| Identification | Back Directory | [Name]
(2R)-3-Cyclopentyl-2-[4-(methanesulfonyl)phenyl]-N-(thiazol-2-yl)propionamide | [CAS]
300353-13-3 | [Synonyms]
Ro 0281675
Ro 28-1675
RO 028-1675;RO 0281675
RO 28-1675 - RO 28-0450, (R)-
(2R)-3-Cyclopentyl-2-[4-(methanesulfonyl)phenyl]-N-(thiazol-2-yl)propionamide
BenzeneacetaMide, α-(cyclopentylMethyl)-4-(Methylsulfonyl)-N-2-thiazolyl-, (αR)- | [Molecular Formula]
C18H22N2O3S2 | [MOL File]
300353-13-3.mol | [Molecular Weight]
378.51 |
| Chemical Properties | Back Directory | [density ]
1.306 | [storage temp. ]
Store at -20°C | [solubility ]
DMSO : 50 mg/mL (132.10 mM; Need ultrasonic) | [form ]
Powder | [pka]
8.65±0.50(Predicted) | [color ]
White to off-white | [InChI]
1S/C18H22N2O3S2/c1-25(22,23)15-8-6-14(7-9-15)16(12-13-4-2-3-5-13)17(21)20-18-19-10-11-24-18/h6-11,13,16H,2-5,12H2,1H3,(H,19,20,21)/t16-/m1/s1 | [InChIKey]
NEQSWPCDHDQINX-MRXNPFEDSA-N | [SMILES]
[S](=O)(=O)(C)c1ccc(cc1)[C@@H](CC3CCCC3)C(=O)Nc2[s]ccn2 |
| Hazard Information | Back Directory | [Uses]
A cell-permeable thiazolyl-propanamide compound that acts as an allosteric glucokinase-(GK) selective activator, increasing Vmax and decreasing [S]1/2 (by 1.5- and 4.3-fold, respectively, at 3 µM; [Glucose] = 5 mM) in human GK enzymatic assays, as well as freeing GK from the inhibitory action of GK regulatory protein (GKRP), resulting in increased GK nuclear-to-cytosol translocation in primary rat hepatocytes (EC50/[Glucose] = 0.16 µM/16.8 mM, 0.27 µM/8.4 mM, 2.2 µM/2.8 mM) and reduced glucose concentration for stimulating insulin secretion from isolated rat pancreatic islets (threshold [glucose] = 3 mM vs 6 mM with or without 3 µM Ro-28-1675). Exhibits in vivo glucose-lowering and insulin-releasing activity in non-diabetic C57BL/6 mice and Wistar rats and is efficacious in several murine (KK/Upj-Ay/J, ob/ob, and diet-induced obese C57BL/6) and rodent (Goto-Kakizaki) type II diabetes mellitus (T2DM) models (10 to 50 mg/kg via p.o.), while efficacy is no longer observed in older hypoinsulinemic db/db mice with blood glucose levels reaching 300 mg/dl. Reported not to affect the activity of hexokinase I or II and display no activity toward GK-independent insulin release from β cells upon 2-Ketoisocaproic acid (α-KIC) stimulation. | [Definition]
ChEBI: (2R)-3-cyclopentyl-2-(4-methylsulfonylphenyl)-N-(2-thiazolyl)propanamide is a member of acetamides. | [Biological Activity]
RO-28-1675 is a potent allosteric activator of glucokinase with EC50 of 54 nM. It can be used in type 2 diabetes research. | [in vitro]
RO-28-1675 can reverse the inhibitory action of the human glucokinase regulatory protein (GKRP).
| [in vivo]
RO-28-1675 (50 mg/kg; po) reduces blood glucose levels in wild-type C57BL/6J mice.
RO-28-1675 (10 mg/kg; po) displays lower clearance and higher oral bioavailability.
| Animal Model: | 10 weeks old male C57BL/6J mice | | Dosage: | 50 mg/kg | | Administration: | Oral administration | | Result: | Reduced blood glucose levels. | | Animal Model: | C57BL/6J mice | | Dosage: | 10 mg/kg | | Administration: | Oral administr ation | | Result: | AUC 0-inf (5150 ng? h/mL), C max (1140 μg/mL) , T max (3.3 hours ), F po (92.8%) with 10 mg/kg orally administered. | | [target]
EC50: 54 nM (glucokinase) |
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| Company Name: |
SPIRO PHARMA
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www.spiropharma.com.cn |
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BOC Sciences
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16314854226 |
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www.bocsci.com |
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Musechem
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+1-800-259-7612 |
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www.musechem.com |
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ChemeGen
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18818260767 |
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https://www.chemegen.com |
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InvivoChem
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13549236410 |
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https://www.invivochem.cn/ |
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