ADIPORON
ADIPORON Basic information
- Product Name:
- ADIPORON
- Synonyms:
-
- SC-396658
- AdipoRon
- 2-(4-benzoylphenoxy)-N-(1-benzylpiperidin-4-yl)acetaMide
- 2-(4-Benzoylphenoxy)-N-[1-(phenylmethyl)-4-piperidinyl]acetamide
- 2-(4-Benzoylphenoxy)-N-[1-(phenylmethyl)-4-piperidinyl]acetamide AdipoRon
- AdipoR agonist
- AdipiRon
- ACETAMIDE, 2-(4-BENZOYLPHENOXY)-N-[1-(PHENYLMETHYL)-4-PIPERIDINYL]-
- CAS:
- 924416-43-3
- MF:
- C27H28N2O3
- MW:
- 428.52
- Product Categories:
-
- Inhibitors
- API
- Mol File:
- 924416-43-3.mol
ADIPORON Chemical Properties
- Melting point:
- 106-108°C
- Boiling point:
- 645.3±55.0 °C(Predicted)
- Density
- 1.21±0.1 g/cm3(Predicted)
- storage temp.
- room temp
- solubility
- DMSO: soluble10mg/mL, clear
- pka
- 13.92±0.20(Predicted)
- form
- powder
- color
- white to beige
- Stability:
- Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 2 months.
- InChI
- InChI=1S/C27H28N2O3/c30-26(28-24-15-17-29(18-16-24)19-21-7-3-1-4-8-21)20-32-25-13-11-23(12-14-25)27(31)22-9-5-2-6-10-22/h1-14,24H,15-20H2,(H,28,30)
- InChIKey
- SHHUPGSHGSNPDB-UHFFFAOYSA-N
- SMILES
- C(NC1CCN(CC2=CC=CC=C2)CC1)(=O)COC1=CC=C(C(=O)C2=CC=CC=C2)C=C1
ADIPORON Usage And Synthesis
Description
Adiponectin expressed by adipocytes exerts antidiabetic effects by binding to adiponectin receptor (AdipoR)1, which activates AMPK pathways, and AdipoR2, which activates PPARα pathways. AdipoRon is an orally active small molecule AdipoR agonist that binds AdipoR1 and AdipoR2 with KD values of 1.8 and 3.1 μM, respectively. At 50 mg/kg, it acts similarly to adiponectin, activating AMPK and PPARα pathways and reducing insulin resistance and glucose intolerance in wild type mice fed a high-
Uses
AdipoRon is an AdipoR agonist and activates AMPK and PPAR-α pathways in the muscle and liver. AdipoRon ameliorated diabetes of genetically obese rodent model db/db mice, and prolonged the shortened lifespan of db/db mice on a high-fat diet. AdipoRon is a promising therapeutic approach for the treatment of obesity-related diseases such as type 2 diabetes.
Biochem/physiol Actions
AdipoRon is an adiponectin agonist that binds to and activates adiponectin receptors AdipoR1 and AdipoR2, activating AMPK and PPAR-α pathways, and ameliorating insulin resistance and glucose intolerance in mice fed a high-fat diet in a manner similar to adiponectin itself. AdipoRon did not affect body weight, but did increase the expression of genes involved in fatty-acid oxidation, decreased tissue triglyceride content, and prolonged the shortened lifespan of db/db mice.
in vivo
AdipoRon (50?mg/kg, i.v.) cuases significant phosphorylation of AMPK in skeletal muscle and liver of wild-type mice but not Adipor1?/??Adipor2?/? double-knockout mice[1]. AdipoRon (0.02, 0.1, and 0.5 mg/kg, i.g.) alleviates D-GalN induced hepatotoxicity in mice, and prevents hepatic architecture distortion against D-GalN challenge. The hepatoprotective potential of AdipoRon is particularly evident in higher dosages (0.1 and 0.5 mg/kg)[2]. Enhanced cardiomyocyte apoptosis in APN-deficient mice is rescued by AdipoRon (50 mg/kg, p.o.) administration. Antiapoptotic effect of AdipoRon is attenuated but not lost in AMPK-DN mice[3].
storage
+4°C
Background
AdipoRon is a small, synthetic molecule that binds both adiponectin receptors AdipoR1 and AdipoR2 with a Kd of approximately 1.8 and 3.1 mM, respectively. This synthetic adiponectin receptor agonist exhibits strong anti-obesity, anti-diabetic, anti-depressant, anti-ischemic, and anti-hypertrophic activities. AdipoRon behaves similarly to adiponectin in muscle and liver tissues of mice that are fed a high-fat diet, reducing insulin resistance and glucose intolerance through activation of the AMPK and PPAR-α pathways. Clinically, AdipoRon can be used to improve post-traumatic stress disorder, anxiety, and systemic sclerosis; it is being evaluated for the treatment of several forms of cancer, including pancreatic ductal adenocarcinoma, myeloma, breast, and ovarian cancer. Treatment of myeloma cell lines with AdipoRon significantly induced expression of the apoptosis-related proteins cleaved caspase-3 and cleaved PARP, and inhibited cell proliferation. A study using a mouse model of hypertension indicated that this AdipoRon treatment could prevent renal fibrosis in hypertensive patients.
References
[1] MIKI OKADA-IWABU. A small-molecule AdipoR agonist for type 2 diabetes and short life in obesity[J]. Nature, 2013, 503 7477: 493-499. DOI:10.1038/nature12656
[2] ARWA FAIRAQ . AdipoRon, an adiponectin receptor agonist, attenuates PDGF-induced VSMC proliferation through inhibition of mTOR signaling independent of AMPK: Implications toward suppression of neointimal hyperplasia[J]. Pharmacological research, 2017, 119: Pages 289-302. DOI:10.1016/j.phrs.2017.02.016
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