Technetium (^99mTc) exametazime

Technetium (^99mTc) exametazime
Clinical data
Trade names	Medi-Exametazim
License data	US FDA: Ceretec;
Routes of; administration	Intravenous
ATC code	V09AA01 (WHO) ; V09HA02 (WHO) (labelled leucocytes);
Legal status
Legal status	US: ℞-only;
Identifiers
	IUPAC name [[(3RS,3'RS)-3,3'-[(2,2-Dimethyltrimethylene)diimino][di-2-butanone]dioximato](3–)-N,N',N'',N''']oxotechnetium (99mTc);
CAS Number	99944-78-2 ;
PubChem CID	9552069;
UNII	3B744AG22N;
Chemical and physical data
Formula	C13H25N4O3Tc
Molar mass	383 g·mol−1
3D model (JSmol)	Interactive image; Interactive image;
Chirality	racemic
	SMILES 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;
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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

^ 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.
^ 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.
^ 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.
^ "Exametazime". PubChem. National Institutes of Health.
^ "Monography in the European Pharmacopoeia" (PDF).

External links

European Association of Nuclear Medicine: Ceretec
GE Healthcare: Ceretec
Exametazime ligand: CID 9552071 from PubChem

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[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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