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  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 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) Y Key:GNOGSFBXBWBTIG-UHFFFAOYSA-N Y
NY  (what is this?)    (verify)

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

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