Tìm theo
Orlistat
Các tên gọi khác (5 ) :
  • (-)-Tetrahydrolipstatin
  • Orlipastat
  • Orlipastatum
  • Tetrahydrolipstatin
  • Xenical
Thuốc Gốc
Small Molecule
CAS: 96829-58-2
ATC: A08AB01
ĐG : A-S Medication Solutions LLC , http://orders.a-smeds.com
CTHH: C29H53NO5
PTK: 495.7348
Orlistat is a drug designed to treat obesity. Its primary function is preventing the absorption of fats from the human diet, thereby reducing caloric intake. Orlistat works by inhibiting pancreatic lipase, an enzyme that breaks down triglycerides in the intestine. Without this enzyme, triglycerides from the diet are prevented from being hydrolyzed into absorbable free fatty acids and are excreted undigested.
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C29H53NO5
Phân tử khối
495.7348
Monoisotopic mass
495.392373811
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
InChI Key
InChIKey=AHLBNYSZXLDEJQ-FWEHEUNISA-N
IUPAC Name
(2S)-1-[(2S,3S)-3-hexyl-4-oxooxetan-2-yl]tridecan-2-yl (2S)-2-formamido-4-methylpentanoate
Traditional IUPAC Name
orlistat
SMILES
CCCCCCCCCCC[C@@H](C[C@@H]1OC(=O)[C@H]1CCCCCC)OC(=O)[C@H](CC(C)C)NC=O
Độ hòa tan
Practically insoluble
logP
8.6
logS
-6.7
pKa (strongest acidic)
12.74
pKa (Strongest Basic)
-0.91
PSA
81.7 Å2
Refractivity
139.94 m3·mol-1
Polarizability
61.12 Å3
Rotatable Bond Count
23
H Bond Acceptor Count
3
H Bond Donor Count
1
Physiological Charge
0
Number of Rings
1
Bioavailability
0
Dược Lực Học : Orlistat is a lipase inhibitor for obesity management that acts by inhibiting the absorption of dietary fats. At the recommended therapeutic dose of 120 mg three times a day, orlistat inhibits dietary fat absorption by approximately 30%. It works by inhibiting pancreatic lipase, an enzyme that breaks down fat in the intestine. Without this enzyme, fat from the diet is excreted undigested and not absorbed by the body. Because some vitamins are fat soluble, the effect of orlistat is to reduce their body absorption. Therefore the drug should only be taken in conjuction with fatty meals, and a multivitamin tablet containing these vitamins (D E K and beta-carotene) should be taken once a day, at least 2 hours before or after taking the drug. In the March 15, 2004 issue of Cancer Research, [1] Steven J. Kridel et al. state that orlistat may also inhibit growth of prostate cancer, and in theory may be useful in treating other cancers, by interfering with the metabolism of fats.
Cơ Chế Tác Dụng : Orlistat is a drug designed to treat obesity. Its primary function is preventing the absorption of fats from the human diet, thereby reducing caloric intake. Orlistat works by inhibiting pancreatic lipase, an enzyme that breaks down triglycerides in the intestine. Without this enzyme, triglycerides from the diet are prevented from being hydrolyzed into absorbable free fatty acids and are excreted undigested. Orlistat is a reversible inhibitor of lipases. It exerts its therapeutic activity in the lumen of the stomach and small intestine by forming a covalent bond with the active serine residue site of gastric and pancreatic lipases. The inactivated enzymes are thus unavailable to hydrolyze dietary fat in the form of triglycerides into absorbable free fatty acids and monoglycerides. As undigested triglycerides are not absorbed, the resulting caloric deficit may have a positive effect on weight control.
Dược Động Học :
▧ Absorption :
Systemic absorption of orlistat is minimal, however systemic absorption of the drug is not needed for activity.
▧ Protein binding :
>99% bound to plasma proteins (lipoproteins and albumin were major binding proteins).
▧ Metabolism :
Metabolized primarily within the gastrointestinal wall forming relatively inactive metabolites. Metabolites M1 (4-member lactone ring hydrolyzed) and M3 (M1 with N-formyl leucine moiety cleaved) accounted for approximately 42% of total radioactivity in plasma. M1 and M3 have an open beta-lactone ring and extremely weak lipase inhibitory activity (1000- and 2500-fold less than orlistat, respectively).
▧ Route of Elimination :
Following a single oral dose of 360 mg 14C-orlistat in both normal weight and obese subjects, fecal excretion of the unabsorbed drug was found to be the major route of elimination. Orlistat and its M1 and M3 metabolites were also subject to biliary excretion.
▧ Half Life :
1 to 2 hours.
Độc Tính : The results of a massive overdose of Xenical are unknown, although the drug seems relatively harmless.
Chỉ Định : For obesity management including weight loss and weight maintenance when used in conjunction with a reduced-calorie diet. Also used to reduce the risk for weight regain after prior weight loss. Use of orlistat is pending revision due to reports of liver-related adverse events.
Tương Tác Thuốc :
  • Acenocoumarol Orlistat may increase the anticoagulant effect of acenocoumarol.
  • Anisindione Orlistat may increase the anticoagulant effect of anisindione.
  • Calcipotriol Orlistat may decrease the serum concentration of fat soluble vitamins like vitamin D. Hence, this applies to calcipotriol, a synthetic derivative of vitamin D. Administer oral fat soluble vitamins at least 2 hours before or after the administration of orlistat. Avoid concomitant administration due to the risk of impaired vitamin absorption. Similar precautions do not apply to parenterally administered fat soluble vitamins.
  • Cholecalciferol Orlistat may decrease the serum concentration of Vitamin D analogs. More specifically, orlistat may impair absorption of Vitamin D analogs such as cholecalciferol. Monitor clinical response (plasma calcium concentrations) to orally administered vitamin D analogs closely if used with orlistat. When this combination must be used, consider administering the vitamin D analog at least 2 hours before or after the administration of orlistat.
  • Cyclosporine Orlistat decreases the effect of cyclosporine
  • Dicoumarol Orlistat may increase the anticoagulant effect of dicumarol.
  • Vitamin A Orlistat may impair the absorption of vitamin A, a fat soluble vitamin. Oral vitamin A should be administered 2 hours prior to or post orlistat administration.
  • Vitamin E Orlistat may impair the absorption of vitamin E, a fat soluble vitamin. Oral vitamin E should be administered 2 hours prior to or post orlistat administration.
  • Warfarin Orlistat may increase the anticoagulant effect of warfarin.
Liều Lượng & Cách Dùng : Capsule - Oral
Dữ Kiện Thương Mại
Giá thị trường
  • Biệt dược thương mại : Xenical 120 mg capsule
    Giá bán buôn : USD >4.44
    Đơn vị tính : capsule
  • Biệt dược thương mại : Alli 60 mg capsule
    Giá bán buôn : USD >0.67
    Đơn vị tính : capsule
Nhà Sản Xuất
  • Công ty :
    Sản phẩm biệt dược : Alli
  • Công ty :
    Sản phẩm biệt dược : Xenical
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB01083
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=3034010
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46508309
ChemSpider
http://www.chemspider.com/Chemical-Structure.2298564.html
BindingDB
http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=24567
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/0004-0256-52
PharmGKB
http://www.pharmgkb.org/drug/PA164776864
Wikipedia
http://en.wikipedia.org/wiki/Orlistat
RxList
http://www.rxlist.com/cgi/generic/orlistat.htm
PDRhealth
http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/xen1529.shtml
Drugs.com
http://www.drugs.com/orlistat.html
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