General Information of Drug (ID: DMQMBZ1)

Drug Name
Rivaroxaban Drug Info
Synonyms XARELTO (TN)
Indication
Disease Entry ICD 11 Status REF
Deep vein thrombosis BD71 Approved [1]
Heparin-induced thrombocytopenia 3B64.12 Approved [2]
Coronavirus Disease 2019 (COVID-19) 1D6Y Phase 3 [3]
Cross-matching ID
PubChem CID
9875401
ChEBI ID
CHEBI:68579
CAS Number
CAS 366789-02-8
TTD Drug ID
DMQMBZ1
VARIDT Drug ID
DR00227
INTEDE Drug ID
DR1431
ACDINA Drug ID
D00601

Molecule-Related Drug Atlas

Molecule-Related Drug Atlas
Molecule Type:
DTT
DTP
DME
DOT
Drug Status:
Approved Drug(s)
Clinical Trial Drug(s)
Drug(s) Targeting Coagulation factor Xa (F10)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Apixaban DM89JLN Thrombosis DB61-GB90 Approved [10]
DU-176b DMCIJBH Atrial fibrillation BC81.3 Approved [11]
Emicizumab DM0AQ83 Factor VIII deficiency 3B10 Approved [12]
BETRIXABAN DM2C4RF Venous thromboembolism BD72 Approved [13]
Lmw heparin DMJPD06 Coagulation defect 3B10.0 Approved [14]
Nadroparin calcium DMBNKST Coagulation defect 3B10.0 Approved [15]
Fondaparinux sodium DMWS3FH Deep vein thrombosis BD71 Approved [16]
Danaparoid DM6CLBN Deep venous clot BD71 Approved [17]
Coagulation Factor IX DM8HBJI Haemophilia B 3B11.0 Approved [18]
Certoparin sodium DMUR94J Deep vein thrombosis BD71 Approved [14]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Transported By P-glycoprotein 1 (ABCB1)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Amoxicillin DMUYNEI Acute otitis media AB00 Approved [19]
Doxorubicin DMVP5YE Acute myelogenous leukaemia 2A41 Approved [20]
Methotrexate DM2TEOL Anterior urethra cancer Approved [21]
Folic Acid DMEMBJC Colorectal carcinoma Approved [22]
Fluorouracil DMUM7HZ Adenocarcinoma 2D40 Approved [21]
Cisplatin DMRHGI9 Adenocarcinoma 2D40 Approved [21]
Progesterone DMUY35B Amenorrhea GA20.0 Approved [23]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [21]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [24]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [25]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Doxorubicin DMVP5YE Acute myelogenous leukaemia 2A41 Approved [26]
Methotrexate DM2TEOL Anterior urethra cancer Approved [27]
Folic Acid DMEMBJC Colorectal carcinoma Approved [28]
Fluorouracil DMUM7HZ Adenocarcinoma 2D40 Approved [29]
Cisplatin DMRHGI9 Adenocarcinoma 2D40 Approved [30]
Progesterone DMUY35B Amenorrhea GA20.0 Approved [31]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [32]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [31]
Sulfasalazine DMICA9H Irritable bowel syndrome DD91.0 Approved [33]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [34]
⏷ 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 [35]
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 [39]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [40]
Etoposide DMNH3PG Acute myelogenous leukaemia 2A41 Approved [41]
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [42]
Prasterone DM67VKL Chronic obstructive pulmonary disease CA22 Approved [36]
Verapamil DMA7PEW Angina pectoris BA40 Approved [43]
Eplerenone DMF0NQR Heart failure BD10-BD13 Approved [61]
Cannabidiol DM0659E Dravet syndrome 8A61.11 Approved [62]
Isotretinoin DM4QTBN Acne vulgaris ED80 Approved [63]
Voriconazole DMAOL2S Aspergillosis 1F20 Approved [64]
Proguanil DMBL79I Malaria 1F40-1F45 Approved [65]
Ivermectin DMDBX5F Intestinal strongyloidiasis due to nematode parasite 1F6B Approved [65]
Loratadine DMF3AN7 Allergy 4A80-4A85 Approved [66]
Nelfinavir mesylate DMFX6G8 N. A. N. A. Approved [67]
Capsaicin DMGMF6V Back pain ME84.Z Approved [68]
Axitinib DMGVH6N Renal cell carcinoma 2C90 Approved [69]
⏷ Show the Full List of 20 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 [44]
Progesterone DMUY35B Amenorrhea GA20.0 Approved [45]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [46]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [47]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [48]
Sulfasalazine DMICA9H Irritable bowel syndrome DD91.0 Approved [49]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [50]
Etoposide DMNH3PG Acute myelogenous leukaemia 2A41 Approved [51]
Verapamil DMA7PEW Angina pectoris BA40 Approved [52]
Sorafenib DMS8IFC Adenocarcinoma 2D40 Approved [47]
Eplerenone DMF0NQR Heart failure BD10-BD13 Approved [61]
Cannabidiol DM0659E Dravet syndrome 8A61.11 Approved [62]
Nelfinavir mesylate DMFX6G8 N. A. N. A. Approved [67]
Ritonavir DMU764S Human immunodeficiency virus infection 1C62 Approved [67]
Ifosfamide DMCT3I8 Adult central nervous system germ cell tumor Approved [70]
Omeprazole DM471KJ Cystic fibrosis CA25 Approved [71]
Thalidomide DM70BU5 Adult T-cell leukemia/lymphoma Approved [72]
Ciclosporin DMAZJFX Graft-versus-host disease 4B24 Approved [73]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [74]
Hydrocortisone DMGEMB7 Acne vulgaris ED80 Approved [75]
⏷ Show the Full List of 20 Drug(s)
Drug(s) Metabolized By Cytochrome P450 2J2 (CYP2J2)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Riociguat DMXBLMP Chronic thromboembolic pulmonary hypertension Approved [53]
Ergocalciferol DMHO0AR Hypoparathyroidism 5A50 Approved [54]
Vorapaxar DMA16BR Myocardial infarction BA41-BA43 Approved [55]
Vitamin D DMWQUC9 N. A. N. A. Approved [54]
Alfacalcidol DM1237M Hyperparathyroidism 5A51 Phase 4 [54]
Ebastine DMH21D9 N. A. N. A. Phase 4 [56]
MANIDIPINE DMJPGUA N. A. N. A. Phase 3 [57]
Carebastine DMUVMWZ Ocular allergy 4A81 Phase 3 [58]
Eperisone DM1SMAI Muscle spasm MB47.3 Phase 3 [59]
H3B-6545 DMIFCY2 Breast cancer 2C60-2C65 Phase 1/2 [60]
⏷ Show the Full List of 10 Drug(s)

Molecular Interaction Atlas of This Drug

Molecular Interaction Atlas

Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Coagulation factor Xa (F10) TTCIHJA FA10_HUMAN Modulator [4]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Breast cancer resistance protein (ABCG2) DTI7UX6 ABCG2_HUMAN Substrate [5]
P-glycoprotein 1 (ABCB1) DTUGYRD MDR1_HUMAN Substrate [6]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4) DE4LYSA CP3A4_HUMAN Substrate [7]
Cytochrome P450 3A5 (CYP3A5) DEIBDNY CP3A5_HUMAN Substrate [8]
Cytochrome P450 2J2 (CYP2J2) DERSX5P CP2J2_HUMAN Substrate [7]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Cytochrome P450 3A4 (CYP3A4) OTQGYY83 CP3A4_HUMAN Biotransformations [9]
Cytochrome P450 3A5 (CYP3A5) OTSXFBXB CP3A5_HUMAN Biotransformations [9]

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: 6388).
2 Rivaroxaban FDA Label
3 Effect of Anticoagulation Therapy on Clinical Outcomes in COVID-19 (COVID-PREVENT)
4 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
5 Absence of both MDR1 (ABCB1) and breast cancer resistance protein (ABCG2) transporters significantly alters rivaroxaban disposition and central nervous system entry. Basic Clin Pharmacol Toxicol. 2013 Mar;112(3):164-70.
6 Downregulation of ABCB1 gene in patients with total hip or knee arthroplasty influences pharmacokinetics of rivaroxaban: a population pharmacokinetic-pharmacodynamic study. Eur J Clin Pharmacol. 2019 Feb 6.
7 Comparative efficacy and safety of the novel oral anticoagulants dabigatran, rivaroxaban and apixaban in preclinical and clinical development. Thromb Haemost. 2010 Mar;103(3):572-85.
8 Pharmacology of the new target-specific oral anticoagulants. J Thromb Thrombolysis. 2013 Aug;36(2):133-40.
9 Mechanism-Based Inactivation of Cytochrome P450 3A4 and 3A5 by the Fibroblast Growth Factor Receptor Inhibitor Erdafitinib. Chem Res Toxicol. 2021 Jul 19;34(7):1800-1813. doi: 10.1021/acs.chemrestox.1c00178. Epub 2021 Jun 30.
10 Pfizer. Product Development Pipeline. March 31 2009.
11 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: 2359).
12 2017 FDA drug approvals.Nat Rev Drug Discov. 2018 Feb;17(2):81-85.
13 Company report (Portola)
14 Natural products as sources of new drugs over the last 25 years. J Nat Prod. 2007 Mar;70(3):461-77.
15 Serum zinc concentrations: contamination from laboratory equipment. JPEN J Parenter Enteral Nutr. 1979 May-Jun;3(3):179-81.
16 Biochemistry and clinical pharmacology of new anticoagulant agents. Pathophysiol Haemost Thromb. 2002 Sep-Dec;32(5-6):218-24.
17 Effect of factor X inhibition on coagulation activation and cytokine induction in human systemic inflammation. J Infect Dis. 2002 Nov 1;186(9):1270-6.
18 Haemophilia B: Christmas disease. Expert Opin Pharmacother. 2005 Aug;6(9):1517-24.
19 Human intestinal transporter database: QSAR modeling and virtual profiling of drug uptake, efflux and interactions. Pharm Res. 2013 Apr;30(4):996-1007.
20 MDR1 (ABCB1) G1199A (Ser400Asn) polymorphism alters transepithelial permeability and sensitivity to anticancer agents. Cancer Chemother Pharmacol. 2009 Jun;64(1):183-8.
21 Mammalian drug efflux transporters of the ATP binding cassette (ABC) family in multidrug resistance: A review of the past decade. Cancer Lett. 2016 Jan 1;370(1):153-64.
22 Folate transporter expression decreases in the human placenta throughout pregnancy and in pre-eclampsia. Pregnancy Hypertens. 2012 Apr;2(2):123-31.
23 Comparative studies on in vitro methods for evaluating in vivo function of MDR1 P-glycoprotein. Pharm Res. 2001 Dec;18(12):1660-8.
24 Antiestrogens and steroid hormones: substrates of the human P-glycoprotein. Biochem Pharmacol. 1994 Jul 19;48(2):287-92.
25 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.
26 Doxorubicin transport by RALBP1 and ABCG2 in lung and breast cancer. Int J Oncol. 2007 Mar;30(3):717-25.
27 Wild-type breast cancer resistance protein (BCRP/ABCG2) is a methotrexate polyglutamate transporter. Cancer Res. 2003 Sep 1;63(17):5538-43.
28 The effect of low pH on breast cancer resistance protein (ABCG2)-mediated transport of methotrexate, 7-hydroxymethotrexate, methotrexate diglutamate, folic acid, mitoxantrone, topotecan, and resveratrol in in vitro drug transport models. Mol Pharmacol. 2007 Jan;71(1):240-9.
29 Role of BCRP as a biomarker for predicting resistance to 5-fluorouracil in breast cancer. Cancer Chemother Pharmacol. 2009 May;63(6):1103-10.
30 Inhibiting the function of ABCB1 and ABCG2 by the EGFR tyrosine kinase inhibitor AG1478. Biochem Pharmacol. 2009 Mar 1;77(5):781-93.
31 Sterol transport by the human breast cancer resistance protein (ABCG2) expressed in Lactococcus lactis. J Biol Chem. 2003 Jun 6;278(23):20645-51.
32 The phytoestrogen genistein enhances multidrug resistance in breast cancer cell lines by translational regulation of ABC transporters. Cancer Lett. 2016 Jun 28;376(1):165-72.
33 Curcumin inhibits the activity of ABCG2/BCRP1, a multidrug resistance-linked ABC drug transporter in mice. Pharm Res. 2009 Feb;26(2):480-7.
34 Imatinib mesylate (STI571) is a substrate for the breast cancer resistance protein (BCRP)/ABCG2 drug pump. Blood. 2004 Nov 1;104(9):2940-2.
35 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.
36 Contribution of human hepatic cytochrome P450 isoforms to regioselective hydroxylation of steroid hormones. Xenobiotica. 1998 Jun;28(6):539-47.
37 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.
38 Isoform-specific regulation of cytochromes P450 expression by estradiol and progesterone. Drug Metab Dispos. 2013 Feb;41(2):263-9.
39 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.
40 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.
41 Effects of morin on the pharmacokinetics of etoposide in rats. Biopharm Drug Dispos. 2007 Apr;28(3):151-6.
42 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.
43 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.
44 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.
45 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.
46 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.
47 Drug Interactions Flockhart Table
48 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.
49 Urinary 6 beta-hydroxycortisol excretion in rheumatoid arthritis. Br J Rheumatol. 1997 Jan;36(1):54-8.
50 Clinical pharmacokinetics of imatinib. Clin Pharmacokinet. 2005;44(9):879-94.
51 Kinetics and regulation of cytochrome P450-mediated etoposide metabolism. Drug Metab Dispos. 2004 Sep;32(9):993-1000.
52 Differential mechanism-based inhibition of CYP3A4 and CYP3A5 by verapamil. Drug Metab Dispos. 2005 May;33(5):664-71.
53 Riociguat (adempas): a novel agent for the treatment of pulmonary arterial hypertension and chronic thromboembolic pulmonary hypertension. P T. 2014 Nov;39(11):749-58.
54 Characterization of rat and human CYP2J enzymes as Vitamin D 25-hydroxylases. Steroids. 2006 Oct;71(10):849-56.
55 Vorapaxar: the missing link in antiplatelet therapy! J Anaesthesiol Clin Pharmacol. 2017 Apr-Jun;33(2):269-270.
56 Identifying a selective substrate and inhibitor pair for the evaluation of CYP2J2 activity. Drug Metab Dispos. 2012 May;40(5):943-51.
57 Inhibitory effects of antihypertensive drugs on human cytochrome P450 2J2 activity: Potent inhibition by azelnidipine and manidipine. Chem Biol Interact. 2019 Jun 1;306:1-9.
58 Characterization of ebastine, hydroxyebastine, and carebastine metabolism by human liver microsomes and expressed cytochrome P450 enzymes: major roles for CYP2J2 and CYP3A. Drug Metab Dispos. 2006 Nov;34(11):1793-7.
59 Characterization of human cytochrome P450 enzymes involved in the biotransformation of eperisone. Xenobiotica. 2009 Jan;39(1):1-10.
60 Nonclinical pharmacokinetics and in vitro metabolism of H3B-6545, a novel selective ERalpha covalent antagonist (SERCA). Cancer Chemother Pharmacol. 2019 Jan;83(1):151-160.
61 The relative role of CYP3A4 and CYP3A5 in eplerenone metabolism. Toxicol Lett. 2019 Oct 15;315:9-13.
62 Characterization of the structural determinants required for potent mechanism-based inhibition of human cytochrome P450 1A1 by cannabidiol. Chem Biol Interact. 2014 May 25;215:62-8.
63 Retinoids activate the RXR/SXR-mediated pathway and induce the endogenous CYP3A4 activity in Huh7 human hepatoma cells. Toxicol Sci. 2006 Jul;92(1):51-60.
64 The novel azole R126638 is a selective inhibitor of ergosterol synthesis in Candida albicans, Trichophyton spp., and Microsporum canis. Antimicrob Agents Chemother. 2004 Sep;48(9):3272-8.
65 Application of higher throughput screening (HTS) inhibition assays to evaluate the interaction of antiparasitic drugs with cytochrome P450s. Drug Metab Dispos. 2001 Jan;29(1):30-5.
66 Cetirizine and loratadine-based antihistamines with 5-lipoxygenase inhibitory activity. Bioorg Med Chem Lett. 2004 Nov 15;14(22):5591-4.
67 Mechanism-based inactivation of CYP3A by HIV protease inhibitors. J Pharmacol Exp Ther. 2005 Feb;312(2):583-91.
68 Studies of the toxicological potential of capsinoids, XIII: inhibitory effects of capsaicin and capsinoids on cytochrome P450 3A4 in human liver microsomes. Int J Toxicol. 2010 Mar;29(2 Suppl):22S-6S.
69 Investigation of the effects of axitinib on the pharmacokinetics of loperamide and its main metabolite N-demethylated loperamide in rats by UPLC-MS/MS. Chem Biol Interact. 2019 Sep 1;310:108744. doi: 10.1016/j.cbi.2019.108744. Epub 2019 Jul 9.
70 Contribution of CYP3A5 to hepatic and renal ifosfamide N-dechloroethylation. Drug Metab Dispos. 2005 Jul;33(7):1074-81. doi: 10.1124/dmd.104.002279. Epub 2005 Apr 8.
71 Use of mRNA expression to detect the induction of drug metabolising enzymes in rat and human hepatocytes. Toxicol Appl Pharmacol. 2009 Feb 15;235(1):86-96.
72 Induction of human cytochrome P450 3A enzymes in cultured placental cells by thalidomide and relevance to bioactivation and toxicity. J Toxicol Sci. 2017;42(3):343-348.
73 Comparison of HepG2 and HepaRG by whole-genome gene expression analysis for the purpose of chemical hazard identification. Toxicol Sci. 2010 May;115(1):66-79.
74 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.
75 Induction of hepatic CYP3A enzymes by pregnancy-related hormones: studies in human hepatocytes and hepatic cell lines. Drug Metab Dispos. 2013 Feb;41(2):281-90.