Basic information
- CAS
103516-75-2- Standard SMILES
C1CCC(C(CC2CCCCN2)C2CCCCC2)CC1.O=C(O)/C=C\C(=O)O- InChIKey
JDZOTSLZMQDFLG-BTJKTKAUSA-N- Molecular formula
- C23H39NO4
- Average molar mass
- 393.6 g/mol
- Monoisotopic mass
- 393.28790873
Overview
PERHEXILINE MALEATE is a small molecule drug with a maximum clinical trial phase of IV that was first approved in 1974. It was withdrawn in at least one region.
Names & identifiers
- Preferred name
- Perhexiline Maleate
- IUPAC
- (Z)-but-2-enedioic acid;2-(2,2-dicyclohexylethyl)piperidine
- English name
- PERHEXILINE MALEATE SALT
- Molecular formula
- C23H39NO4
- Molecular weight
- 393.56
Names & synonyms
Perhexiline maleate6724-53-4Pexid2-(2,2-Dicyclohexylethyl)piperidine maleateDTXSID1021114PexsigNSC-758409K7V8Y90G0HPiperidine, 2-(2,2-dicyclohexylethyl)-, maleate (1:1)Piperidine, 2-(2,2-dicyclohexylethyl)-, (Z)-2-butenedioate (1:1)DTXCID201114RefChem:860306
Show more names
WSM-3978WSM 3978Gperhexilinemaleateperhexilene maleatePERHEXILINE MALEATE SALTPERHEXILINE MALEATE SALT USP/EP/BPPerhexiline maleate, 10 mM in DMSO2-(2,2-dicyclohexylethyl)piperidinemaleate
229-775-5rac Perhexiline MaleatePerhexiline maleate [USAN](Z)-but-2-enedioic acid;2-(2,2-dicyclohexylethyl)piperidineCCRIS 54912-(2,2-Dicyclohexylethyl)piperidine maleate (1:1)Perhexiline maleate, (+)-Perhexiline maleate, (-)-
Database identifiers
- CAS
103516-75-2、103516-76-3、6724-53-4
Properties
Computed structural properties
- Topological polar surface area
- 86.6 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 6
- Heavy atoms
- 28
- Formal charge
- 0
- Complexity
- 364
Experimental & physicochemical properties
Collision Cross Section179.8 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 181 · 181-183°C
- storage temp.
- 2 · 2-8°C
- solubility
- 5 mg/mL · DMSO: ≥5mg/mL
- form
- powder
- color
- white to tan
- InChI
- 1S/C19H35N.C4H4O4/c1-3-9-16(10-4-1)19(17-11-5-2-6-12-17)15-18-13-7-8-14-20-18;5-3(6)1-2-4(7)8/h16-20H,1-15H2;1-2H,(H,5,6)(H,7,8)/b;2-1-
- InChIKey
- JDZOTSLZMQDFLG-BTJKTKAUSA-N
- SMILES
- OC(=O)\C=C/C(O)=O.C1CCC(CC1)C(CC2CCCCN2)C3CCCCC3
- FDA UNII
- 7 V8Y90G0H · K7V8Y90G0H
- UNSPSC Code
- 12352200 · 12352200
- NACRES
- 25 · NA.25
- WGK Germany
- 2 · 2
- RTECS
- 7068000 · TM7068000
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS ClassificationNot Classified
Hazard information
Other Safety InformationIMAP assessments - Piperidine, 2-(2,2-dicyclohexylethyl)-, (Z)-2-butenedioate (1:1): Environment tier I assessment
Hazard Classes and CategoriesNot Classified
Toxicology
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
perhexiline maleate
DILI Positive
DOI:10.1016/j.drudis.2019.09.022
Safety data
- wgk
- 2
- rtecs
- TM7068000
- Toxicity
- LD50 in rats, mice (g/kg): >7, 4.37 orally (Causa, Perri)
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Applications
DescriptionPerhexiline 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.
UsesPERHEXILINE MALEATE SALT is a Vasodilator, used in treatments for angina.
UsesPerhexiline maleate salt has been used to block fatty acid oxidation. It has also been used as 5′adenosinemonophosphate-activatedprotein kinase(AMPK)activator and in worm lifespan assay.
UsesH1 antihistamine
General DescriptionPerhexiline maleate regulatescoronary vasodilatation and blocks exercise-induced tachycardia. It is used to treat angina pectoris and variant angina. Perhexiline maleate functions as a cardiac metabolic agent. It is associated with peripheral neuropathy, high intracranial pressure withpapilledemaand proximal myopathy.
Upstream & downstream products
Upstream raw materials
Suppliers62 total
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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