Basic information
- CAS
27591-69-1- Standard SMILES
CCN(CC)CCOc1ccc2c(c1)C(=O)c1cc(OCCN(CC)CC)ccc1-2- InChIKey
MPMFCABZENCRHV-UHFFFAOYSA-N- Molecular formula
- C25H34N2O3
- Average molar mass
- 410.5 g/mol
- Monoisotopic mass
- 410.25694295
Overview
Tilorone is a member of the class of fluoren-9-ones that is 9H-fluoren-9-one which is substituted by a 2-(diethylamino)ethoxy group at positions 2 and 7. It is an interferon inducer and a selective alpha7 nicotinic acetylcholine receptor (alpha7 nAChR) agonist. Its hydrochloride salt is used as an antiviral drug. It has a role as an antiviral agent, an antineoplastic agent, an interferon inducer, an EC 3.1.1.7 (acetylcholinesterase) inhibitor, a nicotinic acetylcholine receptor agonist and an anti-inflammatory agent. It is a member of fluoren-9-ones, an aromatic ether, a diether and a tertiary amino compound. It is a conjugate base of a tilorone(2+).
Names & identifiers
- Preferred name
- Tilorone
- IUPAC
- 2,7-bis[2-(diethylamino)ethoxy]fluoren-9-one
- English name
- Tilorone
- Molecular formula
- C25H34N2O3
- Molecular weight
- 410.55
Names & synonyms
tilorone27591-97-5Bis-DEAE-fluorenoneTiloronaTiloronum9H-Fluoren-9-one, 2,7-bis[2-(diethylamino)ethoxy]-2,7-Bis(2-(diethylamino)ethoxy)-9H-fluoren-9-oneDTXSID1045958O6W7VEW6KS2,7-bis[2-(diethylamino)ethoxy]-9H-fluoren-9-oneDTXCID90259589H-FLUOREN-9-ONE, 2,7-BIS(2-(DIETHYLAMINO)ETHOXY)-
Show more names
2,TILORONETilorone USP/EP/BPEthylamine fluorenone2,7-Bis[2-(diethylamino)ethoxy]-9-fluorenone
CHEBI:147347Bis DEAE FluorenoneRefChem:933073J05AX192,7-Bis-(2-diethylamino-ethoxy)-fluoren-9-oneTilorone [INN]2,7-Bis-DEAE-fluorenone2,7-bis[2-(diethylamino)ethoxy]fluoren-9-one
Database identifiers
- CAS
27591-69-1、27591-97-5- PubChem CID
- 5475
- DTXSID
DTXSID1045958- ChEMBL
CHEMBL47298- ChEBI
CHEBI:147347
Properties
Computed structural properties
- XLogP
- 4.7
- Topological polar surface area
- 42 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 12
- Heavy atoms
- 30
- Formal charge
- 0
- Complexity
- 477
Experimental & physicochemical properties
Collision Cross Section
195.31 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
219.8 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Boiling point
- 552.3 · 552.3±50.0 °C(Predicted)
- Density
- 1.102 · 1.102±0.06 g/cm3(Predicted)
- pka
- 9.67 · 9.67±0.25(Predicted)
- form
- Solid
- color
- Orange to red
- FDA UNII
- 6 W7VEW6KS · O6W7VEW6KS
- ATC code
- 5 AX19 · J05AX19
Chemistry & industry
Pharmacology
ATC Code
J - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
MeSH Pharmacological Classification
Substances that reduce or suppress INFLAMMATION.
Substances that inhibit or prevent the proliferation of NEOPLASMS.
Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly.
Agents that promote the production and release of interferons. They include mitogens, lipopolysaccharides, and the synthetic polymers Poly A-U and Poly I-C. Viruses, bacteria, and protozoa have been also known to induce interferons.
Applications
UsesTilorone is an orally active antiviral agent and interferon inducer that also has potential antineoplastic, immunomodulatory, and metabolic modulating effects. Tilorone induces an abnormally delayed interferon response and primarily stimulates interferon production in lymphoid tissue. Thus, Tilorone exerts antiviral effects and can be used as a chemotherapeutic agent. Tilorone has the potential to inhibit type 2 diabetes by increasing glucose uptake in vivo and in skeletal muscle cells by enhancing Akt2/AS160 signaling and glucose transporter levels[1][2][3][4][5].
Upstream & downstream products
Downstream products
Suppliers30 total
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Related reactions
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Compound notes
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