Cetilistat

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

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Name
Cetilistat
Accession Number
DB06586
Type
Small Molecule
Groups
Investigational
Description

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.

Structure
Thumb
Synonyms
Not Available
External IDs
ATL-962
Categories
UNII
LC5G1JUA39
CAS number
282526-98-1
Weight
Average: 401.5821
Monoisotopic: 401.292994119
Chemical Formula
C25H39NO3
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

Pharmacology

Indication

Investigated for use/treatment in obesity.

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.

TargetActionsOrganism
UPancreatic triacylglycerol lipaseNot AvailableHumans
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
  1. Padwal R: Cetilistat, a new lipase inhibitor for the treatment of obesity. Curr Opin Investig Drugs. 2008 Apr;9(4):414-21. [PubMed:18393108]
External Links
PubChem Compound
9952916
ChemSpider
8128526
ChEBI
134721
ChEMBL
CHEMBL2103825
Wikipedia
Cetilistat

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentBMI >30 kg/m21
2CompletedTreatmentBMI >30 kg/m2 / Type 2 Diabetes Mellitus1

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
PropertyValueSource
Water Solubility1.25e-05 mg/mLALOGPS
logP8.64ALOGPS
logP9.26ChemAxon
logS-7.5ALOGPS
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area47.89 Å2ChemAxon
Rotatable Bond Count16ChemAxon
Refractivity121.46 m3·mol-1ChemAxon
Polarizability51.21 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9875
Caco-2 permeable+0.5425
P-glycoprotein substrateNon-substrate0.573
P-glycoprotein inhibitor INon-inhibitor0.7204
P-glycoprotein inhibitor IINon-inhibitor0.9269
Renal organic cation transporterNon-inhibitor0.8324
CYP450 2C9 substrateNon-substrate0.8426
CYP450 2D6 substrateNon-substrate0.7453
CYP450 3A4 substrateSubstrate0.5619
CYP450 1A2 substrateInhibitor0.7619
CYP450 2C9 inhibitorNon-inhibitor0.663
CYP450 2D6 inhibitorNon-inhibitor0.9101
CYP450 2C19 inhibitorInhibitor0.6868
CYP450 3A4 inhibitorNon-inhibitor0.8018
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5808
Ames testNon AMES toxic0.6672
CarcinogenicityNon-carcinogens0.9307
BiodegradationNot ready biodegradable0.9914
Rat acute toxicity2.2855 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8825
hERG inhibition (predictor II)Non-inhibitor0.8668
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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
Benzoxazine / Alkyl aryl ether / Benzenoid / Heteroaromatic compound / Lactone / Ether / Azacycle / Oxacycle / Organic oxide / Organooxygen compound
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Triglyceride lipase activity
Specific Function
Not Available
Gene Name
PNLIP
Uniprot ID
P16233
Uniprot Name
Pancreatic triacylglycerol lipase
Molecular Weight
51156.48 Da
References
  1. 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. [PubMed:18500680]

Drug created on March 19, 2008 10:38 / Updated on August 02, 2019 07:52