Cetilistat
Grundinformationen
- CAS
282526-98-1- Standard-SMILES
CCCCCCCCCCCCCCCCOc1nc2ccc(C)cc2c(=O)o1- InChIKey
MVCQKIKWYUURMU-UHFFFAOYSA-N- Summenformel
- C25H39NO3
- Durchschnittliche Molmasse
- 401,6 g/mol
- Monoisotopische Masse
- 401,29299411
Überblick
Cetilistat is a benzoxazine.
Namen und Bezeichner
- Bevorzugter Name
- Cetilistat
- IUPAC
- 2-hexadecoxy-6-methyl-3,1-benzoxazin-4-one
- Englischer Name
- Cetilistat
- Summenformel
- C25H39NO3
- Molmasse
- 401.58
Namen und Synonyme
Cetilistat282526-98-1ATL-962oblean2-(Hexadecyloxy)-6-methyl-4H-3,1-benzoxazin-4-one2-hexadecoxy-6-methyl-3,1-benzoxazin-4-one4H-3,1-Benzoxazin-4-one, 2-(hexadecyloxy)-6-methyl-LC5G1JUA39DTXSID90182506cetilistatumRefChem:575350DTXCID60104997
Weitere Namen anzeigen
New alistatXitelisCetislimCetilstatCetilistaSitilistaXinlisitaNew ristar
2-(hexadecyloxy)-6-methyl-4H-benzo[d][1,3]oxazin-4-oneMFCD09839697Citilistat2-Hexadecyloxy-6-methyl-4H-3,1-benzoxazin-4-oneCetilistat [INN]ATL 962CametorUNII-LC5G1JUA39
Datenbank-Bezeichner
- CAS
282526-98-1- PubChem CID
- 9952916
- DTXSID
DTXSID90182506- ChEMBL
CHEMBL2103825- ChEBI
CHEBI:134721
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 9,8
- Polarare Oberfläche (TPSA)
- 47,9 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 4
- Frei drehbare Bindungen
- 16
- Schwere Atome
- 29
- Formalladung
- 0
- Komplexität
- 477
Experimentelle und physikochemische Eigenschaften
DrugsPharmaceuticals -> Listed in ZINC15
Physikochemische Eigenschaften
- Schmelzpunkt
- 72 to · 72.0 to 76.0 °C
- Siedepunkt
- 509.7 · 509.7±43.0 °C(Predicted)
- Dichte
- 1.02 · 1.02
- storage temp.
- 2 · 2-8°C
- Löslichkeit
- Chloroform (Slightly), Ethyl Acetate (Slightly)
- Aggregatzustand
- Solid
- pka
- 2.96 · 2.96±0.20(Predicted)
- Farbe
- White to Off-White
- 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
- InChIKey
- MVCQKIKWYUURMU-UHFFFAOYSA-N
- SMILES
- N1C2=CC=C(C)C=C2C(=O)OC=1OCCCCCCCCCCCCCCCC
- CAS Datenbank
- 282526 · 282526-98-1(CAS DataBase Reference)
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
Sicherheitsdaten
- hs_code
- 2934.99.4400
Chemie und Industrie
Pharmakologische Informationen
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.
MeSH Pharmacological Classification
Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.
Agents that increase energy expenditure and weight loss by neural and metabolic regulation.
Substances that alter the metabolism of LIPIDS.
Anwendungen
BeschreibungCetilistat (also known as ATL-962) was approved in September 2013 by the Japanese Ministry of Health, Labor and Welfare for the treatment of obesity, limited to patients with both type 2 diabetes mellitus (T2DM) and dyslipidemia, and with a body mass index (BMI)25 kg/m2 in spite of dietary treatment and/or exercise therapy. As with orlistat, cetilistat works via inhibition of pancreatic lipases in the gut to inhibit fat absorption and thereby reduce caloric uptake from diet. The medicinal chemistry program has not been described in the scientific literature, but the patent describing cetilistat also describes the synthesis of analogs with varied aryl substituents and lipophilic tails. The synthesis of cetilistat involves condensation of a hexadecylcarbonochloridate with 2-amino-5-methylbenzoic acid; other analogs were synthesized by varying the carbonochloridate and 2-aminobenzoic acid components. Cetilistat is a potent inhibitor of human and rat pancreatic lipase with IC50s of 15 and 136 nM, respectively, with little inhibition of trypsin or chymotrypsin.
VerwendenA novel pancreatic lipase inhibitor for the treatment of obesity in both diabetic and non-diabetic patients.
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