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Orlistat structure

Orlistat
Orlistat, with the chemical formula C29H53NO5 and CAS registry number 96829-58-2, is a compound known for its use as an anti-obesity medication. It works by inhibiting the absorption of dietary fats in the body, leading to weight loss. Orlistat is commonly prescribed as a treatment for obesity and is available in both prescription and over-the-counter forms. It is typically taken orally and is most effective when used in conjunction with a reduced-calorie diet and exercise. Common side effects of Orlistat include gastrointestinal issues such as oily spotting, flatulence, and fecal urgency. It is important to note that Orlistat should not be used by individuals with certain medical conditions or during pregnancy. Overall, Orlistat is a widely used compound in the management of obesity, offering a potential solution for individuals looking to achieve weight loss goals.
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1. Names and Identifiers
1.1 Name
Orlistat
1.2 Synonyms
(−)-Tetrahydrolipstatin; (-)-TETRAHYDROLIPSTATIN; (1S)-1-{[(2S,3S)-3-hexyl-4-oxooxetan-2-yl]methyl}dodecyl (2S)-2-(formylamino)-4-methylpentanoate; (1S)-1-{[(2S,3S)-3-hexyl-4-oxooxetan-2-yl]methyl}dodecyl N-formyl-L-leucinate; (2S)-1-[(2S)-3-Hexyl-4-oxo-2-oxetanyl]-2-tridecanyl N-formylleucinate; (2S)-1-[(2S,3R)-3-Hexyl-4-oxo-2-oxetanyl]-2-tridecanyl N-formyl-L-leucinate; (2S)-1-[(2S,3S)-3-Hexyl-4-oxo-2-oxetanyl]-2-tridecanyl N-formyl-L-leucinate; (2S)-1-[(2S,3S)-3-Hexyl-4-oxooxetan-2-yl]tridecan-2-yl N-formyl-L-leucinate; (S)-2-FORMYLAMINO-4-METHYL-PENTANOIC ACID (S)-1-[[(2S,3S)-3-HEXYL-4-OXO-2-OXETANYL]METHYL]-DODECYL ESTER; [2S-[2a(R*),3b]]-N-Formyl-L-leucine 1-[(3-hexyl-4-oxo-2-oxetanyl)methyl]dodecyl ester; Alli; Leucine, N-formyl-, (1S)-1-[[(2S)-3-hexyl-4-oxo-2-oxetanyl]methyl]dodecyl ester; L-Leucine, N-formyl-, (1S)-1-[[(2S,3R)-3-hexyl-4-oxo-2-oxetanyl]methyl]dodecyl ester; L-Leucine, N-formyl-, (1S)-1-[[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]methyl]dodecyl ester; MFCD05662360; N-FORMYL-L-LEUCINE (1S)-1-[[(2S,3S)-3-HEXYL-4-OXO-2-OXETANYL]METHYL]DODECYL ESTER; N-Formyl-L-leucine ester with (3S,4S)-3-hexyl-4-[(2S)-2-hydroxytridecyl]-2-oxetanone; Orlipastat; Orlipastatum; Orlistat(FerMentation); Orlistat(synthesis); Orlistat(synthetase/compound); RO-18-0647; Tetrahydrolipstatin; THLP; Xenical;
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1.3 CAS No.
96829-58-2
1.4 CID
3034010
1.5 EINECS
639-755-1
1.6 Molecular Formula
C29H53NO5
1.7 Inchi
InChI=1S/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
1.8 InChkey
AHLBNYSZXLDEJQ-FWEHEUNISA-N
1.9 Canonical Smiles
CCCCCCCCCCCC(CC1C(C(=O)O1)CCCCCC)OC(=O)C(CC(C)C)NC=O
1.10 Isomers Smiles
CCCCCCCCCCC[C@@H](C[C@H]1[C@@H](C(=O)O1)CCCCCC)OC(=O)[C@H](CC(C)C)NC=O
2. Properties
2.1 Solubility
DMSO: 19?mg/mL
2.2 Appearance
solid | white
2.3 Storage
2-8°C
2.4 Chemical Properties
Off-White Solid
2.5 Color/Form
white
2.6 Physical
Solid
2.7 pKa
14.59±0.23(Predicted)
2.8 Water Solubility
DMSO: 19?mg/mL
2.9 Spectral Properties
Specific optical rotation at 20 deg C: -32.0 deg ( c = 1 in chloroform)
Negative optical rotation in ethanol at 529 nm
2.10 StorageTemp
2-8°C
3. Use and Manufacturing
3.1 Description

Orlistat, with the chemical formula C29H53NO5, has the CAS number 96829-58-2. It is a drug used to treat obesity. Orlistat appears as a white to off-white crystalline powder. It has no distinct odor. The basic structure of Orlistat consists of a lipophilic tail and a polar head. This compound is practically insoluble in water. Orlistat is considered safe for use, but it may cause gastrointestinal side effects such as oily spotting, flatulence, and fecal urgency. It works by inhibiting pancreatic lipase, an enzyme that breaks down triglycerides in the intestine, thereby reducing the absorption of dietary fats.

Applicable Fields

Weight Loss: Orlistat is primarily used for weight loss in individuals who are obese or overweight. Its mechanism of action involves reducing the absorption of dietary fats, leading to a decrease in calorie intake and subsequent weight loss.

Storage

ConditionsStore in a cool and dry place.

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3.2 GHS Classification
Signal: Warning
GHS Hazard Statements
Aggregated GHS information provided by 10 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria by 1 of 10 companies. For more detailed information, please visit ECHA C&L website

Of the 4 notification(s) provided by 9 of 10 companies with hazard statement code(s):

H302 (11.11%): Harmful if swallowed [Warning Acute toxicity, oral]
H411 (33.33%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]
H412 (55.56%): Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P264, P270, P273, P301+P312, P330, P391, and P501
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3.3 Methods of Manufacturing
Isolation from fermentation broth of Streptomyces toxyricini: P Hadvary et al, EP 129748; eidem, US 4598089 (1985, 1986 both to Hoffmann-LaRoche)
3.4 Usage
An antiobesity agent. A pancreatic lipase inhibitor. Antiobesity agent.
4. Safety and Handling
4.1 Exposure Standards and Regulations
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription and over-the-counter drug products, incl orlistat, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.
4.2 Octanol/Water Partition Coefficient
log Kow = 8.53
4.3 DisposalMethods
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
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4.4 Formulations/Preparations
/Oral formulations/: Capsules 120 mg Xenical with povidone, (Roche).
Trade name: Xenical
Trade names: Alli.
4.5 Safety

WGK Germany: 3
RTECS: OH3167600

4.6 Specification

Side effects of Orlistat (CAS NO.96829-58-2): The primary side effects of the drug are gastrointestinal-related, and include steatorrhea (oily, loose stools with excessive flatus due to unabsorbed fats reaching the large intestine), fecal incontinence and frequent or urgent bowel movements.

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Hazardous to the aquatic environment, long-term (Chronic) - Category Chronic 3

2.2 GHS label elements, including precautionary statements

Pictogram(s) No symbol.
Signal word

No signal word.

Hazard statement(s)

H412 Harmful to aquatic life with long lasting effects
Precautionary statement(s)
Prevention

P273 Avoid release to the environment.

Response

none

Storage

none

Disposal

P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum
13C NMR : Predict  
1H NMR : Predict  
Predict 1H proton NMR  
7. Computed Properties
8.Other Information
Usage
Orlistat, used in obesity research, is a pancreatic lipase inhibitor that acts locally in the gastrointestinal tract to inhibit lipase. More detailed experiments show that gradually THL affects the retinoblastoma protein pathway and leads to cell-cycle arrest at G1/S boundary. Lipase Inhibitor, THL is an inhibitor of pancreatic and gastric lipase, as well as carboxyl ester lipase (CEL) and diacylglycerol lipase-α (DAGLα). Lipase Inhibitor, THL also activates caspase-3.
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Merck
14,6869
Indications and Usage
Orlistat is an internationally recognized new form of weight loss drug. Its commercial name is Sainike and first went on sale in New Zealand in 1998. Orlistat is a long-term and highly effective specific gastrointestinal lipase inhibitor, and it is insoluble in water, soluble in chloroform, and easily soluble in ethanol.
Orlistat can be used clinically to treat obesity. Usually, a dose of 120mg is taken three times a day within one hour of a meal. Weight loss begins to occur after two weeks of usage. It can be used continuously for 6-12 months, and its effects will cease to increase after daily dosage exceeds 400mg. This drug is suitable to be used in combination with a low-calorie diet by obese and overweight individuals, and it can also be used as long-term treatment for patients who have faced weight-related risk factors. Orlistat has a long-term weight-control effect that reduces and maintains weight and prevents against rebounding. Using Orlistat can lower the occurrences of weight-related risk factors and diseases, including hypercholesterolemia, type-2 diabetes, impaired glucose tolerance, hyperinsulinemia, and hypertension, and it can reduce the fat content in organs. Orlistat also adjusts blood lipid levels: it can decrease serum triglycerides (TG) and low density lipoprotein cholesterol (LDL-C), and it can increase the ratio of high density lipoproteins to low density lipoproteins in obese patients.
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Mechanism of Action
Orlistat is a type of lipase inhibiting weight loss drug and is a hydrated derivative of lipostatin. Orlistat effectively and selectively inhibits stomach lipase and pancreatic lipase, while having no impact on other digestive enzymes (such as amylase, trypsin and chymotrypsin) and on phospholipase, nor does it affect the absorption of carbohydrates, protein and phospholipids. This drug is not absorbed though the gastrointestinal tract and has a reversible inhibiting effect on lipase. Orlistat deactivates enzymes by covalent binding to the serine residue on the active sites of stomach and pancreatic lipase. This prevents the fat in food from being broken down into free fatty acids and diacylglycerol, so it cannot be absorbed, lowering caloric intake and therefore controlling body weight. This drug does not need to be absorbed by the entire body to take effect. Orlistat’s pharmacological activity is dose dependent: a treatment dosage of Orlistat (120mg/d, tid, taken with meals), combined with a low-calorie diet, can reduce up to 30% of fat absorption. In a study comparing normal and obese volunteers, Orlistat was basically not absorbed by the body at all and had a very low blood concentration. After a single oral dosage (the largest being 800mg), the blood concentration of Orlistat in the following 8 hours was <5 ng/ml. Typically, a treatment dosage of Orlistat is only minimally absorbed by the body and will not accumulate in a short treatment period. In an in vitro experiment, Orlistat’s binding rate with other serum proteins exceeded 99% (bound proteins were mainly lipoproteins and albumin), and its binding rate with red blood cells was very low.
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Pharmacokinetics
Minimal absorption when ingested orally, can be metabolized and deactivated in the intestinal tract, metabolizing area is the stomach wall, clearing half-life is about 14-19 hours. A study of obese patients showed that the essentially unabsorbed Orlistat produced two main metabolites in blood: M1(4 lactone ring hydrolysate) and M3 (M1 adhered to an N-leucine cleavage product) compose 42% of total blood concentration. M1 and M3 have extremely weak inhibiting effects on lipase and can both be excreted through bile. About 97% of the drug is excreted through feces, 83% of which is excreted in its original form. The cumulative renal output of Orlistat and its metabolites is lower than 2%, and the complete excretion of the drug (through feces and urine) requires 3-5 days.
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Drug Interactions
May reduce absorption of vitamin A, D and E; take supplements when using this drug. Any preparations containing vitamin A, D or E (such as compound vitamin preparations), should be taken 2 hours after this drug or before bed.
Type-2 diabetes patients may need to decrease dosage of antidiabetic drugs (such as sulfonylurea).
Combined use with cyclosporine may lower the blood concentration of the latter drug.
Combined use with amiodarone may reduce absorption of the latter drug, thus decreasing its curative effects.
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Side Effects
There have been rare cases of Orlistat use leading to elevated transaminase, elevated alkaline phosphatase, and severe hepatitis. There have also been cases of liver failure, some of which required liver transplant surgery or led to death. Orlistat has also had rare reports of allergic reactions, mostly including itchiness, rashes, hives, neurovascular edema, bronchospasm and allergic reactions, as well as very rare reports of herpes. Monitoring of sales also found reports of pancreatitis.
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Warnings and Precautions
Orlistat has led to rare cases of acute hepatocellular necrosis and acute liver failure, some of which required liver transplants or led to death. Thus, prescribing physicians must inform patients to immediately cease use of Orlistat and other suspicious drugs and seek inspection for liver functions if any symptoms or signs of liver function abnormalities occur (such as reduced appetite, itchiness, jaundice, dark urine, light feces, or pain in the upper right quadrant).
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Description
Orlistat is a digestive lipase inhibitor. It inhibits diacylglycerol lipase α (DAGLα), DAGLβ, α/β-hydrolase domain-containing protein 12 (ABHD12), ABHD16A, and platelet-activating factor acetylhydrolase (PAF-AH; IC50s = 0.06, 0.1, 0.08, 0.03, and 0.05 μM, respectively), as well as pancreatic lipase and hormone-sensitive lipase (IC50s = 0.65 and 2.1 μg/ml, respectively) but does not inhibit fatty acid amide hydrolase (FAAH) or KIAA1363 (IC50s = >100 μM for both). Orlistat decreases ionomycin-induced production of the endocannabinoid 2-arachidonoyl glycerol (2-AG) in N18TG2 murine neuroblastoma cells when used at a concentration of 1 μM. It also inhibits fatty acid synthase (FASN; Kiapp = ~0.1 μM for the human enzyme) and the proliferation of PC3 prostate cancer cells in a concentration-dependent manner. Orlistat (10 mg/kg) decreases serum cholesterol levels and total body weight in a mouse model of obesity induced by a high-fat diet. Formulations containing orlistat have been used in the treatment of adult obesity.
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Description
Orlistat was launched in the UK as Xenical for the long-term treatment of obesity, preferably in conjunction with a moderately reduced calorie diet. Orlistat is a tetrahydro-derivative of the natural hypolipaemic lipstatin (from Streptomyces toxyfncini) and can be obtained either by hydrogenation of lipstatine or by several different synthetic ways involving many steps from ( S ) - rnalic acid. Orlistat is a potent inhibitor of gastrointestinal lipases required for the lipolysis and digestion of dietary fat, in particular of pancreatic lipase ; as a result, it prevents the absorption of about one third of the fat contained in food and acts as an effective weight-reducing therapy. The outcomes of several clinical trials involving thousands of obese patients showed that Orlistat promotes a significant weight loss (often between 5 and 10% after one year) and improves cardiovascular risk factors such as total cholesterol, LDL/HDL ratio, blood glucose levels, insulin, blood pressure. Orlistat has minimal systemic absorption, the majority of the compound itself being recovered in the feces ; it does not affect other gastrointestinal processes, or the absorption of other rnacronutrients such as carbohydrates and proteins.
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Chemical Properties
Off-White Solid
Originator
Roche (Switzerland)
Uses
An antiobesity agent. A pancreatic lipase inhibitor. Antiobesity agent.
Uses
antidiabetic
Uses
Orlistat is an antiobesity agent. Orlistat is an pancreatic lipase inhibitor.
Uses
Tetrahydrolipstatin (orlistat) is a semi-synthetic derivative of lipstatin, a metabolite isolated from Streptomyces toxytricini. Tetrahydrolipstatin acts as a potent, irreversible inhibitor of pancreatic lipase. In vivo, it blocks the absorption of triglycerides while allowing fatty acid absorption. Tetrahydrolipstatin is widely used for the treatment of obesity.
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Brand name
Xenical (Roche).
General Description
Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.
Orlistat is a specific lipase inhibitor derived from lipostatin, which is naturally produced by Streptomyces toxytricini. Lipase inhibition induced by orlistat reduces the absorption of dietary fat, thereby contributing to caloric deficit.
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10. Related Questions
What Makes Orlistat a Powerful Tool in Fighting Obesity?Introduction Orlistat, a potent lipase inhibitor, has emerged as a key player in the battle against obesity. Marketed under various brand names like Xenical and Alli, Orlistat's main function is to bl..
What are the product features and advantages of Orlistat?Orlistat is a commonly used pharmaceutical product, widely used to treat specific diseases or symptoms. So, what are the product features and advantages of Orlistat? This article will introduce releva..
Is Orlistat the Safest and Most Effective Weight Loss Pill?Obesity refers to a state where the body weight is significantly above normal, with a thick layer of fat caused by excessive accumulation of triglycerides, especially fat, in the body. Excessive intak..
What is Orlistat and How Does it Work?What is Orlistat? Orlistat is a drug designed to treat obesity. It is marketed under the trade name Xenical by Roche in most countries, and as Alli by GlaxoSmithKline in the United Kingdom and the Uni..
11. Realated Product Infomation
 
1. Names and Identifiers
2. Properties
3. Use and Manufacturing
4. Safety and Handling
5. Msds
6. NMR Spectrum
7. Computational chemical data
8. Other Information
9. Toltal 438 Suppliers
10. Related Questions
11. Realated Product Infomation
 
 
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