Orlistat

Specifications / Handling

More Information
Product Details
Synonyms	Tetrahydrolipstatin; Xenical; Alli; Ro-18-0647
Product Type	Chemical
Properties
Formula	C₂₉H₅₃NO₅
MW	495.7
Merck Index	14: 6869
CAS	96829-58-2
Source/Host Chemicals	Synthetic. Originally isolated from Streptomyces sp.
Purity Chemicals	≥98% (NMR)
Appearance	White to off-white solid.
Solubility	Soluble in DMSO, ethanol or DMF.
Identity	Determined by ¹H-NMR.
InChi Key	AHLBNYSZXLDEJQ-FWEHEUNISA-N
Smiles	[H]C(=O)N[C@@H](CC(C)C)C(=O)O[C@@H](CCCCCCCCCCC)C[C@@H]1OC(=O)[C@H]1CCCCCC
Shipping and Handling
Shipping	AMBIENT
Short Term Storage	+4°C
Long Term Storage	-20°C
Handling Advice	After reconstitution, prepare aliquots and store at -20°C. Protect from light and moisture.
Use/Stability	Stable for at least 2 years after receipt when stored at -20°C.
Documents
MSDS	Download PDF
Product Specification Sheet
Datasheet	Download PDF

Product-specific References

Description

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 α (DAGLα) 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].

Product 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)
The anti-obesity drug orlistat promotes sensitivity to TRAIL by two different pathways in hormone-refractory prostate cancer cells: J. Fujiwara, et al.; Int. J. Oncol. 48, 854 (2016)
The oncogene-dependent resistance to reprogramming unveils cancer therapeutic targets: K. Ito, et al.; Cell Rep. 39, 110721 (2022)

Call	+41 61 926 6040
Fax	+41 61 926 6049