General Information of Drug (ID: DMEV954)

Drug Name
Sulfinpyrazone Drug Info
Synonyms
Anturan; Anturane; Anturanil; Anturano; Anturen; Anturidin; Diphenylpyrazone; Enturan; Enturen; Novopyrazone; Sulfinpirazona; Sulfinpyrazine; Sulfinpyrazon; Sulfinpyrazonum; Sulfoxyphenylpyrazolidin; Sulfoxyphenylpyrazolidine; Sulphinpyrazone; Apo Sulfinpyrazone; Apotex Brand of Sulfinpyrazone; Novartis Brand of Sulfinpyrazone; Nu Pharm Brand of Sulfinpyrazone; Nu Sulfinpyrazone; G 28315; Anturane (TN); Apo-Sulfinpyrazone; G 28,315; Nu-Pharm Brand of Sulfinpyrazone; Nu-Sulfinpyrazone; Sulfinpirazona [INN-Spanish]; Sulfinpyrazone (SPZ); Sulfinpyrazonum [INN-Latin]; USAF GE-13; Sulfinpyrazone [USAN:INN:JAN]; Sulfinpyrazone (JP15/USP/INN); (+/-)-SULFINPYRAZONE; 1,2-Diphenyl-3,5-dioxo-4-(2'-phenyl-sulfinyl-aethyl)-pyrazolidin; 1,2-Diphenyl-3,5-dioxo-4-(2'-phenyl-sulfinyl-aethyl)-pyrazolidin [German]; 1,2-Diphenyl-3,5-dioxo-4-(2-phenylsulfinylethyl) pyrazolidine; 1,2-Diphenyl-3,5-dioxo-4-(2-phenylsulfinylethyl)pyrazolidine; 1,2-Diphenyl-4-(2'-phenylsulfinethyl)-3,5-pyrazolidinedione; 1,2-Diphenyl-4-(2-(phenylsulfinyl)ethyl)-3,5-pyrazolidinedione; 1,2-Diphenyl-4-(phenylsulfinylethyl)-3,5-pyrazolidinedione; 1,2-Diphenyl-4-[2-(phenylsulfinyl)ethyl-3,5-pyrazolidinedione; 1,2-diphenyl-4-[2-(phenylsulfinyl)ethyl]pyrazolidine-3,5-dione; 4-(2-Benzenesulfinylethyl)-1,2-diphenylpyrazolidine-3,5-dione; 4-(Phenylsulfoxyethyl)-1,2-diphenyl-3,5-pyrazolidinedione; 4-[2-(benzenesulfinyl)ethyl]-1,2-diphenylpyrazolidine-3,5-dione
Indication
Disease Entry ICD 11 Status REF
Gout FA25 Approved [1]
Therapeutic Class
Uricosuric Agents
Cross-matching ID
PubChem CID
5342
ChEBI ID
CHEBI:9342
CAS Number
CAS 57-96-5
TTD Drug ID
DMEV954
VARIDT Drug ID
DR00513
INTEDE Drug ID
DR1515

Molecule-Related Drug Atlas

Molecule-Related Drug Atlas
Molecule Type:
DTT
DTP
DME
DOT
Drug Status:
Approved Drug(s)
Investigative Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Benzbromarone DMC3YUA Gout FA25 Approved [12]
XR-9456 DMTUFI1 Discovery agent N.A. Investigative [13]
XR-9504 DMIQP69 Discovery agent N.A. Investigative [13]
XR-9544 DM1OZPN Discovery agent N.A. Investigative [13]
XR-9577 DMIZV6T Discovery agent N.A. Investigative [13]
Pyrrolopyrimidine DMZLFVG Discovery agent N.A. Investigative [14]
Ivermectin DMDBX5F Intestinal strongyloidiasis due to nematode parasite 1F6B Approved [85]
Folic Acid DMEMBJC Colorectal carcinoma Approved [86]
Methotrexate DM2TEOL Anterior urethra cancer Approved [58]
Quercetin DM3NC4M Obesity 5B81 Approved [87]
Docetaxel DMDI269 Advanced cancer 2A00-2F9Z Approved [88]
Irinotecan DMP6SC2 Adenocarcinoma 2D40 Approved [89]
Epirubicin DMPDW6T Solid tumour/cancer 2A00-2F9Z Approved [61]
Doxorubicin DMVP5YE Acute myelogenous leukaemia 2A41 Approved [90]
Colchicine DM2POTE Acute gout flare FA25.0 Approved [91]
Dactinomycin DM2YGNW Adult kidney Wilms tumor Approved [91]
⏷ Show the Full List of 16 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Doxorubicin DMVP5YE Acute myelogenous leukaemia 2A41 Approved [15]
Methotrexate DM2TEOL Anterior urethra cancer Approved [16]
Folic Acid DMEMBJC Colorectal carcinoma Approved [17]
Fluorouracil DMUM7HZ Adenocarcinoma 2D40 Approved [18]
Dinoprostone DMTYOPD Medical abortion JA00.1Z Approved [19]
Cisplatin DMRHGI9 Adenocarcinoma 2D40 Approved [20]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [21]
Sulfasalazine DMICA9H Irritable bowel syndrome DD91.0 Approved [22]
Etoposide DMNH3PG Acute myelogenous leukaemia 2A41 Approved [23]
Oxaliplatin DMQNWRD Adenocarcinoma 2D40 Approved [24]
⏷ 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 [25]
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]
Etoposide DMNH3PG Acute myelogenous leukaemia 2A41 Approved [31]
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [32]
Prasterone DM67VKL Chronic obstructive pulmonary disease CA22 Approved [26]
Verapamil DMA7PEW Angina pectoris BA40 Approved [33]
Eplerenone DMF0NQR Heart failure BD10-BD13 Approved [46]
Cannabidiol DM0659E Dravet syndrome 8A61.11 Approved [47]
Isotretinoin DM4QTBN Acne vulgaris ED80 Approved [48]
Voriconazole DMAOL2S Aspergillosis 1F20 Approved [49]
Proguanil DMBL79I Malaria 1F40-1F45 Approved [50]
Ivermectin DMDBX5F Intestinal strongyloidiasis due to nematode parasite 1F6B Approved [50]
Loratadine DMF3AN7 Allergy 4A80-4A85 Approved [51]
Nelfinavir mesylate DMFX6G8 N. A. N. A. Approved [52]
Capsaicin DMGMF6V Back pain ME84.Z Approved [53]
Axitinib DMGVH6N Renal cell carcinoma 2C90 Approved [54]
⏷ Show the Full List of 20 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 [34]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [35]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [35]
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [5]
Verapamil DMA7PEW Angina pectoris BA40 Approved [36]
Diclofenac DMPIHLS Chronic renal failure GB61.Z Approved [37]
Sorafenib DMS8IFC Adenocarcinoma 2D40 Approved [38]
Quinine DMSWYF5 Malaria 1F40-1F45 Approved [35]
Mycophenolate mofetil DMPQAGE Hepatosplenic T-cell lymphoma Approved [39]
Propofol DMB4OLE Anaesthesia 9A78.6 Approved [40]
Simvastatin DM30SGU Arteriosclerosis BD40 Approved [41]
Cyclophosphamide DM4O2Z7 Advanced cancer 2A00-2F9Z Approved [42]
Lovastatin DM9OZWQ Arteriosclerosis BD40 Approved [41]
Ifosfamide DMCT3I8 Adult central nervous system germ cell tumor Approved [42]
Loratadine DMF3AN7 Allergy 4A80-4A85 Approved [41]
Zafirlukast DMHNQOG Asthma CA23 Approved [41]
Ethinyl Estradiol DMODJ40 Acne vulgaris ED80 Approved [41]
Sorafenib DMS8IFC Adenocarcinoma 2D40 Approved [43]
Dabrafenib DMX6OE3 Melanoma 2C30 Approved [44]
Troglitazone DM3VFPD Diabetic complication 5A2Y Approved [45]
⏷ Show the Full List of 20 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Lopinavir DMITQS0 Human immunodeficiency virus infection 1C62 Approved [55]
Probenecid DMMFWOJ Acute gonococcal cervicitis Approved [56]
Docetaxel DMDI269 Advanced cancer 2A00-2F9Z Approved [57]
Methotrexate DM2TEOL Anterior urethra cancer Approved [58]
Arsenic trioxide DM61TA4 Acute lymphoblastic leukaemia 2A85 Approved [59]
Cholic Acid DM7OKQV Cholelithiasis DC11 Approved [60]
Epirubicin DMPDW6T Solid tumour/cancer 2A00-2F9Z Approved [61]
Cisplatin DMRHGI9 Adenocarcinoma 2D40 Approved [62]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [63]
Phenobarbital DMXZOCG Cluster headache 8A81.0 Approved [64]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Verapamil DMA7PEW Angina pectoris BA40 Approved [65]
Vidarabine DM0N85H Hepatosplenic T-cell lymphoma Approved [65]
Beta-carotene DM0RXBT Vitamin deficiency 5B55-5B71 Approved [66]
Fulvestrant DM0YZC6 Breast cancer 2C60-2C65 Approved [67]
Secobarbital DM14RF5 Epilepsy 8A60-8A68 Approved [68]
Etidronic acid DM1XHYJ Bone Paget disease Approved [65]
Tiaprofenic acid DM23D7J Osteoarthritis FA00-FA05 Approved [65]
Bromperidol DM24XYQ Schizophrenia 6A20 Approved [65]
Simvastatin DM30SGU Arteriosclerosis BD40 Approved [69]
Deoxycholic acid DM3GYAL Subcutaneous fat disorder EF02 Approved [70]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Cytochrome P450 2B6 (CYP2B6)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Sertraline DM0FB1J Coronary heart disease BA80.Z Approved [71]
Ritonavir DMU764S Human immunodeficiency virus infection 1C62 Approved [72]
Rifampicin DM5DSFZ Non-insulin dependent diabetes 5A11 Approved [73]
Thalidomide DM70BU5 Adult T-cell leukemia/lymphoma Approved [74]
Phenytoin DMNOKBV Epilepsy 8A60-8A68 Approved [75]
Clopidogrel DMOL54H Acute coronary syndrome BA41 Approved [76]
Artemisinin DMOY7W3 Malaria 1F40-1F45 Approved [77]
Malathion DMXZ84M Pediculus capitis infestation 1G00.0 Approved [78]
Phenobarbital DMXZOCG Cluster headache 8A81.0 Approved [79]
Permethrin DMZ0Q1G Pediculus capitis infestation 1G00.0 Approved [80]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Bile salt export pump (ABCB11)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Glimepiride DM5FSJA Diabetic complication 5A2Y Approved [81]
Ezetimibe DM7A8TW Atherosclerosis BD40 Approved [7]
Glipizide DMZA5PQ Diabetic complication 5A2Y Approved [7]
Bosentan DMIOGBU Pulmonary arterial hypertension BB01.0 Approved [82]
Indinavir DM0T3YH Human immunodeficiency virus infection 1C62 Approved [81]
Ofloxacin DM0VQN3 Acute gonococcal cervicitis Approved [7]
Primidone DM0WX6I Epilepsy 8A60-8A68 Approved [83]
Gefitinib DM15F0X Colon adenocarcinoma Approved [81]
Drospirenone DM1A9W3 Acne vulgaris ED80 Approved [84]
Nitrendipine DM21C09 Hypertension BA00-BA04 Approved [81]
⏷ 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
Multidrug resistance-associated protein 1 (ABCC1) TTOI92F MRP1_HUMAN Modulator [2]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Multidrug resistance-associated protein 2 (ABCC2) DTFI42L MRP2_HUMAN Substrate [3]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4) DE4LYSA CP3A4_HUMAN Substrate [4]
Cytochrome P450 2C8 (CYP2C8) DES5XRU CP2C8_HUMAN Substrate [5]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
ATP-binding cassette sub-family C member 2 (ABCC2) OTJSIGV5 MRP2_HUMAN Gene/Protein Processing [6]
Bile salt export pump (ABCB11) OTRU7THO ABCBB_HUMAN Gene/Protein Processing [7]
Cytochrome P450 2B6 (CYP2B6) OTOYO4S7 CP2B6_HUMAN Gene/Protein Processing [8]
Cytochrome P450 2C8 (CYP2C8) OTHCWT42 CP2C8_HUMAN Gene/Protein Processing [9]
Cytochrome P450 3A4 (CYP3A4) OTQGYY83 CP3A4_HUMAN Gene/Protein Processing [10]
Multidrug resistance-associated protein 1 (ABCC1) OTGUN89S MRP1_HUMAN Gene/Protein Processing [11]
Nuclear receptor subfamily 1 group I member 2 (NR1I2) OTC5U0N5 NR1I2_HUMAN Gene/Protein Processing [4]

References

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35 Role of cytochrome P450 2C8 in drug metabolism and interactions. Pharmacol Rev. 2016 Jan;68(1):168-241.
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37 Analysis of human cytochrome P450 2C8 substrate specificity using a substrate pharmacophore and site-directed mutants. Biochemistry. 2004 Dec 14;43(49):15379-92.
38 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.
39 PharmGKB summary: mycophenolic acid pathway. Pharmacogenet Genomics. 2014 Jan;24(1):73-9.
40 Possible involvement of multiple human cytochrome P450 isoforms in the liver metabolism of propofol. Br J Anaesth. 1998 Jun;80(6):788-95.
41 Examination of 209 drugs for inhibition of cytochrome P450 2C8. J Clin Pharmacol. 2005 Jan;45(1):68-78.
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43 Differential inhibition of human CYP2C8 and molecular docking interactions elicited by sorafenib and its major N-oxide metabolite. Chem Biol Interact. 2021 Apr 1;338:109401. doi: 10.1016/j.cbi.2021.109401. Epub 2021 Feb 5.
44 Dabrafenib inhibits ABCG2 and cytochrome P450 isoenzymes; potential implications for combination anticancer therapy. Toxicol Appl Pharmacol. 2022 Jan 1;434:115797. doi: 10.1016/j.taap.2021.115797. Epub 2021 Nov 13.
45 Transcriptomic analysis of untreated and drug-treated differentiated HepaRG cells over a 2-week period. Toxicol In Vitro. 2015 Dec 25;30(1 Pt A):27-35.
46 The relative role of CYP3A4 and CYP3A5 in eplerenone metabolism. Toxicol Lett. 2019 Oct 15;315:9-13.
47 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.
48 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.
49 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.
50 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.
51 Cetirizine and loratadine-based antihistamines with 5-lipoxygenase inhibitory activity. Bioorg Med Chem Lett. 2004 Nov 15;14(22):5591-4.
52 Mechanism-based inactivation of CYP3A by HIV protease inhibitors. J Pharmacol Exp Ther. 2005 Feb;312(2):583-91.
53 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.
54 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.
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56 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.
57 Association of genetic polymorphisms in SLCO1B3 and ABCC2 with docetaxel-induced leukopenia. Cancer Sci. 2008 May;99(5):967-72.
58 Methotrexate normalizes up-regulated folate pathway genes in rheumatoid arthritis. Arthritis Rheum. 2013 Nov;65(11):2791-802.
59 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.
60 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.
61 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.
62 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.
63 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.
64 Differential regulation of sinusoidal and canalicular hepatic drug transporter expression by xenobiotics activating drug-sensing receptors in primary human hepatocytes. Drug Metab Dispos. 2006 Oct;34(10):1756-63. doi: 10.1124/dmd.106.010033. Epub 2006 Jul 12.
65 Screening of a chemical library reveals novel PXR-activating pharmacologic compounds. Toxicol Lett. 2015 Jan 5;232(1):193-202. doi: 10.1016/j.toxlet.2014.10.009. Epub 2014 Oct 16.
66 Induction of PXR-mediated metabolism by beta-carotene. Biochim Biophys Acta. 2005 May 30;1740(2):162-9. doi: 10.1016/j.bbadis.2004.11.013. Epub 2004 Dec 8.
67 Lignans, bacteriocides and organochlorine compounds activate the human pregnane X receptor (PXR). Toxicol Appl Pharmacol. 2005 Dec 1;209(2):123-33. doi: 10.1016/j.taap.2005.03.015.
68 Identification and validation of novel human pregnane X receptor activators among prescribed drugs via ligand-based virtual screening. Drug Metab Dispos. 2011 Feb;39(2):337-44. doi: 10.1124/dmd.110.035808. Epub 2010 Nov 10.
69 Identification of HMG-CoA reductase inhibitors as activators for human, mouse and rat constitutive androstane receptor. Drug Metab Dispos. 2005 Jul;33(7):924-9.
70 Acetylated deoxycholic (DCA) and cholic (CA) acids are potent ligands of pregnane X (PXR) receptor. Toxicol Lett. 2017 Jan 4;265:86-96.
71 Cytochrome P450 inhibition potential of new psychoactive substances of the tryptamine class. Toxicol Lett. 2016 Jan 22;241:82-94.
72 Transcriptional profiling suggests that Nevirapine and Ritonavir cause drug induced liver injury through distinct mechanisms in primary human hepatocytes. Chem Biol Interact. 2016 Aug 5;255:31-44.
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74 Thalidomide increases human hepatic cytochrome P450 3A enzymes by direct activation of the pregnane X receptor. Chem Res Toxicol. 2014 Feb 17;27(2):304-308.
75 Human constitutive androstane receptor mediates induction of CYP2B6 gene expression by phenytoin. J Biol Chem. 2004 Jul 9;279(28):29295-301. doi: 10.1074/jbc.M400580200. Epub 2004 Apr 28.
76 Identification of novel agonists by high-throughput screening and molecular modelling of human constitutive androstane receptor isoform 3. Arch Toxicol. 2019 Aug;93(8):2247-2264. doi: 10.1007/s00204-019-02495-6. Epub 2019 Jul 16.
77 Antimalarial artemisinin drugs induce cytochrome P450 and MDR1 expression by activation of xenosensors pregnane X receptor and constitutive androstane receptor. Mol Pharmacol. 2005 Jun;67(6):1954-65.
78 Characterization of human cytochrome P450 induction by pesticides. Toxicology. 2012 Mar 29;294(1):17-26.
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