Orlistat

Orlistat
Klinički podaci
Robne marke	Alli, Xenical
AHFS/Drugs.com	Monografija
Identifikatori
CAS broj	96829-58-2
ATC kod	A08AB01
PubChem	3034010
DrugBank	DB01083
ChemSpider	2298564
ChEMBL	CHEMBL175247
Hemijski podaci
Formula	C29H53NO5
Mol. masa	495,735
SMILES	eMolekuli & PubHem
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; Key: AHLBNYSZXLDEJQ-FWEHEUNISA-N
Farmakokinetički podaci
Poluvreme eliminacije	1 - 2 h
Farmakoinformacioni podaci
Trudnoća	?
Pravni status
Način primene	Oralno

Orlistat je organsko jedinjenje, koje sadrži 29 atoma ugljenika i ima molekulsku masu od 495,735 Da.^[5]^[6]^[7]^[8]^[9]^[10]^[11]^[12]^[13]^[14]^[15]^[16]

Osobine

Osobina	Vrednost
Broj akceptora vodonika	5
Broj donora vodonika	1
Broj rotacionih veza	23
Particioni koeficijent^[17] (ALogP)	8,3
Rastvorljivost^[18] (logS, log(mol/L))	-9,6
Polarna površina^[19] (PSA, Å²)	81,7

Reference

↑ Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today 15 (23-24): 1052-7. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519. edit
↑ Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry 4: 217-241. DOI:10.1016/S1574-1400(08)00012-1.
↑ Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). „Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining”. J Cheminform 2 (1): 3. DOI:10.1186/1758-2946-2-3. PMID 20331846. edit
↑ Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP. (2012). „ChEMBL: a large-scale bioactivity database for drug discovery”. Nucleic Acids Res 40 (Database issue): D1100-7. DOI:10.1093/nar/gkr777. PMID 21948594. edit
↑ Torgerson JS, Hauptman J, Boldrin MN, Sjostrom L: XENical in the prevention of diabetes in obese subjects (XENDOS) study: a randomized study of orlistat as an adjunct to lifestyle changes for the prevention of type 2 diabetes in obese patients. Diabetes Care. 2004 Jan;27(1):155-61. PMID 14693982
↑ Mancini MC, Halpern A: Pharmacological treatment of obesity. Arq Bras Endocrinol Metabol. 2006 Apr;50(2):377-89. Epub 2006 May 23. PMID 16767304
↑ Menendez JA, Vellon L, Lupu R: Antitumoral actions of the anti-obesity drug orlistat (XenicalTM) in breast cancer cells: blockade of cell cycle progression, promotion of apoptotic cell death and PEA3-mediated transcriptional repression of Her2/neu (erbB-2) oncogene. Ann Oncol. 2005 Aug;16(8):1253-67. Epub 2005 May 3. PMID 15870086
↑ Garcia SB, Barros LT, Turatti A, Martinello F, Modiano P, Ribeiro-Silva A, Vespucio MV, Uyemura SA: The anti-obesity agent Orlistat is associated to increase in colonic preneoplastic markers in rats treated with a chemical carcinogen. Cancer Lett. 2006 Aug 28;240(2):221-4. Epub 2005 Dec 27. PMID 16377080
↑ Drew BS, Dixon AF, Dixon JB: Obesity management: update on orlistat. Vasc Health Risk Manag. 2007;3(6):817-21. PMID 18200802
↑ Wong NN, Cheng-Lai A: Orlistat. Heart Dis. 2000 Mar-Apr;2(2):174-81. PMID 11728255
↑ Hvizdos KM, Markham A: Orlistat: a review of its use in the management of obesity. Drugs. 1999 Oct;58(4):743-60. PMID 10551441
↑ Lucas KH, Kaplan-Machlis B: Orlistat--a novel weight loss therapy. Ann Pharmacother. 2001 Mar;35(3):314-28. PMID 11261530
↑ Curran MP, Scott LJ: Orlistat: a review of its use in the management of patients with obesity. Drugs. 2004;64(24):2845-64. PMID 15563254
↑ Ballinger A, Peikin SR: Orlistat: its current status as an anti-obesity drug. Eur J Pharmacol. 2002 Apr 12;440(2-3):109-17. PMID 12007529
↑ Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS (2011). „DrugBank 3.0: a comprehensive resource for omics research on drugs”. Nucleic Acids Res. 39 (Database issue): D1035-41. DOI:10.1093/nar/gkq1126. PMC 3013709. PMID 21059682. edit
↑ David S. Wishart, Craig Knox, An Chi Guo, Dean Cheng, Savita Shrivastava, Dan Tzur, Bijaya Gautam, and Murtaza Hassanali (2008). „DrugBank: a knowledgebase for drugs, drug actions and drug targets”. Nucleic Acids Res 36 (Database issue): D901-6. DOI:10.1093/nar/gkm958. PMC 2238889. PMID 18048412. edit
↑ Ghose, A.K., Viswanadhan V.N., and Wendoloski, J.J. (1998). „Prediction of Hydrophobic (Lipophilic) Properties of Small Organic Molecules Using Fragment Methods: An Analysis of AlogP and CLogP Methods”. J. Phys. Chem. A 102: 3762-3772. DOI:10.1021/jp980230o.
↑ Tetko IV, Tanchuk VY, Kasheva TN, Villa AE. (2001). „Estimation of Aqueous Solubility of Chemical Compounds Using E-State Indices”. Chem Inf. Comput. Sci. 41: 1488-1493. DOI:10.1021/ci000392t. PMID 11749573. edit
↑ Ertl P., Rohde B., Selzer P. (2000). „Fast calculation of molecular polar surface area as a sum of fragment based contributions and its application to the prediction of drug transport properties”. J. Med. Chem. 43: 3714-3717. DOI:10.1021/jm000942e. PMID 11020286. edit

Literatura

Hardman JG, Limbird LE, Gilman AG. (2001). Goodman & Gilman's The Pharmacological Basis of Therapeutics (10 izd.). New York: McGraw-Hill. DOI:10.1036/0071422803. ISBN 0-07-135469-7.
Thomas L. Lemke, David A. Williams, ur. (2007). Foye's Principles of Medicinal Chemistry (6 izd.). Baltimore: Lippincott Willams & Wilkins. ISBN 0-7817-6879-9.

Vanjske veze

	Portal Medicina
	Portal Hemija

Orlistat

[1] Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today 15 (23-24): 1052-7. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519. edit

[2] Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry 4: 217-241. DOI:10.1016/S1574-1400(08)00012-1.

[3] Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). „Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining”. J Cheminform 2 (1): 3. DOI:10.1186/1758-2946-2-3. PMID 20331846. edit

[4] Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP. (2012). „ChEMBL: a large-scale bioactivity database for drug discovery”. Nucleic Acids Res 40 (Database issue): D1100-7. DOI:10.1093/nar/gkr777. PMID 21948594. edit

[5] Torgerson JS, Hauptman J, Boldrin MN, Sjostrom L: XENical in the prevention of diabetes in obese subjects (XENDOS) study: a randomized study of orlistat as an adjunct to lifestyle changes for the prevention of type 2 diabetes in obese patients. Diabetes Care. 2004 Jan;27(1):155-61. PMID 14693982

[6] Mancini MC, Halpern A: Pharmacological treatment of obesity. Arq Bras Endocrinol Metabol. 2006 Apr;50(2):377-89. Epub 2006 May 23. PMID 16767304

[7] Menendez JA, Vellon L, Lupu R: Antitumoral actions of the anti-obesity drug orlistat (XenicalTM) in breast cancer cells: blockade of cell cycle progression, promotion of apoptotic cell death and PEA3-mediated transcriptional repression of Her2/neu (erbB-2) oncogene. Ann Oncol. 2005 Aug;16(8):1253-67. Epub 2005 May 3. PMID 15870086

[8] Garcia SB, Barros LT, Turatti A, Martinello F, Modiano P, Ribeiro-Silva A, Vespucio MV, Uyemura SA: The anti-obesity agent Orlistat is associated to increase in colonic preneoplastic markers in rats treated with a chemical carcinogen. Cancer Lett. 2006 Aug 28;240(2):221-4. Epub 2005 Dec 27. PMID 16377080

[9] Drew BS, Dixon AF, Dixon JB: Obesity management: update on orlistat. Vasc Health Risk Manag. 2007;3(6):817-21. PMID 18200802

[10] Wong NN, Cheng-Lai A: Orlistat. Heart Dis. 2000 Mar-Apr;2(2):174-81. PMID 11728255

[11] Hvizdos KM, Markham A: Orlistat: a review of its use in the management of obesity. Drugs. 1999 Oct;58(4):743-60. PMID 10551441

[12] Lucas KH, Kaplan-Machlis B: Orlistat--a novel weight loss therapy. Ann Pharmacother. 2001 Mar;35(3):314-28. PMID 11261530

[13] Curran MP, Scott LJ: Orlistat: a review of its use in the management of patients with obesity. Drugs. 2004;64(24):2845-64. PMID 15563254

[14] Ballinger A, Peikin SR: Orlistat: its current status as an anti-obesity drug. Eur J Pharmacol. 2002 Apr 12;440(2-3):109-17. PMID 12007529

[15] Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS (2011). „DrugBank 3.0: a comprehensive resource for omics research on drugs”. Nucleic Acids Res. 39 (Database issue): D1035-41. DOI:10.1093/nar/gkq1126. PMC 3013709. PMID 21059682. edit

[16] David S. Wishart, Craig Knox, An Chi Guo, Dean Cheng, Savita Shrivastava, Dan Tzur, Bijaya Gautam, and Murtaza Hassanali (2008). „DrugBank: a knowledgebase for drugs, drug actions and drug targets”. Nucleic Acids Res 36 (Database issue): D901-6. DOI:10.1093/nar/gkm958. PMC 2238889. PMID 18048412. edit

[17] Ghose, A.K., Viswanadhan V.N., and Wendoloski, J.J. (1998). „Prediction of Hydrophobic (Lipophilic) Properties of Small Organic Molecules Using Fragment Methods: An Analysis of AlogP and CLogP Methods”. J. Phys. Chem. A 102: 3762-3772. DOI:10.1021/jp980230o.

[18] Tetko IV, Tanchuk VY, Kasheva TN, Villa AE. (2001). „Estimation of Aqueous Solubility of Chemical Compounds Using E-State Indices”. Chem Inf. Comput. Sci. 41: 1488-1493. DOI:10.1021/ci000392t. PMID 11749573. edit

[19] Ertl P., Rohde B., Selzer P. (2000). „Fast calculation of molecular polar surface area as a sum of fragment based contributions and its application to the prediction of drug transport properties”. J. Med. Chem. 43: 3714-3717. DOI:10.1021/jm000942e. PMID 11020286. edit

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