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

General Information of Drug (ID: DMKBJWP)

Drug Name
Caffeine Drug Info
Synonyms
CFF; Cafamil; Cafecon; Cafeina; Cafeine; Caffedrine; Caffein; Caffeina; Caffenium; Caffine; Cafipel; Coffein; Coffeine; Coffeinum; DHCplus; Dasin; Dexitac; Diurex; Durvitan; Enerjets; Ercatab; Guaranine; Hycomine; Kofein; Koffein; Mateina; Methyltheobromide; Methyltheobromine; Miudol; Nodaca; Organex; Percutafeine; Phensal; Stim; Teina; Thein; Theine; Tirend; Vivarin; Anacin Maximum Strength; Anhydrous caffeine; Caffedrine Caplets; Caffeina [Italian]; Caffeine Pure; Caffeine solution; Coffein [German]; Coffeinum N; Coffeinum Purrum; Component of Cafergot; DHC Plus; Dexitac Stay Alert Stimulant; Eldiatric C; GlaxoSmithKline Brand of Caffeine; Hycomine Compound; Keep Alert; Kofein [Czech]; Koffein [German]; Merck dura Brand of Caffeine; Methylxanthine theophylline; Midol Maximum Strength; Monomethyl derivative of Theophylline; Natural Caffeinum; Nix Nap; No Doz; Nodoz Maximum Strength Caplets; Passauer Brand of Caffeine; Percoffedrinol N; Pierre Fabre Brand of Caffeine; Quick Pep; Republic Drug Brand of Caffeine; Seid Brand of Caffeine; Theobromine Me; Theophylline Me; C 0750; Propoxyphene Compound 65; SK 65 Compound; TNP00310; Thompson Brand 1 of Caffeine; Thompson Brand 2 of Caffeine; Alert-pep; Anhydrous caffeine (JP15); Anhydrous caffeine (TN); Berlin-Chemie Brand of Caffeine; Bristol-Myers Squibb Brand of Caffeine; Cafcit (TN); Caffeine (USP); Caffeine (natural); Caffeine [BAN:JAN]; Caffeine, Monohydrate; Caffeine, anhydrous; Caffeine, synthetic; No-Doz; Pep-Back; Propoxyphene Compound-65; Quick-Pep; Refresh'n; SK-65 Compound; Tri-Aqua; Ultra Pep-Back; Wake-Up; CU-01000012617-3; P-A-C Analgesic Tablets; Theophylline, 7-methyl; Xanthine, 1,3,7-trimethyl; 1,3,7-Trimethyl-2,6-dioxopurine; 1,3,7-Trimethylpurine-2,6-dione; 1,3,7-Trimethylxanthine; 1-3-7-TRIMETHYLXANTHINE; 1-methyltheobromine; 3,7-dihydro-1,3,7-trimethyl-1H-purine; 7-Methyltheophylline
Indication
Disease Entry ICD 11 Status REF
Orthostatic hypotension BA21 Approved [1] , [2]
Therapeutic Class
Antihypertensive Agents
Cross-matching ID
PubChem CID
2519
ChEBI ID
CHEBI:27732
CAS Number
CAS 58-08-2
TTD Drug ID
DMKBJWP
VARIDT Drug ID
DR00593
INTEDE Drug ID
DR0257
ACDINA Drug ID
D00088

Molecule-Related Drug Atlas

Molecule-Related Drug Atlas
Molecule Type:
DTT
DME
Drug Status:
Approved Drug(s)
Clinical Trial Drug(s)
Download the Complete Related Drug List
Drug(s) Metabolized By Cytochrome P450 3A4 (CYP3A4)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Doxorubicin DMVP5YE Solid tumour/cancer 2A00-2F9Z Approved [13]
Progesterone DMUY35B Premature labour JB00 Approved [14]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [15]
Estradiol DMUNTE3 Breast cancer 2C60-2C65 Approved [16]
Acetaminophen DMUIE76 Pain MG30-MG3Z Approved [17]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [18]
Etoposide DMNH3PG Solid tumour/cancer 2A00-2F9Z Approved [19]
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [20]
Prasterone DM67VKL Chronic obstructive pulmonary disease CA22 Approved [14]
Verapamil DMA7PEW Hypertension BA00-BA04 Approved [9]
⏷ 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 Solid tumour/cancer 2A00-2F9Z Approved [21]
Dinoprostone DMTYOPD Medical abortion JA00.1Z Approved [22]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [23]
Estradiol DMUNTE3 Breast cancer 2C60-2C65 Approved [24]
Acetaminophen DMUIE76 Pain MG30-MG3Z Approved [25]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [26]
Etoposide DMNH3PG Solid tumour/cancer 2A00-2F9Z Approved [19]
Oxaliplatin DMQNWRD Colorectal cancer 2B91.Z Approved [27]
Verapamil DMA7PEW Hypertension BA00-BA04 Approved [28]
Diclofenac DMPIHLS Osteoarthritis FA00-FA05 Approved [29]
⏷ 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 Folate-deficiency anemia 3A02.Y Approved [30]
Procainamide DMNMXR8 Ventricular arrhythmias BC71 Approved [31]
Sulfamethoxazole DMB08GE Bacterial infection 1A00-1C4Z Approved [32]
Sulfadiazine DMTW3R8 Rheumatic fever 1B40-1B42 Approved [33]
Tobramycin DMUI0CH Bacterial infection 1A00-1C4Z Approved [34]
Mesalazine DMOL5IU Ulcerative colitis DD71 Approved [35]
Allopurinol DMLPAOB Hyperuricaemia 5C55.Y Approved [36]
Netilmicin DMRD1QK Bacterial infection 1A00-1C4Z Approved [37]
Clonazepam DMTO13J Epilepsy 8A60-8A68 Approved [38]
Hydralazine DMU8JGH Hypertension BA00-BA04 Approved [39]
⏷ 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 Solid tumour/cancer 2A00-2F9Z Approved [40]
Progesterone DMUY35B Premature labour JB00 Approved [41]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [42]
Acetaminophen DMUIE76 Pain MG30-MG3Z Approved [17]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [9]
Quinine DMSWYF5 Malaria 1F40-1F45 Approved [43]
Propofol DMB4OLE Anaesthesia 9A78.6 Approved [44]
Dopamine DMPGUCF Parkinson disease 8A00.0 Approved [45]
Nicotine DMWX5CO Nicotine dependence 6C4A.2 Approved [46]
Propranolol DM79NTF Migraine 8A80 Approved [47]
⏷ 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 Folate-deficiency anemia 3A02.Y Approved [48]
Cisplatin DMRHGI9 Solid tumour/cancer 2A00-2F9Z Approved [49]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [50]
Acetaminophen DMUIE76 Pain MG30-MG3Z Approved [51]
Etoposide DMNH3PG Solid tumour/cancer 2A00-2F9Z Approved [52]
Oxaliplatin DMQNWRD Colorectal cancer 2B91.Z Approved [27]
Verapamil DMA7PEW Hypertension BA00-BA04 Approved [53]
Estrone DM5T6US Menopausal and postmenopausal disorder GA30 Approved [54]
Propofol DMB4OLE Anaesthesia 9A78.6 Approved [55]
Ethanol DMDRQZU Chronic pain MG30 Approved [56]
⏷ 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 Solid tumour/cancer 2A00-2F9Z Approved [21]
Estradiol DMUNTE3 Breast cancer 2C60-2C65 Approved [57]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [57]
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [53]
Verapamil DMA7PEW Hypertension BA00-BA04 Approved [58]
Diclofenac DMPIHLS Osteoarthritis FA00-FA05 Approved [59]
Sorafenib DMS8IFC Hepatocellular carcinoma 2C12.02 Approved [60]
Quinine DMSWYF5 Malaria 1F40-1F45 Approved [57]
Mycophenolate mofetil DMPQAGE Organ transplant rejection NE84 Approved [61]
Propofol DMB4OLE Anaesthesia 9A78.6 Approved [62]
⏷ 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 Premature labour JB00 Approved [63]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [64]
Estradiol DMUNTE3 Breast cancer 2C60-2C65 Approved [65]
Acetaminophen DMUIE76 Pain MG30-MG3Z Approved [53]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [66]
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [53]
Verapamil DMA7PEW Hypertension BA00-BA04 Approved [67]
Diclofenac DMPIHLS Osteoarthritis FA00-FA05 Approved [68]
Estrone DM5T6US Menopausal and postmenopausal disorder GA30 Approved [69]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [70]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Metabolized By Cytochrome P450 1B1 (CYP1B1)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Progesterone DMUY35B Premature labour JB00 Approved [71]
Estradiol DMUNTE3 Breast cancer 2C60-2C65 Approved [72]
Oxaliplatin DMQNWRD Colorectal cancer 2B91.Z Approved [27]
Estrone DM5T6US Menopausal and postmenopausal disorder GA30 Approved [73]
Erythromycin DM4K7GQ Bacterial infection 1A00-1C4Z Approved [74]
Rosuvastatin DMMIQ7G Hypercholesterolaemia 5C80.0 Approved [75]
Vitamin A DMJ2AH4 Night blindness 9D45 Approved [76]
Melatonin DMKWFBT Insomnia 7A00-7A0Z Approved [77]
Theophylline DMRJFN9 Chronic obstructive pulmonary disease CA22 Approved [10]
Flutamide DMK0O7U Prostate cancer 2C82.0 Approved [78]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Targeting Adenosine A2a receptor (ADORA2A)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Istradefylline DM20VSK Parkinson disease 8A00.0 Approved [79]
Regadenoson DM76VHG Radionuclide imaging N.A. Approved [80]
Tozadenant DMATC14 Parkinson disease 8A00.0 Phase 3 [81]
Binodenoson DMVHF8G Hypertension BA00-BA04 Phase 3 [82]
Apadenoson DMD8QTC Coronary artery disease BA80 Phase 3 [83]
Tonapofylline DMBH316 Acute and chronic heart failure BD1Z Phase 2 [84]
Dexefaroxan DMTY4KN Parkinson disease 8A00.0 Phase 2 [85]
AMP-579 DMJ4GPR Hyperlipidaemia 5C80 Phase 2 [86]
BIIB014 DMH7RJ1 Parkinson disease 8A00.0 Phase 2 [87]
MRE-0094 DMQR23W Diabetic foot ulcer BD54 Phase 2 [88]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Targeting Adenosine A1 receptor (ADORA1)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Rolofylline DMSZPR3 Heart failure BD10-BD13 Phase 3 [89]
Tonapofylline DMBH316 Acute and chronic heart failure BD1Z Phase 2 [84]
AMP-579 DMJ4GPR Hyperlipidaemia 5C80 Phase 2 [86]
SELODENOSON DMQM3IX Cardiac arrhythmias BC9Z Phase 2 [90]
Apaxifylline DMQMV9F Cognitive impairment 6D71 Phase 2 [91]
SLV320 DM867BJ Heart failure BD10-BD13 Phase 2 [92]
DTI-0009 DMV84OK Atrial fibrillation BC81.3 Phase 2 [90]
Capadenoson DMYWO62 Atrial fibrillation BC81.3 Phase 2 [93]
BAY 1067197 DM4JGNH Heart failure BD10-BD13 Phase 2 [94]
INO-8875 DMKNA94 Glaucoma/ocular hypertension 9C61 Phase 1/2 [95]
⏷ 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
Adenosine A1 receptor (ADORA1) TTK25J1 AA1R_HUMAN Antagonist [3] , [4]
Adenosine A2a receptor (ADORA2A) TTM2AOE AA2AR_HUMAN Antagonist [3] , [4]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4) DE4LYSA CP3A4_HUMAN Substrate [5]
Cytochrome P450 2E1 (CYP2E1) DEVDYN7 CP2E1_HUMAN Substrate [6]
Cytochrome P450 2D6 (CYP2D6) DECB0K3 CP2D6_HUMAN Substrate [7]
Cytochrome P450 2C9 (CYP2C9) DE5IED8 CP2C9_HUMAN Substrate [8]
Cytochrome P450 1A2 (CYP1A2) DEJGDUW CP1A2_HUMAN Substrate [9]
Cytochrome P450 1B1 (CYP1B1) DE9QHP6 CP1B1_HUMAN Substrate [10]
Cytochrome P450 2C8 (CYP2C8) DES5XRU CP2C8_HUMAN Substrate [11]
RNA cytidine acetyltransferase (hALP) DEZV4AP NAT10_HUMAN Substrate [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: 407).
2 Fatigue: an overview. Am Fam Physician. 2008 Nov 15;78(10):1173-9.
3 Caffeine as a psychomotor stimulant: mechanism of action. Cell Mol Life Sci. 2004 Apr;61(7-8):857-72.
4 Adenosine receptor antagonists intensify the benzodiazepine withdrawal signs in mice. Pharmacol Rep. 2006 Sep-Oct;58(5):643-51.
5 Effect of cytochrome P450 (CYP) inducers on caffeine metabolism in the rat. Pharmacol Rep. 2007 May-Jun;59(3):296-305.
6 CYP2E1 active site residues in substrate recognition sequence 5 identified by photoaffinity labeling and homology modeling. Arch Biochem Biophys. 2007 Mar 1;459(1):59-69.
7 Determinants of interindividual variability and extent of CYP2D6 and CYP1A2 inhibition by paroxetine and fluvoxamine in vivo. J Clin Psychopharmacol. 1998 Jun;18(3):198-207.
8 Monkey liver cytochrome P450 2C9 is involved in caffeine 7-N-demethylation to form theophylline. Xenobiotica. 2013 Dec;43(12):1037-42.
9 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.
10 Oxidation of xenobiotics by recombinant human cytochrome P450 1B1. Drug Metab Dispos. 1997 May;25(5):617-22.
11 PharmGKB summary: caffeine pathway. Pharmacogenet Genomics. 2012 May;22(5):389-95.
12 A population and family study of N-acetyltransferase using caffeine urinary metabolites. Clin Pharmacol Ther. 1993 Aug;54(2):134-41.
13 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.
14 Contribution of human hepatic cytochrome P450 isoforms to regioselective hydroxylation of steroid hormones. Xenobiotica. 1998 Jun;28(6):539-47.
15 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.
16 Isoform-specific regulation of cytochromes P450 expression by estradiol and progesterone. Drug Metab Dispos. 2013 Feb;41(2):263-9.
17 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.
18 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.
19 Effects of morin on the pharmacokinetics of etoposide in rats. Biopharm Drug Dispos. 2007 Apr;28(3):151-6.
20 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.
21 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.
22 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.
23 Endoxifen and other metabolites of tamoxifen inhibit human hydroxysteroid sulfotransferase 2A1 (hSULT2A1). Drug Metab Dispos. 2014 Nov;42(11):1843-50.
24 Cytochrome P450 1A2 (CYP1A2) activity and risk factors for breast cancer: a cross-sectional study. Breast Cancer Res. 2004;6(4):R352-65.
25 PharmGKB summary: pathways of acetaminophen metabolism at the therapeutic versus toxic doses. Pharmacogenet Genomics. 2015 Aug;25(8):416-26.
26 The effect of apigenin on pharmacokinetics of imatinib and its metabolite N-desmethyl imatinib in rats. Biomed Res Int. 2013;2013:789184.
27 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.
28 Identification of P450 enzymes involved in metabolism of verapamil in humans. Naunyn Schmiedebergs Arch Pharmacol. 1993 Sep;348(3):332-7.
29 Metabolism and metabolic inhibition of xanthotoxol in human liver microsomes. Evid Based Complement Alternat Med. 2016;2016:5416509.
30 Arylamine N-acetyltransferase in human red blood cells. Biochem Pharmacol. 1992 Sep 25;44(6):1099-104.
31 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.
32 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.
33 Identification of cytochrome P450 and arylamine N-acetyltransferase isoforms involved in sulfadiazine metabolism. Drug Metab Dispos. 2005 Jul;33(7):969-76.
34 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.
35 NAT1 genotypes do not predict response to mesalamine in patients with ulcerative colitis. Z Gastroenterol. 2008 Mar;46(3):259-65.
36 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.
37 Aminoglycoside resistance resulting from tight drug binding to an altered aminoglycoside acetyltransferase. Antimicrob Agents Chemother. 2003 May;47(5):1577-83.
38 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.
39 Prizidilol, an antihypertensive with precapillary vasodilator and beta-adrenoceptor blocking actions, in primary hypertension. Clin Pharmacol Ther. 1981 May;29(5):588-93.
40 Inhibitory effects of anticancer drugs on dextromethorphan-O-demethylase activity in human liver microsomes. Cancer Chemother Pharmacol. 1993;32(6):491-5.
41 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.
42 CYP2D6 polymorphisms and tamoxifen metabolism: clinical relevance. Curr Oncol Rep. 2010 Jan;12(1):7-15.
43 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.
44 Effects of propofol on human hepatic microsomal cytochrome P450 activities. Xenobiotica. 1998 Sep;28(9):845-53.
45 Pharmacogenetics of schizophrenia. Am J Med Genet. 2000 Spring;97(1):98-106.
46 Roles of CYP2A6 and CYP2B6 in nicotine C-oxidation by human liver microsomes. Arch Toxicol. 1999 Mar;73(2):65-70.
47 Structure-activity relationship for human cytochrome P450 substrates and inhibitors. Drug Metab Rev. 2002 Feb-May;34(1-2):69-82.
48 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.
49 Cytochrome P450 2E1 null mice provide novel protection against cisplatin-induced nephrotoxicity and apoptosis. Kidney Int. 2003 May;63(5):1687-96.
50 Genotoxicity of tamoxifen, tamoxifen epoxide and toremifene in human lymphoblastoid cells containing human cytochrome P450s. Carcinogenesis. 1994 Jan;15(1):5-9.
51 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.
52 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.
53 Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.
54 Novel metabolic pathway of estrone and 17beta-estradiol catalyzed by cytochrome P-450. Drug Metab Dispos. 2000 Feb;28(2):110-2.
55 Inhibition of cytochrome P450 2E1 by propofol in human and porcine liver microsomes. Biochem Pharmacol. 2002 Oct 1;64(7):1151-6.
56 CYP2E1 and clinical features in alcoholics. Neuropsychobiology. 2003;47(2):86-9.
57 Role of cytochrome P450 2C8 in drug metabolism and interactions. Pharmacol Rev. 2016 Jan;68(1):168-241.
58 Differential expression and function of CYP2C isoforms in human intestine and liver. Pharmacogenetics. 2003 Sep;13(9):565-75.
59 Analysis of human cytochrome P450 2C8 substrate specificity using a substrate pharmacophore and site-directed mutants. Biochemistry. 2004 Dec 14;43(49):15379-92.
60 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.
61 PharmGKB summary: mycophenolic acid pathway. Pharmacogenet Genomics. 2014 Jan;24(1):73-9.
62 Possible involvement of multiple human cytochrome P450 isoforms in the liver metabolism of propofol. Br J Anaesth. 1998 Jun;80(6):788-95.
63 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.
64 Tamoxifen inhibits cytochrome P450 2C9 activity in breast cancer patients. J Chemother. 2006 Aug;18(4):421-4.
65 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.
66 Drug-drug interactions with imatinib: an observational study. Medicine (Baltimore). 2016 Oct;95(40):e5076.
67 Drug interactions with calcium channel blockers: possible involvement of metabolite-intermediate complexation with CYP3A. Drug Metab Dispos. 2000 Feb;28(2):125-30.
68 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.
69 A potential role for the estrogen-metabolizing cytochrome P450 enzymes in human breast carcinogenesis. Breast Cancer Res Treat. 2003 Dec;82(3):191-7.
70 A mechanistic approach to antiepileptic drug interactions. Ann Pharmacother. 1998 May;32(5):554-63.
71 Catalytic properties of polymorphic human cytochrome P450 1B1 variants. Carcinogenesis. 1999 Aug;20(8):1607-13.
72 Cytochrome P450 isoforms catalyze formation of catechol estrogen quinones that react with DNA. Metabolism. 2007 Jul;56(7):887-94.
73 A common CYP1B1 polymorphism is associated with 2-OHE1/16-OHE1 urinary estrone ratio. Clin Chem Lab Med. 2005;43(7):702-6.
74 Cytochromes P450 in crustacea. Comp Biochem Physiol C Pharmacol Toxicol Endocrinol. 1998 Nov;121(1-3):157-72.
75 Pharmacokinetics of rosuvastatin when coadministered with rifampicin in healthy males: a randomized, single-blind, placebo-controlled, crossover study. Clin Ther. 2008 Jul;30(7):1283-9.
76 Metabolism of retinoids and arachidonic acid by human and mouse cytochrome P450 1b1. Drug Metab Dispos. 2004 Aug;32(8):840-7.
77 Metabolism of melatonin by human cytochromes p450. Drug Metab Dispos. 2005 Apr;33(4):489-94.
78 Human CYP1B1 and anticancer agent metabolism: mechanism for tumor-specific drug inactivation? J Pharmacol Exp Ther. 2001 Feb;296(2):537-41.
79 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health Human Services. 2019
80 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
81 Tozadenant (SYN115) in patients with Parkinson's disease who have motor fluctuations on levodopa: a phase 2b, double-blind, randomised trial. Lancet Neurol. 2014 Aug;13(8):767-76.
82 Coronary circulation responses to binodenoson, a selective adenosine A2A receptor agonist. Am J Cardiol. 2007 Jun 1;99(11):1507-12.
83 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: 3290).
84 2-Amino-5-benzoyl-4-phenylthiazoles: Development of potent and selective adenosine A1 receptor antagonists. Bioorg Med Chem. 2010 Mar 15;18(6):2195-2203.
85 The pipeline and future of drug development in schizophrenia. Mol Psychiatry. 2007 Oct;12(10):904-22.
86 Adenosine A1/A2a receptor agonist AMP-579 induces acute and delayed preconditioning against in vivo myocardial stunning. Am J Physiol Heart Circ Physiol. 2004 Dec;287(6):H2746-53.
87 Novel pharmacological targets for the treatment of Parkinson's disease. Nat Rev Drug Discov. 2006 Oct;5(10):845-54.
88 Emerging drugs for diabetic foot ulcers. Expert Opin Emerg Drugs. 2006 Nov;11(4):709-24.
89 Association between the PDE4D gene and ischaemic stroke in the Chinese Han population. Clin Sci (Lond). 2009 Aug 17;117(7):265-72.
90 Recent developments in adenosine receptor ligands and their potential as novel drugs. Biochim Biophys Acta. 2011 May;1808(5):1290-308.
91 Trusted, scientifically sound profiles of drug programs, clinical trials, safety reports, and company deals, written by scientists. Springer. 2015. Adis Insight (drug id 800004779)
92 Role of matrix metalloproteinases and their tissue inhibitors as potential biomarkers of left ventricular remodelling in the athlete's heart. Clin Sci (Lond). 2009 Jul 16;117(4):157-64.
93 A1 adenosine receptor agonists and their potential therapeutic applications. Expert Opin Investig Drugs. 2008 Dec;17(12):1901-10.
94 Separation of on-target efficacy from adverse effects through rational design of a bitopic adenosine receptor agonist. Current Issue vol. 111 no. 12 Celine Valant, 4614-4619.
95 INO-8875, a highly selective A1 adenosine receptor agonist: evaluation of chronotropic, dromotropic, and hemodynamic effects in rats. J Pharmacol Exp Ther. 2013 Jan;344(1):59-67.