Iopromide (CHEM016738)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:42:01 UTC
Update Date2016-10-28 10:04:13 UTC
Accession NumberCHEM016738
Identification
Common NameIopromide
ClassSmall Molecule
DescriptionA dicarboxylic acid diamide that consists of N-methylisophthalamide bearing three iodo substituents at positions 2, 4 and 6, a methoxyacetyl substituent at position 5 and two 2,3-dihydroxypropyl groups attached to the amide nitrogens. A water soluble x-ray contrast agent for intravascular administration.
Contaminant Sources
  • STOFF IDENT Compounds
  • Suspected Compounds - Waste Water
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
IopromidaChEBI
IopromidumChEBI
N,N'-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-5-(2-methoxyacetamido)-N-methylisophthalamideChEBI
UltravistChEBI
ProscopeKegg
LopromidHMDB
ClarografHMDB
Ultravist 300HMDB
IopromidHMDB
Chemical FormulaC18H24I3N3O8
Average Molecular Mass791.112 g/mol
Monoisotopic Mass790.870 g/mol
CAS Registry Number73334-07-3
IUPAC NameN-(2,3-dihydroxypropyl)-3-[(2,3-dihydroxypropyl)(methyl)carbamoyl]-5-[(1-hydroxy-2-methoxyethylidene)amino]-2,4,6-triiodobenzene-1-carboximidic acid
Traditional Nameproscope
SMILESCOCC(O)=NC1=C(I)C(C(O)=NCC(O)CO)=C(I)C(C(=O)N(C)CC(O)CO)=C1I
InChI IdentifierInChI=1S/C18H24I3N3O8/c1-24(4-9(28)6-26)18(31)12-13(19)11(17(30)22-3-8(27)5-25)14(20)16(15(12)21)23-10(29)7-32-2/h8-9,25-28H,3-7H2,1-2H3,(H,22,30)(H,23,29)
InChI KeyDGAIEPBNLOQYER-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 4-halobenzoic acids and derivatives. These are benzoic acids or derivatives carrying a halogen atom at the 4-position of the benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct Parent4-halobenzoic acids and derivatives
Alternative Parents
Substituents
  • 4-halobenzoic acid or derivatives
  • 2-halobenzoic acid or derivatives
  • Benzamide
  • Benzoyl
  • Halobenzene
  • Iodobenzene
  • Aryl halide
  • Aryl iodide
  • Vinylogous halide
  • Tertiary carboxylic acid amide
  • Carboxamide group
  • Secondary alcohol
  • Carboximidic acid
  • Carboximidic acid derivative
  • Carboxylic acid derivative
  • Dialkyl ether
  • Ether
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Organohalogen compound
  • Organoiodide
  • Organonitrogen compound
  • Organooxygen compound
  • Primary alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.092 g/LALOGPS
logP-1ALOGPS
logP1.1ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)4.23ChemAxon
pKa (Strongest Basic)2.19ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area175.64 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity146.1 m³·mol⁻¹ChemAxon
Polarizability57.65 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0aor-3000009800-d4eb7c00f7ef4e3c3adaSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00di-0000141900-d1cdbb1581082c3c638aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-006x-0010081900-484ea8ffab12f96d512eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00di-0019760000-3dc5bf91bdb47815fee9Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014j-0059200000-047e7c4128fbfd6816aeSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014j-0397000000-8b00b54a00693ed16a30Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-01bd-2972000000-0565b4327c485775e9e7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0ftr-5930000000-4a161f4b926d1da7163fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00dl-0000081900-4b5238662a76892280cbSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-05fr-0019760000-c5512d68987f36b4b08eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014j-0069200000-62d759cca8eecea14e65Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014j-0297000000-f4e7a88b722caf35d20dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014m-1892000000-99c1943fa38d86cc5f25Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00di-0000041900-31808f9ea15ef7e148c0Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-00di-0019760000-3dc5bf91bdb47815fee9Spectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-00dl-0000081900-4b5238662a76892280cbSpectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-006x-0010081900-484ea8ffab12f96d512eSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-00di-0000041900-5d3e269006c6ded0e39fSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-05fr-0019760000-c5512d68987f36b4b08eSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-00di-0000041900-1e314766cccb8cf739d3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kf-2000001900-d089a3f404ab2418c54fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00fu-6000004900-c670873d53deabb24d02Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056r-3000009100-097a0d506de7b27f6429Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-2000001900-e879a23cf701a7a9851aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05ac-6400003900-e5414049f5dce3c39495Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000f-9100005000-297f8be20ef73659c499Spectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB09156
HMDB IDHMDB0041910
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkIopromide
Chemspider ID3605
ChEBI ID63578
PubChem Compound ID3736
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=20412314
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=20890877
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=20921088
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=21039317
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=21141818
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=21159465
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=21529272
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=21545991
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=21623210
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=21877755
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=21943940
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=22028567
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=22178894
14. Bohm I, Speck U, Schild HH: Pilot study on basophil activation induced by contrast medium. Fundam Clin Pharmacol. 2011 Apr;25(2):267-76. doi: 10.1111/j.1472-8206.2010.00826.x.
15. Lee HC, Chang JG, Yen HW, Liu IH, Lai WT, Sheu SH: Ionic contrast media induced more apoptosis in diabetic kidney than nonionic contrast media. J Nephrol. 2011 May-Jun;24(3):376-80. doi: 10.5301/JN.2010.5784.
16. Kocabay G, Karabay CY: Iopromide-induced encephalopathy following coronary angioplasty. Perfusion. 2011 Jan;26(1):67-70. doi: 10.1177/0267659110385511. Epub 2010 Oct 4.
17. Jensen H, Doughty RW, Grant D, Myhre O: The effects of the iodinated X-ray contrast media iodixanol, iohexol, iopromide, and ioversol on the rat kidney epithelial cell line NRK 52-E. Ren Fail. 2011;33(4):426-33. doi: 10.3109/0886022X.2011.568146.
18. Shin DH, Choi DJ, Youn TJ, Yoon CH, Suh JW, Kim KI, Cho YS, Cho GY, Chae IH, Kim CH: Comparison of contrast-induced nephrotoxicity of iodixanol and iopromide in patients with renal insufficiency undergoing coronary angiography. Am J Cardiol. 2011 Jul 15;108(2):189-94. doi: 10.1016/j.amjcard.2011.03.019. Epub 2011 May 3.
19. Bolognese L, Falsini G, Schwenke C, Grotti S, Limbruno U, Liistro F, Carrera A, Angioli P, Picchi A, Ducci K, Pierli C: Impact of iso-osmolar versus low-osmolar contrast agents on contrast-induced nephropathy and tissue reperfusion in unselected patients with ST-segment elevation myocardial infarction undergoing primary percutaneous coronary intervention (from the Contrast Media and Nephrotoxicity Following Primary Angioplasty for Acute Myocardial Infarction [CONTRAST-AMI] Trial). Am J Cardiol. 2012 Jan 1;109(1):67-74. doi: 10.1016/j.amjcard.2011.08.006. Epub 2011 Sep 22.
20. Cha SH, Kim HS, Lee JY, Kim HO, Park YM: Fixed Drug Eruption due to Iopromide (Ultravist(R)). Ann Dermatol. 2011 Sep;23 Suppl 1:S33-5. doi: 10.5021/ad.2011.23.S1.S33. Epub 2011 Sep 30.