Orlistat (CHEM016817)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:44:34 UTC
Update Date2016-11-09 01:15:28 UTC
Accession NumberCHEM016817
Identification
Common NameOrlistat
ClassSmall Molecule
DescriptionOrlistat is a drug used in the treatment of 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.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(-)-TetrahydrolipostatinChEBI
(2S)-2-Formamido-4-methylpentanoic acid [(2S)-1-[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]tridecan-2-yl] esterChEBI
AlliChEBI
N-Formyl-L-leucine (1S)-1-{[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]methyl}dodecyl esterChEBI
OrlipastatChEBI
OrlistatumChEBI
Ro-18-0647ChEBI
XenicalChEBI
(2S)-2-Formamido-4-methylpentanoate [(2S)-1-[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]tridecan-2-yl] esterGenerator
(-)-TetrahydrolipstatinHMDB
TetrahydrolipstatinHMDB
Roche brand OF orlistatHMDB
THLPHMDB
1-((3-Hexyl-4-oxo-2-oxetanyl)methyl)dodecyl-2-formamido-4-methylvalerateHMDB
GlaxoSmithKline brand OF orlistatHMDB
Hoffmann-la roche brand OF orlistatHMDB
TetrahydrolipastatinHMDB
Chemical FormulaC29H53NO5
Average Molecular Mass495.735 g/mol
Monoisotopic Mass495.392 g/mol
CAS Registry Number96829-58-2
IUPAC Name(2S)-1-[(2S,3S)-3-hexyl-4-oxooxetan-2-yl]tridecan-2-yl (2S)-2-formamido-4-methylpentanoate
Traditional Nameorlistat
SMILESCCCCCCCCCCC[C@@H](C[C@@H]1OC(=O)[C@H]1CCCCCC)OC(=O)[C@H](CC(C)C)NC=O
InChI IdentifierInChI=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 KeyAHLBNYSZXLDEJQ-FWEHEUNISA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as leucine and derivatives. Leucine and derivatives are compounds containing leucine or a derivative thereof resulting from reaction of leucine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentLeucine and derivatives
Alternative Parents
Substituents
  • Leucine or derivatives
  • Alpha-amino acid ester
  • N-formyl-alpha amino acid or derivatives
  • N-formyl-alpha-amino acid
  • Fatty acid ester
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Beta_propiolactone
  • Carboxamide group
  • Carboxylic acid ester
  • Secondary carboxylic acid amide
  • Oxetane
  • Lactone
  • Oxacycle
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility9.2e-05 g/LALOGPS
logP7.61ALOGPS
logP8.11ChemAxon
logS-6.7ALOGPS
pKa (Strongest Acidic)12.74ChemAxon
pKa (Strongest Basic)-0.91ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area81.7 ŲChemAxon
Rotatable Bond Count23ChemAxon
Refractivity139.94 m³·mol⁻¹ChemAxon
Polarizability61.12 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-2902200000-dfdc46fddbbd1d2170e0Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-001i-0000190000-0f2b7ec7f6bc7f95ba46Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-001i-0000390000-65e16678dbfdcc1c64fdSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-00di-0001190000-27c5d161a5754e1434f4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-00di-0001190000-27c5d161a5754e1434f4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0pb9-0971000000-b771a74c99af15873a47Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0pb9-0971000000-b771a74c99af15873a47Spectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-00ps-0394000000-a7e235f00f39832cb26bSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0bti-0289000000-1db53b3f6bf551f35934Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-052o-0922300000-3340cd8d705353e68b6aSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-b8cb3b916515e9d87eebSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-02t9-8904000000-d71719418cae9e9993cdSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-08fr-0459000000-2afd07b05b6499ee680bSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-02tl-0859400000-c74907b45c6c88f27dbfSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-03xr-2914000000-c9c25c9d546bc7dd3cf1Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0002-0105900000-34995f5e283fa1168b24Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-08fr-0459000000-c1482a9118d79780ad8fSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0bti-0289000000-47f99f82e0bf6c110477Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-0900000000-4a9952eba82d4734c89cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-00ps-0394000000-4e5093c320f2bd221805Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0201900000-f738d9eb60da2cb3f8b2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0btd-4903200000-880d8bcbe0e86c1dedeeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4m-9300100000-59ee07367048664d1aeaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-2103900000-12eb6aa4152fd723fd4cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfu-7508900000-d827e3d71bdc755b28a0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002f-9315000000-4c6b30daf1a2bd6ffaf8Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB01083
HMDB IDHMDB0015215
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkOrlistat
Chemspider ID2298564
ChEBI ID94686
PubChem Compound ID3034010
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Hvizdos KM, Markham A: Orlistat: a review of its use in the management of obesity. Drugs. 1999 Oct;58(4):743-60.
2. Lucas KH, Kaplan-Machlis B: Orlistat--a novel weight loss therapy. Ann Pharmacother. 2001 Mar;35(3):314-28.
3. Wong NN, Cheng-Lai A: Orlistat. Heart Dis. 2000 Mar-Apr;2(2):174-81.
4. Ballinger A, Peikin SR: Orlistat: its current status as an anti-obesity drug. Eur J Pharmacol. 2002 Apr 12;440(2-3):109-17.
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.
6. Curran MP, Scott LJ: Orlistat: a review of its use in the management of patients with obesity. Drugs. 2004;64(24):2845-64.
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.
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.
9. Mancini MC, Halpern A: Pharmacological treatment of obesity. Arq Bras Endocrinol Metabol. 2006 Apr;50(2):377-89. Epub 2006 May 23.
10. Drew BS, Dixon AF, Dixon JB: Obesity management: update on orlistat. Vasc Health Risk Manag. 2007;3(6):817-21.
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=27793869
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=28097013
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=28191026
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=28260907
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=28387458
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=28559211
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=28588183
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=28624425