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
Allergic rhinitis	CA08.0	Approved	[1]
Back pain	ME84.Z	Approved	[1]
Cluster headache	8A81.0	Approved	[1]
Common cold	CA00	Approved	[1]
Dysmenorrhea	GA34.3	Approved	[1]
Headache	8A80-8A84	Approved	[1]
Migraine disorder		Approved	[1]
Orthostatic hypotension	BA21	Approved	[2]
Pain	MG30-MG3Z	Approved	[1]

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 Type:

DTT

DME

DOT

Drug Status:

Approved Drug(s)

Clinical Trial Drug(s)

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Drug(s) Targeting Adenosine A2a receptor (ADORA2A)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Istradefylline	DM20VSK	Parkinson disease	8A00.0	Approved	[14]
Regadenoson	DM76VHG	Radionuclide imaging	N.A.	Approved	[15]
Tozadenant	DMATC14	Parkinson disease	8A00.0	Phase 3	[16]
Binodenoson	DMVHF8G	Hypertension	BA00-BA04	Phase 3	[17]
Apadenoson	DMD8QTC	Coronary artery disease	BA80	Phase 3	[18]
Tonapofylline	DMBH316	Acute and chronic heart failure	BD1Z	Phase 2	[19]
Dexefaroxan	DMTY4KN	Parkinson disease	8A00.0	Phase 2	[20]
AMP-579	DMJ4GPR	Hyperlipidaemia	5C80	Phase 2	[21]
BIIB014	DMH7RJ1	Parkinson disease	8A00.0	Phase 2	[22]
MRE-0094	DMQR23W	Diabetic foot ulcer	BD54	Phase 2	[23]
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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	[24]
Tonapofylline	DMBH316	Acute and chronic heart failure	BD1Z	Phase 2	[19]
AMP-579	DMJ4GPR	Hyperlipidaemia	5C80	Phase 2	[21]
SELODENOSON	DMQM3IX	Cardiac arrhythmias	BC9Z	Phase 2	[25]
Apaxifylline	DMQMV9F	Cognitive impairment	6D71	Phase 2	[26]
SLV320	DM867BJ	Heart failure	BD10-BD13	Phase 2	[27]
DTI-0009	DMV84OK	Atrial fibrillation	BC81.3	Phase 2	[25]
Capadenoson	DMYWO62	Atrial fibrillation	BC81.3	Phase 2	[28]
BAY 1067197	DM4JGNH	Heart failure	BD10-BD13	Phase 2	[29]
INO-8875	DMKNA94	Glaucoma/ocular hypertension	9C61	Phase 1/2	[30]
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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	[31]
Progesterone	DMUY35B	Amenorrhea	GA20.0	Approved	[32]
Tamoxifen	DMLB0EZ	Breast cancer	2C60-2C65	Approved	[33]
Estradiol	DMUNTE3	Acne vulgaris	ED80	Approved	[34]
Acetaminophen	DMUIE76	Allergic rhinitis	CA08.0	Approved	[35]
Imatinib	DM7RJXL	Acute lymphoblastic leukaemia	2A85	Approved	[36]
Etoposide	DMNH3PG	Acute myelogenous leukaemia	2A41	Approved	[37]
Zidovudine	DM4KI7O	Human immunodeficiency virus infection	1C62	Approved	[38]
Prasterone	DM67VKL	Chronic obstructive pulmonary disease	CA22	Approved	[32]
Verapamil	DMA7PEW	Angina pectoris	BA40	Approved	[8]
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Drug(s) Metabolized By Cytochrome P450 1A2 (CYP1A2)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Fluorouracil	DMUM7HZ	Adenocarcinoma	2D40	Approved	[39]
Dinoprostone	DMTYOPD	Medical abortion	JA00.1Z	Approved	[40]
Tamoxifen	DMLB0EZ	Breast cancer	2C60-2C65	Approved	[41]
Estradiol	DMUNTE3	Acne vulgaris	ED80	Approved	[42]
Acetaminophen	DMUIE76	Allergic rhinitis	CA08.0	Approved	[43]
Imatinib	DM7RJXL	Acute lymphoblastic leukaemia	2A85	Approved	[44]
Etoposide	DMNH3PG	Acute myelogenous leukaemia	2A41	Approved	[37]
Oxaliplatin	DMQNWRD	Adenocarcinoma	2D40	Approved	[45]
Verapamil	DMA7PEW	Angina pectoris	BA40	Approved	[46]
Diclofenac	DMPIHLS	Chronic renal failure	GB61.Z	Approved	[47]
Zolmitriptan	DM1IB4Q	Migraine	8A80	Approved	[97]
Rofecoxib	DM3P5DA	Osteoarthritis	FA00-FA05	Approved	[97]
Etoricoxib	DM6A4NW	Rheumatoid arthritis	FA20	Approved	[97]
Capsaicin	DMGMF6V	Back pain	ME84.Z	Approved	[98]
Hesperetin	DMKER83	High blood cholesterol level	5C80.00	Approved	[99]
Stiripentol	DMMSDOY	Dravet syndrome	8A61.11	Approved	[100]
Nifedipine	DMSVOZT	Angina pectoris	BA40	Approved	[101]
Zileuton	DMVRIC2	Allergic asthma	CA23.0	Approved	[102]
Nicotine	DMWX5CO	Lung cancer	2C25.0	Approved	[103]
Clonidine	DM6RZ9Q	Attention deficit hyperactivity disorder	6A05.Z	Approved	[13]
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Drug(s) Metabolized By RNA cytidine acetyltransferase (hALP)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Folic Acid	DMEMBJC	Colorectal carcinoma		Approved	[48]
Procainamide	DMNMXR8	Ventricular arrhythmias	BC71	Approved	[49]
Sulfamethoxazole	DMB08GE	Acute otitis media	AB00	Approved	[50]
Sulfadiazine	DMTW3R8	Rheumatic fever	1B40-1B42	Approved	[51]
Tobramycin	DMUI0CH	Bacteremia	1A73	Approved	[52]
Mesalazine	DMOL5IU	Diverticulitis		Approved	[53]
Allopurinol	DMLPAOB	Gout	FA25	Approved	[54]
Netilmicin	DMRD1QK	Bacterial infection	1A00-1C4Z	Approved	[55]
Clonazepam	DMTO13J	Absence epilepsy		Approved	[56]
Hydralazine	DMU8JGH	Chronic heart failure	BD1Z	Approved	[57]
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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	[35]
Imatinib	DM7RJXL	Acute lymphoblastic leukaemia	2A85	Approved	[8]
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]
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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	[68]
Acetaminophen	DMUIE76	Allergic rhinitis	CA08.0	Approved	[69]
Etoposide	DMNH3PG	Acute myelogenous leukaemia	2A41	Approved	[70]
Oxaliplatin	DMQNWRD	Adenocarcinoma	2D40	Approved	[45]
Verapamil	DMA7PEW	Angina pectoris	BA40	Approved	[71]
Estrone	DM5T6US	Acne vulgaris	ED80	Approved	[72]
Propofol	DMB4OLE	Anaesthesia	9A78.6	Approved	[73]
Ethanol	DMDRQZU	Chronic pain	MG30	Approved	[74]
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Drug(s) Metabolized By Cytochrome P450 2C8 (CYP2C8)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Fluorouracil	DMUM7HZ	Adenocarcinoma	2D40	Approved	[39]
Estradiol	DMUNTE3	Acne vulgaris	ED80	Approved	[75]
Imatinib	DM7RJXL	Acute lymphoblastic leukaemia	2A85	Approved	[75]
Zidovudine	DM4KI7O	Human immunodeficiency virus infection	1C62	Approved	[71]
Verapamil	DMA7PEW	Angina pectoris	BA40	Approved	[76]
Diclofenac	DMPIHLS	Chronic renal failure	GB61.Z	Approved	[77]
Sorafenib	DMS8IFC	Adenocarcinoma	2D40	Approved	[78]
Quinine	DMSWYF5	Malaria	1F40-1F45	Approved	[75]
Mycophenolate mofetil	DMPQAGE	Hepatosplenic T-cell lymphoma		Approved	[79]
Propofol	DMB4OLE	Anaesthesia	9A78.6	Approved	[80]
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Drug(s) Metabolized By Cytochrome P450 2C9 (CYP2C9)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Progesterone	DMUY35B	Amenorrhea	GA20.0	Approved	[81]
Tamoxifen	DMLB0EZ	Breast cancer	2C60-2C65	Approved	[82]
Estradiol	DMUNTE3	Acne vulgaris	ED80	Approved	[83]
Acetaminophen	DMUIE76	Allergic rhinitis	CA08.0	Approved	[71]
Imatinib	DM7RJXL	Acute lymphoblastic leukaemia	2A85	Approved	[84]
Zidovudine	DM4KI7O	Human immunodeficiency virus infection	1C62	Approved	[71]
Verapamil	DMA7PEW	Angina pectoris	BA40	Approved	[85]
Diclofenac	DMPIHLS	Chronic renal failure	GB61.Z	Approved	[86]
Estrone	DM5T6US	Acne vulgaris	ED80	Approved	[87]
Valproate	DMCFE9I	Epilepsy	8A60-8A68	Approved	[88]
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Drug(s) Metabolized By Cytochrome P450 1B1 (CYP1B1)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Progesterone	DMUY35B	Amenorrhea	GA20.0	Approved	[89]
Estradiol	DMUNTE3	Acne vulgaris	ED80	Approved	[90]
Oxaliplatin	DMQNWRD	Adenocarcinoma	2D40	Approved	[45]
Estrone	DM5T6US	Acne vulgaris	ED80	Approved	[91]
Erythromycin	DM4K7GQ	Acne vulgaris	ED80	Approved	[92]
Rosuvastatin	DMMIQ7G	Arteriosclerosis	BD40	Approved	[93]
Vitamin A	DMJ2AH4	Night blindness	9D45	Approved	[94]
Melatonin	DMKWFBT	Depression	6A70-6A7Z	Approved	[95]
Theophylline	DMRJFN9	Bronchitis	CA20	Approved	[9]
Flutamide	DMK0O7U	Prostate cancer	2C82.0	Approved	[96]
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Drug(s) Affected By Metallothionein-1A (MT1A)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Cisplatin	DMRHGI9	Adenocarcinoma	2D40	Approved	[104]
Salicyclic acid	DM2F8XZ	Acne vulgaris	ED80	Approved	[105]
Arsenic trioxide	DM61TA4	Acute lymphoblastic leukaemia	2A85	Approved	[106]
Marinol	DM70IK5	Anorexia nervosa cachexia	6B80	Approved	[107]
Valproate	DMCFE9I	Epilepsy	8A60-8A68	Approved	[108]
Zoledronate	DMIXC7G	Adenocarcinoma	2D40	Approved	[109]
Benzoic Acid	DMKB9FI	Alopecia areata	ED70.2	Approved	[105]
Sodium lauryl sulfate	DMLJ634	Constipation	DD91.1	Approved	[105]
Dexamethasone	DMMWZET	Acute adrenal insufficiency		Approved	[110]
Cupric Sulfate	DMP0NFQ	Fungal infection	1F29-1F2F	Approved	[111]
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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]
Adenosine A2a receptor (ADORA2A)	TTM2AOE	AA2AR_HUMAN	Antagonist	[3]

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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	[7]
Cytochrome P450 1A2 (CYP1A2)	DEJGDUW	CP1A2_HUMAN	Substrate	[8]
Cytochrome P450 1B1 (CYP1B1)	DE9QHP6	CP1B1_HUMAN	Substrate	[9]
Cytochrome P450 2C8 (CYP2C8)	DES5XRU	CP2C8_HUMAN	Substrate	[10]
RNA cytidine acetyltransferase (hALP)	DEZV4AP	NAT10_HUMAN	Substrate	[11]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Cytochrome P450 1A2 (CYP1A2)	OTLLBX48	CP1A2_HUMAN	Drug Response	[12]
Metallothionein-1A (MT1A)	OTKBH52X	MT1A_HUMAN	Drug Response	[13]

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References

1	Caffeine 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: 407).
3	Caffeine as a psychomotor stimulant: mechanism of action. Cell Mol Life Sci. 2004 Apr;61(7-8):857-72.
4	Effect of cytochrome P450 (CYP) inducers on caffeine metabolism in the rat. Pharmacol Rep. 2007 May-Jun;59(3):296-305.
5	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.
6	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.
7	Monkey liver cytochrome P450 2C9 is involved in caffeine 7-N-demethylation to form theophylline. Xenobiotica. 2013 Dec;43(12):1037-42.
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	Oxidation of xenobiotics by recombinant human cytochrome P450 1B1. Drug Metab Dispos. 1997 May;25(5):617-22.
10	PharmGKB summary: caffeine pathway. Pharmacogenet Genomics. 2012 May;22(5):389-95.
11	A population and family study of N-acetyltransferase using caffeine urinary metabolites. Clin Pharmacol Ther. 1993 Aug;54(2):134-41.
12	Coffee, CYP1A2 genotype, and risk of myocardial infarction. JAMA. 2006 Mar 8;295(10):1135-41. doi: 10.1001/jama.295.10.1135.
13	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.
14	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health Human Services. 2019
15	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
16	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.
17	Coronary circulation responses to binodenoson, a selective adenosine A2A receptor agonist. Am J Cardiol. 2007 Jun 1;99(11):1507-12.
18	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).
19	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.
20	The pipeline and future of drug development in schizophrenia. Mol Psychiatry. 2007 Oct;12(10):904-22.
21	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.
22	Novel pharmacological targets for the treatment of Parkinson's disease. Nat Rev Drug Discov. 2006 Oct;5(10):845-54.
23	Emerging drugs for diabetic foot ulcers. Expert Opin Emerg Drugs. 2006 Nov;11(4):709-24.
24	Association between the PDE4D gene and ischaemic stroke in the Chinese Han population. Clin Sci (Lond). 2009 Aug 17;117(7):265-72.
25	Recent developments in adenosine receptor ligands and their potential as novel drugs. Biochim Biophys Acta. 2011 May;1808(5):1290-308.
26	Trusted, scientifically sound profiles of drug programs, clinical trials, safety reports, and company deals, written by scientists. Springer. 2015. Adis Insight (drug id 800004779)
27	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.
28	A1 adenosine receptor agonists and their potential therapeutic applications. Expert Opin Investig Drugs. 2008 Dec;17(12):1901-10.
29	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.
30	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.
31	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.
32	Contribution of human hepatic cytochrome P450 isoforms to regioselective hydroxylation of steroid hormones. Xenobiotica. 1998 Jun;28(6):539-47.
33	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.
34	Isoform-specific regulation of cytochromes P450 expression by estradiol and progesterone. Drug Metab Dispos. 2013 Feb;41(2):263-9.
35	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.
36	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.
37	Effects of morin on the pharmacokinetics of etoposide in rats. Biopharm Drug Dispos. 2007 Apr;28(3):151-6.
38	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.
39	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.
40	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.
41	Endoxifen and other metabolites of tamoxifen inhibit human hydroxysteroid sulfotransferase 2A1 (hSULT2A1). Drug Metab Dispos. 2014 Nov;42(11):1843-50.
42	Cytochrome P450 1A2 (CYP1A2) activity and risk factors for breast cancer: a cross-sectional study. Breast Cancer Res. 2004;6(4):R352-65.
43	PharmGKB summary: pathways of acetaminophen metabolism at the therapeutic versus toxic doses. Pharmacogenet Genomics. 2015 Aug;25(8):416-26.
44	The effect of apigenin on pharmacokinetics of imatinib and its metabolite N-desmethyl imatinib in rats. Biomed Res Int. 2013;2013:789184.
45	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.
46	Identification of P450 enzymes involved in metabolism of verapamil in humans. Naunyn Schmiedebergs Arch Pharmacol. 1993 Sep;348(3):332-7.
47	Metabolism and metabolic inhibition of xanthotoxol in human liver microsomes. Evid Based Complement Alternat Med. 2016;2016:5416509.
48	Arylamine N-acetyltransferase in human red blood cells. Biochem Pharmacol. 1992 Sep 25;44(6):1099-104.
49	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.
50	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.
51	Identification of cytochrome P450 and arylamine N-acetyltransferase isoforms involved in sulfadiazine metabolism. Drug Metab Dispos. 2005 Jul;33(7):969-76.
52	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.
53	NAT1 genotypes do not predict response to mesalamine in patients with ulcerative colitis. Z Gastroenterol. 2008 Mar;46(3):259-65.
54	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.
55	Aminoglycoside resistance resulting from tight drug binding to an altered aminoglycoside acetyltransferase. Antimicrob Agents Chemother. 2003 May;47(5):1577-83.
56	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.
57	Prizidilol, an antihypertensive with precapillary vasodilator and beta-adrenoceptor blocking actions, in primary hypertension. Clin Pharmacol Ther. 1981 May;29(5):588-93.
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	Genotoxicity of tamoxifen, tamoxifen epoxide and toremifene in human lymphoblastoid cells containing human cytochrome P450s. Carcinogenesis. 1994 Jan;15(1):5-9.
69	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.
70	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.
71	Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.
72	Novel metabolic pathway of estrone and 17beta-estradiol catalyzed by cytochrome P-450. Drug Metab Dispos. 2000 Feb;28(2):110-2.
73	Inhibition of cytochrome P450 2E1 by propofol in human and porcine liver microsomes. Biochem Pharmacol. 2002 Oct 1;64(7):1151-6.
74	CYP2E1 and clinical features in alcoholics. Neuropsychobiology. 2003;47(2):86-9.
75	Role of cytochrome P450 2C8 in drug metabolism and interactions. Pharmacol Rev. 2016 Jan;68(1):168-241.
76	Differential expression and function of CYP2C isoforms in human intestine and liver. Pharmacogenetics. 2003 Sep;13(9):565-75.
77	Analysis of human cytochrome P450 2C8 substrate specificity using a substrate pharmacophore and site-directed mutants. Biochemistry. 2004 Dec 14;43(49):15379-92.
78	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.
79	PharmGKB summary: mycophenolic acid pathway. Pharmacogenet Genomics. 2014 Jan;24(1):73-9.
80	Possible involvement of multiple human cytochrome P450 isoforms in the liver metabolism of propofol. Br J Anaesth. 1998 Jun;80(6):788-95.
81	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.
82	Tamoxifen inhibits cytochrome P450 2C9 activity in breast cancer patients. J Chemother. 2006 Aug;18(4):421-4.
83	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.
84	Drug-drug interactions with imatinib: an observational study. Medicine (Baltimore). 2016 Oct;95(40):e5076.
85	Drug interactions with calcium channel blockers: possible involvement of metabolite-intermediate complexation with CYP3A. Drug Metab Dispos. 2000 Feb;28(2):125-30.
86	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.
87	A potential role for the estrogen-metabolizing cytochrome P450 enzymes in human breast carcinogenesis. Breast Cancer Res Treat. 2003 Dec;82(3):191-7.
88	A mechanistic approach to antiepileptic drug interactions. Ann Pharmacother. 1998 May;32(5):554-63.
89	Catalytic properties of polymorphic human cytochrome P450 1B1 variants. Carcinogenesis. 1999 Aug;20(8):1607-13.
90	Cytochrome P450 isoforms catalyze formation of catechol estrogen quinones that react with DNA. Metabolism. 2007 Jul;56(7):887-94.
91	A common CYP1B1 polymorphism is associated with 2-OHE1/16-OHE1 urinary estrone ratio. Clin Chem Lab Med. 2005;43(7):702-6.
92	Cytochromes P450 in crustacea. Comp Biochem Physiol C Pharmacol Toxicol Endocrinol. 1998 Nov;121(1-3):157-72.
93	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.
94	Metabolism of retinoids and arachidonic acid by human and mouse cytochrome P450 1b1. Drug Metab Dispos. 2004 Aug;32(8):840-7.
95	Metabolism of melatonin by human cytochromes p450. Drug Metab Dispos. 2005 Apr;33(4):489-94.
96	Human CYP1B1 and anticancer agent metabolism: mechanism for tumor-specific drug inactivation? J Pharmacol Exp Ther. 2001 Feb;296(2):537-41.
97	In vitro inhibition of CYP1A2 by model inhibitors, anti-inflammatory analgesics and female sex steroids: predictability of in vivo interactions. Basic Clin Pharmacol Toxicol. 2008 Aug;103(2):157-65.
98	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.
99	Drug interaction study of flavonoids toward CYP3A4 and their quantitative structure activity relationship (QSAR) analysis for predicting potential effects. Toxicol Lett. 2018 Sep 15;294:27-36.
100	Stiripentol. Expert Opin Investig Drugs. 2005 Jul;14(7):905-11.
101	Inhibition of human cytochrome P450 enzymes by 1,4-dihydropyridine calcium antagonists: prediction of in vivo drug-drug interactions. Eur J Clin Pharmacol. 2000 Feb-Mar;55(11-12):843-52.
102	Mechanism-based inhibition of human liver microsomal cytochrome P450 1A2 by zileuton, a 5-lipoxygenase inhibitor. Drug Metab Dispos. 2003 Nov;31(11):1352-60.
103	Predictive three-dimensional quantitative structure-activity relationship of cytochrome P450 1A2 inhibitors. J Med Chem. 2005 Jun 2;48(11):3808-15.
104	Expression pattern of cisplatin-induced metallothionein isoforms in squamous cell carcinoma. Anticancer Res. 2003 Jan-Feb;23(1A):299-303.
105	A new in vitro method for identifying chemical sensitizers combining peptide binding with ARE/EpRE-mediated gene expression in human skin cells. Cutan Ocul Toxicol. 2010 Sep;29(3):171-92.
106	Arsenic trioxide (ATO) influences the gene expression of metallothioneins in human glioblastoma cells. Biol Trace Elem Res. 2012 Dec;149(3):331-9.
107	Gene expression changes in human small airway epithelial cells exposed to Delta9-tetrahydrocannabinol. Toxicol Lett. 2005 Aug 14;158(2):95-107.
108	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.
109	Zoledronate dysregulates fatty acid metabolism in renal tubular epithelial cells to induce nephrotoxicity. Arch Toxicol. 2018 Jan;92(1):469-485.
110	Identification of mechanisms of action of bisphenol a-induced human preadipocyte differentiation by transcriptional profiling. Obesity (Silver Spring). 2014 Nov;22(11):2333-43.
111	Physiological and toxicological transcriptome changes in HepG2 cells exposed to copper. Physiol Genomics. 2009 Aug 7;38(3):386-401.