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Acetrizoic acid

Acetrizoic acid is a pharmaceutical drug that was used as an iodinated contrast medium for X-ray imaging.[1][2] It was applied in form of its salt, sodium acetrizoate, but is no longer in clinical use.[3]

Acetrizoic acid
Clinical data
Trade namesUrokon, Triurol, Salpix, others
AHFS/Drugs.comInternational Drug Names
ATC code
Identifiers
  • 3-Acetamido-2,4,6-triiodobenzoic acid
CAS Number
  • 85-36-9 N
  • Na salt: 129-63-5
PubChem CID
  • 6806
  • Na salt: 8517
DrugBank
  • DB09347 N
ChemSpider
  • 6547 Y
  • Na salt: 8203
UNII
  • 24256BQV7M
  • Na salt: 5GF4B2I1DD
KEGG
  • D02457 Y
ChEMBL
  • ChEMBL1201327 N
  • Na salt: ChEMBL1201045
CompTox Dashboard (EPA)
  • DTXSID2022549
ECHA InfoCard100.001.455
Chemical and physical data
FormulaC9H6I3NO3
Molar mass556.864 g·mol−1
3D model (JSmol)
  • Interactive image
  • O=C(Nc1c(I)c(c(I)cc1I)C(=O)O)C
  • InChI=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) Y
  • Key:GNOGSFBXBWBTIG-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

Chemistry and mechanism of action edit

The substance has high osmolality and is water-soluble. The three iodine atoms in the molecule readily absorb X-rays and are therefore responsible for its usability as a contrast medium.[3]

History edit

Acetrizoate was developed by V.H. Wallingford of Mallinckrodt, and introduced in 1950;[4] it was employed as a contrast agent for several radiographic studies, including pyelography,[5][6] angiography of the brain, carotid arteries and the aorta,[7][8] and cholecystography.[9][10] It was soon found to be highly toxic to the kidneys and nervous system—work urging caution in its administration was published as early as 1959,[11] 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 sodium diatrizoate, a closely related compound.[4]

Trade names edit

Trade names include Urokon, Triurol and Salpix, as well as Gastrografina and Urografina in Portugal.

References edit

  1. ^ International Drug Names: Acetrizoic acid.
  2. ^ Cheng, K. T. (2004). "5-3-Hydroxy-2-hydroxymethyl-propionamido)-N,N´-dimethyl-N,N´-bis-(2,3-dihydroxypropyl)-2,4,6-triiodoisophthalamide". PMID 20641966. {{cite journal}}: Cite journal requires |journal= (help)
  3. ^ a b "Acetrizoate sodium". Online Medical Dictionary. University of Newcastle upon Tyne. March 5, 2000. Retrieved 2007-11-14.
  4. ^ a b McClennan BL (1990). "Preston M. Hickey memorial lecture. Ionic and nonionic iodinated contrast media: evolution and strategies for use". AJR. American Journal of Roentgenology. 155 (2): 225–33. doi:10.2214/ajr.155.2.2115244. PMID 2115244.
  5. ^ NESBIT RM, LAPIDES J (1950). "Preliminary report on urokon, a new excretory pyelographic medium". J Urol. 63 (6): 1109–12. doi:10.1016/s0022-5347(17)68871-2. PMID 15422724.
  6. ^ EYLER WR, DREW DR, BOHNE AW (1956). "A comparative clinical trial of urographic media: renografin, hypaque, and urokon". Radiology. 66 (6): 871–3. doi:10.1148/66.6.871. PMID 13323329.
  7. ^ LIU P, MURTAGH F, WYCIS HT, SCOTT M (1953). "Report of one hundred carotid angiograms taken with the new contrast medium acetrizoate (urokon) on Chamberlain's biplane stereoscopic angiographic unit". AMA Archives of Neurology & Psychiatry. 69 (5): 651–2. PMID 13039633.
  8. ^ SEAMAN WB, SCHWARTZ HG (1953). "Cerebral arteriography with sodium acetrizoate (urokon sodium) 30%". AMA Archives of Surgery. 67 (5): 741–5. doi:10.1001/archsurg.1953.01260040752012. PMID 13103941.
  9. ^ ORLOFF TL (1955). "Intravenous cholecystography with a new medium; experience with sodium acetrizoate (urokon sodium) seventy per cent". AMA Archives of Surgery. 71 (4): 620–2. doi:10.1001/archsurg.1955.01270160146019. PMID 13258064.
  10. ^ WOOLLEY IM, KEIZUR LW, MAYERHARNISCH G (1957). "Gallbladder visualization following the use of 70 per cent sodium acetrizoate (urokon sodium) for intravenous pyelography". Radiology. 69 (4): 576–7. doi:10.1148/69.4.576. PMID 13485425.
  11. ^ LANCE EM, KILLEN DA, SCOTT HW (1959). "A plea for caution in the use of sodium acetrizoate (urokon) for aortography". Ann Surg. 150 (1): 172. doi:10.1097/00000658-195907000-00022. PMC 1613496. PMID 13661846.

acetrizoic, acid, pharmaceutical, drug, that, used, iodinated, contrast, medium, imaging, applied, form, salt, sodium, acetrizoate, longer, clinical, clinical, datatrade, namesurokon, triurol, salpix, othersahfs, drugs, cominternational, drug, namesatc, codev0. Acetrizoic acid is a pharmaceutical drug that was used as an iodinated contrast medium for X ray imaging 1 2 It was applied in form of its salt sodium acetrizoate but is no longer in clinical use 3 Acetrizoic acidClinical dataTrade namesUrokon Triurol Salpix othersAHFS Drugs comInternational Drug NamesATC codeV08AA07 WHO IdentifiersIUPAC name 3 Acetamido 2 4 6 triiodobenzoic acidCAS Number85 36 9 NNa salt 129 63 5PubChem CID6806Na salt 8517DrugBankDB09347 NChemSpider6547 YNa salt 8203UNII24256BQV7MNa salt 5GF4B2I1DDKEGGD02457 YChEMBLChEMBL1201327 NNa salt ChEMBL1201045CompTox Dashboard EPA DTXSID2022549ECHA InfoCard100 001 455Chemical and physical dataFormulaC 9H 6I 3N O 3Molar mass556 864 g mol 13D model JSmol Interactive imageSMILES O C Nc1c I c c I cc1I C O O CInChI InChI 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 YKey GNOGSFBXBWBTIG UHFFFAOYSA N Y N Y what is this verify Contents 1 Chemistry and mechanism of action 2 History 3 Trade names 4 ReferencesChemistry and mechanism of action editThe substance has high osmolality and is water soluble The three iodine atoms in the molecule readily absorb X rays and are therefore responsible for its usability as a contrast medium 3 History editAcetrizoate was developed by V H Wallingford of Mallinckrodt and introduced in 1950 4 it was employed as a contrast agent for several radiographic studies including pyelography 5 6 angiography of the brain carotid arteries and the aorta 7 8 and cholecystography 9 10 It was soon found to be highly toxic to the kidneys and nervous system work urging caution in its administration was published as early as 1959 11 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 sodium diatrizoate a closely related compound 4 Trade names editTrade names include Urokon Triurol and Salpix as well as Gastrografina and Urografina in Portugal References edit International Drug Names Acetrizoic acid Cheng K T 2004 5 3 Hydroxy 2 hydroxymethyl propionamido N N dimethyl N N bis 2 3 dihydroxypropyl 2 4 6 triiodoisophthalamide PMID 20641966 a href Template Cite journal html title Template Cite journal cite journal a Cite journal requires journal help a b Acetrizoate sodium Online Medical Dictionary University of Newcastle upon Tyne March 5 2000 Retrieved 2007 11 14 a b McClennan BL 1990 Preston M Hickey memorial lecture Ionic and nonionic iodinated contrast media evolution and strategies for use AJR American Journal of Roentgenology 155 2 225 33 doi 10 2214 ajr 155 2 2115244 PMID 2115244 NESBIT RM LAPIDES J 1950 Preliminary report on urokon a new excretory pyelographic medium J Urol 63 6 1109 12 doi 10 1016 s0022 5347 17 68871 2 PMID 15422724 EYLER WR DREW DR BOHNE AW 1956 A comparative clinical trial of urographic media renografin hypaque and urokon Radiology 66 6 871 3 doi 10 1148 66 6 871 PMID 13323329 LIU P MURTAGH F WYCIS HT SCOTT M 1953 Report of one hundred carotid angiograms taken with the new contrast medium acetrizoate urokon on Chamberlain s biplane stereoscopic angiographic unit AMA Archives of Neurology amp Psychiatry 69 5 651 2 PMID 13039633 SEAMAN WB SCHWARTZ HG 1953 Cerebral arteriography with sodium acetrizoate urokon sodium 30 AMA Archives of Surgery 67 5 741 5 doi 10 1001 archsurg 1953 01260040752012 PMID 13103941 ORLOFF TL 1955 Intravenous cholecystography with a new medium experience with sodium acetrizoate urokon sodium seventy per cent AMA Archives of Surgery 71 4 620 2 doi 10 1001 archsurg 1955 01270160146019 PMID 13258064 WOOLLEY IM KEIZUR LW MAYERHARNISCH G 1957 Gallbladder visualization following the use of 70 per cent sodium acetrizoate urokon sodium for intravenous pyelography Radiology 69 4 576 7 doi 10 1148 69 4 576 PMID 13485425 LANCE EM KILLEN DA SCOTT HW 1959 A plea for caution in the use of sodium acetrizoate urokon for aortography Ann Surg 150 1 172 doi 10 1097 00000658 195907000 00022 PMC 1613496 PMID 13661846 nbsp This pharmacology related article is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Acetrizoic acid amp oldid 1203336977, wikipedia, wiki, book, books, library,

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