Rimonabant
Grundinformationen
- CAS
158681-13-1- Standard-SMILES
Cc1c(C(=O)NN2CCCCC2)nn(-c2ccc(Cl)cc2Cl)c1-c1ccc(Cl)cc1- InChIKey
JZCPYUJPEARBJL-UHFFFAOYSA-N- Summenformel
- C22H21Cl3N4O
- Durchschnittliche Molmasse
- 463,8 g/mol
- Monoisotopische Masse
- 462,078094
Namen und Bezeichner
- Bevorzugter Name
- Rimonabant
- IUPAC
- 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-piperidin-1-ylpyrazole-3-carboxamide
- Englischer Name
- Rimonabant
- Summenformel
- C22H21Cl3N4O
- Molmasse
- 463.79
Namen und Synonyme
Rimonabant168273-06-1AcompliaZimulti5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(piperidin-1-yl)-1H-pyrazole-3-carboxamideSR141716SR 141716SR-141716ASR-141716A 2815-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-piperidin-1-ylpyrazole-3-carboxamideDTXSID3046453
Weitere Namen anzeigen
xibuqumrimobrantRimonabanLimonabantrimonabantxUnii-rml78en3xe
RML78EN3XESR-141715-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-1-piperidinyl-1H-pyrazole-3-carboxamideDTXCID1026453CHEBI:349671H-Pyrazole-3-carboxamide, 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-1-piperidinyl-rimonabantumRefChem:389265
Datenbank-Bezeichner
- CAS
158681-13-1、168273-06-1- PubChem CID
- 104850
- DTXSID
DTXSID3046453- ChEMBL
CHEMBL111- ChEBI
CHEBI:34967
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 6,5
- Polarare Oberfläche (TPSA)
- 50,2 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 3
- Frei drehbare Bindungen
- 4
- Schwere Atome
- 30
- Formalladung
- 0
- Komplexität
- 583
Experimentelle und physikochemische Eigenschaften
Solubility2.00e-03 g/L
Physical DescriptionSolid
Physikochemische Eigenschaften
- Schmelzpunkt
- 154.7 °C · 154.7 °C
- Dichte
- 1.41 · 1.41±0.1 g/cm3(Predicted)
- storage temp.
- RT
- Löslichkeit
- Soluble in DMSO (up to 20 mg/ml) or in Ethanol (up to 20 mg/ml).
- pka
- 11.31 · 11.31±0.20(Predicted)
- Aggregatzustand
- solid
- Farbe
- White
- Stabilität
- 1 year · Stable for 1 year from date of purchase as supplied. Protect from moisture. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months.
- InChI
- InChI=1S/C22H21Cl3N4O/c1-14-20(22(30)27-28-11-3-2-4-12-28)26-29(19-10-9-17(24)13-18(19)25)21(14)15-5-7-16(23)8-6-15/h5-10,13H,2-4,11-12H2,1H3,(H,27,30)
- InChIKey
- JZCPYUJPEARBJL-UHFFFAOYSA-N
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
Danger
H361 (50%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]；H371 (50%): May cause damage to organs [Warning Specific target organ toxicity, single exposure]；H372 (50%): Causes damage to organs through prolonged or repeated exposure [Danger Specific target organ toxicity, repeated exposure]；H373 (50%): May causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]；H410 (50%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]
P203, P260, P264, P270, P273, P280, P308+P316, P318, P319, P391, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
Gefahrenhinweise
Hazard Classes and CategoriesRepr. 2 (50%)；STOT SE 2 (50%)；STOT RE 1 (50%)；STOT RE 2 (50%)；Aquatic Chronic 1 (50%)
Sicherheitsdaten
- Alarmwort
- Achtung
- Gefahrenhinweise
- Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code H372
Chemie und Industrie
Pharmakologische Informationen
ATC Code
A - Alimentary tract and metabolism；A08 - Antiobesity preparations, excl. diet products；A08A - Antiobesity preparations, excl. diet products；A08AX - Other antiobesity drugs；A08AX01 - Rimonabant
QA - Alimentary tract and metabolism；QA08 - Antiobesity preparations, excl. diet products；QA08A - Antiobesity preparations, excl. diet products；QA08AX - Other antiobesity drugs；QA08AX01 - Rimonabant
Protein BindingAlmost 100%
Pharmacodynamics
In the RIO-North America trial, 3040 patients were randomized to receive either placebo or one of two doses of rimonabant (5 mg or 20 mg per day). Patients taking 20 mg rimonabant had significant weigh loss, decrease in waist circumference, improved insulin sensitivity, and increases in HDL cholesterol, compared to patients on placebo.
Mechanism of Action
Rimonabant is a specific CB1 cannabinoid receptor antagonist. There is considerable evidence that the endocannabinoid (endogenous cannabinoid) system plays a significant role in appetitive drive and associated behaviours. It is therefore reasonable to hypothesize that the attenuation of the activity of this system would have therapeutic benefit in treating disorders that might have a component of excess appetitive drive or over-activity of the endocannabinoid system, such as obesity, ethanol and other drug abuse, and a variety of central nervous system and other disorders.
Biological Half-Life6 to 9 days with normal BMI and 16 days if BMI is greater than 30
Metabolism/MetabolitesHepatic, CYP3A4 involved.
MeSH Pharmacological Classification
Agents that increase energy expenditure and weight loss by neural and metabolic regulation.
Compounds that inhibit or block the activity of CANNABINOID RECEPTORS.
Zugehörige Reaktionen
5
Notizen zur Verbindung
Wird geladen…