Iobitridol: Difference between revisions

{{short description|Pharmaceutical drug}}

{{cs1 config|name-list-style=vanc}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 444272895

| IUPAC_name = 1-''N'',3-''N-bis''(2,3-dihydroxypropyl)-5-[3-hydroxy-2-(hydroxymethyl)propanamido]-2,4,6-triiodo-1-''N'',3-''N''-dimethylbenzene-1,3-dicarboxamide

| image = Iobitridol.png

<!--Clinical data-->

| tradename = Xenetix

| Drugs.com = {{drugs.com|UK|xenetix-300-300-mgi-ml-solution-for-injection-leaflet}}

| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->

| pregnancy_US = <!-- A / B / C / D / X -->

| pregnancy_category =

| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->

| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII -->

| legal_UK = POM

| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->

| legal_status =

| routes_of_administration = [[Intravenous]], [[joint injection]], [[Drug instillation|instillation into body cavities]]

<!--Pharmacokinetic data-->

| bioavailability =

| protein_bound = ~2%

| metabolism = none

| elimination_half-life = 1.8 hours

| excretion = unchanged via kidneys

<!--Identifiers-->

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 136949-58-1

| ATC_prefix = V08

| ATC_suffix = AB11

| PubChem = 65985

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank = DB12407

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 182ECH14UH

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D01181

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 2107212

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 31701

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 59379

<!--Chemical data-->

| C = 20

| H = 28

| I = 3

| N = 3

| O = 9

| smiles = CN(CC(CO)O)C(=O)c1c(c(c(c(c1I)NC(=O)C(CO)CO)I)C(=O)N(C)CC(CO)O)I

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C20H28I3N3O9/c1-25(3-10(31)7-29)19(34)12-14(21)13(20(35)26(2)4-11(32)8-30)16(23)17(15(12)22)24-18(33)9(5-27)6-28/h9-11,27-32H,3-8H2,1-2H3,(H,24,33)

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = YLPBXIKWXNRACS-UHFFFAOYSA-N

'''Iobitridol''' (trade name '''Xenetix''') is a pharmaceutical drug used as an [[Iodinated contrast|iodine-based]] [[radiocontrast agent]] in [[Radiography|X-ray imaging]].<ref name="Cheng">{{cite journal | vauthors = Cheng KT | title = 5-(3-Hydroxy-2-hydroxymethyl-propionamido)-''N'',''N''´-dimethyl-''N'',''N''´-bis-(2,3-dihydroxypropyl)-2,4,6-triiodoisophthalamide | journal = Molecular Imaging and Contrast Agent Database (MICAD) [Internet] | year = 2004 | pmid = 20641966 | url = https://www.ncbi.nlm.nih.gov/books/NBK25584/ }}</ref> It is injected into blood vessels, joints, or body cavities such as the [[uterus]], and filtered out by the [[kidney]]s.<ref name="AC" /> Its most common adverse effect is [[nausea]]. Severe allergic reactions are rare.<ref name="Cheng" /><ref name="AC" />

The drug received its first marketing approval in 1994 in France<ref name="Guerbet">{{cite web|url=https://www.guerbet.com/products-solutions/contrast-agents/xenetix-scanbag-by-xenetix/|title=Xenetix / ScanBag by Xenetix (Iobitridol)|publisher=[[Guerbet]]|access-date=2021-03-19}}</ref> and is approved for use in many European countries including the UK,<ref>{{cite web|url=https://www.ema.europa.eu/en/documents/psusa/iobitridol-list-nationally-authorised-medicinal-products-psusa/00001761/201904_en.pdf|publisher=[[European Medicines Agency]]|title=Iobitridol: List of nationally authorised medicinal products - PSUSA/00001761/201904|date=2020-04-03}}</ref> but not in the US.<ref name="Cheng" /> It is manufactured by [[Guerbet]].<ref name="Guerbet" />

==Medical uses==

Iobitridol is used for [[intravenous urography]] (imaging of the [[urinary system]] via a vein), [[angiography]] (imaging of blood vessels), [[angiocardiography]] (heart and [[coronary arteries]]), [[arthrography]] (joints), [[hysterosalpingography]] ([[uterus]] and [[fallopian tubes]]), and imaging of the [[cranium]] and the whole body.<ref name="AC">{{cite book|title=Austria-Codex| veditors = Haberfeld H |at=Xenetix 300 (300 mg Jod/ml)-Parenterale Röntgenkontrastmittellösung|publisher=Österreichischer Apothekerverlag|location=Vienna|year=2020|language=de}}</ref> It is approved for use in adults and children.<ref name="McCormack">{{cite journal | vauthors = McCormack PL | title = Iobitridol: a review of its use as a contrast medium in diagnostic imaging | journal = Clinical Drug Investigation | volume = 33 | issue = 2 | pages = 155–66 | date = February 2013 | pmid = 23341290 | doi = 10.1007/s40261-013-0055-3 | s2cid = 5311763 }}</ref>

==Contraindications==

The drug is contraindicated in people with manifest [[hyperthyreosis]] because of its [[iodine]] content. It must not be used to image the uterus or fallopian tubes in pregnant women.<ref name="AC" /><ref name="UK-leaflet" />

==Adverse effects==

Iobitridol is generally well tolerated.<ref name="McCormack" /> The only side effect observed in more than 1% of patients is [[nausea]]. Rare side effects (in fewer than 1 per 10.000 people) include [[anaphylaxis]] (severe allergic reactions), [[circulatory collapse]], [[kidney failure]], [[thyroid]]-related effects, and skin reactions such as [[Stevens–Johnson syndrome]]. Rare side effects in brain imaging include [[convulsion]]s, transient sight disorders, memory loss, and [[coma]].<ref name="AC" /><ref name="UK-leaflet">Xenetix 300 (300 mgI/ml) Solution for Injection: {{drugs.com|UK|xenetix-300-300-mgi-ml-solution-for-injection-leaflet}}. Accessed 2021-03-18.</ref>

==Overdose==

Overdosing is unlikely. It is managed by [[rehydration therapy]] and monitoring of the kidney function for at least three days. If necessary, iobitridol can be removed from the body by [[haemodialysis]].<ref name="AC" /><ref name="UK-leaflet" />

== Interactions ==

Drug interactions are the same as with other iodine-containing contrast agents: patients taking [[diuretics]] are at a higher risk of developing kidney failure under iobitridol unless they receive a water and [[electrolyte]] infusion before imaging.<ref name="AC" /> As the [[diabetes]] drug [[metformin]] is eliminated via the kidneys, it is recommended that people with severe kidney impairment should pause metformin during and after they are given iobitridol.<ref>{{cite web|url=https://www.acr.org/-/media/ACR/Files/Clinical-Resources/Contrast_Media.pdf|title=ACR Manual on Contrast Media|last=American College of Radiology|year=2021|pages=45–46}}</ref>

Certain [[antihypertensive]] (blood pressure lowering) drugs such as [[beta blocker|beta-blocker]]s, [[ACE inhibitor]]s, and [[sartan]]s can prevent the heart from compensating for low blood pressure, with an increased risk of circulatory collapse. [[Iodine-131]], a radioactive [[isotope]] used for thyroid imaging ([[scintigraphy]]) and therapy of [[thyroid cancer]]s, can be less effective when used within several weeks after the application of iobitridol because of residual iodine in the body.<ref name="AC" />

[[Interleukin 2]] cancer therapy has been thought to result in more severe side effects than iobitridol,<ref name="AC" /> but a 2009 literature search has found no such risk.<ref>{{cite journal | vauthors = Boehm I | title = Is interleukin-2 therapy still a risk factor for adverse reactions in concert with iodinated contrast medium injection? | journal = Acta Radiologica | volume = 50 | issue = 7 | pages = 752–3 | date = September 2009 | pmid = 19629773 | doi = 10.1080/02841850903061452 | s2cid = 44833077 }}</ref>

==Pharmacology==

===Mechanism of action===

[[File:BrainMetastasisFromBreastCancer.jpg|thumb|[[CT scan]] of three [[brain metastases]] from breast cancer. Before (left image) and after (right image) injection of an [[iodinated contrast]] agent similar to iobitridol.]]

{{see|Iodinated contrast}}

Iobitridol is an iodine-containing [[radiocontrast agent]].<ref name="AC" /><ref name="McCormack" /> The iodine atoms readily absorb [[X-rays]], resulting in better contrast in [[radiography]] images.<ref>{{cite journal | vauthors = Bae KT | title = Intravenous contrast medium administration and scan timing at CT: considerations and approaches | journal = Radiology | volume = 256 | issue = 1 | pages = 32–61 | date = July 2010 | pmid = 20574084 | doi = 10.1148/radiol.10090908 | doi-access = }}</ref> The quality of images made with this drug is equally good as with other low– or medium–[[osmolarity]] iodinated [[contrast agent]]s such as [[iopamidol]] or [[iohexol]].<ref name="McCormack" />

===Pharmacokinetics===

After [[intravenous infusion]], iobitridol is distributed in the [[circulatory system]] and the [[interstitium]]. The substance is only marginally bound to blood [[plasma protein]]s (to about 2%) and [[membrane protein]]s because the [[hydrophilic]] side chains of the molecule efficiently mask the central iodinated [[benzene]] ring. It is not [[metabolized]] but eliminated in the unchanged form via the kidneys by [[glomerular filtration]] without active secretion or reabsorption. The [[elimination half-life]] is 1.8 hours.<ref name="AC" /><ref name="McCormack" />

In people with kidney failure, the substance is instead eliminated via the [[bile duct]].<ref name="AC" />

==Chemistry==

Of the molecular mass, 45.6% is contributed by the three iodine atoms. Iobitridol is [[nonionic]] but water-soluble,<ref name="Cheng" /> having some [[OH group]]s in its side chains designed to mask the central [[hydrophobic]] benzene ring.<ref name="McCormack" />

The solution has a low osmolarity of 695 (''Xenetix 300'') or 915&nbsp;<abbr title="milliosmole">mOsm</abbr>/kg H₂O (''Xenetix 350''), which means it causes fewer allergic and allergy-like reactions, as well as less [[extravasation]] (leakage of blood vessels) than contrast agents with higher osmolarities.<ref name="AC" /><ref name="McCormack" /><ref>{{cite book|title=Austria-Codex| veditors = Haberfeld H |at=Xenetix 350 (350 mg Jod/ml)-Parenterale Röntgenkontrastmittellösung|publisher=Österreichischer Apothekerverlag|location=Vienna|year=2020|language=de}}</ref>

== References ==

{{reflist}}

[[Category:Iodobenzene derivatives]]