Desethyl KBT-3022
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| Category | Enzyme inhibitors |
| Catalog number | BBF-03762 |
| CAS | 101001-72-3 |
| Molecular Weight | 420.48 |
| Molecular Formula | C23H20N2O4S |
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Description
Desethyl KBT-3022 is the main active metabolite of KBT-3022 which is a potent and long-lasting anti-platelet agent. Desethyl KBT-3022 (1-40 μM) inhibits the thrombin-induced aggregation of washed platelets in a concentration-dependent manner.
Specification
| Synonyms | 2-[2-[4,5-bis(4-methoxyphenyl)-1,3-thiazol-2-yl]pyrrol-1-yl]acetic acid; 2-(4,5-bis(4-methoxylphenyl)thiazol-2-yl)pyrrol-1-ylacetic acid; desethyl KB 3022; desethyl KB-3022; desethyl KBT-3022 |
| Storage | Store at -20°C |
| IUPAC Name | 2-[2-[4,5-bis(4-methoxyphenyl)-1,3-thiazol-2-yl]pyrrol-1-yl]acetic acid |
| Canonical SMILES | COC1=CC=C(C=C1)C2=C(SC(=N2)C3=CC=CN3CC(=O)O)C4=CC=C(C=C4)OC |
| InChI | InChI=1S/C23H20N2O4S/c1-28-17-9-5-15(6-10-17)21-22(16-7-11-18(29-2)12-8-16)30-23(24-21)19-4-3-13-25(19)14-20(26)27/h3-13H,14H2,1-2H3,(H,26,27) |
| InChI Key | KJSPVPWIMGZXOF-UHFFFAOYSA-N |
Properties
| Boiling Point | 630.3±65.0°C at 760 Torr |
| Melting Point | 197.5-200.5°C |
| Density | 1.29±0.1 g/cm3 |
Reference Reading
1. [Determination of the main metabolite (desethyl KBT-3022) of a new antiplatelet agent, KBT-3022 in plasma by gas chromatography]
H Shimada, N Awata, Y Nakada Yakugaku Zasshi . 1992 Jun;112(6):414-7. doi: 10.1248/yakushi1947.112.6_414.
A highly sensitive, accurate and reproducible gas chromatographic method for the determination of a main metabolite, 2-[4,5-bis(4-methoxy-phenyl)thiazol-2-yl] pyrrol-ylacetic acid (desethyl KBT-3022) of a new antiplatelet agent, ethyl 2-[4,5-bis(4-methoxyphenyl)thiazol-2-yl]pyrrol-1-ylacetate (KBT-3022), in the human or dog plasma has been developed. Desethyl KBT-3022 in the plasma was extracted with a mixture of n-hexane and dichloromethane (1:1), and was derivatized using pentafluorobenzyl bromide. The obtained pentafluorobenzyl derivative of desethyl KBT-3022 in the plasma was separated by high-performance liquid chromatography. After the separation, the pentafluorobenzyl derivative of desethyl KBT-3022 was detected by gas chromatography. Gas chromatography was performed with a Ultra 1 column (12 m x 0.22 mm i.d., film thickness 0.33 microns), using an electron capture detector. 2-[2-(4,5-Bis(4-methoxyphenyl)thiazol-2-yl)pyrrol-l-yl]propionic acid was used as an internal standard. The detection limit of desethyl KBT-3022 in the plasma was 0.2 ng/ml. The coefficients of variation were below 5.3%. This method was applied to the determination of the plasma concentration of desethyl KBT-3022 after oral administration of KBT-3022 to dogs.
2. Effect of KBT-3022, a new cyclooxygenase inhibitor, on experimental brain edema in vitro and in vivo
A Yamashita, K Yokota, N Yamamoto, M Oda Eur J Pharmacol . 1996 Feb 22;297(3):225-31. doi: 10.1016/0014-2999(95)00777-6.
The effect of KBT-3022 (ethyl 2-[4,5-bis(4-methoxyphenyl)thiazol-2-yl]pyrrol-1-ylacetate), a new cyclooxygenase inhibitor, on experimental brain edema was studied. In vitro, KBT-3022 (100 microM) and its metabolite desethyl KBT-3022 (10 and 100 microM), but neither acetylsalicylic acid nor indomethacin, inhibited arachidonic acid-induced swelling of guinea pig cortical slices. KBT-3022 (3-100 microM) and desethyl KBT-3022 (3-30 microM), but neither acetylsalicylic acid nor indomethacin, inhibited lipid peroxidation in guinea pig brain homogenate. In vivo, oral administration of KBT-3022 (1, 3 and 10 mg/kg) and indomethacin (10 and 30 mg/kg), but not acetylsalicylic acid, prevented brain edema induced by bilateral carotid occlusion and recirculation in gerbils. Indomethacin then prevented postischemic hyperthermia, but not KBT-3022. KBT-3022 (10 mg/kg) and indomethacin (30 mg/kg) inhibited lactate accumulation in gerbil brain after ischemia and recirculation. These results suggest that KBT-3022 prevents development of both cytotoxic edema in vitro and vasogenic edema in vivo.
3. The mechanism of action of KBT-3022, a new antiplatelet agent
A Yamashita, K Yokota, K Matsuo, M Oda Gen Pharmacol . 1997 Feb;28(2):229-35. doi: 10.1016/s0306-3623(96)00190-5.
1. The mechanism of action of a new antiplatelet agent, KBT-3022 (ethyl 2-[4,5-bis(4-methoxyphenyl)thiazol-2-yl]pyrrol-1-ylacetate) and its active main metabolite, desethyl KBT-3022, was investigated. 2. KBT-3022 and desethyl KBT-3022 inhibited cyclooxygenase from ovine seminal gland with IC50 values of 0.69 and 0.43 microM, respectively. 3. At concentrations higher than those required for cyclooxygenase inhibition, desethyl KBT-3022 inhibited cAMP-phosphodiesterase, specific binding of U46619, and release of phosphatidic acid from thrombin-stimulated platelets. 4. Oral administration of KBT-3022 inhibited the production of thromboxane B2 during blood coagulation more potently than the production of 6-keto-prostaglandin F1 alpha from aortic strips in guinea pigs. 5. These findings suggest that KBT-3022 may inhibit platelet activation principally via the inhibition of cyclooxygenase by desethyl KBT-3022.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
