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 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 N
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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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.