1-N,3-N-bis(2,3-dihydroxypropyl)-5-[N-(2,3-dihydroxypropyl)acetamido]-2,4,6-triiodobenzene-1,3-dicarboxamide

• ChemBase ID: 1188
• Molecular Formular: C19H26I3N3O9
• Molecular Mass: 821.13785
• Monoisotopic Mass: 820.88032343
• SMILES: Ic1c(N(CC(O)CO)C(=O)C)c(I)c(c(I)c1C(=O)NCC(O)CO)C(=O)NCC(O)CO
• Canonical SMILES: OCC(CN(c1c(I)c(C(=O)NCC(CO)O)c(c(c1I)C(=O)NCC(CO)O)I)C(=O)C)O
• InChI: InChI=1S/C19H26I3N3O9/c1-8(29)25(4-11(32)7-28)17-15(21)12(18(33)23-2-9(30)5-26)14(20)13(16(17)22)19(34)24-3-10(31)6-27/h9-11,26-28,30-32H,2-7H2,1H3,(H,23,33)(H,24,34)
• InChIKey: NTHXOOBQLCIOLC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-N,3-N-bis(2,3-dihydroxypropyl)-5-[N-(2,3-dihydroxypropyl)acetamido]-2,4,6-triiodobenzene-1,3-dicarboxamide
• IUPAC Traditional name: iohexol
• Brand Name: Exypaque; Histodenz; Nycodenz; Omnipaque
• Synonyms: 5-(N-2,3-Dihydroxypropylacetamido)-2,4,6-triiodo-N,N′-bis(2,3-dihydroxypropyl)isophthalamide; Histodenz™; Nycodenz; 5-(N-2-3-DIHYDROXYPROPYL-ACETMIDO)-2,4,6-TRIIODO-N,N'-bis-(2,3-DIHYDROXYPROPYL)-ISOPHTHALAMIDE; 5-[N-(2,3-Dihydroxypropyl)acetamido]-2,4,6-triiodo-N,N′-bis(2,3-dihydroxypropyl)isophthalamide; Iohexol

Database IDs

• CAS Number: 66108-95-0
• EC Number: 266-164-2
• MDL Number: MFCD00077732
• Beilstein Number: 2406632
• PubChem SID: 160964650; 24893646; 46506178; 24863593
• PubChem CID: 3730

CALCULATED PROPERTIES

JChem

• Acid pKa: 11.731379
• H Acceptors: 9
• H Donor: 8
• LogD (pH = 5.5): -1.9508227
• LogD (pH = 7.4): -1.9508405
• Log P: -1.9508225
• Molar Refractivity: 148.839 cm^3
• Polarizability: 57.81681 Å^3
• Polar Surface Area: 199.89 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -2.82
• LOG S: -3.01
• Solubility (Water): 7.96e-01 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): -3.05 [HANSCH,C & LEO,AJ (1985)]

Safety Information

• Storage Condition: 0°C
• RTECS: CZ2205000
• German water hazard class: 1
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C; room temp

Product Information

• Purity: ≥98.0% (HPLC)
• Cation Traces: Ca: ≤10 mg/kg; Cd: ≤5 mg/kg; Co: ≤5 mg/kg; Cr: ≤5 mg/kg; Cu: ≤5 mg/kg; Fe: ≤5 mg/kg; K: ≤50 mg/kg; Mg: ≤5 mg/kg; Mn: ≤5 mg/kg; Na: ≤50 mg/kg; Ni: ≤5 mg/kg; Pb: ≤5 mg/kg; Zn: ≤5 mg/kg
• Antion Traces: chloride (Cl-): ≤100 mg/kg; sulfate (SO42-): ≤100 mg/kg
• Loss on Drying: ≤5% loss on drying
• Empirical Formula (Hill Notation): C19H26I3N3O9

DETAILS

MP Biomedicals - 02157750

Useful as a nonionic density gradient medium.

DrugBank - DB01362

• Drug Groups: approved
• Description: Iohexol is an effective non-ionic, water-soluble contrast agent which is used in myelography, arthrography, nephroangiography, arteriography, and other radiographic procedures. Its low systemic toxicity is the combined result of low chemotoxicity and low osmolality. [PubChem]
• Indication: Iohexol ia used in myelography, arthrography, nephroangiography, arteriography, and other radiographic procedures.
• Pharmacology: Iohexol is an effective non-ionic, water-soluble contrast agent which is used in myelography, arthrography, nephroangiography, arteriography, and other radiographic procedures. Its low systemic toxicity is the combined result of low chemotoxicity and low osmolality.
• Toxicity: Non-ionic radiocontrast agents like iohexol are cytotoxic to renal cells. The toxic effects include apoptosis, cellular energy failure, disruption of calcium homeostasis, and disturbance of tubular cell polarity, and are thought to be linked to oxidative stress.
• Affected Organisms: Humans and other mammals
• Absorption: Small amounts are absorbed through the bladder via intravesical instillation. Following intrauterine instillation, the majority of the medium within the uterine cavity is discharged into the vagina immediately upon termination of procedure. However, any medium retained in the uterine or peritoneal cavity is absorbed systemically within 60 minutes. May not be absorbed for up to 24 hours if tubes are obstructed and dilated.
• Half Life: Intrathecal half-life is 3.4 hours (mean). Intravascular is approximately 2 hours (with normal renal function).
• Elimination: Iohexol is absorbed from cerebrospinal fluid (CSF) into the bloodstream and is eliminated by renal excretion. No significant metabolism, deiodination, or biotransformation occurs.
• Distribution: * 350-849 mL/kg
• Clearance: * 109 mL/min [Adult patients receiving 16-18 ml of iohexol (180 mgI/mL) by lumbar intrathecal injection]
• References: Kawada TK: Iohexol and iopamidol: second-generation nonionic radiographic contrast media. Drug Intell Clin Pharm. 1985 Jul-Aug;19(7-8):525-9. [Pubmed] ; Shaw DD, Potts DG: Toxicology of iohexol. Invest Radiol. 1985 Jan-Feb;20(1 Suppl):S10-3. [Pubmed]
• External Links: Wikipedia

Sigma Aldrich - D2158

Application
Useful as a nonionic density gradient medium.
法律信息
Histodenz is a trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - 37890

Application
A non-ionic iodinated gradient medium1,2

REFERENCES

• Rickwood, D., et al., Anal. Biochem. , 123 : 23 (1982).
• Kawada TK: Iohexol and iopamidol: second-generation nonionic radiographic contrast media. Drug Intell Clin Pharm. 1985 Jul-Aug;19(7-8):525-9. Pubmed
• Shaw DD, Potts DG: Toxicology of iohexol. Invest Radiol. 1985 Jan-Feb;20(1 Suppl):S10-3. Pubmed