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Iopromid

Iopromide

HCID 3736
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GrundinformationenNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
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Grundinformationen

CAS
73334-07-3
Standard-SMILES
COCC(=O)Nc1c(I)c(C(=O)NCC(O)CO)c(I)c(C(=O)N(C)CC(O)CO)c1I
InChIKey
DGAIEPBNLOQYER-UHFFFAOYSA-N
Summenformel
C18H24I3N3O8
Durchschnittliche Molmasse
791,1 g/mol
Monoisotopische Masse
790,8698

Namen und Bezeichner

Bevorzugter Name
Iopromide
IUPAC
1-N,3-N-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-5-[(2-methoxyacetyl)amino]-3-N-methylbenzene-1,3-dicarboxamide
Lokaler Name
Iopromid
Englischer Name
Iopromide
Summenformel
C18H24I3N3O8
Molmasse
791.11

Namen und Synonyme

iopromide73334-07-3UltravistIopromidumIopromidaProscopeUltravist 300iopromidUltravist 370Ultravist 150Ultravist 240ZK 35760
Weitere Namen anzeigen
1,3-benzenedicarboxamide,n,n’-bis(2,3-dihydroxypropyl)-5-((methoxyacetyl)aminoN1,N3-Bis(2,3-dihydroxypropyl)-2,4,6-triiodo-5-(2-methoxyacetamido)-N1-methylisophthalamideshl414coproMide
DTXSID0023163Ultravist (pharmacy bulk)712BAC33MZZK-35760N,N'-Bis(2,3-dihydroxypropyl)-2,4,6-triiodo-5-(2-methoxyacetamido)-N-methylisophthalamideDTXCID503163CHEBI:63578Ultravist 300 In Plastic Container

Datenbank-Bezeichner

CAS
73334-07-3
PubChem CID
3736
DTXSID
DTXSID0023163
ChEMBL
CHEMBL1725
ChEBI
CHEBI:63578
UNII
712BAC33MZ
EC Number

Eigenschaften

Berechnete Struktureigenschaften

XLogP
-2,1
Polarare Oberfläche (TPSA)
169 Ų
H-Brücken-Donoren
6
H-Brücken-Akzeptoren
8
Frei drehbare Bindungen
11
Schwere Atome
32
Formalladung
0
Komplexität
647

Experimentelle und physikochemische Eigenschaften

LogP-2.05
Ionization Efficiency · 6 Einträge

Positive

2.7

2.7

Agilent XCT

Electrospray ionization

formic acid (5.3nM)

Collision Cross Section223.51 Ų [M+H]+;212.3 Ų [M-H]-

Physikochemische Eigenschaften

Schmelzpunkt
broad (160C transition)
Siedepunkt
840.9 · 840.9±65.0 °C(Predicted)
Dichte
2.173 · 2.173±0.06 g/cm3(Predicted)
storage temp.
2 · Keep in dark place,Sealed in dry,2-8°C
Löslichkeit
Freely soluble in water and in dimethyl sulfoxide, practically insoluble in ethanol (96 per cent) and in acetone.
pka
10.62 · 10.62±0.70(Predicted)
Aggregatzustand
Solid
Farbe
White to off-white

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 6 Einträge

This chemical does not meet GHS hazard criteria for 2.4% (1 of 41) of reports.

Warning

H400 (95.1%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard];H410 (97.6%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

P273, P391, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 41 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Reported as not meeting GHS hazard criteria per 1 of 41 reports by companies.;There are 3 notifications provided by 40 of 41 reports by companies with hazard statement code(s).;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Gefahrenhinweise

Hazard Classes and CategoriesAquatic Acute 1 (95.1%);Aquatic Chronic 1 (97.6%)

Toxikologische Informationen

Effects During Pregnancy and Lactation · 1 Eintrag

◉ Summary of Use during Lactation;Intravenous iodinated contrast media are poorly excreted into breastmilk and poorly absorbed orally so they are not likely to reach the bloodstream of the infant or cause any adverse effects in breastfed infants. Guidelines developed by several professional organizations state that breastfeeding need not be disrupted after a nursing mother receives an iodine-containing contrast medium. However, because there is no published experience with iopromide during breastfeeding, other agents may be preferred, especially while nursing a newborn or preterm infant.;◉ Effects in Breastfed Infants;Relevant published information was not found as of the revision date.;◉ Effects on Lactation and Breastmilk;Relevant published information was not found as of the revision date.

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 3 Einträge

V08AB05

V - Various;V08 - Contrast media;V08A - X-ray contrast media, iodinated;V08AB - Watersoluble, nephrotropic, low osmolar x-ray contrast media;V08AB05 - Iopromide

QV - Various;QV08 - Contrast media;QV08A - X-ray contrast media, iodinated;QV08AB - Watersoluble, nephrotropic, low osmolar x-ray contrast media;QV08AB05 - Iopromide

Protein BindingThe plasma protein binding of iopromide is 1%.
Pharmacodynamics · 1 Eintrag

After intravenous injection, opacification of the renal parenchyma begins within 1 minute. Excretion of the contrast agent becomes apparent in 1 to 3 minutes with optimal contrast in the calyces and collecting system occurring between 5 and 15 minutes. In nephropathic conditions, particularly when excretory capacity has been altered, the excretion rate varies unpredictably and opacification may be delayed for several hours after injection. the degree of contrast enhancement is related to the iodine concentration in the tissue of interest.

Mechanism of Action · 1 Eintrag

Iopromide is a nonionic iodinated, water-soluble, radiographic contrast medium that is available in two stable, ready-to-use solutions of different concentrations (i.e., 300 mg I/mL and 370 mg I/mL). Following intravascular injection, iopromide provides radiographic opacification of the vasculature and extracellular space in the path of flow of the agent, allowing diagnostic assessment of the limbs and internal organs until significant dilution occurs.

Biological Half-Life · 1 Eintrag

After intravenous administration to healthy adult subjects, the plasma iopromide concentration-time profile shows an initial distribution phase with a half-life of 0.24 hours; a main elimination phase with a half-life of 2 hours; and a terminal elimination phase with a half-life of 6.2 hours.

Metabolism/MetabolitesIopromide does not undergo significant metabolism, deiodination, or biotransformation.

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Notizen zur Verbindung

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Auf dieser SeiteGrundinformationenNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
277-385-9
Nikkaji
J11.916D
Stabilität
Hygroscopic
Major Application
clinical
InChI
InChI=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)
InChIKey
DGAIEPBNLOQYER-UHFFFAOYSA-N
SMILES
C1(C(N(CC(O)CO)C)=O)=C(I)C(NC(COC)=O)=C(I)C(C(NCC(O)CO)=O)=C1I
CAS Datenbank
73334 · 73334-07-3(CAS DataBase Reference)
EPA chemische Informationen
1 · 1,3-Benzenedicarboxamide, N1,N3-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-5-[(2-methoxyacetyl)amino]-N1-methyl- (73334-07-3)

Sicherheitsdaten

wgk
3
ridadr
UN 3077 9 / PGIII
hs_code
2924296000
RTECS-Nr.
CZ2230000
risk_code
50/53
Toxizität
LD50 in mice, rats (g iodine/kg body weight): 16.5, 11.4 i.v. (Muetzel)
hazard_code
N
safety_code
60-61
hazard_class
9
Speicherklasse
11 - Combustible Solids
Hazard Classifications
Aquatic Acute 1Aquatic Chronic 1
FDA Pharmacological Classification · 6 Einträge

712BAC33MZ

IOPROMIDE

Established Pharmacologic Class [EPC] - Radiographic Contrast Agent

Mechanisms of Action [MoA] - X-Ray Contrast Activity

Iopromide is a Radiographic Contrast Agent. The mechanism of action of iopromide is as a X-Ray Contrast Activity.

IOPROMIDE

MeSH Pharmacological ClassificationSubstances used to allow enhanced visualization of tissues.
Absorption, Distribution and Excretion · 4 Einträge

Immediately following intravascular injection, iopromide reaches peak plasma concentrations and is then rapidly distributed throughout the extracellular fluid compartment. It displays little tendency to bind to serum or plasma proteins. Iodinated contrast agents cross a disrupted blood-brain barrier.

The amounts excreted unchanged in urine represent 97% of the dose in adult healthy subjects. Only 2% of the dose is recovered in the feces. Similar recoveries in urine and feces are observed in middle-aged and elderly patients. This finding suggests that, compared to the renal route, biliary and/or gastrointestinal excretion is not important for iopromide. During the slower terminal phase, only 3% of the dose is eliminated; 97% of the dose is disposed of during the earlier phases, the largest part of which occurs during the main elimination phase. The ratio of the renal clearance of iopromide to the creatinine clearance is 0.82, suggesting that iopromide is mainly excreted by glomerular filtration. Additional tubular reabsorption is possible.

The total volume of distribution at steady state is about 16 L, suggesting distribution into extracellular space.

The mean total and renal clearances are 107 mL/min and 104 mL/min, respectively.

Verwendung und Herstellung

Uses · 1 Eintrag

Use (kg) in Switzerland (2009): >5000;Use (kg; approx.) in Germany (2009): >25000;Use (kg; exact) in Germany (2009): 46863;Consumption (g per capita) in Switzerland (2009): 0.64;Consumption (g per capita; approx.) in Germany (2009): 0.31;Consumption (g per capita; exact) in Germany (2009): 0.57;Excretion rate: 0.92;Calculated removal (%): 8.8

Anwendungen

BeschreibungIopromide is a non-ionic, water-soluble X-ray contrast agent for intravascular administration. Iopromide can cause acute kidney injury and is used in animal models of contrast-induced nephropathy.

VerwendenLabelled Iopromide. Nonionic, injectable radio-contrast medium. Diagnostic aid (radiopaque medium).

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

1,3-Benzenedicarboxamide, N3-[2,3-bis(acetyloxy)propyl]-N1-(2,3-dihydroxypropyl)-2,4,6-triiodo-5-[(2-methoxyacetyl)amino]-N1-methyl-3-(Methylamino)propan-1,2-diol

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Ergänzende Hinweise · 1 Eintrag

DefinitionChEBI: A 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 ater soluble x-ray contrast agent for intravascular administration.