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Iocetamic acid

Iocetamic acid structure

CAS No:
16034-77-8
Formula:
C12H13I3N2O3
Chemical Name:
Iocetamic acid
Synonyms:
Propanoic acid,3-[acetyl(3-amino-2,4,6-triiodophenyl)amino]-2-methyl-;β-Alanine,N-acetyl-N-(3-amino-2,4,6-triiodophenyl)-2-methyl-;3-[Acetyl(3-amino-2,4,6-triiodophenyl)amino]-2-methylpropanoic acid;N-Acetyl-N-(3-amino-2,4,6-triiodophenyl)-2-methyl-β-alanine;Iocetamic acid;N-Acetyl-N-(3-amino-2,4,6-triiodophenyl)-β-aminoisobutyric acid;Cholebrine;N-(3-Amino-2,4,6-triiodophenyl)-3-acetamido-2-methylpropionic acid;DRC 1201;MP 620;Cholimil;25312-12-3
Categories:
Active Pharmaceutical Ingredients > Diagnostic Agents

Description

3-(N-acetyl-3-amino-2,4,6-triiodoanilino)-2-methylpropanoic acid is an aromatic amide.|Iocetamic acid is a diagnostic aid (radiopaque medium)

Iocetamic acid Basic Attributes

Molecular Weight：

613.95663

Exact Mass：

613.96

EC Number：

240-173-1

DSSTox ID：

DTXSID2023149

Color/Form：

WHITE TO LIGHT CREAM-COLORED POWDER

ATC Code：

V - Various

HScode：

2924299090

Characteristics

PSA：

83.63000

XLogP3：

3.73740

Density：

2.2000 (rough estimate)

Melting Point：

224-225 °C

Boiling Point：

658.2±55.0 °C(Predicted)

Flash Point：

351.9ºC

Refractive Index：

1.7400 (estimate)

Water Solubility：

SLIGHTLY SOL IN ALCOHOL

Vapor Pressure：

3.21E-18mmHg at 25°C

Toxicity：

LD50 in rats (g/kg): 7.1 orally; 0.70 i.v. (Janbroers)

Odor：

ODORLESS OR HAS FAINT ACETIC ACID ODOR

Safety Information

Stability/Shelf Life：

Stable. Incompatible with strong oxidizing agents.

Precautionary statement(s)：

P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, P501

Hazard Statements：

H302

GHS Classification：

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, and P501|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Drug Information

Therapeutic Uses：

Contrast Media|AN ORAL CHOLECYSTOGRAPHIC AGENT INDICATED FOR RADIOGRAPHIC VISUALIZATION OF GALL BLADDER. ... CONTRACTION OF GALL BLADDER ALSO MAY PROVIDE VISUALIZATION OF BILIARY DUCTS.|TYROPANOATE 3 G, IOCETAMIC ACID 4.5 G, IOPANOIC ACID 3 G & IOCETAMIC ACID 3 G, WERE EVALUATED IN 800 PT. IOCETAMIC ACID IS AS RELIABLE & EFFECTIVE AS TYROPANOATE OR IOPANOIC ACID IN CHOLECYSTOGRAPHY. 3 G DOSE PRODUCES CHOLECYSTOGRAMS AS SATISFACTORY AS 4.5 G WITH LOWER INCIDENCE OF CRAMPS.

Drug Warnings：

IT IS CONTRAINDICATED IN PT WITH ACUTE NEPHRITIS AND UREMIA, SINCE IT IS ELIMINATED BY THE KIDNEYS. IT SHOULD NOT BE ADMIN WHEN DISORDERS OF THE GI TRACT EXIST WHICH PREVENT ABSORPTION OF THE MEDIUM.

Absorption：

...RAPIDLY ABSORBED FOLLOWING ORAL ADMIN, CONJUGATED WITH GLUCURONIC ACID IN LIVER, SECRETED INTO BILE AS RADIOPAQUE GLUCURONIDE, & CONCN IN THE FUNCTIONING GALL BLADDER.

Metabolism/Metabolites：

...CONJUGATED WITH GLUCURONIC ACID IN LIVER...

Human Toxicity Excerpts：

MEDIA USED FOR GI ROENTGENOGRAPHY & AGENTS ADMIN ORALLY MAY CAUSE NAUSEA, VOMITING, & DIARRHEA. ACUTE TUBULAR NECROSIS HAS BEEN REPORTED TO BE THE CONSEQUENCE OF INGESTION OF CERTAIN GALLBLADDER DYES. /IODINATED CONTRAST MEDIA/|OUT OF 2,200 EXAM WITH IOCETAMIC ACID, 4 CASES OF SEVERE SKIN REACTIONS WERE REPORTED. EVEN THOUGH INCIDENCE OF SKIN REACTIONS WAS 1.8%, ITS SEVERITY INDUCED THE USE OF ANOTHER AGENT FOR ORAL CHOLECYSTOGRAPHY.|ONSET OF ACUTE IODIDE POISONING MAY OCCUR IMMEDIATELY OR SEVERAL HR AFTER ADMIN. ANGIOEDEMA IS OUTSTANDING SYMPTOM, & SWELLING OF LARYNX MAY LEAD TO SUFFOCATION. MULTIPLE CUTANEOUS HEMORRHAGES MAY BE PRESENT. ALSO MANIFESTATIONS OF SERUM-SICKNESS TYPE HYPERSENSITIVITY, SUCH AS FEVER, ARTHRALGIA, LYMPH NODE ENLARGEMENT, & EOSINOPHILIA, MAY APPEAR. THROMBOTIC THROMBOCYTOPENIC PURPURA & FATAL PERIARTERITIS NODOSA ATTRIBUTED TO HYPERSENSITIVITY TO IODIDE HAS BEEN DESCRIBED. /IODINE PREPN/|THE FIRST CASE OF SEVERE THROMBOCYTOPENIA OCCURRED IN AN ADULT MALE AFTER INGESTION OF A WIDELY USED CHOLECYSTOGRAPHIC MEDIUM, IOCETAMIC ACID.

MeSH Entry Terms：

Cholebrine

Iocetamic acid Use and Manufacturing

Methods of Manufacturing

M-NITROANILINE IS HEATED WITH METHACRYLIC ACID & RESULTING N-(3-NITROPHENYL)-2-METHYL-BETA-ALANINE IS N-ACETYLATED WITH A MIXT OF ACETIC ANHYDRIDE & ACETIC ACID. AFTER REDUCING NO2 TO NH2 WITH AID OF RANEY NICKEL, IODINATION IS EFFECTED WITH NAICL2.

Uses

Diagnostic aid (radiopaque medium).

Manufacturing Info：

NETHERLAND PATENT APPLS 6,515,305; 6,607,275 (BOTH 1967 TO DAGRA), CA 67, 108422M (1967); 69, 10263B (1968); KORVER, REC TRAV CHIM 87, 308 (1968).

Laboratory Methods：

A CHEMICAL METHOD IS PRESENTED FOR THE MEASUREMENT OF URINARY IODIDE IN PATIENTS RECEIVING IODINE-CONTAINING CONTRAST AGENTS. THE ADMIN OF A NUMBER OF CONTRAST AGENTS TO PATIENTS, INCLUDING IOCETAMIC ACID, RESULTED IN AN URINARY IODIDE-RELEASE OF UP TO 5.9% OF THE ADMINISTERED DOSE OF ORGANIC IODIDE.

Use Classification：

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

Computed Properties

Molecular Weight:613.96
XLogP3:2.6
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:4
Exact Mass:613.8060
Monoisotopic Mass:613.8060
Topological Polar Surface Area:83.6
Heavy Atom Count:20
Complexity:383
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes