Iohexol

{{Short description|Chemical compound}} {{Use dmy dates|date=March 2024}} {{Infobox drug | Verifiedfields = changed | verifiedrevid = 461935422 | image = Iohexol.svg | image_class = skin-invert-image | alt =

| tradename = Iodaque, Hexopaque, Oraltag, others | Drugs.com = {{drugs.com|CONS|iohexol}} | DailyMedID = Iohexol | pregnancy_AU =  | routes_of_administration = Intrathecal, intravascular, by mouth, intracavital, rectal | ATC_prefix = V08 | ATC_suffix = AB02

| legal_AU =  | legal_AU_comment = | legal_BR =  | legal_BR_comment = | legal_CA = Rx-only | legal_CA_comment = <ref>{{cite web | title=Product monograph brand safety updates | website=Health Canada | date=February 2024 | url=https://www.canada.ca/en/health-canada/services/drugs-health-products/drug-products/drug-product-database/label-safety-assessment-update/product-monograph-brand-safety-updates.html | access-date=24 March 2024}}</ref><ref>{{cite web | title=Regulatory Decision Summary for Omnipaque | website=Drug and Health Products Portal | date=29 December 2023 | url=https://dhpp.hpfb-dgpsa.ca/review-documents/resource/RDS1710787451238 | access-date=2 April 2024}}</ref> | legal_DE =  | legal_DE_comment = | legal_NZ =  | legal_NZ_comment = | legal_UK =  | legal_UK_comment = | legal_US = Rx-only | legal_US_comment = | legal_EU = | legal_EU_comment = | legal_UN =  | legal_UN_comment = | legal_status = Rx-only

| CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 66108-95-0 | PubChem = 3730 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = DB01362 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 3599 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 4419T9MX03 | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = D01817 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 31709 | ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL = 1200455 | synonyms = 5-[N-(2,3-Dihydroxypropyl)acetamido]-2,4,6-triiodo-N,N'-bis(2,3-dihydroxypropyl)isophthalamide

| IUPAC_name = 1-''N'',3-''N''-Bis(2,3-dihydroxypropyl)-5-[''N''-(2,3-dihydroxypropyl)acetamido]-2,4,6-triiodobenzene-1,3-dicarboxamide | C=19 | H=26 | I=3 | N=3 | O=9 | smiles = O=C(N(c1c(I)c(c(I)c(c1I)C(=O)NCC(O)CO)C(=O)NCC(O)CO)CC(O)CO)C | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 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) | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = NTHXOOBQLCIOLC-UHFFFAOYSA-N | melting_point = 174 | melting_high = 180 }}

'''Iohexol''', sold under the trade names '''Omnipaque''' and '''Iodaque''' among others, is a contrast agent used for X-ray imaging.<ref name=WHO2008/> This includes when visualizing arteries, veins, ventricles of the brain, the urinary system, and joints, as well as during computed tomography (CT scan).<ref name=WHO2008/> It is given by mouth, injection into a vein, or into a body cavity.<ref name=Ric2015/>

Side effects include vomiting, skin flushing, headache, itchiness, kidney problems, and low blood pressure.<ref name=WHO2008/> Less commonly allergic reactions or seizures may occur.<ref name=WHO2008/> Allergies to povidone-iodine or shellfish do not affect the risk of side effects more than other allergies.<ref name=ACR2017>{{cite book|title=ACR Manual on Contrast Media v10.3. 2017|date=2017|publisher=American College of Radiology|isbn=9781559030120|page=6|url=https://www.acr.org/-/media/ACR/Files/Clinical-Resources/Contrast_Media.pdf|access-date=1 January 2018|url-status=live|archive-url=https://web.archive.org/web/20180101145210/https://www.acr.org/-/media/ACR/Files/Clinical-Resources/Contrast_Media.pdf|archive-date=1 January 2018}}</ref> Use in the later part of pregnancy may cause hypothyroidism in the baby.<ref>{{cite book| vauthors = Briggs GG, Freeman RK, Yaffe SJ |title=Drugs in Pregnancy and Lactation: A Reference Guide to Fetal and Neonatal Risk|date=2011|publisher=Lippincott Williams & Wilkins|isbn=9781608317080|page=761|url=https://books.google.com/books?id=OIgTE4aynrMC&pg=PA761|language=en|url-status=live|archive-url=https://web.archive.org/web/20170101161434/https://books.google.ca/books?id=OIgTE4aynrMC&pg=PA761|archive-date=1 January 2017}}</ref> Iohexol is an iodinated non-ionic radiocontrast agent.<ref name=WHO2008>{{cite book | title = WHO Model Formulary 2008 | year = 2009 | isbn = 9789241547659 | vauthors = ((World Health Organization)) | veditors = Stuart MC, Kouimtzi M, Hill SR | hdl = 10665/44053 | author-link = World Health Organization | publisher = World Health Organization | hdl-access=free |pages=317–8 }}</ref> It is in the low osmolar family.<ref>{{cite book| vauthors = Sutton D, Young JW |title=A Short Textbook of Clinical Imaging|date=2012|publisher=Springer Science & Business Media|isbn=9781447117551|page=235|url=https://books.google.com/books?id=muflBwAAQBAJ&pg=PA235|language=en|url-status=live|archive-url=https://web.archive.org/web/20170101161432/https://books.google.ca/books?id=muflBwAAQBAJ&pg=PA235|archive-date=1 January 2017}}</ref>

Iohexol was approved for medical use in 1985.<ref>{{cite book| vauthors = Broe ME, Porter GA, Bennett WM, Verpooten GA |title=Clinical Nephrotoxins: Renal Injury from Drugs and Chemicals|date=2013|publisher=Springer Science & Business Media|isbn=9789401590884|page=325|url=https://books.google.com/books?id=tkPwCAAAQBAJ&pg=PA325|language=en|url-status=live|archive-url=https://web.archive.org/web/20170101001423/https://books.google.ca/books?id=tkPwCAAAQBAJ&pg=PA325|archive-date=1 January 2017}}</ref> It is on the World Health Organization's List of Essential Medicines.<ref name="WHO21st">{{cite book | vauthors = ((World Health Organization)) | title = World Health Organization model list of essential medicines: 21st list 2019 | year = 2019 | hdl = 10665/325771 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO | hdl-access=free }}</ref><ref name=Ric2015>{{cite book| vauthors = Hamilton R |title=Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition|date=2015|publisher=Jones & Bartlett Learning|isbn=9781284057560|page=171}}</ref>

==Chemistry== The osmolality of iohexol ranges from 322 mOsm/kg—approximately 1.1 times that of blood plasma—to 844 mOsm/kg, almost three times that of blood.<ref>{{cite web | url = http://dailymed.nlm.nih.gov/dailymed/fdaDrugXsl.cfm?id=3465&type=display | archive-url = https://archive.today/20120707232939/http://dailymed.nlm.nih.gov/dailymed/fdaDrugXsl.cfm?id=3465&type=display | url-status = dead | archive-date = 7 July 2012 | title = Omnipaque (Iohexol) injection. Product label | author = GE Healthcare | author-link = GE Healthcare |date=May 2006 | access-date = 28 March 2007 | publisher = U.S. National Library of Medicine | work = DailyMed}}</ref> Despite this difference, iohexol is still considered a low-osmolality contrast agent; the osmolality of older agents, such as diatrizoate, may be more than twice as high.<ref>{{cite web | url = http://dailymed.nlm.nih.gov/dailymed/fdaDrugXsl.cfm?id=997&type=display | title = Hypaque (Diatrizoate Meglumine and Diatrizoate Sodium) injection, solution. Product label | author = Amersham Health | date = April 2006 | access-date = 29 March 2007 | publisher = U.S. National Library of Medicine | work = DailyMed | url-status = dead | archive-url = https://web.archive.org/web/20110523223457/http://dailymed.nlm.nih.gov/dailymed/fdaDrugXsl.cfm?id=997&type=display | archive-date = 23 May 2011 }}</ref>

==Adverse effects== The most common side effects after intravenous injections are: pain at the site of injection (3%), blurring of vision (2%), nausea (2%), arrhythmia (2%), taste perversion (1%), hypotension (0.7%), and vomiting (0.7%).<ref name="Omnipaque"/>

==Society and culture==

===Naming=== It is sold under the brand name Omnipaque.<ref>{{cite web | url=https://www.hpra.ie/img/uploaded/swedocuments/666c85d0-2222-42f9-873f-a269d151e198.pdf | title=Omnipaque | publisher=Health Products Regulatory Authority | location=Ireland | date=January 2018 | access-date=31 July 2020 | archive-date=28 August 2021 | archive-url=https://web.archive.org/web/20210828130526/https://www.hpra.ie/homepage/site-tools/error-page | url-status=dead }}</ref> It is also sold as a density gradient medium under the names Accudenz, Histodenz, and Nycodenz.<ref>{{cite web | url = https://www.sigmaaldrich.com/content/dam/sigma-aldrich/docs/Sigma/Product_Information_Sheet/d2158pis.pdf | title = HistoDenz | id = D2158 | archive-url = https://web.archive.org/web/20151120190729/https://www.sigmaaldrich.com/content/dam/sigma-aldrich/docs/Sigma/Product_Information_Sheet/d2158pis.pdf | archive-date = 20 November 2015 | work = Product information sheet | publisher = Sigma-Aldrich | access-date = 19 November 2015 }}</ref><ref>{{cite web | url = http://www.axis-shield-density-gradient-media.com/Leaflet%20Nycodenz.pdf | title = Nycodenz®: A universal density gradient medium | archive-url = https://web.archive.org/web/20150226092521/http://www.axis-shield-density-gradient-media.com/Leaflet%20Nycodenz.pdf | archive-date=26 February 2015 | publisher = Axis-Shield Density Gradient Media. | access-date = 19 November 2015 }}</ref>

===Available forms=== It is available in various concentrations, from 140<ref name="Omnipaque">{{cite web |title=Highlights of prescribing information for Omnipaque |url=https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/018956s101lbl.pdf |publisher=US Food and Drug Administration |access-date=13 December 2022 |archive-url=https://web.archive.org/web/20220620004252/https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/018956s101lbl.pdf |archive-date=20 June 2022 |url-status=dead }}</ref> to 350<ref name="AC">{{cite book|title=Austria-Codex| veditors = Haberfeld H |at=Omnipaque 350 mg J/ml Infusionsflasche|publisher=Österreichischer Apothekerverlag|location=Vienna|year=2020|language=German}}</ref> milligrams of iodine per milliliter.<ref name="Omnipaque"/> Iohexol can given as intrathecal, intravascular, oral, rectal, intraarticular, or into the body cavity.<ref name="Omnipaque"/>

== References== {{Reflist}}

Category:Benzamides Category:Iodobenzene derivatives Category:Radiocontrast agents Category:World Health Organization essential medicines Category:Wikipedia medicine articles ready to translate