2-(2,2-Dicyclohexylethyl)piperidiniumhydrogenmaleat
rac Perhexiline Maleate · Pexid · WSM-3978 · WSM 3978G · perhexilinemaleate · perhexilene maleate · PERHEXILINE MALEATE SALT · PERHEXILINE MALEATE SALT USP/EP/BP
Identifikatoren & physikalische Daten
| CAS No. | 103516-75-2 |
|---|---|
| Summenformel | C23H39NO4 |
| Durchschnittliche Molmasse | 393,6 g/mol |
| Monoisotopische Masse | 393,28790873 g/mol |
| SMILES | C1CCC(C(CC2CCCCN2)C2CCCCC2)CC1.O=C(O)/C=C\C(=O)O |
| InChIKey | JDZOTSLZMQDFLG-BTJKTKAUSA-N |
| PubChem CID | 5284439 |
| ChEMBL | CHEMBL1334033 |
| ChEBI | CHEBI:232991 |
| EC No. | 229-775-5 |
| DTXSID | DTXSID1021114 |
| Lokaler Name | 2-(2,2-Dicyclohexylethyl)piperidiniumhydrogenmaleat |
Chemische & physikalische Eigenschaften
| Polarare Oberfläche (TPSA) | 86,6 |
|---|---|
| H-Brücken-Donoren | 3 |
| H-Brücken-Akzeptoren | 5 |
| Frei drehbare Bindungen | 6 |
| Schwere Atome | 28 |
| Formalladung | 0 |
| Komplexität | 364 |
| Collision Cross Section | 179.8 Ų [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards] |
| Schmelzpunkt | 181-183°C |
| Lagerbedingungen | 2-8°C |
| Löslichkeit | DMSO: ≥5mg/mL |
| Aggregatzustand | powder |
| Farbe | white to tan |
| InChI | 1S/C19H35N.C4H4O4/c1-3-9-16(10-4-1)19(17-11-5-2-6-12-17)15-18-13-7-8-14-20-185-3(6)1-2-4(7)8/h16-20H,1-15H21-2H,(H,5,6)(H,7,8)/b2-1- |
| InChIKey | JDZOTSLZMQDFLG-BTJKTKAUSA-N |
| SMILES | OC(=O)\C=C/C(O)=O.C1CCC(CC1)C(CC2CCCCN2)C3CCCCC3 |
Sicherheit & Vorschriften
| GHS-Einstufung | Not Classified |
|---|---|
| Weitere Sicherheitsinformationen | IMAP assessments - Piperidine, 2-(2,2-dicyclohexylethyl)-, (Z)-2-butenedioate (1:1): Environment tier I assessment |
| Hazard Classes and Categories | Not Classified |
| Drug Induced Liver Injury | Drug-Induced Liver Injury Severity and Toxicity (DILIst)perhexiline maleateDILI PositiveDOI:10.1016/j.drudis.2019.09.022 |
| Wassergefährdungsklasse (WGK) | 2 |
| RTECS-Nr. | TM7068000 |
| Toxizität | LD50 in rats, mice (g/kg): >7, 4.37 orally (Causa, Perri) |
| Lagerklasse | 11 - Combustible Solids |
Anwendungen & Verwendung
Beschreibung
Perhexiline is a carnitine palmitoyltransferase 1 (CPT1) and CPT2 inhibitor that was originally developed as an anti-anginal drug in the 1970s. It inhibits rat heart and liver CPT1 (IC50 = 77 and 148 μM, respectively) and rat heart CPT2 (IC50 = 79 μM). Inhibition of CPT reduces uptake of long-chain fatty acids into the mitochondria, thereby shifting cellular metabolism from β-oxidation to glycolysis. Perhexilin inhibits mTORC1 signaling at 10 μM and induces autophagy ~7-fold at a concentration of 10 μM in MCF-7 cells.
Verwenden
PERHEXILINE MALEATE SALT is a Vasodilator, used in treatments for angina.