| Revision as of 19:55, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 466617398 of page Acetrizoic_acid for the Chem/Drugbox validation project (updated: 'CAS_number'). |
Latest revision as of 20:49, 28 November 2024 edit Headbomb (talk | contribs)Edit filter managers, Autopatrolled, Extended confirmed users, Page movers, File movers, New page reviewers, Pending changes reviewers, Rollbackers, Template editors454,330 edits ce |
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{{Short description|Chemical compound}} |
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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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{{Drugbox |
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{{Drugbox |
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| Verifiedfields = changed |
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| verifiedrevid = 448208161 |
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| verifiedrevid = 477239789 |
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| IUPAC_name = 3-Acetamido-2,4,6-triiodobenzoic acid |
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| IUPAC_name = 3-Acetamido-2,4,6-triiodobenzoic acid |
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| image = Acetrizoic acid.png |
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| image = Acetrizoic acid.png |
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| alt2 = Space-filling model |
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| alt2 = Space-filling model |
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<!--Clinical data--> |
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<!--Clinical data--> |
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| tradename = |
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| tradename = Urokon, Triurol, Salpix, others |
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| Drugs.com = {{Drugs.com|international|acetrizoic-acid}} |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| pregnancy_US = <!-- A / B / C / D / X --> |
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| pregnancy_US = <!-- A / B / C / D / X --> |
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| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> |
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| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> |
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| legal_status = |
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| legal_status = |
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| routes_of_administration = |
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| routes_of_administration = |
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<!--Pharmacokinetic data--> |
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<!--Pharmacokinetic data--> |
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| metabolism = |
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| metabolism = |
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| elimination_half-life = |
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| elimination_half-life = |
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| excretion = |
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| excretion = |
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<!--Identifiers--> |
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<!--Identifiers--> |
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| index2_label= ] salt |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number_Ref = {{cascite|changed|CAS}} |
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| CAS_number = <!-- blanked - oldvalue: 85-36-9 --> |
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| CAS_number = 85-36-9 |
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| CAS_number2 = 129-63-5 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 24256BQV7M |
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| UNII2 = 5GF4B2I1DD |
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| ATC_prefix = V08 |
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| ATC_prefix = V08 |
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| ATC_suffix = AA07 |
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| ATC_suffix = AA07 |
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| PubChem = 6806 |
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| PubChem = 6806 |
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| PubChem2 = 8517 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank_Ref = {{drugbankcite|changed|drugbank}} |
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| DrugBank = |
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| DrugBank = DB09347 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 6547 |
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| ChemSpiderID = 6547 |
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| ChemSpiderID2 = 8203 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = 1201327 |
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| ChEMBL2 = 1201045 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = D02457 |
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| KEGG = D02457 |
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<!--Chemical data--> |
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<!--Chemical data--> |
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| C=9 | H=6 | I=3 | N=1 | O=3 |
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| C=9 | H=6 | I=3 | N=1 | O=3 |
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| molecular_weight = 556.86 g/mol |
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| smiles = O=C(Nc1c(I)c(c(I)cc1I)C(=O)O)C |
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| smiles = O=C(Nc1c(I)c(c(I)cc1I)C(=O)O)C |
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| InChI = 1/C9H6I3NO3/c1-3(14)13-8-5(11)2-4(10)6(7(8)12)9(15)16/h2H,1H3,(H,13,14)(H,15,16) |
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| InChIKey = GNOGSFBXBWBTIG-UHFFFAOYAG |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C9H6I3NO3/c1-3(14)13-8-5(11)2-4(10)6(7(8)12)9(15)16/h2H,1H3,(H,13,14)(H,15,16) |
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| StdInChI = 1S/C9H6I3NO3/c1-3(14)13-8-5(11)2-4(10)6(7(8)12)9(15)16/h2H,1H3,(H,13,14)(H,15,16) |
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| StdInChIKey = GNOGSFBXBWBTIG-UHFFFAOYSA-N |
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| StdInChIKey = GNOGSFBXBWBTIG-UHFFFAOYSA-N |
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}} |
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}} |
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'''Acetrizoic acid''' is a pharmaceutical drug that was used as an ] medium for ].<ref>{{Drugs.com|international|acetrizoic-acid}}: Acetrizoic acid.</ref><ref>{{cite journal|pmid=20641966|year=2004|last1=Cheng|first1=K. T.|title=5-3-Hydroxy-2-hydroxymethyl-propionamido)-''N'',''N''´-dimethyl-''N'',''N''´-bis-(2,3-dihydroxypropyl)-2,4,6-triiodoisophthalamide}}</ref> It was applied in form of its salt, sodium acetrizoate, but is no longer in clinical use.<ref name="cancerweb">{{cite web | url = http://cancerweb.ncl.ac.uk/cgi-bin/omd?acetrizoate+sodium | title = Acetrizoate sodium | date = March 5, 2000 | access-date = 2007-11-14 | publisher = ] | work = Online Medical Dictionary}}</ref> |
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==Chemistry and mechanism of action== |
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The substance has high ] and is ]. The three ] atoms in the molecule readily absorb X-rays and are therefore responsible for its usability as a contrast medium.<ref name="cancerweb" /> |
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==History== |
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Acetrizoate was developed by V.H. Wallingford of ], and introduced in 1950;<ref name=McClennan>{{cite journal |author=McClennan BL |title=Preston M. Hickey memorial lecture. Ionic and nonionic iodinated contrast media: evolution and strategies for use |journal=AJR. American Journal of Roentgenology |volume=155 |issue=2 |pages=225–33 |year=1990 |pmid=2115244 |doi=10.2214/ajr.155.2.2115244}}</ref> it was employed as a contrast agent for several radiographic studies, including ],<ref>{{cite journal |vauthors=NESBIT RM, LAPIDES J |title=Preliminary report on urokon, a new excretory pyelographic medium |journal=J Urol |volume=63 |issue=6 |pages=1109–12 |year=1950 |doi=10.1016/s0022-5347(17)68871-2 |pmid=15422724 }}</ref><ref>{{cite journal |vauthors=EYLER WR, DREW DR, BOHNE AW |title=A comparative clinical trial of urographic media: renografin, hypaque, and urokon |journal=Radiology |volume=66 |issue=6 |pages=871–3 |year=1956 |pmid=13323329 |doi=10.1148/66.6.871}}</ref> ] of the ], ] arteries and the ],<ref>{{cite journal |vauthors=LIU P, MURTAGH F, WYCIS HT, SCOTT M |title=Report of one hundred carotid angiograms taken with the new contrast medium acetrizoate (urokon) on Chamberlain's biplane stereoscopic angiographic unit |journal=A.M.A. Archives of Neurology & Psychiatry |volume=69 |issue=5 |pages=651–2 |year=1953 |pmid=13039633 }}</ref><ref>{{cite journal |vauthors=SEAMAN WB, SCHWARTZ HG |title=Cerebral arteriography with sodium acetrizoate (urokon sodium) 30% |journal=A.M.A. Archives of Surgery |volume=67 |issue=5 |pages=741–5 |year=1953 |pmid=13103941 |doi=10.1001/archsurg.1953.01260040752012}}</ref> and ].<ref>{{cite journal |author=ORLOFF TL |title=Intravenous cholecystography with a new medium; experience with sodium acetrizoate (urokon sodium) seventy per cent |journal=A.M.A. Archives of Surgery |volume=71 |issue=4 |pages=620–2 |year=1955 |pmid=13258064 |doi=10.1001/archsurg.1955.01270160146019}}</ref><ref>{{cite journal |vauthors=WOOLLEY IM, KEIZUR LW, MAYERHARNISCH G |title=Gallbladder visualization following the use of 70 per cent sodium acetrizoate (urokon sodium) for intravenous pyelography |journal=Radiology |volume=69 |issue=4 |pages=576–7 |year=1957 |pmid=13485425 |doi=10.1148/69.4.576}}</ref> It was soon found to be highly toxic to the ]s and ]—work urging caution in its administration was published as early as 1959,<ref>{{cite journal |vauthors=LANCE EM, KILLEN DA, SCOTT HW |title=A plea for caution in the use of sodium acetrizoate (urokon) for aortography |journal=Ann Surg |volume=150 |issue=1 |pages=172 |year=1959 |pmid=13661846 |doi=10.1097/00000658-195907000-00022 |pmc=1613496}}</ref> after reports of adverse reactions ranging from hypersensitivity to brain damage—and was eventually replaced by other agents with higher efficacy and lower toxicity, such as ], a closely related compound.<ref name=McClennan/> |
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==Trade names== |
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Trade names include Urokon, Triurol and Salpix, as well as Gastrografina and Urografina in Portugal. |
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==References== |
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{{reflist}} |
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{{Contrast media}} |
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{{pharma-stub}} |