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

General Information of Drug (ID: DMPRI8G)

Drug Name
Buprenorphine Drug Info
Synonyms
Buprel; Buprenex; Buprenophine; Buprenorfina; Buprenorphinum; Probuphine; Temgesic; Buprenorphine Hcl; RX 6029M; Buprenex (TN); Buprenorfina [INN-Spanish]; Buprenorphine [INN:BAN]; Buprenorphinum [INN-Latin]; Subutex (TN); Temgesic (TN); Buprenorphine (JAN/INN); RX-6029-M; Suboxone (TN); [5alpha,7alpha(S)]-17-(Cyclopropylmethyl)-alpha-(1,1-dimethylethyl)-4,5-epoxy-18,19-dihydro-3-hydroxy-6-methoxy-alpha-methyl-6,14-ethenomorphinan-7-methanol; (-)-buprenorphine; (5alpha,6beta,14beta,18R)-17-(cyclopropylmethyl)-18-[(1S)-1-hydroxy-1,2,2-trimethylpropyl]-6-(methyloxy)-18,19-dihydro-4,5-epoxy-6,14-ethenomorphinan-3-ol; (5alpha,6beta,14beta,18R)-17-(cyclopropylmethyl)-18-[(2S)-2-hydroxy-3,3-dimethylbutan-2-yl]-6-methoxy-18,19-dihydro-4,5-epoxy-6,14-ethenomorphinan-3-ol; 17-Cyclopropylmethyl-4,5alpha-epoxy-7alpha-((S)-1-hydroxy-1,2,2-trimethylpropyl-6-methoxy-6,14-endo-ethanomorphinan-3-ol; 17-cyclopropylmethyl-4,5alpha-epoxy-7alpha-((S)-1-hydroxy-1,2,2-trimethylpropyl)-6-methoxy-6,14-endo-ethanomorphinan-3-ol; 2-(N-Cyclopropylmethyl-4,5alpha-epoxy-3-hydroxy-6-methoxy-6,14-endo-ethanomorphinan-7alpha-yl)-3,3-dimethyl-2-butanol; 2-(N-cyclopropylmethyl-4,5alpha-epoxy-3-hydroxy-6-methoxy-6,14-endo-ethanomorphinan-6alpha-yl)-3,3-dimethyl-2-butanol; 21-(Cyclopropyl-7alpha-((S)-1-hydroxy-1,2,2-trimethylpropyl-6,14-endo-ethano-6,7,8,14-tetrahydrooripavine; 21-cyclopropyl-7alpha-(2-hydroxy-3,3-dimethyl-2-butyl)-6,14-endo-ethano-6,7,8,14-tetrahydrooripavine; 21-cyclopropyl-7alpha-[(S)-1-hydroxy-1,2,2-trimethylpropyl]-6,14-endo-ethano-6,7,8,14-tetrahydrooripavine; 6,14-Ethenomorphinan-7-methanol; 6,14-Ethenomorphinan-7-methanol, 17-(cyclopropylmethyl)-alpha-(1,1-dimethylethyl)-4,5-epoxy-18,19-dihydro-3-hydroxy-6-methoxy-alpha-methyl-, (alphaS,5alpha,7alpha)-(9CI); 6029-M
Indication
Disease Entry ICD 11 Status REF
Opioid dependence 6C43.2Z Approved [1]
Pain MG30-MG3Z Approved [2]
Psychiatric disorder 6E8Z Phase 3 [3]
Migraine 8A80 Phase 2 [4]
Chronic pain MG30 Investigative [1]
Therapeutic Class
Analgesics
Cross-matching ID
PubChem CID
644073
ChEBI ID
CHEMBL3216
CAS Number
CAS 52485-79-7
TTD Drug ID
DMPRI8G
INTEDE Drug ID
DR0246
ACDINA Drug ID
D00082

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 Opioid receptor mu (MOP)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Morphine DMRMS0L Advanced cancer 2A00-2F9Z Approved [15]
Hydromorphone DMHP21E Back pain ME84.Z Approved [16]
Tapentadol hydrochloride DMXLSH3 Acute pain MG31 Approved [17]
Fentanyl DM8WAHT Analgesia MB40.8 Approved [18]
Alfentanil DMVO0UB Anaesthesia 9A78.6 Approved [19]
Naloxegol DML0B41 Opioid-induced constipation DB32.1 Approved [20]
Eluxadoline DMYZ0P1 Diarrhea-predominant irritable bowel syndrome DD91.01 Approved [21]
Nalfurafine hcl DMA9DHW Uremic pruritus EC90.10 Approved [22]
Oxycodone DMXLKHV Osteoarthritis FA00-FA05 Approved [23]
Methylnaltrexone bromide DMZTGN2 Opioid-induced constipation DB32.1 Approved [17]
⏷ 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 [24]
Progesterone DMUY35B Amenorrhea GA20.0 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 [30]
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [31]
Prasterone DM67VKL Chronic obstructive pulmonary disease CA22 Approved [25]
Verapamil DMA7PEW Angina pectoris BA40 Approved [8]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Metabolized By UDP-glucuronosyltransferase 1A1 (UGT1A1)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [32]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [33]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [34]
Etoposide DMNH3PG Acute myelogenous leukaemia 2A41 Approved [35]
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [36]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [37]
Mycophenolate mofetil DMPQAGE Hepatosplenic T-cell lymphoma Approved [38]
Metronidazole DMTIVEN Abscess Approved [39]
Propofol DMB4OLE Anaesthesia 9A78.6 Approved [40]
Ethanol DMDRQZU Chronic pain MG30 Approved [41]
⏷ 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 [42]
Progesterone DMUY35B Amenorrhea GA20.0 Approved [43]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [44]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [28]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [8]
Quinine DMSWYF5 Malaria 1F40-1F45 Approved [45]
Propofol DMB4OLE Anaesthesia 9A78.6 Approved [46]
Dopamine DMPGUCF Acromegaly 5A60.0 Approved [47]
Nicotine DMWX5CO Lung cancer 2C25.0 Approved [48]
Propranolol DM79NTF Angina pectoris BA40 Approved [49]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Metabolized By Cytochrome P450 3A5 (CYP3A5)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Doxorubicin DMVP5YE Acute myelogenous leukaemia 2A41 Approved [50]
Progesterone DMUY35B Amenorrhea GA20.0 Approved [51]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [52]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [53]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [54]
Sulfasalazine DMICA9H Irritable bowel syndrome DD91.0 Approved [55]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [56]
Etoposide DMNH3PG Acute myelogenous leukaemia 2A41 Approved [57]
Verapamil DMA7PEW Angina pectoris BA40 Approved [58]
Sorafenib DMS8IFC Adenocarcinoma 2D40 Approved [53]
⏷ 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 [59]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [53]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [53]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [53]
Prasterone DM67VKL Chronic obstructive pulmonary disease CA22 Approved [60]
Verapamil DMA7PEW Angina pectoris BA40 Approved [61]
Sorafenib DMS8IFC Adenocarcinoma 2D40 Approved [53]
Quinine DMSWYF5 Malaria 1F40-1F45 Approved [53]
Irinotecan DMP6SC2 Adenocarcinoma 2D40 Approved [53]
Metronidazole DMTIVEN Abscess Approved [62]
⏷ 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 [60]
Diclofenac DMPIHLS Chronic renal failure GB61.Z Approved [63]
Propofol DMB4OLE Anaesthesia 9A78.6 Approved [64]
Phenytoin DMNOKBV Epilepsy 8A60-8A68 Approved [60]
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 [60]
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 [70]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [71]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [71]
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [60]
Verapamil DMA7PEW Angina pectoris BA40 Approved [72]
Diclofenac DMPIHLS Chronic renal failure GB61.Z Approved [73]
Sorafenib DMS8IFC Adenocarcinoma 2D40 Approved [74]
Quinine DMSWYF5 Malaria 1F40-1F45 Approved [71]
Mycophenolate mofetil DMPQAGE Hepatosplenic T-cell lymphoma Approved [75]
Propofol DMB4OLE Anaesthesia 9A78.6 Approved [64]
⏷ 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 [76]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [77]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [78]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [60]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [79]
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [60]
Verapamil DMA7PEW Angina pectoris BA40 Approved [80]
Diclofenac DMPIHLS Chronic renal failure GB61.Z Approved [81]
Estrone DM5T6US Acne vulgaris ED80 Approved [82]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [83]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Mitogen-activated protein kinase 3 (MAPK3)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Cisplatin DMRHGI9 Adenocarcinoma 2D40 Approved [84]
Progesterone DMUY35B Amenorrhea GA20.0 Approved [85]
Cannabidiol DM0659E Dravet syndrome 8A61.11 Approved [86]
Sertraline DM0FB1J Coronary heart disease BA80.Z Approved [87]
Beta-carotene DM0RXBT Vitamin deficiency 5B55-5B71 Approved [88]
Fulvestrant DM0YZC6 Breast cancer 2C60-2C65 Approved [89]
Secobarbital DM14RF5 Epilepsy 8A60-8A68 Approved [90]
Gefitinib DM15F0X Colon adenocarcinoma Approved [91]
Fexofenadine DM17ONX Allergic rhinitis CA08.0 Approved [92]
Hydrogen peroxide DM1NG5W Infectious disease 1A00-CA43.1 Approved [93]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Mitogen-activated protein kinase 1 (MAPK1)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Ethanol DMDRQZU Chronic pain MG30 Approved [94]
Progesterone DMUY35B Amenorrhea GA20.0 Approved [85]
Carvedilol DMHTEAO Chronic heart failure BD1Z Approved [95]
Paclitaxel DMLB81S Breast carcinoma Approved [96]
Etoposide DMNH3PG Acute myelogenous leukaemia 2A41 Approved [97]
Cisplatin DMRHGI9 Adenocarcinoma 2D40 Approved [84]
Urokinase DM0GOUD Myocardial infarction BA41-BA43 Approved [98]
Cannabidiol DM0659E Dravet syndrome 8A61.11 Approved [99]
Sertraline DM0FB1J Coronary heart disease BA80.Z Approved [87]
Beta-carotene DM0RXBT Vitamin deficiency 5B55-5B71 Approved [88]
⏷ 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
Opioid receptor mu (MOP) TTKWM86 OPRM_HUMAN Agonist [5]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4) Main DME DE4LYSA CP3A4_HUMAN Substrate [6]
Cytochrome P450 2D6 (CYP2D6) DECB0K3 CP2D6_HUMAN Substrate [7]
Cytochrome P450 2C9 (CYP2C9) DE5IED8 CP2C9_HUMAN Substrate [8]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DEYGVN4 UD11_HUMAN Substrate [9]
Cytochrome P450 3A5 (CYP3A5) Main DME DEIBDNY CP3A5_HUMAN Substrate [10]
Cytochrome P450 2C8 (CYP2C8) DES5XRU CP2C8_HUMAN Substrate [11]
Cytochrome P450 3A7 (CYP3A7) DERD86B CP3A7_HUMAN Substrate [8]
Cytochrome P450 2C18 (CYP2C18) DEZMWRE CP2CI_HUMAN Substrate [12]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Mitogen-activated protein kinase 1 (MAPK1) OTH85PI5 MK01_HUMAN Post-Translational Modifications [13]
Mitogen-activated protein kinase 3 (MAPK3) OTCYKGKO MK03_HUMAN Post-Translational Modifications [13]
UDP-glucuronosyltransferase 1A1 OTH1C8OJ UD11_HUMAN Biotransformations [14]

References

1 Buprenorphine FDA Label
2 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: 1670).
3 ClinicalTrials.gov (NCT02510014) Safety and Tolerability Study of Depot Buprenorphine in Treatment Seeking Subjects With Opioid Use Disorder.
4 ClinicalTrials.gov (NCT00941304) Study of BEMA Buprenorphine in the Treatment of Dental Pain. U.S. National Institutes of Health.
5 Buprenorphine is a weak partial agonist that inhibits opioid receptor desensitization. J Neurosci. 2009 Jun 3;29(22):7341-8.
6 Drug interactions of clinical importance among the opioids, methadone and buprenorphine, and other frequently prescribed medications: a review. Am J Addict. 2010 Jan-Feb;19(1):4-16.
7 Effect of nonspecific binding to microsomes and metabolic elimination of buprenorphine on the inhibition of cytochrome P4502D6. Biol Pharm Bull. 2005 Feb;28(2):212-6.
8 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.
9 Contribution of the different UDP-glucuronosyltransferase (UGT) isoforms to buprenorphine and norbuprenorphine metabolism and relationship with the main UGT polymorphisms in a bank of human liver microsomes. Drug Metab Dispos. 2010 Jan;38(1):40-5.
10 Buprenorphine pharmacology review: update on transmucosal and long-acting formulations. J Addict Med. 2019 Mar/Apr;13(2):93-103.
11 Buprenorphine in cancer pain. Support Care Cancer. 2005 Nov;13(11):878-87.
12 In vitro metabolism study of buprenorphine: evidence for new metabolic pathways. Drug Metab Dispos. 2005 May;33(5):689-95.
13 opioid receptor agonist-selective regulation of interleukin-4 in T lymphocytes. J Neuroimmunol. 2013 Oct 15;263(1-2):35-42. doi: 10.1016/j.jneuroim.2013.07.012. Epub 2013 Jul 25.
14 The effect of incubation conditions on the enzyme kinetics of udp-glucuronosyltransferases. Drug Metab Dispos. 2003 Jun;31(6):762-7. doi: 10.1124/dmd.31.6.762.
15 Antianalgesia: stereoselective action of dextro-morphine over levo-morphine on glia in the mouse spinal cord.J Pharmacol Exp Ther.2005 Sep;314(3):1101-8.
16 Clinical pipeline report, company report or official report of signaturerx.
17 2008 FDA drug approvals. Nat Rev Drug Discov. 2009 Feb;8(2):93-6.
18 The ChEMBL database in 2017. Nucleic Acids Res. 2017 Jan 4;45(D1):D945-D954.
19 Concentration-effect relationship of intravenous alfentanil and ketamine on peripheral neurosensory thresholds, allodynia and hyperalgesia of neuropathic pain. Pain. 2001 Mar;91(1-2):177-87.
20 2014 FDA drug approvals. Nat Rev Drug Discov. 2015 Feb;14(2):77-81.
21 Molecular characterization of eluxadoline as a potential ligand targeting mu-delta opioid receptor heteromers.Biochem Pharmacol.2014 Dec 1;92(3):448-56.
22 Drug design and synthesis of a novel kappa opioid receptor agonist with an oxabicyclo[2.2.2]octane skeleton and its pharmacology. Bioorg Med Chem Lett. 2010 Jan 1;20(1):121-4.
23 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. (Target id: 319).
24 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.
25 Contribution of human hepatic cytochrome P450 isoforms to regioselective hydroxylation of steroid hormones. Xenobiotica. 1998 Jun;28(6):539-47.
26 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.
27 Isoform-specific regulation of cytochromes P450 expression by estradiol and progesterone. Drug Metab Dispos. 2013 Feb;41(2):263-9.
28 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.
29 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.
30 Effects of morin on the pharmacokinetics of etoposide in rats. Biopharm Drug Dispos. 2007 Apr;28(3):151-6.
31 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.
32 Functional significance of UDP-glucuronosyltransferase variants in the metabolism of active tamoxifen metabolites. Cancer Res. 2009 Mar 1;69(5):1892-900.
33 Functional characterization of human and cynomolgus monkey UDP-glucuronosyltransferase 1A1 enzymes. Life Sci. 2010 Aug 14;87(7-8):261-8.
34 Effect of UDP-glucuronosyltransferase (UGT) 1A polymorphism (rs8330 and rs10929303) on glucuronidation status of acetaminophen. Dose Response. 2017 Sep 11;15(3):1559325817723731.
35 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.
36 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.
37 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.
38 Characterization of rat intestinal microsomal UDP-glucuronosyltransferase activity toward mycophenolic acid. Drug Metab Dispos. 2006 Sep;34(9):1632-9.
39 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.
40 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.
41 Identification and preliminary characterization of UDP-glucuronosyltransferases catalyzing formation of ethyl glucuronide. Anal Bioanal Chem. 2014 Apr;406(9-10):2325-32.
42 Inhibitory effects of anticancer drugs on dextromethorphan-O-demethylase activity in human liver microsomes. Cancer Chemother Pharmacol. 1993;32(6):491-5.
43 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.
44 CYP2D6 polymorphisms and tamoxifen metabolism: clinical relevance. Curr Oncol Rep. 2010 Jan;12(1):7-15.
45 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.
46 Effects of propofol on human hepatic microsomal cytochrome P450 activities. Xenobiotica. 1998 Sep;28(9):845-53.
47 Pharmacogenetics of schizophrenia. Am J Med Genet. 2000 Spring;97(1):98-106.
48 Roles of CYP2A6 and CYP2B6 in nicotine C-oxidation by human liver microsomes. Arch Toxicol. 1999 Mar;73(2):65-70.
49 Structure-activity relationship for human cytochrome P450 substrates and inhibitors. Drug Metab Rev. 2002 Feb-May;34(1-2):69-82.
50 Drug related genetic polymorphisms affecting adverse reactions to methotrexate, vinblastine, doxorubicin and cisplatin in patients with urothelial cancer. J Urol. 2008 Dec;180(6):2389-95.
51 Human prostate CYP3A5: identification of a unique 5'-untranslated sequence and characterization of purified recombinant protein. Biochem Biophys Res Commun. 1999 Jul 14;260(3):676-81.
52 Polymorphisms in cytochrome P4503A5 (CYP3A5) may be associated with race and tumor characteristics, but not metabolism and side effects of tamoxifen in breast cancer patients. Cancer Lett. 2005 Jan 10;217(1):61-72.
53 Drug Interactions Flockhart Table
54 Induction of hepatic CYP2E1 by a subtoxic dose of acetaminophen in rats: increase in dichloromethane metabolism and carboxyhemoglobin elevation. Drug Metab Dispos. 2007 Oct;35(10):1754-8.
55 Urinary 6 beta-hydroxycortisol excretion in rheumatoid arthritis. Br J Rheumatol. 1997 Jan;36(1):54-8.
56 Clinical pharmacokinetics of imatinib. Clin Pharmacokinet. 2005;44(9):879-94.
57 Kinetics and regulation of cytochrome P450-mediated etoposide metabolism. Drug Metab Dispos. 2004 Sep;32(9):993-1000.
58 Differential mechanism-based inhibition of CYP3A4 and CYP3A5 by verapamil. Drug Metab Dispos. 2005 May;33(5):664-71.
59 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.
60 Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.
61 Prediction of cytochrome P450 3A inhibition by verapamil enantiomers and their metabolites. Drug Metab Dispos. 2004 Feb;32(2):259-66.
62 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.
63 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.
64 Possible involvement of multiple human cytochrome P450 isoforms in the liver metabolism of propofol. Br J Anaesth. 1998 Jun;80(6):788-95.
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 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.
71 Role of cytochrome P450 2C8 in drug metabolism and interactions. Pharmacol Rev. 2016 Jan;68(1):168-241.
72 Differential expression and function of CYP2C isoforms in human intestine and liver. Pharmacogenetics. 2003 Sep;13(9):565-75.
73 Analysis of human cytochrome P450 2C8 substrate specificity using a substrate pharmacophore and site-directed mutants. Biochemistry. 2004 Dec 14;43(49):15379-92.
74 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.
75 PharmGKB summary: mycophenolic acid pathway. Pharmacogenet Genomics. 2014 Jan;24(1):73-9.
76 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.
77 Tamoxifen inhibits cytochrome P450 2C9 activity in breast cancer patients. J Chemother. 2006 Aug;18(4):421-4.
78 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.
79 Drug-drug interactions with imatinib: an observational study. Medicine (Baltimore). 2016 Oct;95(40):e5076.
80 Drug interactions with calcium channel blockers: possible involvement of metabolite-intermediate complexation with CYP3A. Drug Metab Dispos. 2000 Feb;28(2):125-30.
81 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.
82 A potential role for the estrogen-metabolizing cytochrome P450 enzymes in human breast carcinogenesis. Breast Cancer Res Treat. 2003 Dec;82(3):191-7.
83 A mechanistic approach to antiepileptic drug interactions. Ann Pharmacother. 1998 May;32(5):554-63.
84 Treatment with anticancer agents induces dysregulation of specific Wnt signaling pathways in human ovarian luteinized granulosa cells in vitro. Toxicol Sci. 2013 Nov;136(1):183-92. doi: 10.1093/toxsci/kft175. Epub 2013 Aug 16.
85 Progesterone increases csk homologous kinase in HMC-1560 human mast cells and reduces cell proliferation. J Cell Biochem. 2007 Dec 1;102(5):1271-80. doi: 10.1002/jcb.21357.
86 Cannabidiol upregulates melanogenesis through CB1 dependent pathway by activating p38 MAPK and p42/44 MAPK. Chem Biol Interact. 2017 Aug 1;273:107-114. doi: 10.1016/j.cbi.2017.06.005. Epub 2017 Jun 7.
87 Sertraline, an antidepressant, induces apoptosis in hepatic cells through the mitogen-activated protein kinase pathway. Toxicol Sci. 2014 Feb;137(2):404-15. doi: 10.1093/toxsci/kft254. Epub 2013 Nov 5.
88 Growth stimulation of human pulmonary adenocarcinoma cells and small airway epithelial cells by beta-carotene via activation of cAMP, PKA, CREB and ERK1/2. Int J Cancer. 2006 Mar 15;118(6):1370-80. doi: 10.1002/ijc.21537.
89 Estrogen and pure antiestrogen fulvestrant (ICI 182 780) augment cell-matrigel adhesion of MCF-7 breast cancer cells through a novel G protein coupled estrogen receptor (GPR30)-to-calpain signaling axis. Toxicol Appl Pharmacol. 2014 Mar 1;275(2):176-81. doi: 10.1016/j.taap.2014.01.005. Epub 2014 Jan 17.
90 Inhibition of activator protein 1 by barbiturates is mediated by differential effects on mitogen-activated protein kinases and the small G proteins ras and rac-1. J Pharmacol Exp Ther. 2004 Dec;311(3):1232-40. doi: 10.1124/jpet.104.071332. Epub 2004 Jul 19.
91 Growth of hormone-dependent MCF-7 breast cancer cells is promoted by constitutive caveolin-1 whose expression is lost in an EGF-R-mediated manner during development of tamoxifen resistance. Breast Cancer Res Treat. 2010 Feb;119(3):575-91. doi: 10.1007/s10549-009-0355-8. Epub 2009 Mar 15.
92 Effect of histamine H1 receptor antagonists on TARC/CCL17 and MDC/CCL22 production from CD14+ cells induced by antigenic stimulation in vitro. Int Arch Allergy Immunol. 2011;155(1):38-51. doi: 10.1159/000318720. Epub 2010 Nov 25.
93 SIRT3 Mediates the Antioxidant Effect of Hydrogen Sulfide in Endothelial Cells. Antioxid Redox Signal. 2016 Feb 20;24(6):329-43. doi: 10.1089/ars.2015.6331. Epub 2015 Nov 10.
94 Downregulation of mitogen-activated protein kinases (MAPKs) in chronic ethanol-induced fatty liver. Toxicol Mech Methods. 2020 Jul;30(6):407-416. doi: 10.1080/15376516.2020.1747126. Epub 2020 Apr 1.
95 A unique mechanism of beta-blocker action: carvedilol stimulates beta-arrestin signaling. Proc Natl Acad Sci U S A. 2007 Oct 16;104(42):16657-62. doi: 10.1073/pnas.0707936104. Epub 2007 Oct 9.
96 The stent-eluting drugs sirolimus and paclitaxel suppress healing of the endothelium by induction of autophagy. Am J Pathol. 2009 Nov;175(5):2226-34.
97 Modulation of apoptosis in HaCaT keratinocytes via differential regulation of ERK signaling pathway by flavonoids. J Biol Chem. 2005 Sep 9;280(36):31498-507. doi: 10.1074/jbc.M505537200. Epub 2005 Jul 13.
98 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.
99 Cannabidiol Modulates the Immunophenotype and Inhibits the Activation of the Inflammasome in Human Gingival Mesenchymal Stem Cells. Front Physiol. 2016 Nov 24;7:559. doi: 10.3389/fphys.2016.00559. eCollection 2016.