[(1S)-1-[[(2S)-3-hexyl-4-oxo-oxetan-2-yl]methyl]dodecyl] (2S)-2-formamido-4-methyl-pentanoate

[(1S)-1-[[(2S)-3-hexyl-4-oxo-oxetan-2-yl]methyl]dodecyl] (2S)-2-formamido-4-methyl-pentanoate - Names and Identifiers

Name	Orlistat
Synonyms	XENICAL Orlistat ORLISTAT RO-18-0647 Orlipastat Orlistat(synthesis) Orlistat(FerMentation) (-)-TETRAHYDROLIPSTATIN (-)-Tetrahydrolipstatin(EquivalentToOrlistat) (1S)-1-{[(2R,3S)-3-hexyl-4-oxooxetan-2-yl]methyl}dodecyl N-formyl-D-leucinate N-FORMYL-L-LEUCINE (1S)-1-[[(2S,3S)-3-HEXYL-4-OXO-2-OXETANYL]METHYL]DODECYL ESTER [(1S)-1-[[(2S)-3-hexyl-4-oxo-oxetan-2-yl]methyl]dodecyl] (2S)-2-formamido-4-methyl-pentanoate (S)-2-FORMYLAMINO-4-METHYL-PENTANOIC ACID (S)-1-[[(2S,3S)-3-HEXYL-4-OXO-2-OXETANYL]METHYL]-DODECYL ESTER
CAS	96829-58-2
EINECS	639-755-1
InChI	InChI=1/C29H53NO5/c1-5-7-9-11-12-13-14-15-16-18-24(34-29(33)26(30-22-31)20-23(3)4)21-27-25(28(32)35-27)19-17-10-8-6-2/h22-27H,5-21H2,1-4H3,(H,30,31)/t24-,25?,26-,27-/m0/s1
InChIKey	AHLBNYSZXLDEJQ-FWEHEUNISA-N

[(1S)-1-[[(2S)-3-hexyl-4-oxo-oxetan-2-yl]methyl]dodecyl] (2S)-2-formamido-4-methyl-pentanoate - Physico-chemical Properties

Molecular Formula	C29H53NO5
Molar Mass	495.73
Density	0.976±0.06 g/cm3(Predicted)
Melting Point	<50 °C
Boling Point	615.9±30.0 °C(Predicted)
Specific Rotation(α)	D20 -32.0° (c = 1 in chloroform)
Flash Point	326.3°C
Solubility	Almost insoluble in water, easily soluble in chloroform, easily soluble in methanol and ethanol, easy to pyrolysis
Vapor Presure	4.23E-15mmHg at 25°C
Appearance	White powder or solid
Color	white
Merck	14,6869
pKa	14.59±0.23(Predicted)
Storage Condition	2-8°C
Stability	Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 1 week.
Refractive Index	1.469
MDL	MFCD05662360

[(1S)-1-[[(2S)-3-hexyl-4-oxo-oxetan-2-yl]methyl]dodecyl] (2S)-2-formamido-4-methyl-pentanoate - Risk and Safety

WGK Germany	3
RTECS	OH3167600
HS Code	29322090

[(1S)-1-[[(2S)-3-hexyl-4-oxo-oxetan-2-yl]methyl]dodecyl] (2S)-2-formamido-4-methyl-pentanoate - Reference

Reference

1. Li Qiang, Xu Tianren, Lu Chang, etc. Inhibitory effect of Hawthorn decoction pieces on pancreatic lipase activity [J]. Pharmaceutical Research, 2020, v.39(05):19-23.
2. Zhang Dan, Yao Zhengying, Hou Beiwei, et al. Study on the inhibitory effect of the extract from the leaves of Frost Mulberry on the activity of pancreatic lipase [J]. Science and Technology of food industry, 2017, 038(003):52-56.
3. Zhang Dan, Yao Zhengying, Hou Beiwei, Zhang Weiming, Sun Lijun. Inhibitory effect of perfume lotus extract on pancreatic lipase activity [J]. Food Science and Technology, 2017,42(03):227-231.
4. Chen Yongli, Huang Junyan, Wang Ling, Yao Kai, Jia Dongying. Chemical composition of mulberry leaf polysaccharide and its inhibitory effect on pancreatic lipase [J]. Food Science and Technology, 2021,46(03):162-166.
5. [IF = 6.165] Sha Li et al."Mechanistic insights into the inhibition of colorectal lipase by apigenin: Inhibitory interaction, conformational change and molecular docking studies. J Mol Liq. 2021 Aug;335:116505
6. [IF = 5.396] Hang Xu et al."The ameliorative effect of the Pyracantha fortuneana (Maxim.) H. L. Li extract on intestinal barrier dysfunction through modulating glycolipid digestion and gut microbiota in high fat diet-fed rats."Food Funct. 2019 Oct;10(10):6517-6532
7. [IF=4.451] Sha Li et al."Kaempferol inhibits the activity of pancreatic lipase and its synergistic effect with orlistat."J Funct Foods. 2020 Sep;72:104041
8. [IF=3.167] Hao-Xiang Gao et al."Potential of phenolic compounds in Ligustrum robustum (Rxob.) Blume as antioxidant and lipase inhibitors: Multi-spectroscopic methods and molecular docking."J Food Sci. 2022 Feb;87(2):651-663

[(1S)-1-[[(2S)-3-hexyl-4-oxo-oxetan-2-yl]methyl]dodecyl] (2S)-2-formamido-4-methyl-pentanoate - Reference Information

New weight loss and lipid-lowering drug	orlistat is an internationally recognized new weight loss and lipid-lowering drug, it was first listed in New Zealand in 1998, with sales of US $0.146 billion that year and US $0.538 billion in 2007. orlistat currently accounts for 80% of the global weight loss market, with sales of US $80 million in Hong Kong alone. Orlistat is a long-acting and potent specific gastrointestinal lipase inhibitor, white or off-white powder at room temperature, insoluble in water, soluble in chloroform, soluble in ethanol, enzymes are inactivated by the formation of covalent bonds with the active serine sites of gastric and pancreatic lipases in the lumen of the stomach and small intestine. Fat in food can not be decomposed into free fatty acids and monoacylglycerol, so fat can not be absorbed and utilized, thereby reducing the body's calorie intake, weight control. The drug does not need to be absorbed through the whole body to exert its efficacy. At the usual doses, the absorption of fat can be inhibited by 30%. It is rarely absorbed after oral administration, and can be metabolized and inactivated in the intestine. The metabolic site is in the wall of the gastrointestinal tract, and the elimination half-life is about 14 to 19 hours. About 97% of this product with fecal excretion, of which 83% to the original form of discharge. Orlistat can be clinically applied to obesity and hyperlipidemia. Under normal circumstances, a single oral 120mg, three times a day, in a meal or 1 hour after meals. 2 weeks after taking the drug can begin to lose weight. Can be taken continuously for 6 to 12 months, such as the dose increased to 400mg per day or more, the effect is no longer enhanced. Figure 1 shows the Yining man orlistat tablets produced by Zhejiang Haizheng Pharmaceutical.
properties	white crystalline powder, almost insoluble in water, soluble in chloroform, easily soluble in methanol and ethanol, easy to pyrolysis, the melting point was 40 °c to 42 °c. Its molecule is a diastereomer containing four chiral centers, at a wavelength of 529nm, and its ethanol solution has a negative optical rotation.
mechanism of action	orlistat is a long-acting, potent and specific gastrointestinal lipase inhibitor, the lipase active serine site in the small intestine cavity forms a covalent bond, which makes the above two enzymes inactive. The inactivated enzyme cannot decompose the fat in the food into free fatty acids and glycerol that can be absorbed by the human body, thereby reducing fat intake, play a role in weight loss. In addition, it has been found that Orlistat can inhibit intestinal absorption of cholesterol by inhibiting Niemann-Pick C1-like protein 1(niemann-pickC1-like1,NPC1L1).
pharmacological action	orlistat is a kind of antiobesity drug, which is a hydration derivative of lipstatin, can reduce the absorption of food fat, resulting in weight loss. This product has a strong and selective inhibition of gastric lipase and pancreatic lipase, no effect on other digestive enzymes (amylase, trypsin, chymotrypsin) and phospholipase, does not affect carbohydrates, absorption of proteins and phospholipids. The drug is not absorbed by the gastrointestinal tract, the inhibitory effect on lipase is reversible. orlistat mainly inactivates enzymes in the gastrointestinal tract by covalently binding to serine residues at the active sites of gastric lipase and pancreatic lipase, inhibiting triacylglycerol hydrolysis, reduce the intake of monoglycerides and free fatty acids, thereby controlling body weight. The pharmacological activity of orlistat was dose-dependent. The therapeutic dose of orlistat (120 mg/ d,tid, taken with meals) combined with a low calorie balanced diet could reduce fat absorption by 30%. Studies in normal-weight and obese volunteers have shown that orlistat is essentially not absorbed by the body and that plasma concentrations of the drug are very low after a single oral dose (maximum dose 800mg), plasma concentrations of orlistat were <5ng/ml within 8H. Generally, the systemic absorption of orlistat by the body at the therapeutic dose is very small, and there is no accumulation in the short-term treatment. In vitro, the binding rate of orlistat to plasma protein is more than 99% (lipoprotein and albumin are the main binding proteins), and orlistat rarely binds to red blood cells. Studies in obese patients have shown that very rarely absorbed orlistat has 2 major metabolites in plasma, M1(4-ring lactone ring hydrolysate). And M3(M1 attached to a cleavage product of N-formyl leucine) accounted for 42% of the total plasma concentration. The inhibition of M1 and M3 on lipase was very weak. Unabsorbed orlistat is excreted mainly through feces, accounting for about 97% of the dose taken, of which 83% is the prototype drug, and the cumulative renal excretion of orlistat and its metabolites is less than 2%, drug excretion (feces and urine) requires 3 ~ 5d. M1 and M3 can be excreted by bile. This product also has the function of regulating blood lipid: it can reduce triglyceride (TG) and low density lipoprotein cholesterol LDL-C in serum of obese patients and increase the ratio of high density lipoprotein to low density lipoprotein.
indications	This product is suitable for obese and overweight people in combination with a mild low-calorie diet, include long-term treatment of patients who have developed risk factors associated with obesity. This product has the effect of long-term weight control (weight loss, weight maintenance and prevention of rebound). Taking orlistat reduces risk factors associated with obesity and other obesity-related conditions by Incidence Rate, including hypercholesterolemia, type II diabetes, impaired glucose tolerance, hyperinsulinemia, hypertension, and can reduce the fat content in the organs.
adverse reactions	rare reports of elevated transaminases, elevated alkaline phosphatase, and severe hepatitis have been reported with Orlistat use, and cases of liver failure, some of which require liver transplantation or may directly lead to death. Orlistat has also been reported to have rare allergic reactions, the main clinical manifestations of which are pruritus, rash, urticaria, angioneurotic edema, bronchospasm and anaphylaxis. Post-marketing surveillance also found reports of pancreatitis.
drug interaction	reduces the absorption of vitamins A, D and E. The use of this product can be supplemented at the same time. If you are taking preparations containing vitamins A, D and E (such as some compound vitamin preparations), you should take the product 2 hours after taking the product or before going to bed. Patients with type 2 diabetes may need to reduce the dose of oral hypoglycemic agents (such as sulfonylureas). In combination with cyclosporine can cause a decrease in the plasma concentration of the latter. When amiodarone is used, the absorption of the latter may be reduced and the efficacy may be reduced.
usage and dosage	the combination of a micro-low energy diet is suitable for the long-term treatment of obese and overweight people, including those who have developed risk factors associated with obesity. Has the effect of long-term weight control (weight loss, weight maintenance and prevention of rebound). Risk factors associated with obesity and other diseases associated with obesity may also be reduced by Incidence Rate, including hypercholesterolemia, type 2 diabetes. Adults: The recommended dose is one 120mg capsule taken orally with a meal or one hour after a meal. If there is no meal or no fat in the food, you can omit a dose. The effect of long-term treatment (including weight control and improvement of risk factors) is sustainable. The patient's diet should be balanced, micro low energy, about 30% of the heat from fat, food should be rich in fruits and vegetables. Fat, carbohydrate, and protein intake should be distributed over three daily meals. There was no evidence that more than 120mg three times daily enhanced efficacy. No dose adjustment is required in the elderly.
note	due to rare reports of acute hepatocellular necrosis or severe liver injury with acute liver failure, some of these cases require liver transplantation or may directly lead to death, so the prescribing doctor should instruct the patient to take after any symptoms and signs of liver dysfunction (such as loss of appetite, itching, jaundice, dark urine, light stool, right upper quadrant pain), should immediately stop orlistat and other suspicious drugs, and liver function tests.
Use	Orlistat is a general purpose lipase inhibitor that acts on PL in human duodenal fluid, the IC50 was 122 ng/ml.
toxic substance data	information provided by: pubchem.ncbi.nlm.nih.gov (external link)

Last Update：2024-04-10 22:29:15

[(1S)-1-[[(2S)-3-hexyl-4-oxo-oxetan-2-yl]methyl]dodecyl] (2S)-2-formamido-4-methyl-pentanoate

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[(1S)-1-[[(2S)-3-hexyl-4-oxo-oxetan-2-yl]methyl]dodecyl] (2S)-2-formamido-4-methyl-pentanoate

[(1S)-1-[[(2S)-3-hexyl-4-oxo-oxetan-2-yl]methyl]dodecyl] (2S)-2-formamido-4-methyl-pentanoate

Orlistat

CAS: 96829-58-2

Molecular Formula: C29H53NO5

[(1S)-1-[[(2S)-3-hexyl-4-oxo-oxetan-2-yl]methyl]dodecyl] (2S)-2-formamido-4-methyl-pentanoate - Names and Identifiers

[(1S)-1-[[(2S)-3-hexyl-4-oxo-oxetan-2-yl]methyl]dodecyl] (2S)-2-formamido-4-methyl-pentanoate - Physico-chemical Properties

[(1S)-1-[[(2S)-3-hexyl-4-oxo-oxetan-2-yl]methyl]dodecyl] (2S)-2-formamido-4-methyl-pentanoate - Risk and Safety

[(1S)-1-[[(2S)-3-hexyl-4-oxo-oxetan-2-yl]methyl]dodecyl] (2S)-2-formamido-4-methyl-pentanoate - Reference

[(1S)-1-[[(2S)-3-hexyl-4-oxo-oxetan-2-yl]methyl]dodecyl] (2S)-2-formamido-4-methyl-pentanoate - Reference Information

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[(1S)-1-[[(2S)-3-hexyl-4-oxo-oxetan-2-yl]methyl]dodecyl] (2S)-2-formamido-4-methyl-pentanoate Request for Quotation

Orlistat

CAS: 96829-58-2

Molecular Formula: C29H53NO5

[(1S)-1-[[(2S)-3-hexyl-4-oxo-oxetan-2-yl]methyl]dodecyl] (2S)-2-formamido-4-methyl-pentanoate - Names and Identifiers

[(1S)-1-[[(2S)-3-hexyl-4-oxo-oxetan-2-yl]methyl]dodecyl] (2S)-2-formamido-4-methyl-pentanoate - Physico-chemical Properties

[(1S)-1-[[(2S)-3-hexyl-4-oxo-oxetan-2-yl]methyl]dodecyl] (2S)-2-formamido-4-methyl-pentanoate - Risk and Safety

[(1S)-1-[[(2S)-3-hexyl-4-oxo-oxetan-2-yl]methyl]dodecyl] (2S)-2-formamido-4-methyl-pentanoate - Reference

[(1S)-1-[[(2S)-3-hexyl-4-oxo-oxetan-2-yl]methyl]dodecyl] (2S)-2-formamido-4-methyl-pentanoate - Reference Information

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[(1S)-1-[[(2S)-3-hexyl-4-oxo-oxetan-2-yl]methyl]dodecyl] (2S)-2-formamido-4-methyl-pentanoate