CGP-12388 - CAS 108929-47-1
Catalog number: 108929-47-1
Category: Inhibitor
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Molecular Formula:
Molecular Weight:
Adrenergic Receptor
CGP-12388 is a beta-adrenoceptor antagonist-derived radioligands. It is used for cardiac PET imaging due to its high hydrophilicity and affinity to beta-adrenoceptor.
Solid powder
4-(3-(Isopropylamino)-2-Hydroxypropoxy)-2H-Benzimidazol-2-One;Cgp 12388; Cgp-12388; Cgp12388;2H-Benzimidazol-2-one, 4-(3-(isopropylamino)-2-hydroxypropoxy)-;4-[2-hydroxy-3-(propan-2-ylamino)propoxy]benzimidazol-2-one
10 mM in DMSO
-20°C Freezer
CGP-12388 is used for cardiac PET imaging due to its high hydrophilicity and affinity to beta-adrenoceptor.
Quality Standard:
In-house standard
Shelf Life:
2 month in rt, long time
Boiling Point:
367.8±37.0 °C | Condition: Press: 760 Torr
1.202±0.06 g/cm3 | Condition: Temp: 20 °C Press: 760 Torr
Canonical SMILES:
1.Synthesis and evaluation of (S)-4-(3-(2'-[11C]isopropylamino)-2-hydroxypropoxy) -2H-benzimidazol -2-one ((S)-[11C]CGP 12388) and (S)-4-(3-((1'-[18F]-fluoroisopropyl)amino)-2-hydroxypropoxy) -2H- benzimidazol-2-one ((S)-[18F]fluoro-CGP 12388) for visualization of beta-adrenoceptors with positron emission tomography.
Elsinga PH;van Waarde A;Jaeggi KA;Schreiber G;Heldoorn M;Vaalburg W J Med Chem. 1997 Nov 7;40(23):3829-35.
The beta-adrenoceptor antagonist (S)-[11C]CGP 12177 (4-(3-(tert-butylamino)-2-hydroxypropoxy)-2H-benzimidazol -2[11C]- one) is a generally accepted radioligand for cardiac and pulmonary PET studies. The synthesis of [11C]CGP 12177 is a laborious and often troublesome procedure. Therefore, (S)-CGP 12388 (4-(3-(isopropylamino)-2-hydroxypropoxy) -2H-benzimidazol-2-one), 5, the isopropyl analogue of CGP 12177, has been labeled with carbon-11 in the isopropyl group via a reductive alkylation by [11C]acetone (3) of the corresponding (S)-desisopropyl compound 2. The fluoro-substituted analogue of (S)-CGP 12388 was prepared by reacting 2 with [18F]fluoroacetone (4). (S)-[11C]CGP 12388 (5) was easily prepared via a one-pot procedure. The radiochemical yield of (S)-[11C]CGP 12388 (600-800 Ci/mmol, EOS) was 18% (EOB) with a total synthesis time of 35 min, whereas (S)-[18F]fluoro-CGP 12388 (6) (> 2000 Ci/mmol, EOS) was synthesized in 105 min with a radiochemical yield of 12% (EOB). Biodistribution studies in rats demonstrated specific binding to beta-adrenoceptors of (S)-[18F]fluoro-CGP 12388 and (S)-[11C]CGP 12388 in lung and heart. The lungs were clearly visualized with PET studies of rats. Total/nonspecific binding at 60 min postinjection was 5.
2.Positron emission tomography studies of human airways using an inhaled beta-adrenoceptor antagonist, S-11C-CGP 12388.
van Waarde A;Maas B;Doze P;Slart RH;Frijlink HW;Vaalburg W;Elsinga PH Chest. 2005 Oct;128(4):3020-7.
OBJECTIVES: ;Positron emission tomography (PET) scanning may provide information on changes in the density and affinity of airway beta-adrenoceptors in lung diseases. However, the injection of a radiolabeled beta-blocker results in a pulmonary PET signal that reflects the binding of the ligand in the alveoli and not in the airways. Better discrimination between alveolar and airway beta-adrenoceptors may be possible with an inhaled radioligand.;DESIGN: ;A nebulizer was used to administer the antagonist S-11C-CGP12388 in aerosol form. Eight volunteers inhaled the tracer twice, at baseline and after pretreatment with a beta-adrenergic drug. In both PET scan studies, a dynamic scan of the lungs was followed by a whole-body scan to assess the inhaled dose. Pulmonary uptake was quantified using a region-of-interest-based analysis.;SETTING: ;University hospital.;PARTICIPANTS: ;Healthy volunteers.;INTERVENTIONS: ;Pretreatment consisted either of inhaled salbutamol (400 microg, 20 min before the scan), or orally administered pindolol (3 x 5 mg during a period of 16 h before PET scanning).;RESULTS: ;Drug pretreatment did not affect pulmonary deposition of the radioligand. The agonist salbutamol accelerated the monoexponential washout of 11C not only in the peripheral lung (mainly alveoli), but also in the central lung (mainly airways) and in the main bronchi.
3.Measurement of myocardial beta-adrenoceptor density in clinical studies: a role for positron emission tomography?
de Jong RM;Blanksma PK;van Waarde A;van Veldhuisen DJ Eur J Nucl Med Mol Imaging. 2002 Jan;29(1):88-97. Epub 2001 Nov 6.
The beta-adrenoceptor (beta-AR) plays an important role in the regulation of heart function and has been extensively studied in recent decades. In vitro studies have shown down-regulation of beta-AR density in heart failure and cardiac conditions that may lead to heart failure. As in vitro measurements on cardiac tissue samples do not allow longitudinal and regional assessment of myocardial beta-ARs in humans, new methods are being developed to measure beta-ARs in vivo using positron emission tomography (PET). Studies using PET and the radioligand [(11)C]CGP 12177 have shown promising results that are in agreement with those of in vitro studies. However, the radiochemical synthesis of [(11)C]CGP 12177 is very demanding, preventing its widespread use. Hence, new radioligands are being developed using simpler methods of radiochemical synthesis. ( S)-[(11)C]CGP 12388 has been presented as a promising new radioligand. So far, in vivo measurements of beta-AR density using PET have mainly been performed to confirm in vitro studies. Using the full potential of PET, performance of regional measurements and longitudinal studies might add further knowledge on the pathophysiological role of the beta-AR in cardiac disease and the effect of interventions.
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CAS 108929-47-1 CGP-12388

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