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Tilorone

CAS No.27591-97-5
Chemical Name:Tilorone
CBNumber:CB3875201
Molecular Formula:C25H34N2O3
Formula Weight:410.55
MOL File:27591-97-5.mol

Tilorone Property

Boiling point 552.3±50.0 °C(Predicted)
Density 1.102±0.06 g/cm3(Predicted)
pka 9.67±0.25(Predicted)
form Solid
color Orange to red
FDA UNII O6W7VEW6KS
ATC code J05AX19

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
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Tilorone Chemical Properties,Usage,Production

Uses Tilorone 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].
Definition ChEBI: 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 interferon inducer, an antineoplastic agent, an anti-inflammatory agent and a nicotinic acetylcholine receptor agonist. It is a member of fluoren-9-ones, a tertiary amino compound, an aromatic ether and a diether. It is a conjugate base of a tilorone(2+).

in vivo

Tilorone (50-250 mg/kg; po; single dose) can induce a delayed but not prolonged interferon response; and affects circulating interferon levels in a dose-dependent manner^[1].
The maximum tolerated single dose of Tilorone in mice is 100 mg/kg; pharmacokinetic results of Tilorone (2, 10 mg/kg; ip) in mice indicate that Tilorone has a high absorption rate and is The half-life in mice is 18 hours, but exposure in male mice is higher^[2].
Tilorone (25-50 mg/kg; ip; once daily for 8 days ) protects 90% of Ebola virus-infected mice from lethal challenge^[2].
Tilorone (25 mg/kg; iv; single dose) enhances immunity in small Uptake of the radiolabeled glucose analog ¹⁸F-fluoro-2-deoxyglucose in rats^[3].

Animal Model:	6-week-old female mouse^[1]
Dosage:	250 mg/kg
Administration:	po; single dose
Result:	Resulted in correspondingly lower levels of circulating interferon, although moderately high levels were obtained (2,500 units/ml) with as little as 50 mg/kg. Interferon production was not detected in the upper gastrointestinal tract.

Animal Model:	Ebola virus disease (EVD) infected mouse model^[2]
Dosage:	25 mg/kg, 30 mg/kg, 50 mg/kg
Administration:	ip; once daily for 8 days
Result:	Showed was fully protective effect at 30 mg/kg, starting 2 or 24 h postchallenge and continuing through day 7 postinfection.

Animal Model:	C57BL/6 mouse^[3]
Dosage:	25 mg/kg
Administration:	IV; in 100?μL saline via the lateral tail vein
Result:	Significant increased in the SUV mean of skeletal muscle, adipose tissue, and liver.

References [1] Stringfellow D A, et al. Tilorone hydrochloride: an oral interferon-inducing agent[J]. Antimicrobial agents and chemotherapy, 1972, 2(2): 73-78. DOI:10.1128/AAC.2.2.73
[2] Ekins S, et al. Efficacy of tilorone dihydrochloride against Ebola virus infection[J]. Antimicrobial agents and chemotherapy, 2018, 62(2): 10.1128/aac. 01711-17. DOI:10.1128/AAC.01711-17
[3] Kohler Z M, et al. Tilorone increases glucose uptake in vivo and in skeletal muscle cells by enhancing Akt2/AS160 signaling and glucose transporter levels[J]. Journal of Cellular Physiology, 2023, 238(5): 1080-1094. DOI:10.1002/jcp.30998
[4] Wissing M D, et al. Small-molecule screening of PC3 prostate cancer cells identifies tilorone dihydrochloride to selectively inhibit cell growth based on cyclin-dependent kinase 5 expression[J]. Oncology reports, 2014, 32(1): 419-424.