Amidotrizoic acid

Structural formula
General
Non-proprietary name	Amidotrizoic acid
other names	3,5-bis (acetamido) -2,4,6-triiodobenzoic acid ( IUPAC )
Molecular formula	C 11 H 9 I 3 N 2 O 4
External identifiers / databases
EC number	204-223-6
ECHA InfoCard	100.003.840
PubChem	2140
ChemSpider	2055
DrugBank	DB00271
Wikidata	Q411511
Drug information
ATC code	V08 AA01
Drug class	X-ray contrast media
properties
Molar mass	613.91 g · mol -1
Melting point	> 300 ° C
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
Toxicological data	8900 mg kg −1 ( LD 50 , mouse , iv )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Amidotrizoic acid ( amidotrizoate , 3,5-bis (acetamido) -2,4,6-triiodobenzoic acid) is a water-soluble, kidney-permeable, highly osmolar, iodine-containing contrast medium used in radiology .

links

Amidotrizoic acid is used medicinally in the form of various salts:

Meglumine amidotrizoate
Sodium amidotrizoate
L- lysine amidotrizoate

The respective formulations (solutions for oral intake, injection , instillation ) differ in their osmolality (it is 5 to 8 times higher than that of the blood), in their sodium and iodine content and in their viscosity , which determines the type of application becomes.

Applications

Amidotrizoate-containing contrast media are used for various purposes.

Visualization of the gastrointestinal tract , especially if a perforation is suspected. In contrast to contrast media containing barium sulfate , amidotrizoate does not lead to the dreaded chemical peritonitis when it escapes into the abdominal cavity . Highly concentrated contrast media can be used (for example 10 g sodium amidotrizoate and 66 g meglumine amidotrizoate per 100 ml contrast media; trade names Gastrografin ^® , Gastrolux ^® ).

Representations in the urological / endoscopic area: for example the urinary drainage system using retrograde urethrography , the joints using arthrography , or the biliary tract, gall bladder and pancreatic duct using endoscopic retrograde cholangiopancreatography . Depending on the area of application, solutions of various osmolality and viscosity are used (for example 60 g of L-lysine amidotrizoate per 100 ml of contrast medium; trade name Peritrast Infusio ^® 300/60% ).

On July 1, 2000, the Federal Institute for Drugs and Medical Devices (BfArM) revoked the approval of ionic, strongly hypertonic contrast media (diatrizoate = amidotrizoate, ioxitalamate) for intravascular administration. The justification for this measure lies in the negative benefit-risk assessment of these contrast media. The low-osmolar and especially the non-ionic contrast media are clearly better tolerated due to their reduced osmotoxic and chemotoxic effects.

Structure-activity relationships

The carboxy group is responsible for salt formation and thus for solubility and excretion with the urine. The three symmetrically arranged iodine atoms produce the desired contrast density. The acetylamino groups reduce the lipophilicity of the basic substance and cause a drastic decrease in protein binding . High protein binding is believed to be responsible for membrane damage, inhibition of enzymes and other side effects.

literature

W. Forth, D. Henschler, W. Rummel: General and special pharmacology and toxicology . 9th edition. URBAN & FISCHER, Munich 2005, ISBN 3-437-42521-8 .

Individual evidence

↑ Entry on amidotrizoic acid. In: Römpp Online . Georg Thieme Verlag, accessed on May 30, 2014.
↑ ^a ^b Data sheet Diatrizoic acid from Sigma-Aldrich , accessed on November 18, 2019 ( PDF ).
↑ Entry on amidotrizoic acid in the ChemIDplus database of the United States National Library of Medicine (NLM) .
↑ BfArM Risk Information: Revocation of ionic X-ray contrast media (amidotrizoic acid, iotalamic acid) for intravascular use ordered on July 1, 2000 (accessed on June 6, 2015).

Trade names

Monopreparations

Gastrografin (D, CH), Gastrolux (D), Gastrolux CT (D), Gastrolux RE (D), Gastrovue (Dom. Rep.), Peritrast (D, A), Urolux Retro (D)

Combination preparations

Ethibloc (D),

[1] Entry on amidotrizoic acid. In: Römpp Online . Georg Thieme Verlag, accessed on May 30, 2014.

[Sigma-2] Data sheet Diatrizoic acid from Sigma-Aldrich , accessed on November 18, 2019 ( PDF ).

[ChemIDplus-3] Entry on amidotrizoic acid in the ChemIDplus database of the United States National Library of Medicine (NLM) .

[4] BfArM Risk Information: Revocation of ionic X-ray contrast media (amidotrizoic acid, iotalamic acid) for intravascular use ordered on July 1, 2000 (accessed on June 6, 2015).