Chemistry:Iotrolan

Short description: Chemical compound

Iotrolan

Clinical data
Trade names	Isovist
AHFS/Drugs.com	International Drug Names
Pregnancy category	Contraindicated
ATC code	V08AB06 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Protein binding	Negligible
Excretion	99% via kidneys
Identifiers
IUPAC name 2,4,6-triiodo-5-{N-methyl-2-[methyl({2,4,6-triiodo-3,5-bis[(1,3,4-trihydroxybutan-2-yl)carbamoyl]phenyl})carbamoyl]acetamido}-1-N,3-N-bis(1,3,4-trihydroxybutan-2-yl)benzene-1,3-dicarboxamide
CAS Number	79770-24-4 Y
PubChem CID	3738
ChemSpider	3607
UNII	16FL47B687
KEGG	D01714 Y
ChEMBL	ChEMBL1200555 N
Chemical and physical data
Formula	C37H48I6N6O18
Molar mass	1626.242 g·mol−1
3D model (JSmol)	Interactive image
SMILES CN(c1c(c(c(c(c1I)C(=O)NC(CO)C(CO)O)I)C(=O)NC(CO)C(CO)O)I)C(=O)CC(=O)N(C)c2c(c(c(c(c2I)C(=O)NC(CO)C(CO)O)I)C(=O)NC(CO)C(CO)O)I
InChI InChI=1S/C37H48I6N6O18/c1-48(32-28(40)22(34(64)44-12(4-50)16(58)8-54)26(38)23(29(32)41)35(65)45-13(5-51)17(59)9-55)20(62)3-21(63)49(2)33-30(42)24(36(66)46-14(6-52)18(60)10-56)27(39)25(31(33)43)37(67)47-15(7-53)19(61)11-57/h12-19,50-61H,3-11H2,1-2H3,(H,44,64)(H,45,65)(H,46,66)(H,47,67) Key:XUHXFSYUBXNTHU-UHFFFAOYSA-N
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Iotrolan (trade name Isovist) is an iodine-containing radiocontrast agent, a substance used to improve the visibility of body structures on images obtained by X-ray techniques.

(As of 2021), it is unknown whether it is still marketed anywhere in the world.

Medical uses

It is particularly used to image spaces surrounding the central nervous system, such as the ventricles, after injection into the cerebrospinal fluid; and also for angiography (imaging of blood vessels), urography (imaging of the urinary tract) and hysterosalpingography (imaging of uterus and fallopian tubes). It can also be used to image joint spaces and in endoscopic retrograde cholangiopancreatography (ERCP).

Contraindications

Hysterosalpingography is contraindicated during pregnancy and during acute inflammation in the pelvic region.

Adverse effects

The most common side effects are nausea and vomiting. Redness and a hot feeling of the skin is relatively common when the medication is injected into a vein. When injected into the cerebrospinal fluid, headache is among the most common adverse effects, and sometimes confusion or hallucinations can occur. Allergy-like reactions such as fever, hypotension (low blood pressure) and shock have also been observed.

Interactions

Drug interactions are similar to other iodine-containing contrast agents. Iodine-131, a radioactive isotope used for thyroid imaging (scintigraphy) and therapy of thyroid cancers, can be less effective when used within two to six weeks after application of iotrolan because of residual iodine in the body. Iotrolan can slow down the excretion of the diabetes drug metformin, potentially resulting in lactic acidosis.

Chemistry and mechanism of action

Further information: Iodinated contrast

Chemically, the substance is a dimer of a triiodinated isophthalic acid derivative. The iodine atoms readily absorb X-rays, improving the contrast in X-ray images of the body. It is non-ionic but water soluble.