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Benzbromarone information


Benzbromarone
Clinical data
AHFS/Drugs.comInternational Drug Names
ATC code
  • M04AB03 (WHO)
Identifiers
IUPAC name
  • (3,5-dibromo-4-hydroxyphenyl)-(2-ethyl-1-benzofuran-3-yl)methanone
CAS Number
  • 3562-84-3 ☒N
PubChem CID
  • 2333
ChemSpider
  • 2243 checkY
UNII
  • 4POG0RL69O
ChEBI
  • CHEBI:3023 checkY
ChEMBL
  • ChEMBL388590 checkY
CompTox Dashboard (EPA)
  • DTXSID4022652 Edit this at Wikidata
ECHA InfoCard100.020.573 Edit this at Wikidata
Chemical and physical data
FormulaC17H12Br2O3
Molar mass424.088 g·mol−1
3D model (JSmol)
  • Interactive image
Melting point161 to 163 °C (322 to 325 °F)
SMILES
  • Brc1cc(cc(Br)c1O)C(=O)c2c3ccccc3oc2CC
InChI
  • InChI=1S/C17H12Br2O3/c1-2-13-15(10-5-3-4-6-14(10)22-13)16(20)9-7-11(18)17(21)12(19)8-9/h3-8,21H,2H2,1H3 checkY
  • Key:WHQCHUCQKNIQEC-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Benzbromarone is a uricosuric agent and non-competitive inhibitor of xanthine oxidase[1] used in the treatment of gout, especially when allopurinol, a first-line treatment, fails or produces intolerable adverse effects. It is structurally related to the antiarrhythmic amiodarone.[2]

Benzbromarone is highly effective and well tolerated,[3][4][5][6] and clinical trials as early as 1981 and in April 2008 have suggested it is superior to both allopurinol, a non-uricosuric xanthine oxidase inhibitor, and probenecid, another uricosuric drug.[7][8]

  1. ^ Sinclair DS, Fox IH (December 1975). "The pharmacology of hypouricemic effect of benzbromarone". The Journal of Rheumatology. 2 (4): 437–45. PMID 1206675.
  2. ^ Kumar V, Locuson CW, Sham YY, Tracy TS (October 2006). "Amiodarone analog-dependent effects on CYP2C9-mediated metabolism and kinetic profiles". Drug Metabolism and Disposition. 34 (10): 1688–96. doi:10.1124/dmd.106.010678. PMID 16815961.
  3. ^ Heel RC, Brogden RN, Speight TM, Avery GS (November 1977). "Benzbromarone: a review of its pharmacological properties and therapeutic use in gout and hyperuricaemia". Drugs. 14 (5): 349–66. doi:10.2165/00003495-197714050-00002. PMID 338280. S2CID 8198915.
  4. ^ Masbernard A, Giudicelli CP (May 1981). "Ten years' experience with benzbromarone in the management of gout and hyperuricaemia" (PDF). South African Medical Journal = Suid-Afrikaanse Tydskrif vir Geneeskunde. 59 (20): 701–6. PMID 7221794.
  5. ^ Perez-Ruiz F, Alonso-Ruiz A, Calabozo M, Herrero-Beites A, García-Erauskin G, Ruiz-Lucea E (September 1998). "Efficacy of allopurinol and benzbromarone for the control of hyperuricaemia. A pathogenic approach to the treatment of primary chronic gout". Annals of the Rheumatic Diseases. 57 (9): 545–9. doi:10.1136/ard.57.9.545. PMC 1752740. PMID 9849314.
  6. ^ Reinders MK, van Roon EN, Houtman PM, Brouwers JR, Jansen TL (September 2007). "Biochemical effectiveness of allopurinol and allopurinol-probenecid in previously benzbromarone-treated gout patients". Clinical Rheumatology. 26 (9): 1459–65. doi:10.1007/s10067-006-0528-3. PMID 17308859.
  7. ^ Schepers GW (1981). "Benzbromarone therapy in hyperuricaemia; comparison with allopurinol and probenecid". The Journal of International Medical Research. 9 (6): 511–5. doi:10.1177/030006058100900615. PMID 7033016. S2CID 33337546.
  8. ^ Reinders MK, van Roon EN, Jansen TL, Delsing J, Griep EN, Hoekstra M, et al. (January 2009). "Efficacy and tolerability of urate-lowering drugs in gout: a randomised controlled trial of benzbromarone versus probenecid after failure of allopurinol". Annals of the Rheumatic Diseases. 68 (1): 51–6. doi:10.1136/ard.2007.083071. PMID 18250112.

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Benzbromarone

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Benzbromarone is a uricosuric agent and non-competitive inhibitor of xanthine oxidase used in the treatment of gout, especially when allopurinol, a first-line...

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Gout suppressants

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allopurinol and Febuxostat, and uricosuric agents, such as probenecid and benzbromarone. Induction therapy of gout targets to relieve acute pain and inflammation...

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Uricosuric

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other medications. The primary uricosuric drugs include probenecid, benzbromarone and sulfinpyrazone. Drugs with other primary uses, that have known uricosuric...

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ATC code M04

Last Update:

Allopurinol, combinations M04AB01 Probenecid M04AB02 Sulfinpyrazone M04AB03 Benzbromarone M04AB04 Isobromindione M04AB05 Lesinurad M04AC01 Colchicine M04AC02...

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Uric acid

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XOTooltip Xanthine oxidase Allopurinol Amflutizole Benzbromarone Caffeic acid Cinnamaldehyde Cinnamomum osmophloeum Febuxostat Myo-inositol Kaempferol...

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Nucleotide

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XOTooltip Xanthine oxidase Allopurinol Amflutizole Benzbromarone Caffeic acid Cinnamaldehyde Cinnamomum osmophloeum Febuxostat Myo-inositol Kaempferol...

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Caffeine

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XOTooltip Xanthine oxidase Allopurinol Amflutizole Benzbromarone Caffeic acid Cinnamaldehyde Cinnamomum osmophloeum Febuxostat Myo-inositol Kaempferol...

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Quercetin

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XOTooltip Xanthine oxidase Allopurinol Amflutizole Benzbromarone Caffeic acid Cinnamaldehyde Cinnamomum osmophloeum Febuxostat Myo-inositol Kaempferol...

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Purine

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XOTooltip Xanthine oxidase Allopurinol Amflutizole Benzbromarone Caffeic acid Cinnamaldehyde Cinnamomum osmophloeum Febuxostat Myo-inositol Kaempferol...

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Dotinurad

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by inhibiting URAT1/SLC22A12 receptor. It is a structural analog of Benzbromarone. Kuriyama S (March 2020). "Dotinurad: a novel selective urate reabsorption...

Word Count : 251

Hyperuricemia

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interfering with xanthine oxidase.[citation needed] Uricosuric agents (benzbromarone, benziodarone, probenecid, lesinurad, sulfinpyrazone, ethebencid, zoxazolamine...

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Fenethylline

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XOTooltip Xanthine oxidase Allopurinol Amflutizole Benzbromarone Caffeic acid Cinnamaldehyde Cinnamomum osmophloeum Febuxostat Myo-inositol Kaempferol...

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Methotrexate

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XOTooltip Xanthine oxidase Allopurinol Amflutizole Benzbromarone Caffeic acid Cinnamaldehyde Cinnamomum osmophloeum Febuxostat Myo-inositol Kaempferol...

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Inositol

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XOTooltip Xanthine oxidase Allopurinol Amflutizole Benzbromarone Caffeic acid Cinnamaldehyde Cinnamomum osmophloeum Febuxostat Myo-inositol Kaempferol...

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Ivermectin

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XOTooltip Xanthine oxidase Allopurinol Amflutizole Benzbromarone Caffeic acid Cinnamaldehyde Cinnamomum osmophloeum Febuxostat Myo-inositol Kaempferol...

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Gout

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prevent further episodes of gout, including probenecid, febuxostat, benzbromarone, and colchicine. Long term medications are not recommended until a person...

Word Count : 7831

Adenosine

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XOTooltip Xanthine oxidase Allopurinol Amflutizole Benzbromarone Caffeic acid Cinnamaldehyde Cinnamomum osmophloeum Febuxostat Myo-inositol Kaempferol...

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Phenolphthalein

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XOTooltip Xanthine oxidase Allopurinol Amflutizole Benzbromarone Caffeic acid Cinnamaldehyde Cinnamomum osmophloeum Febuxostat Myo-inositol Kaempferol...

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Theophylline

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XOTooltip Xanthine oxidase Allopurinol Amflutizole Benzbromarone Caffeic acid Cinnamaldehyde Cinnamomum osmophloeum Febuxostat Myo-inositol Kaempferol...

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Theobromine

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XOTooltip Xanthine oxidase Allopurinol Amflutizole Benzbromarone Caffeic acid Cinnamaldehyde Cinnamomum osmophloeum Febuxostat Myo-inositol Kaempferol...

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Nucleoside

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XOTooltip Xanthine oxidase Allopurinol Amflutizole Benzbromarone Caffeic acid Cinnamaldehyde Cinnamomum osmophloeum Febuxostat Myo-inositol Kaempferol...

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Benziodarone

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vasodilator. Bufeniode has the same aromatic substitution pattern. Amiodarone Benzbromarone, the brominated analogue of benziodarone, used as an uricosuric Dronedarone...

Word Count : 55

Allopurinol

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XOTooltip Xanthine oxidase Allopurinol Amflutizole Benzbromarone Caffeic acid Cinnamaldehyde Cinnamomum osmophloeum Febuxostat Myo-inositol Kaempferol...

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Cytidine monophosphate

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XOTooltip Xanthine oxidase Allopurinol Amflutizole Benzbromarone Caffeic acid Cinnamaldehyde Cinnamomum osmophloeum Febuxostat Myo-inositol Kaempferol...

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Pentoxifylline

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XOTooltip Xanthine oxidase Allopurinol Amflutizole Benzbromarone Caffeic acid Cinnamaldehyde Cinnamomum osmophloeum Febuxostat Myo-inositol Kaempferol...

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Cytosine

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XOTooltip Xanthine oxidase Allopurinol Amflutizole Benzbromarone Caffeic acid Cinnamaldehyde Cinnamomum osmophloeum Febuxostat Myo-inositol Kaempferol...

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Coomassie brilliant blue

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XOTooltip Xanthine oxidase Allopurinol Amflutizole Benzbromarone Caffeic acid Cinnamaldehyde Cinnamomum osmophloeum Febuxostat Myo-inositol Kaempferol...

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Cilostazol

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XOTooltip Xanthine oxidase Allopurinol Amflutizole Benzbromarone Caffeic acid Cinnamaldehyde Cinnamomum osmophloeum Febuxostat Myo-inositol Kaempferol...

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