Synonym
Ro 18-0647; Ro18-0647; Ro-18-0647; Ro 180647; Ro180647; Ro-180647; Ro 18-0647/002; Orlistat, Alli, Tetrahydrolipastatin, Tetrahydrolipstatin, THLP, Xenical
IUPAC/Chemical Name
[(2S)-1-[(2S,3S)-3-hexyl-4-oxooxetan-2-yl]tridecan-2-yl] (2S)-2-formamido-4-methylpentanoate
InChi Key
AHLBNYSZXLDEJQ-FWEHEUNISA-N
InChi Code
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
SMILES Code
CC(C)C[C@H](NC=O)C(O[C@@H](CCCCCCCCCCC)C[C@@H]([C@@H]1CCCCCC)OC1=O)=O
Purity
>99% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
Orlistat is a lipase inhibitor for obesity management that acts by inhibiting the absorption of dietary fats.
In vitro activity:
When labeled with [1-13C]d-glucose and [1,2-13C2]choline, common metabolic differences between control and orlistat-treated H441, H1975, and PC14 cells were observed, such as increased accumulation of β-glucose (Glu-β) and β-fructose 1,6-bisphosphate (βF16P) (Fig. 3c; Fig. S2 in the “Electronic Supplementary Material”) and decreased levels of de novo FA and de novo and total phosphatidylcholine (Ptd.Cho.) However, H3255 cells did not exhibit any of the metabolic changes observed in H441, H1975, and PC14 cell lines. In orlistat-treated H3255 cells, a significant increase in the level of membrane phospholipids (CL/Ptd.EA, Ptd.serine, and sphingomyelin) was observed by 31P MRS, but no significant changes in de novo FA were observed by 13C MRS (Fig. S2 in the “Electronic Supplementary Material”). In contrast, orlistat-treated H441, H1975, and PC14 cells exhibited a significant decrease in membrane phospholipid levels, including Ptd.inositol (Fig. 3d; Fig. S2 in the “Electronic Supplementary Material”).
Reference: Evid Based Complement Alternat Med. 2020 Apr 8;2020:9818349. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3591534/
In vivo activity:
The assessment of serum lipid and metabolic profiles were carried out for all groups. There were significant increases for the levels of TC, TG, LDL, CRI I and II, and leptin but significant decrease for the levels of HDL and adiponectin in the OB (obese rats administered with distilled water) group as compared to the Normal group. Daily oral administration of orlistat in the obese rats in concomitant to HFD (high fat diet) for six weeks significantly decreased the levels of TC, TG, LDL, CRI-I, CRI-II, and leptin but significantly increased the levels of HDL and adiponectin compared to the OB group (Table 2).
Reference: Antioxidants (Basel). 2021 Feb; 10(2): 251. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7915029/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
10.0 |
20.20 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
495.73
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Hitakarun A, Khongwichit S, Wikan N, Roytrakul S, Yoksan S, Rajakam S, Davidson AD, Smith DR. Evaluation of the antiviral activity of orlistat (tetrahydrolipstatin) against dengue virus, Japanese encephalitis virus, Zika virus and chikungunya virus. Sci Rep. 2020 Jan 30;10(1):1499. doi: 10.1038/s41598-020-58468-8. PMID: 32001767; PMCID: PMC6992670.
2. Sankaranarayanapillai M, Zhang N, Baggerly KA, Gelovani JG. Metabolic shifts induced by fatty acid synthase inhibitor orlistat in non-small cell lung carcinoma cells provide novel pharmacodynamic biomarkers for positron emission tomography and magnetic resonance spectroscopy. Mol Imaging Biol. 2013 Apr;15(2):136-47. doi: 10.1007/s11307-012-0587-6. PMID: 22886728; PMCID: PMC3591534.
3. Othman ZA, Zakaria Z, Suleiman JB, Ghazali WSW, Mohamed M. Anti-Atherogenic Effects of Orlistat on Obesity-Induced Vascular Oxidative Stress Rat Model. Antioxidants (Basel). 2021 Feb 6;10(2):251. doi: 10.3390/antiox10020251. PMID: 33562069; PMCID: PMC7915029.
4. Ke J, An Y, Cao B, Lang J, Wu N, Zhao D. Orlistat-Induced Gut Microbiota Modification in Obese Mice. Evid Based Complement Alternat Med. 2020 Apr 8;2020:9818349. doi: 10.1155/2020/9818349. PMID: 32328145; PMCID: PMC7168719.
In vitro protocol:
1. Hitakarun A, Khongwichit S, Wikan N, Roytrakul S, Yoksan S, Rajakam S, Davidson AD, Smith DR. Evaluation of the antiviral activity of orlistat (tetrahydrolipstatin) against dengue virus, Japanese encephalitis virus, Zika virus and chikungunya virus. Sci Rep. 2020 Jan 30;10(1):1499. doi: 10.1038/s41598-020-58468-8. PMID: 32001767; PMCID: PMC6992670.
2. Sankaranarayanapillai M, Zhang N, Baggerly KA, Gelovani JG. Metabolic shifts induced by fatty acid synthase inhibitor orlistat in non-small cell lung carcinoma cells provide novel pharmacodynamic biomarkers for positron emission tomography and magnetic resonance spectroscopy. Mol Imaging Biol. 2013 Apr;15(2):136-47. doi: 10.1007/s11307-012-0587-6. PMID: 22886728; PMCID: PMC3591534.
In vivo protocol:
1. Othman ZA, Zakaria Z, Suleiman JB, Ghazali WSW, Mohamed M. Anti-Atherogenic Effects of Orlistat on Obesity-Induced Vascular Oxidative Stress Rat Model. Antioxidants (Basel). 2021 Feb 6;10(2):251. doi: 10.3390/antiox10020251. PMID: 33562069; PMCID: PMC7915029.
2. Ke J, An Y, Cao B, Lang J, Wu N, Zhao D. Orlistat-Induced Gut Microbiota Modification in Obese Mice. Evid Based Complement Alternat Med. 2020 Apr 8;2020:9818349. doi: 10.1155/2020/9818349. PMID: 32328145; PMCID: PMC7168719.
1: Derosa G, Maffioli P, Sahebkar A. Improvement of plasma adiponectin, leptin and C-reactive protein concentrations by orlistat: a systematic review and meta-analysis. Br J Clin Pharmacol. 2016 May;81(5):819-34. doi: 10.1111/bcp.12874. Epub 2016 Mar 6. Review. PubMed PMID: 26717446; PubMed Central PMCID: PMC4834599.
2: Aldekhail NM, Logue J, McLoone P, Morrison DS. Effect of orlistat on glycaemic control in overweight and obese patients with type 2 diabetes mellitus: a systematic review and meta-analysis of randomized controlled trials. Obes Rev. 2015 Dec;16(12):1071-80. doi: 10.1111/obr.12318. Epub 2015 Sep 8. Review. PubMed PMID: 26345590.
3: Halpern B, Halpern A. Safety assessment of FDA-approved (orlistat and lorcaserin) anti-obesity medications. Expert Opin Drug Saf. 2015 Feb;14(2):305-15. doi: 10.1517/14740338.2015.994502. Epub 2015 Jan 7. Review. PubMed PMID: 25563411.
4: Sumithran P, Proietto J. Benefit-risk assessment of orlistat in the treatment of obesity. Drug Saf. 2014 Aug;37(8):597-608. doi: 10.1007/s40264-014-0210-7. Review. PubMed PMID: 25064699.
5: Beyea MM, Garg AX, Weir MA. Does orlistat cause acute kidney injury? Ther Adv Drug Saf. 2012 Apr;3(2):53-7. doi: 10.1177/2042098611429985. Review. PubMed PMID: 25083225; PubMed Central PMCID: PMC4110847.
6: García Díaz E, Martín Folgueras T. Systematic review of the clinical efficacy of sibutramine and orlistat in weigth loss, quality of life and its adverse effects in obese adolescents. Nutr Hosp. 2011 May-Jun;26(3):451-7. doi: 10.1590/S0212-16112011000300004. Review. PubMed PMID: 21892560.
7: Johansson K, Sundström J, Neovius K, Rössner S, Neovius M. Long-term changes in blood pressure following orlistat and sibutramine treatment: a meta-analysis. Obes Rev. 2010 Nov;11(11):777-91. doi: 10.1111/j.1467-789X.2009.00693.x. Review. PubMed PMID: 20025693.
8: Ahmed MH. Orlistat and calcium oxalate crystalluria: an association that needs consideration. Ren Fail. 2010;32(8):1019-21. doi: 10.3109/0886022X.2010.501929. Review. PubMed PMID: 20722574.
9: McClendon KS, Riche DM, Uwaifo GI. Orlistat: current status in clinical therapeutics. Expert Opin Drug Saf. 2009 Nov;8(6):727-44. Review. PubMed PMID: 19998527.
10: [Pharmacological sheet. Orlistat, oral administration (Xenical, Alli). ]. J Pharm Belg. 2009 Jun;(2):67-8. Review. French. PubMed PMID: 19739531.
11: Coutinho W. The first decade of sibutramine and orlistat: a reappraisal of their expanding roles in the treatment of obesity and associated conditions. Arq Bras Endocrinol Metabol. 2009 Mar;53(2):262-70. Review. PubMed PMID: 19466219.
12: Paragh G, Bajnok L. [The role of orlistat in the treatment of obesity]. Orv Hetil. 2005 Mar 13;146(11):493-8. Review. Hungarian. PubMed PMID: 15813187.
13: Kiortsis DN, Filippatos TD, Elisaf MS. The effects of orlistat on metabolic parameters and other cardiovascular risk factors. Diabetes Metab. 2005 Feb;31(1):15-22. Review. PubMed PMID: 15803108.
14: Curran MP, Scott LJ. Spotlight on orlistat in the management of patients with obesity. Treat Endocrinol. 2005;4(2):127-9. Review. PubMed PMID: 15783249.
15: Foxcroft DR, Milne R. Orlistat for the treatment of obesity: rapid review and cost-effectiveness model. Obes Rev. 2000 Oct;1(2):121-6. Review. PubMed PMID: 12119985.
16: Ballinger A, Peikin SR. Orlistat: its current status as an anti-obesity drug. Eur J Pharmacol. 2002 Apr 12;440(2-3):109-17. Review. PubMed PMID: 12007529.
17: Wong NN, Cheng-Lai A. Orlistat. Heart Dis. 2000 Mar-Apr;2(2):174-81. Review. PubMed PMID: 11728255.
18: O'Meara S, Riemsma R, Shirran L, Mather L, ter Riet G. A rapid and systematic review of the clinical effectiveness and cost-effectiveness of orlistat in the management of obesity. Health Technol Assess. 2001;5(18):1-81. Review. PubMed PMID: 11399238.
19: Ballinger A. Orlistat in the treatment of obesity. Expert Opin Pharmacother. 2000 May;1(4):841-7. Review. PubMed PMID: 11249520.
20: Hauptman J. Orlistat: selective inhibition of caloric absorption can affect long-term body weight. Endocrine. 2000 Oct;13(2):201-6. Review. PubMed PMID: 11186221.
