| Revision as of 20:35, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,055 edits Saving copy of the {{drugbox}} taken from revid 471677885 of page Alfuzosin for the Chem/Drugbox validation project (updated: 'DrugBank'). |
Latest revision as of 00:19, 23 November 2024 edit 98.149.97.245 (talk) →Brand names |
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{{Short description|Chemical compound alfa1-blocker}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}} |
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{{Use dmy dates|date=April 2022}} |
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{{Drugbox |
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{{Drugbox |
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| Verifiedfields = changed |
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| Watchedfields = changed |
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| class = ] |
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| verifiedrevid = 456679205 |
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| verifiedrevid = 477247048 |
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| IUPAC_name = ''N''-propyl] tetrahydrofuran- 2-carboxamide |
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| image = Alfuzosin.svg |
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| image = Alfuzosin.svg |
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| width = 275 |
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<!--Clinical data--> |
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| alt = <!--Clinical data--> |
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| pronounce = {{IPAc-en|æ|l|ˈ|f|juː|z|oʊ|s|ɪ|n}} {{respell|al|FEW|zoh-sin}} |
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| tradename = Uroxatral |
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| tradename = Uroxatral, others |
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| Drugs.com = {{drugs.com|monograph|alfuzosin-hydrochloride}} |
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| Drugs.com = {{drugs.com|monograph|alfuzosin-hydrochloride}} |
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| MedlinePlus = a604002 |
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| MedlinePlus = a64002 |
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| DailyMedID = Alfuzosin |
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| pregnancy_AU = B2 |
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| pregnancy_AU = B2 |
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| routes_of_administration = ] |
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| pregnancy_US = B |
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| legal_UK = POM |
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| legal_UK = POM |
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| legal_US = Rx-only |
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| legal_US = Rx-only |
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| routes_of_administration = Oral |
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<!--Pharmacokinetic data--> |
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<!--Pharmacokinetic data-->| bioavailability = 49% |
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| bioavailability = 49% |
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| protein_bound = 82–90% |
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| metabolism = ] (]-mediated) |
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| protein_bound = 82%-90% |
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| metabolism = ] (]-mediated) |
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| elimination_half-life = 10 hours |
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| elimination_half-life = 10 hours |
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| excretion = Fecal (69%) and ] (24%) |
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| excretion = ] (69%) and ] (24%) |
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<!--Identifiers--> |
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<!--Identifiers-->| IUPHAR_ligand = 7109 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = 81403-80-7 |
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| CAS_number = 81403-80-7 |
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| ATC_suffix = CA01 |
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| ATC_suffix = CA01 |
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| PubChem = 2092 |
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| PubChem = 2092 |
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| DrugBank_Ref = {{drugbankcite|changed|drugbank}} |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = DB00346 |
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| DrugBank = DB00346 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChEMBL = 709 |
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| ChEMBL = 709 |
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<!--Chemical data-->| IUPAC_name = (''RS'')-''N''-propyl] tetrahydrofuran- 2-carboxamide |
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<!--Chemical data--> |
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| C=19 | H=27 | N=5 | O=4 |
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| C = 19 |
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| H = 27 |
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| molecular_weight = 389.449 g/mol |
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| N = 5 |
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| O = 4 |
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| smiles = O=C(NCCCN(c2nc1cc(OC)c(OC)cc1c(n2)N)C)C3OCCC3 |
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| smiles = O=C(NCCCN(c2nc1cc(OC)c(OC)cc1c(n2)N)C)C3OCCC3 |
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| InChI = 1/C19H27N5O4/c1-24(8-5-7-21-18(25)14-6-4-9-28-14)19-22-13-11-16(27-3)15(26-2)10-12(13)17(20)23-19/h10-11,14H,4-9H2,1-3H3,(H,21,25)(H2,20,22,23) |
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| InChIKey = WNMJYKCGWZFFKR-UHFFFAOYAD |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C19H27N5O4/c1-24(8-5-7-21-18(25)14-6-4-9-28-14)19-22-13-11-16(27-3)15(26-2)10-12(13)17(20)23-19/h10-11,14H,4-9H2,1-3H3,(H,21,25)(H2,20,22,23) |
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| StdInChI = 1S/C19H27N5O4/c1-24(8-5-7-21-18(25)14-6-4-9-28-14)19-22-13-11-16(27-3)15(26-2)10-12(13)17(20)23-19/h10-11,14H,4-9H2,1-3H3,(H,21,25)(H2,20,22,23) |
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| StdInChIKey = WNMJYKCGWZFFKR-UHFFFAOYSA-N |
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| StdInChIKey = WNMJYKCGWZFFKR-UHFFFAOYSA-N |
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}} |
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}} |
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<!-- Definition and medical uses --> |
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'''Alfuzosin''', sold under the brand name '''Uroxatral''' among others, is a ] of the ] class. It is used to treat ] (BPH).<ref>{{cite journal | vauthors = Lepor H | title = Alpha-blockers for the Treatment of Benign Prostatic Hyperplasia | journal = The Urologic Clinics of North America | volume = 43 | issue = 3 | pages = 311–23 | date = August 2016 | pmid = 27476124 | pmc = 2213889 | doi = 10.1016/j.ucl.2016.04.009 }}</ref> |
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<!-- Side effects and mechanisms --> |
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As an ] of the ], it works by relaxing the muscles in the ] and ] neck, making urination easier. |
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<!-- Society and culture --> |
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Alfuzosin was patented in 1978 and approved for medical use in 1988.<ref>{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=455 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA455 }}</ref> It was approved in the US for benign prostatic hyperplasia in 2003. In 2020, it was the 336th-most commonly prescribed medication in the United States, with more than 700{{nbsp}}thousand prescriptions.<ref>{{cite web | title = The Top 300 of 2020 | url = https://clincalc.com/DrugStats/Top300Drugs.aspx | website = ClinCalc | access-date = 7 October 2022}}</ref><ref>{{cite web | title = Alfuzosin - Drug Usage Statistics | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/Alfuzosin | access-date = 7 October 2022}}</ref> |
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== Side effects == |
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The most common side effects are ] (due to ]), ], ], ], and abdominal disturbances. Side effects include ], ], and ].<ref>{{cite web|url= https://medlineplus.gov/druginfo/meds/a604002.html#side-effects|title=Alfuzosin|publisher=]|agency=]|date=15 April 2016}}</ref> Adverse effects of alfuzosin are similar to that of ], but with 70% lower rate of ].<ref name=HillsLiu2015>{{cite journal | vauthors = Liu C, Zeng G, Kang R, Wu W, Li J, Chen K, Wan SP | title = Efficacy and Safety of Alfuzosin as Medical Expulsive Therapy for Ureteral Stones: A Systematic Review and Meta-Analysis | journal = PLOS ONE | volume = 10 | issue = 8 | pages = e0134589 | year = 2015 | pmid = 26244843 | pmc = 4526635 | doi = 10.1371/journal.pone.0134589 | bibcode = 2015PLoSO..1034589L | doi-access = free }}{{CC-notice|cc=by4|url=http://journals.plos.org/plosone/article?id=10.1371/journal.pone.0134589|authors=Chenli Liu, Guohua Zeng, Ran Kang, Wenqi Wu, Jiasheng Li, Kang Chen and Show P. Wan}}</ref> |
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== Chemistry == |
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Alfuzosin contains a ], so is ], with two ]ic forms, (''R'')- and (''S'')-alfuzosin. The drug is used as a ], (''RS'')-alfuzosin, a 1:1 mixture of the (''R'')- and (''S'')- forms.<ref name="Rote Liste">Rote Liste Service GmbH (Hrsg.): ''Rote Liste 2017 - Arzneimittelverzeichnis für Deutschland (einschließlich EU-Zulassungen und bestimmter Medizinprodukte)''. Rote Liste Service GmbH, Frankfurt/Main, 2017, Aufl. 57, S. 159, {{ISBN|978-3-946057-10-9}}.</ref> |
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{| class="wikitable" style="text-align:center" |
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|- class="hintergrundfarbe6" |
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! colspan="2"| Enantiomers of alfuzosin |
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| ]<br /><small>]: 123739-69-5</small> |
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| ]<br /><small>CAS number.: 123739-70-8</small> |
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It is provided as the ] salt. |
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==Society and culture== |
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===Brand names=== |
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It is sold under the brand names Alfosoft, Uroxatral,<ref>{{Cite web |title=Alfuzosin (Oral Route) Description and Brand Names - Mayo Clinic |url=https://www.mayoclinic.org/drugs-supplements/alfuzosin-oral-route/description/drg-20061611 |access-date=2022-09-21 |website=www.mayoclinic.org}}</ref> Xatral, Prostetrol,<ref>{{Cite web |title=Prostetrol 10mg 30 tablet |url=https://royalph.com/en/prostetrol-10mg-30tab.html |access-date=2022-09-21 |website=royalph.com |language=en}}</ref> and Alfural.<ref>{{Cite web |title=Γαληνός - Φάρμακο - ALFURAL |url=https://www.galinos.gr/web/drugs/main/drugs/alfural |access-date=2022-09-21 |website=www.galinos.gr |language=el}}</ref>{{Unreliable source?|date=September 2022}} |
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==Synthesis== |
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The nitration of veratraldehyde (1) gives 6-Nitroveratraldehyde (2). Oxidation of the aldehyde to the acid, halogenation with thionyl chloride and amide formation with ammonia gives 4,5-dimethoxy-2-nitrobenzamide (3). Béchamp reduction of the nitro group gives 2-amino-4,5-dimethoxybenzamide (4). Reaction with urea leads to 6,7-Dimethoxyquinazoline-2,4-dione (5). Halogenation with phosphoryl chloride gives 2,4-Dichloro-6,7-dimethoxyquinazoline (6). Treatment with one equivalent of ammonia yields 4-Amino-2-chloro-6,7-dimethoxyquinazoline (7). |
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Synthesis:<ref>Cazor, JL; Borg, F.; Dimsdale, M.; Alfuzosin hydrochloride. Drugs Fut 1986, 11, 10, 821.</ref><ref>Manoury, Philippe M.; Binet, Jean L.; Dumas, Andre P.; Lefevre-Borg, Francoise; Cavero, Icilio (1986). "Synthesis and antihypertensive activity of a series of 4-amino-6,7-dimethoxyquinazoline derivatives". Journal of Medicinal Chemistry 29 (1): 19–25. doi:10.1021/jm00151a003.</ref> Patent:<ref>Philippe M. Manoury, US4315007 (1982 to Synthelabo SA); CA, 96, 162737e.</ref> New patent:<ref>Keshav Deo, et al. WO2009001369 (to Alembic Ltd.).</ref> Radiolabelled:<ref>{{cite journal | vauthors=((Allen, J.)) | journal=Journal of Labelled Compounds and Radiopharmaceuticals | title=A synthesis of alfuzosine hydrochloride | volume=20 | issue=11 | pages=1283–1286 | date= November 1983 | doi=10.1002/jlcr.2580201109}}</ref>]] |
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The reaction of 2-Tetrahydrofuroic Acid (8) with Ethyl chloroformate (9) gives Ethoxycarbonyl oxolane-2-carboxylate, PC10997775 (10). Treatment of the mixed anhydride with 3-Methylaminopropionitrile (11) gives N-(2-Cyanoethyl)tetrahydro-N-methyl-2-furancarboxamide (12). Catalytic hydrogenation gives N-(3-Aminopropyl)tetrahydro-N-methyl-2-furancarboxamide (13). Migration of the amide methyl group to the terminal position gives N-oxolane-2-carboxamide (14). Convergent synthesis between the two coutnerparts completed the synthesis of Alfuzosin (15). |
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==References== |
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{{Reflist}} |
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{{Drugs used in benign prostatic hypertrophy}} |
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{{Adrenergic receptor modulators}} |
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{{Portal bar | Medicine | Viruses}} |
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