Technetium (99mTc) exametazime

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.
Technetium (99mTc) exametazime
Clinical data
Trade namesCeretec
License data
Routes of
administration		Intravenous
ATC code
Legal status
Legal status
Identifiers
  • [[(3RS,3'RS)-3,3'-[(2,2-Dimethyltrimethylene)diimino][di-2-butanone]dioximato](3–)-N,N',N'',N''']oxotechnetium (99mTc)
CAS Number
PubChem CID
UNII
Chemical and physical data
FormulaC13H25N4O3Tc
Molar mass383 g·mol−1
3D model (JSmol)
Chiralityracemic
  • CC1(C)CN2[Tc]3(N4C1)([N](O[H]O[N]3=C(C)[C@H]4C)=C(C)[C@H]2C)=O

  • CC1(C)CN2[Tc]3(N4C1)([N](O[H]O[N]3=C(C)[C@@H]4C)=C(C)[C@@H]2C)=O
 ☒NcheckY (what is this?)  (verify)

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. Moretti JL, Defer G, Cinotti L, Cesaro P, Degos JD, Vigneron N, et al. (1990). ""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. doi:10.1007/BF01566007. PMID 2307169. S2CID 11934803.
  2. Weldon MJ, Joseph AE, French A, Saverymuttu SH, Maxwell JD (October 1995). "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. doi:10.1136/gut.37.4.557. PMC 1382910. PMID 7489945.
  3. Ui K, Yamaguchi T (December 1991). "[Therapy and diagnosis of emergency shock patients]". Nihon Naika Gakkai Zasshi. The Journal of the Japanese Society of Internal Medicine. 80 (12): 1892–6. doi:10.2169/naika.80.1892. PMID 1804909.
  4. "Exametazime". PubChem. National Institutes of Health.
  5. "Monography in the European Pharmacopoeia" (PDF).
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