Basic information
- CAS
55242-55-2- Standard SMILES
CCCn1cnc2c1c(=O)n(CCCCC(C)=O)c(=O)n2C- InChIKey
RBQOQRRFDPXAGN-UHFFFAOYSA-N- Molecular formula
- C15H22N4O3
- Average molar mass
- 306.36 g/mol
- Monoisotopic mass
- 306.16919056
Overview
Propentofylline is an oxopurine.
Names & identifiers
- Preferred name
- Propentofylline
- IUPAC
- 3-methyl-1-(5-oxohexyl)-7-propylpurine-2,6-dione
- English name
- PROPENTOFYLLINE
- Molecular formula
- C15H22N4O3
- Molecular weight
- 306.36
Names & synonyms
Show more names
Database identifiers
- CAS
55242-55-2- PubChem CID
- 4938
- DTXSID
DTXSID4045189- ChEMBL
CHEMBL1079905- ChEBI
CHEBI:32061- UNII
- 5RTA398U4H
- EC Number
- 611-242-7
- Nikkaji
- J22.661K
Properties
Computed structural properties
- XLogP
- 0.7
- Topological polar surface area
- 75.5 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 7
- Heavy atoms
- 22
- Formal charge
- 0
- Complexity
- 454
Experimental & physicochemical properties
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]
Physicochemical properties
- Melting point
- 64 · 64-66°C
- Boiling point
- 541.4 · 541.4±56.0 °C(Predicted)
- Density
- 1.25 · 1.25±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · Sealed in dry,Store in freezer, under -20°C
- solubility
- 2 O: · H2O: soluble12.4mg/mL
- pka
- 0.58 · 0.58±0.70(Predicted)
- form
- solid
- color
- white
- Water Solubility
- 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
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 5 RTA398U4H · 5RTA398U4H
- ATC code
- 6 BC02 · N06BC02
- UNSPSC Code
- 41106305 · 41106305
- NACRES
- 77 · NA.77
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302+H312+H332
- Precautionary statements
- 261 · P261-P264-P280-P301+P312-P302+P352+P312-P304+P340+P312
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xn
- Risk Statements
- 20 · 20/21/22
- WGK Germany
- 3 · 3
- RTECS
- 8438700 · UO8438700
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 4 DermalAcute · Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 Oral
- Toxicity
- 50 in · 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)
Safety & regulation
GHS classification
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.
Hazard information
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- rtecs
- UO8438700
- Toxicity
- 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)
- risk_code
- 20/21/22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302+H312+H332
- Hazard Classifications
- Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 Oral
- Precautionary statements
- P261-P264-P280-P301+P312-P302+P352+P312-P304+P340+P312
Chemistry & industry
Pharmacology
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.
Uses & manufacturing
Applications
DescriptionPropentofylline is a nootropic indicated for cerebrovascular disorders. Other indications currently under investigation include senile dementia, stroke and hypoxia.
UsesA c-AMP phosphodiesterase inhibitor. A nerve growth factor stimulator. An adenosine transport inhibitor. A non-selective adenosine receptor antagonist. Nootropic.
Upstream & downstream products
Upstream raw materials
Suppliers31 total
Additional notes
DefinitionChEBI: Propentofylline is an oxopurine.
Related reactions
Compound notes
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