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Orlistat

CAS No.
96829-58-2
Chemical Name:
Orlistat
Synonyms
Orlistate;XENICAL;Orlistat Powder;aolisita;Orlipastat, Orlistat;N-FORMYL-L-LEUCINE (1S)-1-[[(2S,3S)-3-HEXYL-4-OXO-2-OXETANYL]METHYL]DODECYL ESTER;(S)-2-FORMYLAMINO-4-METHYL-PENTANOIC ACID (S)-1-[[(2S,3S)-3-HEXYL-4-OXO-2-OXETANYL]METHYL]-DODECYL ESTER;Alisit;CS-836;oristat
CBNumber:
CB2431985
Molecular Formula:
C29H53NO5
Molecular Weight:
495.73
MDL Number:
MFCD05662360
MOL File:
96829-58-2.mol
Last updated:2024-04-26 17:21:34

Orlistat Properties

Melting point <50 °C
Boiling point 615.9±30.0 °C(Predicted)
alpha D20 -32.0° (c = 1 in chloroform)
Density 0.976±0.06 g/cm3(Predicted)
storage temp. 2-8°C
solubility DMSO: 19 mg/mL
form solid
pka 14.59±0.23(Predicted)
color white
Merck 14,6869
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.
InChIKey AHLBNYSZXLDEJQ-FWEHEUNISA-N
SMILES C(O[C@H](C[C@H]1[C@H](CCCCCC)C(=O)O1)CCCCCCCCCCC)(=O)[C@H](CC(C)C)NC=O
CAS DataBase Reference 96829-58-2(CAS DataBase Reference)
FDA UNII 95M8R751W8
ATC code A08AB01

Pharmacokinetic data

Protein binding >99%
Excreted unchanged in urine 0-4%
Biological half-life 1-2 / Unchanged

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H302-H412
Precautionary statements  P273
WGK Germany  3
RTECS  OH3167600
HS Code  29322090
NFPA 704
0
2 0

Orlistat price More Price(47)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich O4139 Orlistat ≥98%, solid 96829-58-2 25mg $162 2024-03-01 Buy
Sigma-Aldrich 1478800 Orlistat United States Pharmacopeia (USP) Reference Standard 96829-58-2 200mg $584.4 2024-03-01 Buy
TCI Chemical O0381 Orlistat >97.0%(HPLC)(N) 96829-58-2 100mg $48 2024-03-01 Buy
TCI Chemical O0381 Orlistat >97.0%(HPLC)(N) 96829-58-2 1g $50 2024-03-01 Buy
Alfa Aesar J62999 Orlistat, 98% 96829-58-2 50mg $70.65 2024-03-01 Buy
Product number Packaging Price Buy
O4139 25mg $162 Buy
1478800 200mg $584.4 Buy
O0381 100mg $48 Buy
O0381 1g $50 Buy
J62999 50mg $70.65 Buy

Orlistat Chemical Properties,Uses,Production

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.

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.

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.

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.

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.

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).

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.

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.

Chemical Properties

Off-White Solid

Originator

Roche (Switzerland)

Uses

Orlistat is an antiobesity agent. Orlistat is an pancreatic lipase inhibitor.

Uses

antidiabetic

Uses

An antiobesity agent. A pancreatic lipase inhibitor. Antiobesity agent.

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.

Definition

ChEBI: Orlistat is a carboxylic ester resulting from the formal condensation of the carboxy group of N-formyl-L-leucine with the hydroxy group of (3S,4S)-3-hexyl-4-[(2S)-2-hydroxytridecyl]oxetan-2-one. A pancreatic lipase inhibitor, it is used as an anti-obesity drug. It has a role as an EC 3.1.1.3 (triacylglycerol lipase) inhibitor, a bacterial metabolite, an EC 2.3.1.85 (fatty acid synthase) inhibitor and an anti-obesity agent. It is a beta-lactone, a L-leucine derivative, a member of formamides and a carboxylic ester.

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.

Biological Activity

Hypolipemic pancreatic, gastric and carboxylester lipase inhibitor. Exhibits no activity at phospholipase A 2 , liver esterase, trypsin and chymotrypsin. Inhibits the thioesterase domain of fatty acid synthase, leading to cell cycle arrest at the G 1 /S boundary in vitro . Prevents the absorption of approximately one third of fat from food and exhibits progastrokinetic, antiobesity and antihypercholesterolemic activity in vivo .

Biochem/physiol Actions

Orlistat, used in obesity research, is a pancreatic lipase inhibitor that acts locally in the gastrointestinal tract to inhibit lipase.

Clinical Use

Adjunct in obesity

Drug interactions

Potentially hazardous interactions with other drugs
Acarbose: avoid concomitant administration.
Amiodarone: possibly slightly reduces absorption.1
Anticoagulants: monitor INR more frequently (due to reduction in vitamin K absorption).1
Antiepileptics: possible increased risk of convulsions.
Antivirals: absorption of abacavir, atazanavir, darunavir, didanosine, efavirenz, elvitegravir, emtricitabine, enfuvirtide, etravirine, fosamprenavir, indinavir, lamivudine, lopinavir, maraviroc, nevirapine, raltegravir, rilpivirine, ritonavir, saquinavir, stavudine, tenofovir, tipranavir and zidovudine possibly reduced.
Ciclosporin: possibly reduces absorption of ciclosporin.
Tacrolimus: possibly reduces absorption of tacrolimus.1
Thyroid hormones: possible increased risk of hypothyroidism with levothyroxine.
Vitamins: may reduce the absorption of fat soluble vitamins.

Metabolism

Orlistat is minimally absorbed and has no defined systemic pharmacokinetics. The metabolism of orlistat occurs mainly within the gastrointestinal wall to form 2 major inactive metabolites, M1 (4-member lactone ring hydrolysed) and M3 (M1 with N-formyl leucine moiety cleaved).
Faecal excretion of the unabsorbed drug is the major route of elimination. Approximately 97% of the administered dose is excreted in faeces and 83% of that as unchanged orlistat.

storage

+4°C

References

1) Bisogno et al. (2006), Development of the first potent and specific inhibitors of endocannabinoid biosynthesis; Biochim. Biophys. Acta, 1761 205 2) Hadvary et al. (1991), The lipase inhibitor tetrahydrolipstatin bind covalently to the putative active site serine of pancreatic lipase; J. Biol. Chem., 266 2021 3) Kridel et al. (2004), Orlistat is a novel inhibitor of fatty acid synthase with antitumor activity; Cancer Res., 64 2070 4) Ballinger and Peikin (2002), Orlistat: it’s current status as an anti-obesity drug; Eur. J. Pharmacol., 440 109

Orlistat Preparation Products And Raw materials

Raw materials

Preparation Products

Global( 730)Suppliers
Supplier Tel Email Country ProdList Advantage
Hong Kong Excellence Biotechnology Co., Ltd.
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Xi'an ZB Biotech Co.,Ltd
+8618591943808 sales01@xazbbio.com China 816 58
Wuhan Haorong Biotechnology Co.,ltd
+8618565342920 sales@chembj.net China 270 58
Shanghai Aosiris new Material Technology Co., LTD
86-15139564871 +8615139564871 wrjmoon2000@163.com China 357 58
Sigma Audley
+86-18336680971 +86-18126314766 nova@sh-teruiop.com China 525 58
Apeloa production Co.,Limited
+86-19131931000 +86-19131931000 admin@apcl.com.cn China 231 58
Hebei Yanxi Chemical Co., Ltd.
+8617531190177 peter@yan-xi.com China 6011 58
Sinoway Industrial co., ltd.
0592-5800732; +8613806035118 xie@china-sinoway.com China 992 58
Anhui Yiao New Material Technology Co., Ltd
+86-199-55145978 +8619955145978 sales8@anhuiyiao.com China 253 58

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View Lastest Price from Orlistat manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Orlistat pictures 2024-05-22 Orlistat
96829-58-2
US $0.00 / KG 1KG 99% 20 TONS Jinan Jianfeng Chemical Co., Ltd
Orlistat pictures 2024-05-21 Orlistat
96829-58-2
US $10.00 / kg 1kg 99% 10000 tons Hunan aslsen technology co.,ltd
Orlistat pictures 2024-05-21 Orlistat
96829-58-2
US $0.00-0.00 / kg 1kg 99% 500 Wuhan Haorong Biotechnology Co.,Ltd
  • Orlistat pictures
  • Orlistat
    96829-58-2
  • US $0.00 / KG
  • 99%
  • Jinan Jianfeng Chemical Co., Ltd
  • Orlistat pictures
  • Orlistat
    96829-58-2
  • US $10.00 / kg
  • 99%
  • Hunan aslsen technology co.,ltd
  • Orlistat pictures
  • Orlistat
    96829-58-2
  • US $0.00-0.00 / kg
  • 99%
  • Wuhan Haorong Biotechnology Co.,Ltd

Orlistat Spectrum

RO-18-0647 (-)-TETRAHYDROLIPSTATIN ORLISTAT Orlistat(synthesis) Orlistat(FerMentation) S,S,S,S-Orlistat (2S)-1-[(2S,3S)-3-hexyl-4-oxooxetan-2-yl]tridecan-2-yl (2S)-2-forMaMido-4-Methylpentanoate oristat N-formyl-(1S)-1-[[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]methyl]dodecyl ester L-Leucine Orlistat N-Formyl-L-leucine (1S)-1-[[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]methyl]dodecyl ester Orlistat, >=98% Olistat Lipase Inhibitor, THL HY-B0218 Orlipastat Orlistat,()-Tetrahydrolipstatin, N-Formyl-L-leucine (1S)-1-[[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]methyl]dodecyl ester, Ro-18-0647 Orlistat (200 mg) ORLISTAT (BULK MATERIAL) ORLISTAT PELLETS 50% (-)-Tetrahydrolipstatin(EquivalentToOrlistat) Xenical, (-)-Tetrahydrolipstatin, N-Formyl-L-leucine (1S)-1-[[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]methyl]dodecyl Ester, Orlistat, Tetrahydolipstat ORLIPASTATUM Ro 18-0647/002 (-)-Tetrahydrolipstatin, Ro-18-0647, N-Formyl-L-leucine (1S)-1-[[(2S,3S)-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 N-Formyl-L-leucine (1S)-1-[[(2S)-3α-hexyl-4-oxooxetan-2β-yl]methyl]dodecyl ester N-Formyl-L-leucine (S)-1-[[(2S)-3α-hexyl-4-oxooxetane-2β-yl]methyl]dodecyl ester Orlistat(synthetase/compound) Orlistat, 97%, General lipase inhibitor Alisit Orlistat Weight Loss Steroids Western wuming CS-836 Orlistat Tablets Orlistat Orlistat Orlistat> Qrlistat (S)-(S)-1-((2S,3S)-3-Hexyl-4-oxooxetan-2-yl)tridecan-2-yl 2-formamido-4-methylpentanoate Orlistat Solution in Acetonitrile, 1000 ug/ml Orlistat powder for lose weight Orlista hot selling Orlistat ORLISTAT PALLET Orlistat USP/EP/BP Horse meriton Orlistat Impurity 29 Xenical Orlistat Orlistat (Tetrahydrolipstatin) Prompt Delivery Orlistat D7Q: What is Orlistat D7 Q: What is the CAS Number of Orlistat D7 Q: What is the storage condition of Orlistat D7 Q: What are the applications of Orlistat D7 OrlistatQ: What is Orlistat Q: What is the CAS Number of Orlistat Q: What is the storage condition of Orlistat Q: What are the applications of Orlistat Orlistat (1478800) (S)-2-FORMYLAMINO-4-METHYL-PENTANOIC ACID (S)-1-[[(2S,3S)-3-HEXYL-4-OXO-2-OXETANYL]METHYL]-DODECYL ESTER N-FORMYL-L-LEUCINE (1S)-1-[[(2S,3S)-3-HEXYL-4-OXO-2-OXETANYL]METHYL]DODECYL ESTER Orlipastat, Orlistat Orlistat Powder XENICAL