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

General Information of Drug (ID: DMAYL0T)

Drug Name
Phenylbutazone Drug Info
Synonyms
Alindor; Alkabutazona; Alqoverin; Anerval; Anpuzone; Antadol; Anuspiramin; Arthrizon; Artizin; Artrizin; Artrizone; Artropan; Azdid; Azobutyl; Azolid; Benzone; Betazed; Bizolin; Bunetzone; Busone; Butacompren; Butacote; Butadion; Butadiona; Butadione; Butadionum; Butagesic; Butalgina; Butalidon; Butaluy; Butaphen; Butapirazol; Butapirazole; Butapyrazole; Butarecbon; Butartril; Butartrina; Butatron; Butazina; Butazolidin; Butazolidine; Butazona; Bute; Butidiona; Butone; Butoz; Butylpyrin; Buvetzone; Buzon;Chembutazone; Cotylbutazone; Digibutina; Diossidone; Diozol; Diphebuzol; Diphenylbutazone; Ecobutazone; Elmedal; Equipalazone; Equiphen; Eributazone; Esteve; Febuzina; Fenartil; Fenibutal; Fenibutasan; Fenibutazona; Fenibutol; Fenilbutazon; Fenilbutazona; Fenilbutazone; Fenilbutina; Fenilbutine; Fenilidina; Fenotone; Fenylbutazon; Flexazone; Intalbut; Intrabutazone; Intrazone; Ipsoflame; Kadol; Lingel; Malgesic; Mephabutazon; Mephabutazone; Merizone; Nadazone; Nadozone; Novophenyl; Phebuzin; Phebuzine; Phenbutazol; Phenbutazone; Phenopyrine; Phenylbutaz; Phenylbutazon; Phenylbutazonum; Phenyzene; Phenyzone; Praecirheumin; Pyrabutol; Pyrazolidin; Rectofasa; Reudo; Reudox; Reumasyl; Reumazin; Reumazol; Reumune; Reumuzol; Reupolar; Robizone; Rubatone; Scanbutazone; Schemergen; Schemergin; Shigrodin; Tazone; Tencodyne; Tetnor; Tevcodyne; Therazone; Ticinil; Todalgil; Uzone; Wescozone; Zolaphen; Zolidinum; Alka Butazolidin; Art rizin; Buta phen; Butyl pyrin; Equi bute; Exrheudon N; Fe nilbutine; Fenilbutazone [DCIT]; Phenyl butazone; Phenylbutazon [German]; Pirarreumol B; A 7514; Bizolin 200; G 13871; P 8386; P1686; P1Z; AZOLID (TN); Apo-Phenylbutazone; Butiwas-Simple; Component of Azolid-A; DA-192; Fenilbutazona [INN-Spanish]; G 13,871; Ia-But; Mepha-Butazon; Neo-zoline; Phenyl-Mobuzon; Phenylbutazonum [INN-Latin]; Robizon-V; Robizone-V; Usaf ge-15; VAC-10; B.T.Z; Phen-Buta-Vet; R-3-ZON; B.t.z.; Bute, Butazolidin, Butatron, Phenylbutazone; Phenylbutazone (JP15/USP/INN); Phenylbutazone [USAN:INN:BAN:JAN]; 1,2-Diphenyl-2,3-dioxo-4-N-butylpyrazoline; 1,2-Diphenyl-3,5-dioxo-4-butylpyrazolidine; 1,2-Diphenyl-4-butyl-3,5-dioxopyrazolidine; 1,2-Diphenyl-4-butyl-3,5-pyrazolidinedione; 1,2-diphenyl-3,5-dioxo-4-n-butylpyrazoline; 3,5-Dioxe-4 buty-1, diphenyl-pyrazolidine; 3,5-Dioxo-1,2-diphenyl-4-N-butylpyrazolidine; 3,5-Dioxo-1,2-diphenyl-4-n-butyl-pyrazolidin; 3,5-dioxo-4-butyl-1-diphenyl-pyrazolidine; 4-BUTYL-1,2-DIPHENYL-PYRAZOLIDINE-3,5-DIONE; 4-Butyl-1,2-diphenyl-3,5-dioxopyrazolidine; 4-Butyl-1,2-diphenyl-3,5-pyrazolidinedione; 4-Butyl-1,2-diphenylpyrazolidine-3,5-dione; 4-n-Butyl-1,2-diphenyl-3,5-pyrazolidinedione
Indication
Disease Entry ICD 11 Status REF
Chronic pain MG30 Approved [1]
Therapeutic Class
Analgesics
Cross-matching ID
PubChem CID
4781
ChEBI ID
CHEBI:48574
CAS Number
CAS 50-33-9
TTD Drug ID
DMAYL0T
VARIDT Drug ID
DR00560
INTEDE Drug ID
DR1281

Molecule-Related Drug Atlas

Molecule-Related Drug Atlas
Molecule Type:
DTT
DME
DOT
Drug Status:
Approved Drug(s)
Download the Complete Related Drug List
Drug(s) Targeting Prostaglandin G/H synthase 2 (COX-2)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Ibuprofen DM8VCBE Dysmenorrhea GA34.3 Approved [7]
Naproxen DMZ5RGV Bursitis Approved [8]
Etodolac DM6WJO9 Osteoarthritis FA00-FA05 Approved [9]
Indomethacin DMSC4A7 Bursitis Approved [10]
Celecoxib DM6LOQU Dysmenorrhea GA34.3 Approved [11]
Nabumetone DMAT2XH Osteoarthritis FA00-FA05 Approved [12]
Rofecoxib DM3P5DA Osteoarthritis FA00-FA05 Approved [13]
Flurbiprofen DMGN4BY Osteoarthritis FA00-FA05 Approved [14]
Eicosapentaenoic acid/docosa-hexaenoic acid DMMUCG4 Hypertriglyceridemia 5C80.1 Approved [15]
Aminosalicylic Acid DMENSL5 Crohn disease DD70 Approved [10]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Metabolized By UDP-glucuronosyltransferase 1A1 (UGT1A1)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [16]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [17]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [18]
Etoposide DMNH3PG Acute myelogenous leukaemia 2A41 Approved [19]
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [20]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [21]
Mycophenolate mofetil DMPQAGE Hepatosplenic T-cell lymphoma Approved [22]
Metronidazole DMTIVEN Abscess Approved [23]
Propofol DMB4OLE Anaesthesia 9A78.6 Approved [24]
Ethanol DMDRQZU Chronic pain MG30 Approved [25]
⏷ 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 [26]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [27]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [28]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [29]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [30]
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [29]
Verapamil DMA7PEW Angina pectoris BA40 Approved [31]
Diclofenac DMPIHLS Chronic renal failure GB61.Z Approved [32]
Estrone DM5T6US Acne vulgaris ED80 Approved [33]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [34]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Cytochrome P450 3A4 (CYP3A4)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Eplerenone DMF0NQR Heart failure BD10-BD13 Approved [35]
Cannabidiol DM0659E Dravet syndrome 8A61.11 Approved [36]
Isotretinoin DM4QTBN Acne vulgaris ED80 Approved [37]
Voriconazole DMAOL2S Aspergillosis 1F20 Approved [38]
Proguanil DMBL79I Malaria 1F40-1F45 Approved [39]
Ivermectin DMDBX5F Intestinal strongyloidiasis due to nematode parasite 1F6B Approved [39]
Loratadine DMF3AN7 Allergy 4A80-4A85 Approved [40]
Nelfinavir mesylate DMFX6G8 N. A. N. A. Approved [41]
Capsaicin DMGMF6V Back pain ME84.Z Approved [42]
Axitinib DMGVH6N Renal cell carcinoma 2C90 Approved [43]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By L-selectin (SELL)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Meclofenamic acid DM05FXR Ankylosing spondylitis FA92.0 Approved [6]
Meloxicam DM2AR7L Arthritis FA20 Approved [6]
Methotrexate DM2TEOL Anterior urethra cancer Approved [44]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [45]
Erythromycin DM4K7GQ Acne vulgaris ED80 Approved [46]
Aspirin DM672AH Acute coronary syndrome BA41 Approved [6]
Thalidomide DM70BU5 Adult T-cell leukemia/lymphoma Approved [47]
Nabumetone DMAT2XH Osteoarthritis FA00-FA05 Approved [6]
Ciclosporin DMAZJFX Graft-versus-host disease 4B24 Approved [48]
Flufenamic Acid DMC8VNH Dysmenorrhea GA34.3 Approved [6]
⏷ 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
Prostaglandin G/H synthase 2 (COX-2) TTVKILB PGH2_HUMAN Inhibitor [2]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 2C9 (CYP2C9) DE5IED8 CP2C9_HUMAN Substrate [3]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DEYGVN4 UD11_HUMAN Substrate [4]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Cytochrome P450 3A4 (CYP3A4) OTQGYY83 CP3A4_HUMAN Gene/Protein Processing [5]
L-selectin (SELL) OT6RAJZR LYAM1_HUMAN Gene/Protein Processing [6]

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: 7270).
2 COX-1 and COX-2 inhibition in horse blood by phenylbutazone, flunixin, carprofen and meloxicam: an in vitro analysis. Pharmacol Res. 2005 Oct;52(4):302-6.
3 Metabolism of sulfinpyrazone sulfide and sulfinpyrazone by human liver microsomes and cDNA-expressed cytochrome P450s. Drug Metab Dispos. 2001 May;29(5):701-11.
4 Identification of human UDP-glucuronosyltransferase isoform(s) responsible for the C-glucuronidation of phenylbutazone. Arch Biochem Biophys. 2006 Oct 1;454(1):72-9.
5 A reporter gene assay to assess the molecular mechanisms of xenobiotic-dependent induction of the human CYP3A4 gene in vitro. Xenobiotica. 1999 Mar;29(3):269-79.
6 Structure-function relationship and role of tumor necrosis factor-alpha-converting enzyme in the down-regulation of L-selectin by non-steroidal anti-inflammatory drugs. J Biol Chem. 2002 Oct 11;277(41):38212-21. doi: 10.1074/jbc.M205142200. Epub 2002 Jul 29.
7 Maternal toxicity of nonsteroidal anti-inflammatory drugs as an important factor affecting prenatal development. Reprod Toxicol. 2009 Sep;28(2):239-44.
8 Comparative inhibitory activity of rofecoxib, meloxicam, diclofenac, ibuprofen, and naproxen on COX-2 versus COX-1 in healthy volunteers. J Clin Pharmacol. 2000 Oct;40(10):1109-20.
9 Membranous nephropathy associated with the relatively selective cyclooxygenase-2 inhibitor, etodolac, in a patient with early rheumatoid arthritis. Intern Med. 2007;46(13):1055-8.
10 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
11 Pfizer. Product Development Pipeline. March 31 2009.
12 Renal effects of nabumetone, a COX-2 antagonist: impairment of function in isolated perfused rat kidneys contrasts with preserved renal function in vivo. Exp Nephrol. 2001;9(6):387-96.
13 Privileged structures: a useful concept for the rational design of new lead drug candidates. Mini Rev Med Chem. 2007 Nov;7(11):1108-19.
14 Flurbiprofen, a cyclooxygenase inhibitor, protects mice from hepatic ischemia/reperfusion injury by inhibiting GSK-3 signaling and mitochondrial permeability transition.Mol Med.2012 Sep 25;18:1128-35.
15 Cox-2 inhibitory effects of naturally occurring and modified fatty acids. J Nat Prod. 2001 Jun;64(6):745-9.
16 Functional significance of UDP-glucuronosyltransferase variants in the metabolism of active tamoxifen metabolites. Cancer Res. 2009 Mar 1;69(5):1892-900.
17 Functional characterization of human and cynomolgus monkey UDP-glucuronosyltransferase 1A1 enzymes. Life Sci. 2010 Aug 14;87(7-8):261-8.
18 Effect of UDP-glucuronosyltransferase (UGT) 1A polymorphism (rs8330 and rs10929303) on glucuronidation status of acetaminophen. Dose Response. 2017 Sep 11;15(3):1559325817723731.
19 UDP-glucuronosyltransferase 1A1 is the principal enzyme responsible for etoposide glucuronidation in human liver and intestinal microsomes: structural characterization of phenolic and alcoholic glucuronides of etoposide and estimation of enzyme kinetics. Drug Metab Dispos. 2007 Mar;35(3):371-80.
20 Interindividual variability in pharmacokinetics of generic nucleoside reverse transcriptase inhibitors in TB/HIV-coinfected Ghanaian patients: UGT2B7*1c is associated with faster zidovudine clearance and glucuronidation. J Clin Pharmacol. 2009 Sep;49(9):1079-90.
21 Effect of aging on glucuronidation of valproic acid in human liver microsomes and the role of UDP-glucuronosyltransferase UGT1A4, UGT1A8, and UGT1A10. Drug Metab Dispos. 2009 Jan;37(1):229-36.
22 Characterization of rat intestinal microsomal UDP-glucuronosyltransferase activity toward mycophenolic acid. Drug Metab Dispos. 2006 Sep;34(9):1632-9.
23 Drug-drug interactions for UDP-glucuronosyltransferase substrates: a pharmacokinetic explanation for typically observed low exposure (AUCi/AUC) ratios. Drug Metab Dispos. 2004 Nov;32(11):1201-8.
24 Substrate-dependent modulation of UDP-glucuronosyltransferase 1A1 (UGT1A1) by propofol in recombinant human UGT1A1 and human liver microsomes. Basic Clin Pharmacol Toxicol. 2007 Sep;101(3):211-4.
25 Identification and preliminary characterization of UDP-glucuronosyltransferases catalyzing formation of ethyl glucuronide. Anal Bioanal Chem. 2014 Apr;406(9-10):2325-32.
26 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.
27 Tamoxifen inhibits cytochrome P450 2C9 activity in breast cancer patients. J Chemother. 2006 Aug;18(4):421-4.
28 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.
29 Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.
30 Drug-drug interactions with imatinib: an observational study. Medicine (Baltimore). 2016 Oct;95(40):e5076.
31 Drug interactions with calcium channel blockers: possible involvement of metabolite-intermediate complexation with CYP3A. Drug Metab Dispos. 2000 Feb;28(2):125-30.
32 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.
33 A potential role for the estrogen-metabolizing cytochrome P450 enzymes in human breast carcinogenesis. Breast Cancer Res Treat. 2003 Dec;82(3):191-7.
34 A mechanistic approach to antiepileptic drug interactions. Ann Pharmacother. 1998 May;32(5):554-63.
35 The relative role of CYP3A4 and CYP3A5 in eplerenone metabolism. Toxicol Lett. 2019 Oct 15;315:9-13.
36 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.
37 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.
38 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.
39 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.
40 Cetirizine and loratadine-based antihistamines with 5-lipoxygenase inhibitory activity. Bioorg Med Chem Lett. 2004 Nov 15;14(22):5591-4.
41 Mechanism-based inactivation of CYP3A by HIV protease inhibitors. J Pharmacol Exp Ther. 2005 Feb;312(2):583-91.
42 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.
43 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.
44 The contribution of methotrexate exposure and host factors on transcriptional variance in human liver. Toxicol Sci. 2007 Jun;97(2):582-94.
45 Differential modulation of PI3-kinase/Akt pathway during all-trans retinoic acid- and Am80-induced HL-60 cell differentiation revealed by DNA microarray analysis. Biochem Pharmacol. 2004 Dec 1;68(11):2177-86.
46 The in vitro effects of quinupristin/dalfopristin, erythromycin and levofloxacin at low concentrations on the expression of different cell adhesion molecules on the surface of endothelial cells (Eahy926). Toxicology. 2006 Jan 20;218(1):30-8. doi: 10.1016/j.tox.2005.09.014. Epub 2005 Nov 16.
47 Immunological consequences of thalidomide treatment in Sj?gren's syndrome. Ann Rheum Dis. 2006 Jan;65(1):112-4. doi: 10.1136/ard.2005.038406.
48 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.