Chemistry:Technetium (99mTc) exametazime

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Short description: Chemical compound


Technetium (99mTc) exametazime
Tc-99m exametazime skeletal.svg
Clinical data
Trade namesCeretec
License data
Pregnancy
category
  • US: C (Risk not ruled out)
Routes of
administration
Intravenous
ATC code
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
UNII
Chemical and physical data
FormulaC13H25N4O3Tc
Molar mass383 g·mol−1
3D model (JSmol)
Chiralityracemic
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Technetium (99mTc) exametazime is a radiopharmaceutical sold under the trade name Ceretec, and is used by nuclear medicine physicians for the detection of altered regional cerebral perfusion in stroke[1] and other cerebrovascular diseases. It can also be used for the labelling of leukocytes to localise intra-abdominal infections[2] and inflammatory bowel disease.[3] Exametazime (the part without technetium) is sometimes referred to as hexamethylpropylene amine oxime or HMPAO, although correct chemical names are:[4]

  • (NE)-N-[(3R)-3-[[3-[[(2R,3E)-3-hydroxyiminobutan-2-yl]amino]-2,2-dimethylpropyl]amino]butan-2-ylidene]hydroxylamine
  • or 3,3'-((2,2,-dimethyl-1,3-propanediyl)diimino)bis-2-butanone dioxime.

Chemistry

One of the two enantiomers of exametazime

The drug consists of exametazime as a chelating agent for the radioisotope technetium-99m. Both enantiomeric forms of exametazime are used—the drug is racemic.[5] The third stereoisomer of this structure, the meso form, is not included.

References

  1. ""Luxury perfusion" with 99mTc-HMPAO and 123I-IMP SPECT imaging during the subacute phase of stroke". European Journal of Nuclear Medicine 16 (1): 17–22. 1990. doi:10.1007/BF01566007. PMID 2307169. 
  2. "Comparison of 99m technetium hexamethylpropylene-amine oxime labelled leucocyte with 111-indium tropolonate labelled granulocyte scanning and ultrasound in the diagnosis of intra-abdominal abscess". Gut 37 (4): 557–64. October 1995. doi:10.1136/gut.37.4.557. PMID 7489945. 
  3. "[Therapy and diagnosis of emergency shock patients]". Nihon Naika Gakkai Zasshi. The Journal of the Japanese Society of Internal Medicine 80 (12): 1892–6. December 1991. doi:10.2169/naika.80.1892. PMID 1804909. 
  4. "Exametazime". National Institutes of Health. https://pubchem.ncbi.nlm.nih.gov/compound/9552071#section=Deprecated-CAS. 
  5. "Monography in the European Pharmacopoeia". http://library.njucm.edu.cn/yaodian/ep/EP5.0/12_monographs_on_radiopharmaceutical_preparations/Technetium%20(99mTc)%20exametazime%20injection.pdf. 

External links