General Information of Drug (ID: DMK7CYX)

Drug Name
Vadimezan Drug Info
Synonyms DMXAA; AS-1404; ASA-404; R-1564; 5,6-MeXAA; 5,6-dimethylxanthenone-4-acetic acid
Indication
Disease Entry ICD 11 Status REF
Solid tumour/cancer 2A00-2F9Z Phase 2 [1]
Cross-matching ID
PubChem CID
123964
ChEBI ID
CHEBI:75934
CAS Number
CAS 117570-53-3
TTD Drug ID
DMK7CYX
INTEDE Drug ID
DR1664

Molecule-Related Drug Atlas

Molecule-Related Drug Atlas
Molecule Type:
DTT
DME
DOT
Drug Status:
Approved Drug(s)
Clinical Trial Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Sulfasalazine DMICA9H Irritable bowel syndrome DD91.0 Approved [7]
Triptolide DMCMDVR Autoimmune diabetes 5A10 Phase 3 [8]
Laquinimod DM3IWS8 Lupus 4A40 Phase 3 [9]
Edasalonexent DMYVBF6 Duchenne dystrophy 8C70 Phase 3 [10]
MD1003 DMVZ57G Multiple sclerosis 8A40 Phase 3 [10]
CAT 1004 DMQBP7R Duchenne dystrophy 8C70 Phase 2 [11]
Parthenolide DMCQBFT N. A. N. A. Phase 2 [12]
Recoflavone DMCSR8I Inflammatory bowel disease DD72 Phase 2 [13]
CZEN-002 DMUDMHA Fungal infection 1F29-1F2F Phase 2 [14]
XP-23829 DMELUYN Multiple sclerosis 8A40 Phase 2 [15]
⏷ 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 Adenocarcinoma 2D40 Approved [16]
Dinoprostone DMTYOPD Medical abortion JA00.1Z Approved [17]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [18]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [19]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [20]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [21]
Etoposide DMNH3PG Acute myelogenous leukaemia 2A41 Approved [22]
Oxaliplatin DMQNWRD Adenocarcinoma 2D40 Approved [23]
Verapamil DMA7PEW Angina pectoris BA40 Approved [24]
Diclofenac DMPIHLS Chronic renal failure GB61.Z Approved [25]
Zolmitriptan DM1IB4Q Migraine 8A80 Approved [40]
Rofecoxib DM3P5DA Osteoarthritis FA00-FA05 Approved [40]
Etoricoxib DM6A4NW Rheumatoid arthritis FA20 Approved [40]
Capsaicin DMGMF6V Back pain ME84.Z Approved [41]
Hesperetin DMKER83 High blood cholesterol level 5C80.00 Approved [42]
Stiripentol DMMSDOY Dravet syndrome 8A61.11 Approved [43]
Nifedipine DMSVOZT Angina pectoris BA40 Approved [44]
Zileuton DMVRIC2 Allergic asthma CA23.0 Approved [45]
Nicotine DMWX5CO Lung cancer 2C25.0 Approved [46]
Clonidine DM6RZ9Q Attention deficit hyperactivity disorder 6A05.Z Approved [47]
⏷ Show the Full List of 20 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [26]
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [27]
Diclofenac DMPIHLS Chronic renal failure GB61.Z Approved [28]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [29]
Mycophenolate mofetil DMPQAGE Hepatosplenic T-cell lymphoma Approved [30]
Ibuprofen DM8VCBE Dysmenorrhea GA34.3 Approved [28]
PITAVASTATIN CALCIUM DM1UJO0 Dyslipidemia 5C80-5C81 Approved [31]
Troglitazone DM3VFPD Diabetic complication 5A2Y Approved [32]
Ezetimibe DM7A8TW Atherosclerosis BD40 Approved [33]
Simvastatin DM30SGU Arteriosclerosis BD40 Approved [34]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [35]
Diclofenac DMPIHLS Chronic renal failure GB61.Z Approved [36]
Sorafenib DMS8IFC Adenocarcinoma 2D40 Approved [37]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [28]
Mycophenolate mofetil DMPQAGE Hepatosplenic T-cell lymphoma Approved [38]
Propofol DMB4OLE Anaesthesia 9A78.6 Approved [28]
Ibuprofen DM8VCBE Dysmenorrhea GA34.3 Approved [28]
Troglitazone DM3VFPD Diabetic complication 5A2Y Approved [39]
Nateglinide DMLK2QH Diabetic complication 5A2Y Approved [28]
Haloperidol DM96SE0 Delirium Approved [28]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Ivermectin DMDBX5F Intestinal strongyloidiasis due to nematode parasite 1F6B Approved [48]
Folic Acid DMEMBJC Colorectal carcinoma Approved [49]
Methotrexate DM2TEOL Anterior urethra cancer Approved [50]
Quercetin DM3NC4M Obesity 5B81 Approved [51]
Docetaxel DMDI269 Advanced cancer 2A00-2F9Z Approved [52]
Irinotecan DMP6SC2 Adenocarcinoma 2D40 Approved [53]
Epirubicin DMPDW6T Solid tumour/cancer 2A00-2F9Z Approved [54]
Doxorubicin DMVP5YE Acute myelogenous leukaemia 2A41 Approved [55]
Colchicine DM2POTE Acute gout flare FA25.0 Approved [56]
Dactinomycin DM2YGNW Adult kidney Wilms tumor Approved [56]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Lopinavir DMITQS0 Human immunodeficiency virus infection 1C62 Approved [57]
Sulfinpyrazone DMEV954 Gout FA25 Approved [58]
Probenecid DMMFWOJ Acute gonococcal cervicitis Approved [59]
Docetaxel DMDI269 Advanced cancer 2A00-2F9Z Approved [60]
Methotrexate DM2TEOL Anterior urethra cancer Approved [50]
Arsenic trioxide DM61TA4 Acute lymphoblastic leukaemia 2A85 Approved [61]
Cholic Acid DM7OKQV Cholelithiasis DC11 Approved [62]
Epirubicin DMPDW6T Solid tumour/cancer 2A00-2F9Z Approved [54]
Cisplatin DMRHGI9 Adenocarcinoma 2D40 Approved [63]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [64]
⏷ 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
Nuclear factor NF-kappa-B (NFKB) TTSXVID NFKB1_HUMAN; NFKB2_HUMAN; TF65_HUMAN; RELB_HUMAN; REL_HUMAN Modulator [2]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 1A2 (CYP1A2) DEJGDUW CP1A2_HUMAN Substrate [3]
UDP-glucuronosyltransferase 2B7 (UGT2B7) DEB3CV1 UD2B7_HUMAN Substrate [3]
UDP-glucuronosyltransferase 1A9 (UGT1A9) DE85D2P UD19_HUMAN Substrate [4]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
ATP-binding cassette sub-family C member 2 (ABCC2) OTJSIGV5 MRP2_HUMAN Regulation of Drug Effects [5]
Cytochrome P450 1A2 (CYP1A2) OTLLBX48 CP1A2_HUMAN Biotransformations [6]
Multidrug resistance-associated protein 1 (ABCC1) OTGUN89S MRP1_HUMAN Regulation of Drug Effects [5]

References

1 ClinicalTrials.gov (NCT01057342) Paclitaxel, Carboplatin, and Dimethylxanthenone Acetic Acid in Treating Patients With Extensive-Stage Small Cell Lung Cancer. U.S. National Institutes of Health.
2 Auckland Cancer Society Research Centre report
3 Preclinical factors affecting the interindividual variability in the clearance of the investigational anti-cancer drug 5,6-dimethylxanthenone-4-acetic acid. Biochem Pharmacol. 2003 Jun 1;65(11):1853-65.
4 Predicting pharmacokinetics and drug interactions in patients from in vitro and in vivo models: the experience with 5,6-dimethylxanthenone-4-acetic acid (DMXAA), an anti-cancer drug eliminated mainly by conjugation. Drug Metab Rev. 2002 Nov;34(4):751-90.
5 Transport of the investigational anti-cancer drug 5,6-dimethylxanthenone-4-acetic acid and its acyl glucuronide by human intestinal Caco-2 cells. Eur J Pharm Sci. 2005 Apr;24(5):513-24. doi: 10.1016/j.ejps.2005.01.006.
6 Inhibition of human CYP1A2 oxidation of 5,6-dimethyl-xanthenone-4-acetic acid by acridines: a molecular modelling study. Clin Exp Pharmacol Physiol. 2005 Aug;32(8):633-9.
7 Emerging drugs for rheumatoid arthritis. Expert Opin Emerg Drugs. 2008 Mar;13(1):175-96.
8 Functional p53 is required for triptolide-induced apoptosis and AP-1 and nuclear factor-kappaB activation in gastric cancer cells. Oncogene. 2001 Nov 29;20(55):8009-18.
9 Reduced astrocytic NF- B activation by laquinimod protects from cuprizone-induced demyelination. Acta Neuropathol. 2012 Sep;124(3):411-24.
10 Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
11 Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
12 Hypoxia-induced neutrophil survival is mediated by HIF-1alpha-dependent NF-kappaB activity. J Exp Med. 2005 Jan 3;201(1):105-15.
13 DA-6034, a derivative of flavonoid, prevents and ameliorates dextran sulfate sodium-induced colitis and inhibits colon carcinogenesis. Exp Biol Med (Maywood). 2008 Feb;233(2):180-91.
14 US patent application no. US20100278784 A1.
15 Trusted, scientifically sound profiles of drug programs, clinical trials, safety reports, and company deals, written by scientists. Springer. 2015. Adis Insight (drug id 800036491)
16 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.
17 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.
18 Endoxifen and other metabolites of tamoxifen inhibit human hydroxysteroid sulfotransferase 2A1 (hSULT2A1). Drug Metab Dispos. 2014 Nov;42(11):1843-50.
19 Cytochrome P450 1A2 (CYP1A2) activity and risk factors for breast cancer: a cross-sectional study. Breast Cancer Res. 2004;6(4):R352-65.
20 PharmGKB summary: pathways of acetaminophen metabolism at the therapeutic versus toxic doses. Pharmacogenet Genomics. 2015 Aug;25(8):416-26.
21 The effect of apigenin on pharmacokinetics of imatinib and its metabolite N-desmethyl imatinib in rats. Biomed Res Int. 2013;2013:789184.
22 Effects of morin on the pharmacokinetics of etoposide in rats. Biopharm Drug Dispos. 2007 Apr;28(3):151-6.
23 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.
24 Identification of P450 enzymes involved in metabolism of verapamil in humans. Naunyn Schmiedebergs Arch Pharmacol. 1993 Sep;348(3):332-7.
25 Metabolism and metabolic inhibition of xanthotoxol in human liver microsomes. Evid Based Complement Alternat Med. 2016;2016:5416509.
26 Metabolism and transport of tamoxifen in relation to its effectiveness: new perspectives on an ongoing controversy. Future Oncol. 2014 Jan;10(1):107-22.
27 Determination of UDP-glucuronosyltransferase UGT2B7 activity in human liver microsomes by ultra-performance liquid chromatography with MS detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2008 Jul 1;870(1):84-90.
28 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.
29 Pharmacokinetic and pharmacodynamic interaction of lorazepam and valproic acid in relation to UGT2B7 genetic polymorphism in healthy subjects. Clin Pharmacol Ther. 2008 Apr;83(4):595-600.
30 PharmGKB summary: mycophenolic acid pathway. Pharmacogenet Genomics. 2014 Jan;24(1):73-9.
31 Pitavastatin: a review in hypercholesterolemia. Am J Cardiovasc Drugs. 2017 Apr;17(2):157-168.
32 Troglitazone glucuronidation in human liver and intestine microsomes: high catalytic activity of UGT1A8 and UGT1A10. Drug Metab Dispos. 2002 Dec;30(12):1462-9.
33 Ezetimibe: a review of its metabolism, pharmacokinetics and drug interactions. Clin Pharmacokinet. 2005;44(5):467-94.
34 Pharmacogenomics of statins: understanding susceptibility to adverse effects. Pharmgenomics Pers Med. 2016 Oct 3;9:97-106.
35 Polymorphic expression of UGT1A9 is associated with variable acetaminophen glucuronidation in neonates: a population pharmacokinetic and pharmacogenetic study. Clin Pharmacokinet. 2018 Oct;57(10):1325-1336.
36 Glucuronidation of nonsteroidal anti-inflammatory drugs: identifying the enzymes responsible in human liver microsomes. Drug Metab Dispos. 2005 Jul;33(7):1027-35.
37 Pharmacokinetic interaction involving sorafenib and the calcium-channel blocker felodipine in a patient with hepatocellular carcinoma. Invest New Drugs. 2011 Dec;29(6):1511-4.
38 The evolution of population pharmacokinetic models to describe the enterohepatic recycling of mycophenolic acid in solid organ transplantation and autoimmune disease. Clin Pharmacokinet. 2011 Jan;50(1):1-24.
39 The UDP-glucuronosyltransferase 1A9 enzyme is a peroxisome proliferator-activated receptor alpha and gamma target gene. J Biol Chem. 2003 Apr 18;278(16):13975-83.
40 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.
41 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.
42 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.
43 Stiripentol. Expert Opin Investig Drugs. 2005 Jul;14(7):905-11.
44 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.
45 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.
46 Predictive three-dimensional quantitative structure-activity relationship of cytochrome P450 1A2 inhibitors. J Med Chem. 2005 Jun 2;48(11):3808-15.
47 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.
48 Characterization of multidrug transporter-mediated efflux of avermectins in human and mouse neuroblastoma cell lines. Toxicol Lett. 2015 Jun 15;235(3):189-98. doi: 10.1016/j.toxlet.2015.04.005. Epub 2015 Apr 9.
49 Folate concentration dependent transport activity of the Multidrug Resistance Protein 1 (ABCC1). Biochem Pharmacol. 2004 Apr 15;67(8):1541-8.
50 Methotrexate normalizes up-regulated folate pathway genes in rheumatoid arthritis. Arthritis Rheum. 2013 Nov;65(11):2791-802.
51 Influence of redox-active compounds and PXR-activators on human MRP1 and MRP2 gene expression. Toxicology. 2002 Feb 28;171(2-3):137-46.
52 Enhanced in vitro invasiveness and drug resistance with altered gene expression patterns in a human lung carcinoma cell line after pulse selection with anticancer drugs. Int J Cancer. 2004 Sep 10;111(4):484-93. doi: 10.1002/ijc.20230.
53 Clinical determinants of response to irinotecan-based therapy derived from cell line models. Clin Cancer Res. 2008 Oct 15;14(20):6647-55.
54 Co-encapsulation of chrysophsin-1 and epirubicin in PEGylated liposomes circumvents multidrug resistance in HeLa cells. Chem Biol Interact. 2015 Dec 5;242:13-23. doi: 10.1016/j.cbi.2015.08.023. Epub 2015 Sep 1.
55 Upregulation of multi drug resistance genes in doxorubicin resistant human acute myelogeneous leukemia cells and reversal of the resistance. Hematology. 2007 Dec;12(6):511-7. doi: 10.1080/10245330701562535.
56 Functional analysis of MRP1 cloned from bovine. FEBS Lett. 2002 Jun 19;521(1-3):211-3. doi: 10.1016/s0014-5793(02)02816-8.
57 Functional defect caused by the 4544G>A SNP in ABCC2: potential impact for drug cellular disposition. Pharmacogenet Genomics. 2011 Dec;21(12):884-93. doi: 10.1097/FPC.0b013e32834d672b.
58 Role of multidrug resistance protein 2 (MRP2, ABCC2) in alkylating agent detoxification: MRP2 potentiates glutathione S-transferase A1-1-mediated resistance to chlorambucil cytotoxicity. J Pharmacol Exp Ther. 2004 Jan;308(1):260-7. doi: 10.1124/jpet.103.057729. Epub 2003 Oct 20.
59 MRP2 (ABCC2) transports taxanes and confers paclitaxel resistance and both processes are stimulated by probenecid. Int J Cancer. 2005 Sep 20;116(5):824-9. doi: 10.1002/ijc.21013.
60 Association of genetic polymorphisms in SLCO1B3 and ABCC2 with docetaxel-induced leukopenia. Cancer Sci. 2008 May;99(5):967-72.
61 In vitro study of transporters involved in intestinal absorption of inorganic arsenic. Chem Res Toxicol. 2012 Feb 20;25(2):446-53. doi: 10.1021/tx200491f. Epub 2012 Jan 26.
62 Potency of individual bile acids to regulate bile acid synthesis and transport genes in primary human hepatocyte cultures. Toxicol Sci. 2014 Oct;141(2):538-46. doi: 10.1093/toxsci/kfu151. Epub 2014 Jul 23.
63 Evaluation of drug transporters' significance for multidrug resistance in head and neck squamous cell carcinoma. Head Neck. 2011 Jul;33(7):959-68. doi: 10.1002/hed.21559. Epub 2010 Aug 24.
64 Gene expression analysis of precision-cut human liver slices indicates stable expression of ADME-Tox related genes. Toxicol Appl Pharmacol. 2011 May 15;253(1):57-69.