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Acetrizoic acid

Acetrizoic acid structure

CAS No:
85-36-9
Formula:
C9H6I3NO3
Chemical Name:
Acetrizoic acid
Synonyms:
Benzoic acid,3-(acetylamino)-2,4,6-triiodo-;Benzoic acid,3-acetamido-2,4,6-triiodo-;3-(Acetylamino)-2,4,6-triiodobenzoic acid;3-Acetamido-2,4,6-triiodobenzoic acid;2,4,6-Triiodo-3-acetamidobenzoic acid;Acetrizoic acid;Urokon;3-Acetylamino-2,4,6-triiodobenzoic acid;Opacaron;Urokonic acid
Categories:
Active Pharmaceutical Ingredients > Diagnostic Agents

Description

Acetrizoic acid is a molecule used as a contrast medium.

Acetrizoic acid is an aminobenzoic acid.|Acetrizoic acid presents the molecular formula of 3-acetamidol-2,4,6-triiodobenzoic acid and it is the first monomeric ionic compound used as an X-ray contrast agent. It was first synthesized by Wallingford in 1953 and it was filled in the FDA by the Johnson & Johnson subsidiary, Cilag Chemie AG, on February 8th, 1978. Acetrizoic acid presents, in the FDA records, a category of drug substance with an inactive status.|An iodinated radiographic contrast medium used as acetrizoate sodium in HYSTEROSALPINGOGRAPHY.

Acetrizoic acid Basic Attributes

Molecular Weight：

556.86

Exact Mass：

556.86

EC Number：

201-600-7

UNII：

24256BQV7M

NSC Number：

758681

DSSTox ID：

DTXSID2022549

ATC Code：

V - Various

HScode：

2924299090

Characteristics

PSA：

66.4

XLogP3：

2.6

Density：

2.8±0.1 g/cm3

Melting Point：

280-280.5 °C (decomp)

Boiling Point：

547.1

Flash Point：

284.7±30.1 °C

Refractive Index：

1.802

Water Solubility：

1.28g/L(25 ºC)

Toxicity：

Oral-mouse LD50: 20000mg/kg; intravenous-mouse LD50: 8000 mg/kg

Flammability characteristics：

Flammable; decomposes by heating to release toxic nitrogen oxides, iodide fumes

Safety Information

hazard class code：

36/37/38

safety instructions：

26-36/37/39

RTECS Number：

DG0887000

Storage features：

Warehouse ventilated, low temperature and dry

Precautionary statement(s)：

P264, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, P362

Hazard Statements：

H315

GHS Classification：

|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P264, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, and P362|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Toxicity

Toxicity class：

practically nontoxic

Toxicity Summary：

In preclinical studies performed in rodents, the LD50 after oral or intravenous administration was 2 g/kg and 8 g/kg respectively.

Protein Binding：

The radiographic agents such as acetrizoic acid are carried free in plasma in which less than 5% of the injected dose is protein bound.

Drug Information

Drug Indication：

Acetrizoic acid indication was to be used as a contrast agent for X-ray. Some information indicates its nephrotropic property as one of the characteristics for the utilization of acetrizoic acid. The X-ray imaging depends on the difference in tissue density which is provided by an X-ray attenuation between the area of interest and the surrounding tissue. The use of contrast agents will provoke a contrast enhancement or opacification and it will improve the differentiation of pathological processes from normal tissue.

MeSH：

Substances used to allow enhanced visualization of tissues. (See all compounds classified as Contrast Media.)

Absorption：

After intravenous administration, acetrizoic acid gets largely distributed in the extracellular fluid space. Radiographic agents like acetrizoic agents present variations in the plasma concentration depending on the dose and injection rate. After 5 minutes of administration, about 80% of the administered dose will stay outside of the intravascular compartment. There are some exceptions to the diffusion, such as the brain, neural tissue and testes where the tight junctions do not allow extravascularization.|After intravenous administration, acetrizoic acid is mainly excreted unchanged by the kidney. The elimination pathway is handled by a glomerular filtration and concentration by tubular resorption of water. The excreted dose is of about 83% of the administered dose after 3 hours and of about 100% at 24 hours.

Metabolism/Metabolites：

The majority of the administered dose of acetrizoic acid remains unchanged.

Biological Half-Life：

When water-soluble contrast agents, such as acetrizoic acid, are administered, it is reported a half-life of approximate 4 hours.

Mechanism of Action：

Iodine, a big component in acetrizoic acid, is an element with a high atomic density. This property causes attenuation of X-rays within the diagnostic energy spectrum. Thus, acetrizoic acid is a water-soluble and reasonably safe iodinated contrast agent that can be intravenously administered for clinical applications.

MeSH Entry Terms：

Acetrizoate Sodium

Acetrizoic acid Use and Manufacturing

Uses

radiopaque agent

Use Classification：

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

Computed Properties

Molecular Weight:556.86
XLogP3:2.6
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:556.7482
Monoisotopic Mass:556.7482
Topological Polar Surface Area:66.4
Heavy Atom Count:16
Complexity:300
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

Sodium benzoate

Benzene

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Acetrizoic acid

CAS No.: 85-36-9

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Acetrizoic acid 85-36-9

CAS No.: 85-36-9

Grade: Pharmaceutical Grade

Content: 99%

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