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ProductsBack/Orlistat [96829-58-2]
Chemical Structure
Chemical Structure
Chemical Structure

Orlistat [96829-58-2]

Research Use Only
AG-CN2-0050
AdipoGen Life Sciences
CAS Number96829-58-2
DownloadMSDS
Product group Chemicals
Estimated Purity>98%
Molecular Weight495.7
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Overview

  • Supplier
    AdipoGen Life Sciences
  • Product Name
    Orlistat
  • Delivery Days Customer
    10
  • CAS Number
    96829-58-2
  • Certification
    Research Use Only
  • Estimated Purity
    >98%
  • Molecular Formula
    C29H53NO5
  • Molecular Weight
    495.7
  • Scientific Description
    Chemical. CAS: 96829-58-2. Formula: C29H53NO5. MW: 495.7. Synthetic. Originally isolated from Streptomyces sp. Hypolipemic cell permeable and irreversible pancreatic, gastric and carboxylester lipase inhibitor. Anti-obesity and antihypercholesterolemic compound. Antitumor compound by inhibition of the thioesterase domain of fatty acid synthase (FASN). Anti-proliferative. Causes cell cycle arrest at G1 phase. Apoptosis inducer through caspase-3 activation. Sn-1-selective-diacylglycerol lipases alpha (DAGLalpha) inhibitor. Targets serine hydrolases in the nervous system, such as diacylglycerol lipase (DAGL), which is responsible for the conversion of DAG to 2-AG. Partially inhibits the hydrolysis of triglycerides and lowers the absorption of dietary fat, promoting weight loss. Promotes the sensitivity to TRAIL in cancer cells by ROS-mediated pathways. - Hypolipemic cell permeable and irreversible pancreatic, gastric and carboxylester lipase inhibitor [1-3]. Anti-obesity and antihypercholesterolemic compound [2, 5, 11]. Antitumor compound by inhibition of the thioesterase domain of fatty acid synthase (FASN) [4, 6, 9, 10]. Anti-proliferative [4, 6, 9, 10]. Causes cell cycle arrest at G1 phase. Apoptosis inducer through caspase-3 activation [6, 10]. Sn-1-selective-diacylglycerol lipases alpha (DAGLalpha) inhibitor. Targets serine hydrolases in the nervous system, such as diacylglycerol lipase (DAGL), which is responsible for the conversion of DAG to 2-AG [7]. Partially inhibits the hydrolysis of triglycerides and lowers the absorption of dietary fat, promoting weight loss [8]. Promotes the sensitivity to TRAIL in cancer cells by ROS-mediated pathways [11].
  • SMILES
    [H]C(=O)N[C@@H](CC(C)C)C(=O)O[C@@H](CCCCCCCCCCC)C[C@@H]1OC(=O)[C@H]1CCCCCC
  • Storage Instruction
    -20°C,2°C to 8°C
  • UNSPSC
    12352200

References

  • Interactions of lipoprotein lipase with the active-site inhibitor tetrahydrolipstatin (Orlistat): A. Lookene, et al.; Eur. J. Biochem. 222, 395 (1994)
  • Mode of action of orlistat: R. Guerciolini; Int. J Obes. Relat. Metab. Disord. 2, S12 (1997) (Review)
  • Degree of in vivo inhibition of human gastric and pancreatic lipases by Orlistat (Tetrahydrolipstatin, THL) in the stomach and small intestine: B. Sternby, et al.; Clin. Nutr. 21, 395 (2002)
  • Orlistat is a novel inhibitor of fatty acid synthase with antitumor activity: S.J. Kridel, et al.; Cancer Res. 64, 2070 (2004)
  • The use of orlistat in the treatment of obesity, dyslipidaemia and Type 2 diabetes: R.H. Nelson & J.M. Miles; Expert Opin. Pharmacother. 6, 2483 (2005) (Review)
  • Antitumoral actions of the anti-obesity drug orlistat (XenicalTM) in breast cancer cells: blockade of cell cycle progression, promotion of apoptotic cell death and PEA3-mediated transcriptional repression of Her2/neu (erbB-2) oncogene: J.A. Menendez, et al.; Ann. Oncol. 16, 1253 (2005)
  • Development of the first potent and specific inhibitors of endocannabinoid biosynthesis: T. Bisogno, et al.; Biochim. Biophys. Acta 1761, 205 (2006)
  • Orlistat accelerates gastric emptying and attenuates GIP release in healthy subjects: F.Y. Enc, et al.; Am. J. Physiol. Gastrointest. Liver Physiol. 296, G482 (2008)
  • Fatty acid synthase inhibition with Orlistat promotes apoptosis and reduces cell growth and lymph node metastasis in a mouse melanoma model: M.A. Carvalho, et al.; Int. J. Cancer. 123, 2557 (2008)
  • Antitumor effect of orlistat, a fatty acid synthase inhibitor, is via activation of caspase-3 on human colorectal carcinoma-bearing animal: H.Y. Chuang, et al.; Biomed. Pharmacother. 65, 286 (2011)