Cetilistat
Explore a selection of our essential drug information below, or:
Identification
- Generic Name
- Cetilistat
- DrugBank Accession Number
- DB06586
- Background
Cetilistat is a novel inhibitor of pancreatic lipase being developed by Alizyme for the treatment of obesity and associated co-morbidities, including type 2 diabetes.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
- Weight
- Average: 401.5821
Monoisotopic: 401.292994119 - Chemical Formula
- C25H39NO3
- Synonyms
- Cetilistat
- External IDs
- ATL-962
Pharmacology
- Indication
Investigated for use/treatment in obesity.
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- Pharmacodynamics
Not Available
- Mechanism of action
Cetilistat is a gastrointestinal lipase inhibitor that blocks fat digestion and absorption, leading to reduced energy intake, and thus weight loss. It is distinct from most other anti-obesity agents as it does not act on the brain to reduce appetite, but acts peripherally. The compound remains in the gastrointestinal tract with no significant absorption into the body.
Target Actions Organism AEndothelial lipase modulatorHumans AGastric triacylglycerol lipase modulatorHumans UPancreatic triacylglycerol lipase Not Available Humans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as benzoxazines. These are organic compounds containing a benzene fused to an oxazine ring (a six-membered aliphatic ring with four carbon atoms, one oxygen atom, and one nitrogen atom).
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Benzoxazines
- Sub Class
- Not Available
- Direct Parent
- Benzoxazines
- Alternative Parents
- Alkyl aryl ethers / Benzenoids / Heteroaromatic compounds / Lactones / Oxacyclic compounds / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives
- Substituents
- Alkyl aryl ether / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Benzoxazine / Ether / Heteroaromatic compound / Hydrocarbon derivative / Lactone / Organic nitrogen compound
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- LC5G1JUA39
- CAS number
- 282526-98-1
- InChI Key
- MVCQKIKWYUURMU-UHFFFAOYSA-N
- InChI
- InChI=1S/C25H39NO3/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-19-28-25-26-23-18-17-21(2)20-22(23)24(27)29-25/h17-18,20H,3-16,19H2,1-2H3
- IUPAC Name
- 2-(hexadecyloxy)-6-methyl-4H-3,1-benzoxazin-4-one
- SMILES
- CCCCCCCCCCCCCCCCOC1=NC2=C(C=C(C)C=C2)C(=O)O1
References
- General References
- Padwal R: Cetilistat, a new lipase inhibitor for the treatment of obesity. Curr Opin Investig Drugs. 2008 Apr;9(4):414-21. [Article]
- External Links
- PubChem Compound
- 9952916
- ChemSpider
- 8128526
- ChEBI
- 134721
- ChEMBL
- CHEMBL2103825
- ZINC
- ZINC000014128264
- Wikipedia
- Cetilistat
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data2 Completed Treatment Diabetes Mellitus, Noninsulin Dependent / Obesity 1 somestatus stop reason just information to hide 1 Completed Treatment Obesity 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 1.25e-05 mg/mL ALOGPS logP 8.64 ALOGPS logP 9.26 Chemaxon logS -7.5 ALOGPS pKa (Strongest Basic) -4.4 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 47.89 Å2 Chemaxon Rotatable Bond Count 16 Chemaxon Refractivity 121.46 m3·mol-1 Chemaxon Polarizability 51.21 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.9875 Caco-2 permeable + 0.5425 P-glycoprotein substrate Non-substrate 0.573 P-glycoprotein inhibitor I Non-inhibitor 0.7204 P-glycoprotein inhibitor II Non-inhibitor 0.9269 Renal organic cation transporter Non-inhibitor 0.8324 CYP450 2C9 substrate Non-substrate 0.8426 CYP450 2D6 substrate Non-substrate 0.7453 CYP450 3A4 substrate Substrate 0.5619 CYP450 1A2 substrate Inhibitor 0.7619 CYP450 2C9 inhibitor Non-inhibitor 0.663 CYP450 2D6 inhibitor Non-inhibitor 0.9101 CYP450 2C19 inhibitor Inhibitor 0.6868 CYP450 3A4 inhibitor Non-inhibitor 0.8018 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.5808 Ames test Non AMES toxic 0.6672 Carcinogenicity Non-carcinogens 0.9307 Biodegradation Not ready biodegradable 0.9914 Rat acute toxicity 2.2855 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8825 hERG inhibition (predictor II) Non-inhibitor 0.8668
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0udi-9121600000-a76a155430d07d522781 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0059-0901000000-10e28afca961e68dbb9d Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4l-9112000000-432cc3ab68f2575cc54c Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-0914000000-650f83401662cde08359 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0ue9-0901000000-08a22a8c5e98e3fb56d8 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-052f-9121000000-d48ec3f524ffd276d0c6 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 234.8155295 predictedDarkChem Lite v0.1.0 [M-H]- 207.01784 predictedDeepCCS 1.0 (2019) [M+H]+ 234.7086295 predictedDarkChem Lite v0.1.0 [M+H]+ 210.32271 predictedDeepCCS 1.0 (2019) [M+Na]+ 235.6657295 predictedDarkChem Lite v0.1.0 [M+Na]+ 218.08199 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Modulator
- General Function
- Exerts both phospholipase and triglyceride lipase activities (PubMed:10192396, PubMed:10318835, PubMed:12032167). More active as a phospholipase than a triglyceride lipase (PubMed:12032167). Hydrolyzes triglycerides, both with short-chain fatty acyl groups (tributyrin) and long-chain fatty acyl groups (triolein) with similar levels of activity toward both types of substrates (PubMed:12032167). Hydrolyzes high density lipoproteins (HDL) more efficiently than other lipoproteins (PubMed:10192396, PubMed:12032167)
- Specific Function
- 1-acyl-2-lysophosphatidylserine acylhydrolase activity
- Gene Name
- LIPG
- Uniprot ID
- Q9Y5X9
- Uniprot Name
- Endothelial lipase
- Molecular Weight
- 56794.275 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Modulator
- General Function
- Catalyzes the hydrolysis of triacylglycerols to yield free fatty acids, diacylglycerol, monoacylglycerol, and glycerol (PubMed:10358049, PubMed:2243091). Shows a preferential hydrolysis at the sn-3 position of triacylglycerol (PubMed:2243091)
- Specific Function
- lipid binding
- Gene Name
- LIPF
- Uniprot ID
- P07098
- Uniprot Name
- Gastric triacylglycerol lipase
- Molecular Weight
- 45237.375 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Plays an important role in fat metabolism. It preferentially splits the esters of long-chain fatty acids at positions 1 and 3, producing mainly 2-monoacylglycerol and free fatty acids, and shows considerably higher activity against insoluble emulsified substrates than against soluble ones
- Specific Function
- all-trans-retinyl-palmitate hydrolase, all-trans-retinol forming activity
- Gene Name
- PNLIP
- Uniprot ID
- P16233
- Uniprot Name
- Pancreatic triacylglycerol lipase
- Molecular Weight
- 51156.48 Da
References
- Yamada Y, Kato T, Ogino H, Ashina S, Kato K: Cetilistat (ATL-962), a novel pancreatic lipase inhibitor, ameliorates body weight gain and improves lipid profiles in rats. Horm Metab Res. 2008 Aug;40(8):539-43. doi: 10.1055/s-2008-1076699. Epub 2008 May 21. [Article]
Drug created at March 19, 2008 16:38 / Updated at October 03, 2024 04:25