Iocetamic Acid
Basic information
- CAS
16034-77-8- Standard SMILES
CC(=O)N(CC(C)C(=O)O)c1c(I)cc(I)c(N)c1I- InChIKey
GSVQIUGOUKJHRC-UHFFFAOYSA-N- Molecular formula
- C12H13I3N2O3
- Average molar mass
- 613.96 g/mol
- Monoisotopic mass
- 613.806
Overview
3-(N-acetyl-3-amino-2,4,6-triiodoanilino)-2-methylpropanoic acid is an aromatic amide.
Names & identifiers
- Preferred name
- Iocetamic Acid
- IUPAC
- 3-(N-acetyl-3-amino-2,4,6-triiodoanilino)-2-methylpropanoic acid
- English name
- IOCETAMIC ACID (200 MG)
- Molecular formula
- C12H13I3N2O3
- Molecular weight
- 613.96
Names & synonyms
IOCETAMIC ACIDCholebrine16034-77-8CholimilColebrinaMP-620DTXSID2023149DRC 1201MP 620FA675Q0E3E3-(N-(3-Amino-2,4,6-triiodophenyl)acetamido)-2-methylpropanoic acidN-Acetyl-N-(3-amino-2,4,6-triiodophenyl)-2-methyl-beta-alanine
Show more names
3-(N-acetyl-3-amino-2,4,6-triiodoanilino)-2-methylpropanoic acidmp620drc1201iocetamiciocetamicacidIOCETAMIC ACID (200 MG)IOCETAMIC ACID (200 MG) USP/EP/BP
Propanoic acid, 3-(acetyl(3-amino-2,4,6-triiodophenyl)amino)-2-methyl-DTXCID303149N-Acetyl-N-(3-amino-2,4,6-triiodophenl)-2-methyl-beta-alaninebeta-Alanine, N-acetyl-N-(3-amino-2,4,6-triiodophenyl)-2-methyl-N-Acetyl-N-(2,4,6-triiodo-3-aminophenyl)-beta-aminoisobutyric acidN-Acetyl-N-(3-amino-2,4,6-triiodophenyl)-beta-aminoisobutyric acid3-(Acetyl-(3-amino-2,4,6-triiodophenyl)amino)-2-methylpropanoic acidPropionic acid, 3-(acetyl-(3-amino-2,4,6-triiodophenyl)amino)-2-methyl-
Database identifiers
- CAS
16034-77-8- PubChem CID
- 27648
- DTXSID
DTXSID2023149- ChEMBL
CHEMBL1200770- ChEBI
CHEBI:91662- UNII
- FA675Q0E3E
- EC Number
- 240-173-1
- Nikkaji
- J9.024G
Properties
Computed structural properties
- XLogP
- 2.6
- Topological polar surface area
- 83.6 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 4
- Heavy atoms
- 20
- Formal charge
- 0
- Complexity
- 383
Experimental & physicochemical properties
OdorODORLESS OR HAS FAINT ACETIC ACID ODOR
Color/FormWHITE TO LIGHT CREAM-COLORED POWDER
Solubility
PRACTICALLY INSOL IN WATER; SOMEWHAT SOL IN ETHER, BENZENE; SLIGHTLY SOL IN ACETONE, CHLOROFORM
SLIGHTLY SOL IN ALCOHOL
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Melting Point
224-225 °C
ALSO REPORTED MP RANGE 191-212 °C; CONSISTS OF 2 ISOMERS HAVING MELTING POINTS 232 °C & 200-201 °C & PKA'S OF 4.25 & 4.0 RESPECTIVELY; THE LOWER MELTING COMPD IS APPROX TWO TIMES AS SOLUBLE
Stability/Shelf LifeUNSTABLE IN LIGHT
Physicochemical properties
- Melting point
- 224 · 224-225° (NL 6515305); mp range 191-212° (Korver); Consists of 2 isomers having mps 232° and 200-201°
- Boiling point
- 658.2 · 658.2±55.0 °C(Predicted)
- Density
- 2.2 · 2.2000 (rough estimate)
- refractive index
- 1.74 · 1.7400 (estimate)
- pka
- 4 · 4.0(at 25℃)
- Water Solubility
- 5.286 g/L · 5.286g/L(37 ºC)
- Stability
- Stable. Incompatible with strong oxidizing agents.
- FDA UNII
- 675 Q0E3E · FA675Q0E3E
- ATC code
- 8 AC07 · V08AC07
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H332-H335-H312-H302
- Precautionary statements
- 264 · P264-P280-P305+P351+P338-P337+P313P-P264-P280-P302+P352-P321-P332+P313-P362-P261-P271-P304+P340-P312-P280-P302+P352-P312-P322-P363-P501-P264-P270-P301+P312-P330-P501
- Hazardous Substances Data
- 16034 · 16034-77-8(Hazardous Substances Data)
- Toxicity
- 50 in · LD50 in rats (g/kg): 7.1 orally; 0.70 i.v. (Janbroers)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Toxicology
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.
Safety data
- Toxicity
- LD50 in rats (g/kg): 7.1 orally; 0.70 i.v. (Janbroers)
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H315-H319-H332-H335-H312-H302
- Precautionary statements
- P264-P280-P305+P351+P338-P337+P313P-P264-P280-P302+P352-P321-P332+P313-P362-P261-P271-P304+P340-P312-P280-P302+P352-P312-P322-P363-P501-P264-P270-P301+P312-P330-P501
- Hazardous Substances Data
- 16034-77-8(Hazardous Substances Data)
Chemistry & industry
Pharmacology
ATC Code
V - Various
QV - Various
Metabolism/Metabolites...CONJUGATED WITH GLUCURONIC ACID IN LIVER...
Absorption, Distribution and Excretion...RAPIDLY ABSORBED FOLLOWING ORAL ADMIN, CONJUGATED WITH GLUCURONIC ACID IN LIVER, SECRETED INTO BILE AS RADIOPAQUE GLUCURONIDE, & CONCN IN THE FUNCTIONING GALL BLADDER.
Uses & manufacturing
UsesMEDICATION
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.
General Manufacturing InformationNETHERLAND 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).
Applications
UsesDiagnostic aid (radiopaque medium).
Upstream & downstream products
Upstream raw materials
Additional notes
DefinitionChEBI: 3-(N-acetyl-3-amino-2,4,6-triiodoanilino)-2-methylpropanoic acid is an aromatic amide.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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