaenoic acid/docosa-hexaenoic acid DMMUCG4 Hypertriglyceridemia 5C80.1 Approved [98]
Fluconazole DMOWZ6B Cryptococcal meningitis Approved [89]
Quinine DMSWYF5 Malaria 1F40-1F45 Approved [90]
⏷ Show the Full List of 20 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 [81]
Progesterone DMUY35B Amenorrhea GA20.0 Approved [73]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [82]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [83]
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [43]
Verapamil DMA7PEW Angina pectoris BA40 Approved [84]
Diclofenac DMPIHLS Chronic renal failure GB61.Z Approved [53]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [80]
Quinine DMSWYF5 Malaria 1F40-1F45 Approved [85]
Propofol DMB4OLE Anaesthesia 9A78.6 Approved [47]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Flavin-containing monooxygenase 3 (FMO3)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Ciclosporin DMAZJFX Graft-versus-host disease 4B24 Approved [99]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [100]
Temozolomide DMKECZD Adenocarcinoma 2D40 Approved [101]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [102]
Almogran DM7I64Z Migraine 8A80 Approved [103]
Ranitidine DM0GUSX Gastric ulcer DA60 Approved [104]
Methimazole DM25FL8 Hyperthyroidism 5A02 Approved [105]
Sulindac DM2QHZU Acute myelogenous leukaemia 2A41 Approved [106]
Docetaxel DMDI269 Advanced cancer 2A00-2F9Z Approved [107]
Clozapine DMFC71L Schizophrenia 6A20 Approved [108]
⏷ 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
Dopamine D2 receptor (D2R) TTEX248 DRD2_HUMAN Modulator [2]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
P-glycoprotein 1 (ABCB1) DTUGYRD MDR1_HUMAN Substrate [3]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4) DE4LYSA CP3A4_HUMAN Substrate [4]
Cytochrome P450 2E1 (CYP2E1) DEVDYN7 CP2E1_HUMAN Substrate [5]
Cytochrome P450 2D6 (CYP2D6) DECB0K3 CP2D6_HUMAN Substrate [6]
Cytochrome P450 2C9 (CYP2C9) DE5IED8 CP2C9_HUMAN Substrate [6]
Cytochrome P450 1A1 (CYP1A1) DE6OQ3W CP1A1_HUMAN Substrate [4]
Mephenytoin 4-hydroxylase (CYP2C19) DEGTFWK CP2CJ_HUMAN Substrate [6]
Cytochrome P450 2A6 (CYP2A6) DEJVYAZ CP2A6_HUMAN Substrate [4]
Cytochrome P450 1A2 (CYP1A2) DEJGDUW CP1A2_HUMAN Substrate [7]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Cytochrome P450 2C9 (CYP2C9) OTGLBN29 CP2C9_HUMAN Biotransformations [6]
Cytochrome P450 3A4 (CYP3A4) OTQGYY83 CP3A4_HUMAN Biotransformations [6]
Flavin-containing monooxygenase 3 (FMO3) OT1G2EV3 FMO3_HUMAN Biotransformations [6]

References

1 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2 Synthesis and in vitro binding of N-phenyl piperazine analogs as potential dopamine D3 receptor ligands. Bioorg Med Chem. 2005 Jan 3;13(1):77-87.
3 Identification of P-glycoprotein substrates and inhibitors among psychoactive compounds--implications for pharmacokinetics of selected substrates. J Pharm Pharmacol. 2004 Aug;56(8):967-75.
4 The metabolism of the piperazine-type phenothiazine neuroleptic perazine by the human cytochrome P-450 isoenzymes. Eur Neuropsychopharmacol. 2004 May;14(3):199-208.
5 Effects of phenothiazine neuroleptics on the rate of caffeine demethylation and hydroxylation in the rat liver. Pol J Pharmacol. 2001 Nov-Dec;53(6):615-21.
6 Cytochrome P-450 enzymes and FMO3 contribute to the disposition of the antipsychotic drug perazine in vitro. Psychopharmacology (Berl). 2000 Sep;151(4):312-20.
7 Perazine as a potent inhibitor of human CYP1A2 but not CYP3A4. Pol J Pharmacol. 2002 Jul-Aug;54(4):407-10.
8 The Detection of Dopamine Gene Receptors (DRD1-DRD5) Expression on Human Peripheral Blood Lymphocytes by Real Time PCR. Iran J Allergy Asthma Immunol. 2004 Dec;3(4):169-74.
9 Dopaminergic synapses in the matrix of the ventrolateral striatum after chronic haloperidol treatment. Synapse. 2002 Aug;45(2):78-85.
10 CYP2D6 and DRD2 genes differentially impact pharmacodynamic sensitivity and time course of prolactin response to perphenazine. Pharmacogenet Genomics. 2007 Nov;17(11):989-93.
11 Screening of domperidone in wastewater by high performance liquid chromatography and solid phase extraction methods. Talanta. 2006 Jan 15;68(3):928-31.
12 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: 3639).
13 Receptor reserve-dependent properties of antipsychotics at human dopamine D2 receptors. Eur J Pharmacol. 2009 Apr 1;607(1-3):35-40.
14 [The benzamides tiapride, sulpiride, and amisulpride in treatment for Tourette's syndrome]. Nervenarzt. 2007 Mar;78(3):264, 266-8, 270-1.
15 Modulatory role of dopamine D2 receptors and fundamental role of L-type Ca2+ channels in the induction of long-term potentiation in the basolateral... Eur J Pharmacol. 2009 Mar 15;606(1-3):90-3.
16 Hughes B: 2009 FDA drug approvals. Nat Rev Drug Discov. 2010 Feb;9(2):89-92.
17 Randomized clinical comparison of perospirone and risperidone in patients with schizophrenia: Kansai Psychiatric Multicenter Study. Psychiatry Clin Neurosci. 2009 Jun;63(3):322-8.
18 Human intestinal transporter database: QSAR modeling and virtual profiling of drug uptake, efflux and interactions. Pharm Res. 2013 Apr;30(4):996-1007.
19 MDR1 (ABCB1) G1199A (Ser400Asn) polymorphism alters transepithelial permeability and sensitivity to anticancer agents. Cancer Chemother Pharmacol. 2009 Jun;64(1):183-8.
20 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.
21 Folate transporter expression decreases in the human placenta throughout pregnancy and in pre-eclampsia. Pregnancy Hypertens. 2012 Apr;2(2):123-31.
22 Comparative studies on in vitro methods for evaluating in vivo function of MDR1 P-glycoprotein. Pharm Res. 2001 Dec;18(12):1660-8.
23 Antiestrogens and steroid hormones: substrates of the human P-glycoprotein. Biochem Pharmacol. 1994 Jul 19;48(2):287-92.
24 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.
25 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.
26 Contribution of human hepatic cytochrome P450 isoforms to regioselective hydroxylation of steroid hormones. Xenobiotica. 1998 Jun;28(6):539-47.
27 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.
28 Isoform-specific regulation of cytochromes P450 expression by estradiol and progesterone. Drug Metab Dispos. 2013 Feb;41(2):263-9.
29 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.
30 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.
31 Effects of morin on the pharmacokinetics of etoposide in rats. Biopharm Drug Dispos. 2007 Apr;28(3):151-6.
32 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.
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 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.
35 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.
36 Endoxifen and other metabolites of tamoxifen inhibit human hydroxysteroid sulfotransferase 2A1 (hSULT2A1). Drug Metab Dispos. 2014 Nov;42(11):1843-50.
37 Cytochrome P450 1A2 (CYP1A2) activity and risk factors for breast cancer: a cross-sectional study. Breast Cancer Res. 2004;6(4):R352-65.
38 PharmGKB summary: pathways of acetaminophen metabolism at the therapeutic versus toxic doses. Pharmacogenet Genomics. 2015 Aug;25(8):416-26.
39 The effect of apigenin on pharmacokinetics of imatinib and its metabolite N-desmethyl imatinib in rats. Biomed Res Int. 2013;2013:789184.
40 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.
41 Identification of P450 enzymes involved in metabolism of verapamil in humans. Naunyn Schmiedebergs Arch Pharmacol. 1993 Sep;348(3):332-7.
42 Metabolism and metabolic inhibition of xanthotoxol in human liver microsomes. Evid Based Complement Alternat Med. 2016;2016:5416509.
43 Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.
44 Genotoxicity of tamoxifen, tamoxifen epoxide and toremifene in human lymphoblastoid cells containing human cytochrome P450s. Carcinogenesis. 1994 Jan;15(1):5-9.
45 Psychotropic drug interactions with valproate. Clin Neuropharmacol. 2005 Mar-Apr;28(2):96-101.
46 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.
47 Possible involvement of multiple human cytochrome P450 isoforms in the liver metabolism of propofol. Br J Anaesth. 1998 Jun;80(6):788-95.
48 CYP2A6- and CYP2A13-catalyzed metabolism of the nicotine delta-5'(1')iminium ion. J Pharmacol Exp Ther. 2012 Nov;343(2):307-15.
49 Allelic variants of human cytochrome P450 1A1 (CYP1A1): effect of T461N and I462V substitutions on steroid hydroxylase specificity. Pharmacogenetics. 2000 Aug;10(6):519-30.
50 Metabolism of tamoxifen by recombinant human cytochrome P450 enzymes: formation of the 4-hydroxy, 4'-hydroxy and N-desmethyl metabolites and isomerization of trans-4-hydroxytamoxifen. Drug Metab Dispos. 2002 Aug;30(8):869-74.
51 Cytochrome P450 isoforms catalyze formation of catechol estrogen quinones that react with DNA. Metabolism. 2007 Jul;56(7):887-94.
52 Preferred orientations in the binding of 4'-hydroxyacetanilide (acetaminophen) to cytochrome P450 1A1 and 2B1 isoforms as determined by 13C- and 15N-NMR relaxation studies. J Med Chem. 1994 Mar 18;37(6):860-7.
53 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.
54 A common CYP1B1 polymorphism is associated with 2-OHE1/16-OHE1 urinary estrone ratio. Clin Chem Lab Med. 2005;43(7):702-6.
55 Cytochromes P450 in crustacea. Comp Biochem Physiol C Pharmacol Toxicol Endocrinol. 1998 Nov;121(1-3):157-72.
56 Disruption of endogenous regulator homeostasis underlies the mechanism of rat CYP1A1 mRNA induction by metyrapone. Biochem J. 1998 Apr 1;331 ( Pt 1):273-81.
57 Pharmacogenomics in drug-metabolizing enzymes catalyzing anticancer drugs for personalized cancer chemotherapy. Curr Drug Metab. 2007 Aug;8(6):554-62.
58 Inhibitory effects of anticancer drugs on dextromethorphan-O-demethylase activity in human liver microsomes. Cancer Chemother Pharmacol. 1993;32(6):491-5.
59 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.
60 CYP2D6 polymorphisms and tamoxifen metabolism: clinical relevance. Curr Oncol Rep. 2010 Jan;12(1):7-15.
61 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.
62 Effects of propofol on human hepatic microsomal cytochrome P450 activities. Xenobiotica. 1998 Sep;28(9):845-53.
63 Pharmacogenetics of schizophrenia. Am J Med Genet. 2000 Spring;97(1):98-106.
64 Roles of CYP2A6 and CYP2B6 in nicotine C-oxidation by human liver microsomes. Arch Toxicol. 1999 Mar;73(2):65-70.
65 Structure-activity relationship for human cytochrome P450 substrates and inhibitors. Drug Metab Rev. 2002 Feb-May;34(1-2):69-82.
66 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.
67 Cytochrome P450 2E1 null mice provide novel protection against cisplatin-induced nephrotoxicity and apoptosis. Kidney Int. 2003 May;63(5):1687-96.
68 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.
69 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.
70 Novel metabolic pathway of estrone and 17beta-estradiol catalyzed by cytochrome P-450. Drug Metab Dispos. 2000 Feb;28(2):110-2.
71 Inhibition of cytochrome P450 2E1 by propofol in human and porcine liver microsomes. Biochem Pharmacol. 2002 Oct 1;64(7):1151-6.
72 CYP2E1 and clinical features in alcoholics. Neuropsychobiology. 2003;47(2):86-9.
73 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.
74 Tamoxifen inhibits cytochrome P450 2C9 activity in breast cancer patients. J Chemother. 2006 Aug;18(4):421-4.
75 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.
76 Drug-drug interactions with imatinib: an observational study. Medicine (Baltimore). 2016 Oct;95(40):e5076.
77 Drug interactions with calcium channel blockers: possible involvement of metabolite-intermediate complexation with CYP3A. Drug Metab Dispos. 2000 Feb;28(2):125-30.
78 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.
79 A potential role for the estrogen-metabolizing cytochrome P450 enzymes in human breast carcinogenesis. Breast Cancer Res Treat. 2003 Dec;82(3):191-7.
80 A mechanistic approach to antiepileptic drug interactions. Ann Pharmacother. 1998 May;32(5):554-63.
81 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.
82 Cytochrome P450 pharmacogenetics and cancer. Oncogene. 2006 Mar 13;25(11):1679-91.
83 CYP2C19*17 is associated with decreased breast cancer risk. Breast Cancer Res Treat. 2009 May;115(2):391-6.
84 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.
85 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.
86 The relative role of CYP3A4 and CYP3A5 in eplerenone metabolism. Toxicol Lett. 2019 Oct 15;315:9-13.
87 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.
88 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.
89 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.
90 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.
91 Cetirizine and loratadine-based antihistamines with 5-lipoxygenase inhibitory activity. Bioorg Med Chem Lett. 2004 Nov 15;14(22):5591-4.
92 Mechanism-based inactivation of CYP3A by HIV protease inhibitors. J Pharmacol Exp Ther. 2005 Feb;312(2):583-91.
93 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.
94 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.
95 Comparative effects of thiazolidinediones on in vitro P450 enzyme induction and inhibition. Drug Metab Dispos. 2003 Apr;31(4):439-46.
96 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.
97 Potential of pranlukast and zafirlukast in the inhibition of human liver cytochrome P450 enzymes. Xenobiotica. 2004 May;34(5):429-38.
98 The inhibitory effect of polyunsaturated fatty acids on human CYP enzymes. Life Sci. 2006 Nov 25;79(26):2432-40.
99 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.
100 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.
101 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.
102 Multiple microRNAs function as self-protective modules in acetaminophen-induced hepatotoxicity in humans. Arch Toxicol. 2018 Feb;92(2):845-858.
103 Identification of the human liver enzymes involved in the metabolism of the antimigraine agent almotriptan. Drug Metab Dispos. 2003 Apr;31(4):404-11.
104 Evaluation of fresh and cryopreserved hepatocytes as in vitro drug metabolism tools for the prediction of metabolic clearance. Drug Metab Dispos. 2004 Nov;32(11):1247-53. doi: 10.1124/dmd.104.000026. Epub 2004 Jul 30.
105 Identification and functional analysis of common human flavin-containing monooxygenase 3 genetic variants. J Pharmacol Exp Ther. 2007 Jan;320(1):266-73. doi: 10.1124/jpet.106.112268. Epub 2006 Oct 18.
106 Genetic polymorphisms of human flavin monooxygenase 3 in sulindac-mediated primary chemoprevention of familial adenomatous polyposis. Clin Cancer Res. 2004 Dec 15;10(24):8357-62. doi: 10.1158/1078-0432.CCR-04-1073.
107 Pharmacogenomics variation in drug metabolizing enzymes and transporters in relation to docetaxel toxicity in Lebanese breast cancer patients: paving the way for OMICs in low and middle income countries. OMICS. 2013 Jul;17(7):353-67. doi: 10.1089/omi.2013.0019. Epub 2013 Jun 11.
108 Interindividual variation in relative CYP1A2/3A4 phenotype influences susceptibility of clozapine oxidation to cytochrome P450-specific inhibition in human hepatic microsomes. Drug Metab Dispos. 2008 Dec;36(12):2547-55. doi: 10.1124/dmd.108.023671. Epub 2008 Sep 22.