Acetrizoic acid

Acetrizoic acid
Clinical data
Trade names	Urokon, Triurol, Salpix, others
AHFS/Drugs.com	International Drug Names
ATC code	V08AA07 (WHO) ;
Identifiers
	IUPAC name 3-Acetamido-2,4,6-triiodobenzoic acid;
CAS Number	85-36-9 ; Na salt: 129-63-5;
PubChem CID	6806; Na salt: 8517;
DrugBank	DB09347 ;
ChemSpider	6547 ; Na salt: 8203;
UNII	24256BQV7M; Na salt: 5GF4B2I1DD;
KEGG	D02457 ;
ChEMBL	ChEMBL1201327 ; Na salt: ChEMBL1201045;
CompTox Dashboard (EPA)	DTXSID2022549 ;
ECHA InfoCard	100.001.455
Chemical and physical data
Formula	C9H6I3NO3
Molar mass	556.864 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(Nc1c(I)c(c(I)cc1I)C(=O)O)C;
	InChI 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) ; Key:GNOGSFBXBWBTIG-UHFFFAOYSA-N ;
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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]

Chemistry and mechanism of action

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

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

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

References

^ 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. {{cite journal}}: 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". A.M.A. Archives of Neurology & Psychiatry. 69 (5): 651–2. PMID 13039633.
^ SEAMAN WB, SCHWARTZ HG (1953). "Cerebral arteriography with sodium acetrizoate (urokon sodium) 30%". A.M.A. 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". A.M.A. 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.

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[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)

[cancerweb-3] "Acetrizoate sodium". Online Medical Dictionary. University of Newcastle upon Tyne. March 5, 2000. Retrieved 2007-11-14.

[McClennan-4] 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". A.M.A. Archives of Neurology & Psychiatry. 69 (5): 651–2. PMID 13039633.

[8] SEAMAN WB, SCHWARTZ HG (1953). "Cerebral arteriography with sodium acetrizoate (urokon sodium) 30%". A.M.A. 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". A.M.A. 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.

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