(2R)-3-Cyclopentyl-2-[4-(methanesulfonyl)phenyl]-N-(thiazol-2-yl)propionamide
- Product Name
- (2R)-3-Cyclopentyl-2-[4-(methanesulfonyl)phenyl]-N-(thiazol-2-yl)propionamide
- CAS No.
- 300353-13-3
- Chemical Name
- (2R)-3-Cyclopentyl-2-[4-(methanesulfonyl)phenyl]-N-(thiazol-2-yl)propionamide
- Synonyms
- Ro 28-1675;Ro 0281675;RO281675,RO 28 1675;RO 028-1675;RO 0281675;RO 28-1675 (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)-
- CBNumber
- CB42516200
- Molecular Formula
- C18H22N2O3S2
- Formula Weight
- 378.51
- MOL File
- 300353-13-3.mol
(2R)-3-Cyclopentyl-2-[4-(methanesulfonyl)phenyl]-N-(thiazol-2-yl)propionamide Property
- 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
Safety
- WGK Germany
- WGK 3
- Storage Class
- 11 - Combustible Solids
N-Bromosuccinimide Price
- Product number
- 5.09665
- Product name
- Glucokinase Activator III, Ro-28-1675
- Packaging
- 10mg
- Price
- $263
- Updated
- 2026/03/19
- Product number
- Axon1356
- Product name
- RO28-1675-RO28-0450,(R)-
- Purity
- 99%
- Packaging
- 2mg
- Price
- $115.5
- Updated
- 2021/12/16
- Product number
- Axon1356
- Product name
- RO28-1675-RO28-0450,(R)-
- Purity
- 99%
- Packaging
- 5mg
- Price
- $159.5
- Updated
- 2021/12/16
- Product number
- CS-2016
- Product name
- RO-28-1675
- Purity
- 99.95%
- Packaging
- 5mg
- Price
- $258
- Updated
- 2021/12/16
- Product number
- API0004737
- Product name
- (R)-3-CYCLOPENTYL-2-(4-METHANESULFONYL-PHENYL)-N-THIAZOL-2-YL-PROPIONAMIDE
- Purity
- 95.00%
- Packaging
- 2MG
- Price
- $262
- Updated
- 2021/12/16
(2R)-3-Cyclopentyl-2-[4-(methanesulfonyl)phenyl]-N-(thiazol-2-yl)propionamide Chemical Properties,Usage,Production
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)
(2R)-3-Cyclopentyl-2-[4-(methanesulfonyl)phenyl]-N-(thiazol-2-yl)propionamide Preparation Products And Raw materials
Raw materials
Preparation Products
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