Propentofylline
Grundinformationen
- CAS
55242-55-2- Standard-SMILES
CCCn1cnc2c1c(=O)n(CCCCC(C)=O)c(=O)n2C- InChIKey
RBQOQRRFDPXAGN-UHFFFAOYSA-N- Summenformel
- C15H22N4O3
- Durchschnittliche Molmasse
- 306,36 g/mol
- Monoisotopische Masse
- 306,16919056
Überblick
Propentofylline is an oxopurine.
Namen und Bezeichner
- Bevorzugter Name
- Propentofylline
- IUPAC
- 3-methyl-1-(5-oxohexyl)-7-propylpurine-2,6-dione
- Englischer Name
- PROPENTOFYLLINE
- Summenformel
- C15H22N4O3
- Molmasse
- 306.36
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
55242-55-2- PubChem CID
- 4938
- DTXSID
DTXSID4045189- ChEMBL
CHEMBL1079905- ChEBI
CHEBI:32061- UNII
- 5RTA398U4H
- EC Number
- 611-242-7
- Nikkaji
- J22.661K
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 0,7
- Polarare Oberfläche (TPSA)
- 75,5 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 4
- Frei drehbare Bindungen
- 7
- Schwere Atome
- 22
- Formalladung
- 0
- Komplexität
- 454
Experimentelle und physikochemische Eigenschaften
Collision Cross Section
178.88 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
168.3 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physikochemische Eigenschaften
- Schmelzpunkt
- 64 · 64-66°C
- Siedepunkt
- 541.4 · 541.4±56.0 °C(Predicted)
- Dichte
- 1.25 · 1.25±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · Sealed in dry,Store in freezer, under -20°C
- Löslichkeit
- 2 O: · H2O: soluble12.4mg/mL
- pka
- 0.58 · 0.58±0.70(Predicted)
- Aggregatzustand
- solid
- Farbe
- white
- Wasserlöslichkeit
- 2 O: · H2O: 12.4mg/mL
- InChI
- 1S/C15H22N4O3/c1-4-8-18-10-16-13-12(18)14(21)19(15(22)17(13)3)9-6-5-7-11(2)20/h10H,4-9H2,1-3H3
- InChIKey
- RBQOQRRFDPXAGN-UHFFFAOYSA-N
- SMILES
- CCCn1cnc2N(C)C(=O)N(CCCCC(C)=O)C(=O)c12
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
This chemical does not meet GHS hazard criteria for 1.1% (1 of 95) of reports.
Warning
H302 (98.9%): Harmful if swallowed [Warning Acute toxicity, oral]
P260, P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P319, P321, P330, P362+P364, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 95 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Sicherheitsdaten
- wgk
- 3
- RTECS-Nr.
- UO8438700
- risk_code
- 20/21/22
- Toxizität
- LD50 in male, female mice, male, female rats (mg/kg): 900, 780, 1150, 940 orally; 168, 170, 180, 195 i.v.; 375, 346, 199, 196 i.p.; 450, 508, 400, 338 s.c. (Inazu)
- hazard_code
- Xn
- Speicherklasse
- 11 - Combustible Solids
- Hazard Classifications
- Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 Oral
Chemie und Industrie
Pharmakologische Informationen
ATC Code
N - Nervous system
QN - Nervous system
QC - Cardiovascular system
Mechanism of Action
Propentofylline is a xanthine derivative and phosphodiesterase inhibitor with purported neuroprotective effects. It inhibits both phosphodiesterase and adenosine uptake. Phosphodiesterase has shown to associated with age-related memory impairment and Alzheimer's disease. β-Amyloid protein 1–42 (β42) can induce apoptosis in the cultured hippocampal neurons, suggesting that it plays an important role in causing neurodegeneration in Alzheimer's disease. Propentofylline is also capable of activating a cAMP–PKA system, depressing the caspase cascade and modifying Bcl-2 family proteins. Propentofylline blocked both the apoptotic features induced by β42 and further induced an anti-apoptotic protein, Bcl-2. It suggests that the protection of propentofylline on the β42-induced neurotoxicity is caused by enhancing anti-apoptotic action through cAMP–PKA system.
MeSH Pharmacological Classification
Drugs intended to prevent damage to the brain or spinal cord from ischemia, stroke, convulsions, or trauma. Some must be administered before the event, but others may be effective for some time after. They act by a variety of mechanisms, but often directly or indirectly minimize the damage produced by endogenous excitatory amino acids.
Verwendung und Herstellung
Anwendungen
BeschreibungPropentofylline is a nootropic indicated for cerebrovascular disorders. Other indications currently under investigation include senile dementia, stroke and hypoxia.
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