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

General Information of Drug (ID: DMDO279)

Drug Name
Phenprocoumon Drug Info
Synonyms
Falithiom; Falithrom; Fencumar; Fenprocoumona; Fenprocumon; Fenprocumone; Liquamar; Marcoumar; Marcumar; Marcuphen; Phenprocoumalol; Phenprocoumarol; Phenprocoumarole; Phenprocoumone; Phenprocoumonum; Phenprocumone; Phenprocumonum; Phenprogramma; Phenylpropylhydroxycumarinum; Fenprocumone [DCIT]; Hexal Brand of Phenprocoumon; Roche Brand of Phenprocoumon; Worwag Brand of Phenprocoumon; U29342; Falithrom (TN); Fenprocoumona [INN-Spanish]; Liquamar (TN); Marcoumar (TN); Marcumar (TN); Phenprocoumone [INN-French]; Phenprocoumonum [INN-Latin]; Ro 1-4849; Phenprocoumon (USAN/INN); Phenprocoumon [USAN:INN:BAN]; 2-hydroxy-3-(1-phenylpropyl)chromen-4-one; 3-(1'-Phenyl-propyl)-4-oxycoumarin; 3-(1'-Phenyl-propyl)-4-oxycoumarin [German]; 3-(1-Phenylpropyl)-4-hydroxycoumarin; 3-(alpha-Ethylbenzyl)-4-hydroxycoumarin; 3-(alpha-Phenylpropyl)-4-hydroxycoumarin; 4-Hydroxy-3-(1-phenylpropyl)-2H-1-benzopyran-2-one; 4-Hydroxy-3-(1-phenylpropyl)-2H-chromen-2-one
Indication
Disease Entry ICD 11 Status REF
Myocardial infarction BA41-BA43 Approved [1]
Thrombosis DB61-GB90 Approved [2]
Venous thromboembolism BD72 Investigative [1]
Therapeutic Class
Anticoagulants
Cross-matching ID
PubChem CID
54680692
ChEBI ID
CHEBI:50438
CAS Number
CAS 435-97-2
TTD Drug ID
DMDO279
VARIDT Drug ID
DR01279
INTEDE Drug ID
DR1279

Molecule-Related Drug Atlas

Molecule-Related Drug Atlas
Molecule Type:
DTT
DTP
DME
DOT
Drug Status:
Approved Drug(s)
Clinical Trial Drug(s)
Download the Complete Related Drug List
Drug(s) Targeting Vitamin K epoxide reductase complex 1 (VKORC1)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Warfarin DMJYCVW Atrial fibrillation BC81.3 Approved [3]
Acenocoumarol DMH75KV Thrombosis DB61-GB90 Approved [9]
Dicumarol DMFQCB1 Bleeding disorder GA20-GA21 Approved [10]
Phenindione DM2PYNR Coagulation defect 3B10.0 Approved [3]
Tecarfarin DMTCR2O Cerebrovascular ischaemia 8B1Z Phase 3 [11]
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 [12]
Doxorubicin DMVP5YE Acute myelogenous leukaemia 2A41 Approved [13]
Methotrexate DM2TEOL Anterior urethra cancer Approved [14]
Folic Acid DMEMBJC Colorectal carcinoma Approved [15]
Fluorouracil DMUM7HZ Adenocarcinoma 2D40 Approved [14]
Cisplatin DMRHGI9 Adenocarcinoma 2D40 Approved [14]
Progesterone DMUY35B Amenorrhea GA20.0 Approved [16]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [14]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [17]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [18]
⏷ 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 [19]
Progesterone DMUY35B Amenorrhea GA20.0 Approved [20]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [21]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [22]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [23]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [24]
Etoposide DMNH3PG Acute myelogenous leukaemia 2A41 Approved [25]
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [26]
Prasterone DM67VKL Chronic obstructive pulmonary disease CA22 Approved [20]
Verapamil DMA7PEW Angina pectoris BA40 Approved [27]
⏷ 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 [28]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [29]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [29]
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [30]
Verapamil DMA7PEW Angina pectoris BA40 Approved [31]
Diclofenac DMPIHLS Chronic renal failure GB61.Z Approved [32]
Sorafenib DMS8IFC Adenocarcinoma 2D40 Approved [33]
Quinine DMSWYF5 Malaria 1F40-1F45 Approved [29]
Mycophenolate mofetil DMPQAGE Hepatosplenic T-cell lymphoma Approved [34]
Propofol DMB4OLE Anaesthesia 9A78.6 Approved [35]
⏷ 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 [36]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [37]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [38]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [30]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [39]
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [30]
Verapamil DMA7PEW Angina pectoris BA40 Approved [40]
Diclofenac DMPIHLS Chronic renal failure GB61.Z Approved [41]
Estrone DM5T6US Acne vulgaris ED80 Approved [42]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [43]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Heat shock factor protein 1 (HSF1)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Hydrogen peroxide DM1NG5W Infectious disease 1A00-CA43.1 Approved [44]
SPI-1005 DM6XFHS Reperfusion injury ND56.Z Approved [7]
Imipramine DM2NUH3 Depression 6A70-6A7Z Approved [7]
Sulindac DM2QHZU Acute myelogenous leukaemia 2A41 Approved [45]
Simvastatin DM30SGU Arteriosclerosis BD40 Approved [46]
Ceftazidime DM41GRA Bacteremia 1A73 Approved [7]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [47]
Chlorpheniramine DM5URA2 Allergic rhinitis CA08.0 Approved [7]
Ethacrynic acid DM60QMR Edema MG29 Approved [7]
Arsenic trioxide DM61TA4 Acute lymphoblastic leukaemia 2A85 Approved [7]
⏷ 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
Vitamin K epoxide reductase complex 1 (VKORC1) TTEUC8H VKOR1_HUMAN Inhibitor [3]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
P-glycoprotein 1 (ABCB1) DTUGYRD MDR1_HUMAN Substrate [4]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4) DE4LYSA CP3A4_HUMAN Substrate [5]
Cytochrome P450 2C9 (CYP2C9) Main DME DE5IED8 CP2C9_HUMAN Substrate [6]
Cytochrome P450 2C8 (CYP2C8) DES5XRU CP2C8_HUMAN Substrate [5]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Heat shock factor protein 1 (HSF1) OTYNJ4KP HSF1_HUMAN Gene/Protein Processing [7]
Vitamin K epoxide reductase complex subunit 1 OTOJNJRD VKOR1_HUMAN Gene/Protein Processing [8]
Vitamin K epoxide reductase complex subunit 1-like protein 1 OT7QSEWT VKORL_HUMAN Gene/Protein Processing [8]

References

1 Phenprocoumon FDA Label
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4 Role of P-glycoprotein in the uptake/efflux transport of oral vitamin K antagonists and rivaroxaban through the Caco-2 cell model. Basic Clin Pharmacol Toxicol. 2013 Oct;113(4):259-65.
5 Identification of cytochromes P450 2C9 and 3A4 as the major catalysts of phenprocoumon hydroxylation in vitro. Eur J Clin Pharmacol. 2004 May;60(3):173-82.
6 Genetic polymorphisms of cytochrome P450 2C9 causing reduced phenprocoumon (S)-7-hydroxylation in vitro and in vivo. Xenobiotica. 2004 Sep;34(9):847-59.
7 A Gene Expression Biomarker Predicts Heat Shock Factor 1 Activation in a Gene Expression Compendium. Chem Res Toxicol. 2021 Jul 19;34(7):1721-1737. doi: 10.1021/acs.chemrestox.0c00510. Epub 2021 Jun 25.
8 VKORC1 and VKORC1L1 have distinctly different oral anticoagulant dose-response characteristics and binding sites. Blood Adv. 2018 Mar 27;2(6):691-702.
9 Evaluation of a reverse-hybridization StripAssay for the detection of genetic polymorphisms leading to acenocoumarol sensitivity. Mol Biol Rep. 2010 Apr;37(4):1693-7.
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11 Tecarfarin, a novel vitamin K reductase antagonist, is not affected by CYP2C9 and CYP3A4 inhibition following concomitant administration of fluconazole in healthy participants. J Clin Pharmacol. 2011Apr;51(4):561-74.
12 Human intestinal transporter database: QSAR modeling and virtual profiling of drug uptake, efflux and interactions. Pharm Res. 2013 Apr;30(4):996-1007.
13 MDR1 (ABCB1) G1199A (Ser400Asn) polymorphism alters transepithelial permeability and sensitivity to anticancer agents. Cancer Chemother Pharmacol. 2009 Jun;64(1):183-8.
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18 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.
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21 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.
22 Isoform-specific regulation of cytochromes P450 expression by estradiol and progesterone. Drug Metab Dispos. 2013 Feb;41(2):263-9.
23 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.
24 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.
25 Effects of morin on the pharmacokinetics of etoposide in rats. Biopharm Drug Dispos. 2007 Apr;28(3):151-6.
26 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.
27 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.
28 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.
29 Role of cytochrome P450 2C8 in drug metabolism and interactions. Pharmacol Rev. 2016 Jan;68(1):168-241.
30 Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.
31 Differential expression and function of CYP2C isoforms in human intestine and liver. Pharmacogenetics. 2003 Sep;13(9):565-75.
32 Analysis of human cytochrome P450 2C8 substrate specificity using a substrate pharmacophore and site-directed mutants. Biochemistry. 2004 Dec 14;43(49):15379-92.
33 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.
34 PharmGKB summary: mycophenolic acid pathway. Pharmacogenet Genomics. 2014 Jan;24(1):73-9.
35 Possible involvement of multiple human cytochrome P450 isoforms in the liver metabolism of propofol. Br J Anaesth. 1998 Jun;80(6):788-95.
36 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.
37 Tamoxifen inhibits cytochrome P450 2C9 activity in breast cancer patients. J Chemother. 2006 Aug;18(4):421-4.
38 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.
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41 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.
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43 A mechanistic approach to antiepileptic drug interactions. Ann Pharmacother. 1998 May;32(5):554-63.
44 NRF2 transcriptionally activates the heat shock factor 1 promoter under oxidative stress and affects survival and migration potential of MCF7 cells. J Biol Chem. 2018 Dec 14;293(50):19303-19316. doi: 10.1074/jbc.RA118.003376. Epub 2018 Oct 11.
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46 Simvastatin induces heat shock factor 1 in vascular endothelial cells. Atherosclerosis. 2006 Oct;188(2):265-73. doi: 10.1016/j.atherosclerosis.2005.10.045. Epub 2005 Dec 20.
47 Transcriptional and Metabolic Dissection of ATRA-Induced Granulocytic Differentiation in NB4 Acute Promyelocytic Leukemia Cells. Cells. 2020 Nov 5;9(11):2423. doi: 10.3390/cells9112423.