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 = {{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}}{{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}}
| 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
| bioavailability =
| protein_bound = Low
| metabolism = Nil
| elimination_half-life = Variable
| excretion = Kidney, unchanged
| 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 name Iodaque among others, is a contrast agent used for X-ray imaging. This includes when visualizing arteries, veins, ventricles of the brain, the urinary system, and joints, as well as during computed tomography (CT scan). It is given by mouth, injection into a vein, or into a body cavity.
Side effects include vomiting, skin flushing, headache, itchiness, kidney problems, and low blood pressure. Less commonly allergic reactions or seizures may occur. Allergies to povidone-iodine or shellfish do not affect the risk of side effects more than other allergies.{{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}} Use in the later part of pregnancy may cause hypothyroidism in the baby.{{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}} Iohexol is an iodinated non-ionic radiocontrast agent.{{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 }} It is in the low osmolar family.{{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}}
Iohexol was approved for medical use in 1985.{{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}} It is on the World Health Organization's List of Essential Medicines.{{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 }}{{cite book| vauthors = Hamilton R |title=Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition|date=2015|publisher=Jones & Bartlett Learning|isbn=9781284057560|page=171}}
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.{{cite web | url = http://dailymed.nlm.nih.gov/dailymed/fdaDrugXsl.cfm?id=3465&type=display | 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}} 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.{{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 = live | 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 }}
Adverse effects
Society and culture
=Naming=
It is sold under the brand name Omnipaque.{{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 }} It is also sold as a density gradient medium under the names Accudenz, Histodenz, and Nycodenz.{{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 }}{{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 }}
=Available forms=
It is available in various concentrations, from 140{{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/20220711204218if_/https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/018956s101lbl.pdf |archive-date=11 July 2022}} to 350{{cite book|title=Austria-Codex| veditors = Haberfeld H |at=Omnipaque 350 mg J/ml Infusionsflasche|publisher=Österreichischer Apothekerverlag|location=Vienna|year=2020|language=German}} milligrams of iodine per milliliter. Iohexol can given as intrathecal, intravascular, oral, rectal, intraarticular, or into the body cavity.
References
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Category:Iodobenzene derivatives