TILORONE HYDROCHLORIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C25H34N2O3.2ClH
Molecular Weight	483.471
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.Cl.CCN(CC)CCOC1=CC=C2C(=C1)C(=O)C3=C2C=CC(OCCN(CC)CC)=C3

InChI

InChIKey=BSVYJQAWONIOOU-UHFFFAOYSA-N

InChI=1S/C25H34N2O3.2ClH/c1-5-26(6-2)13-15-29-19-9-11-21-22-12-10-20(30-16-14-27(7-3)8-4)18-24(22)25(28)23(21)17-19;;/h9-12,17-18H,5-8,13-16H2,1-4H3;2*1H

HIDE SMILES / InChI

Description
Sources: https://www.rlsnet.ru/mnn_index_id_2731.htm
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/27809794 | https://www.ncbi.nlm.nih.gov/pubmed/24841903

Tilorone (trade names Amixin, Lavomax and others) is the first recognized synthetic, small molecular weight compound that is an orally active interferon inducer. Tilorone induces the formation of interferons (alpha, beta, gamma) by intestinal epithelial cells, hepatocytes, T-lymphocytes, and granulocytes. After ingestion, the maximum production of interferon is determined in the sequence of the intestine - liver - blood after 4-24 hours. Activates the stem cells of the bone marrow, stimulates humoral immunity, increases the production of IgM, IgA, IgG, affects the antibody formation, reduces the degree of immunosuppression, restores the ratio of T-helperers / T-suppressors. The mechanism of antiviral action is associated with the inhibition of translation of virus-specific proteins in infected cells, thereby suppressing the replication of the virus. Effective against influenza viruses and viruses that cause ARVI, hepato- and herpesviruses, incl. CMV and others. The mechanism of antiviral action is associated with the inhibition of translation of virus-specific proteins in infected cells, thereby suppressing the replication of the virus.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
interferon-alpha production 2 Target ID: GO:0032607 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26633340	Activator 1430

Conditions

Condition	Modality	Highest Phase	Product
Hepatitis A 2 Sources: https://www.rlsnet.ru/mnn_index_id_2731.htm	Primary	Approved 8429	Amixin Approved Use Unknown
Hepatitis B 57 Sources: https://www.rlsnet.ru/mnn_index_id_2731.htm	Primary	Approved 8429	Amixin Approved Use Unknown
Hepatitis C 42 Sources: https://www.rlsnet.ru/mnn_index_id_2731.htm	Primary	Approved 8429	Amixin Approved Use Unknown
Cytomegalovirus infection 6 Sources: https://www.rlsnet.ru/mnn_index_id_2731.htm	Primary	Approved 8429	Amixin Approved Use Unknown

PubMed

Title	Date	PubMed
Antiviral activity and induction of interferon-like substance by quinacrine and acranil.	1973 May	4790609
Bis-basic-substituted polycyclic aromatic compounds. A new class of antiviral agents. 3. 2,7-Bis(aminoacyl)fluorenes and -fluorenones.	1974 Aug	4367594
Antiviral activity of BL-3849A, a low-molecular-weight oral interferon inducer.	1976 Oct	185953
Effects of tilorone hydrochloride on experimental flavivirus infections in mice.	1977 Mar	17279
Antiviral and interferon-inducing properties of interferon inducers administered with prostaglandins.	1980 Mar	6158913
α7 Nicotinic Receptor Agonists: Potential Therapeutic Drugs for Treatment of Cognitive Impairments in Schizophrenia and Alzheimer's Disease.	2010 May 27	21249164
Development of a multiparametric cell-based protocol to screen and classify the hepatotoxicity potential of drugs.	2012 May	22331495

Patents

Sample Use Guides

In Vivo Use Guide

Treatment of viral hepatitis A - on the first day of 125 mg 2 times, then - 125 mg after 48 hours. The course - 1.25 g (10 tables.). Treatment of acute hepatitis B - the first two days of 125 mg, then 125 mg after 48 hours, the course of treatment - 2 g (16 table). With prolonged course of hepatitis B, 125 mg twice a day on the first day, then 125 mg after 48 hours. The course of treatment is 2.5 g (20 tablets). Acute hepatitis C - 125 mg / day for the first 2 days of treatment, then 125 mg after 48 hours. The course of treatment is 2.5 g (20 tablets).

Route of Administration: Oral

In Vitro Use Guide

MTS assays were performed to measure the antiproliferative effect of tilorone treatment. Tilorone dihydrochloride (Sigma-Aldrich) was stored as a 10 mM stock solution in DMSO at -20˚C. One thousand PC3 cells were plated in 96-well plates containing 100 μl complete RPMI media. At circa 50% confluence, tilorone dihydrochloride was administered. For experiments the compound was diluted in complete RPMI media to obtain the desired final concentration. After treatment for 72 h (tilorone monotherapy), MTS reagent was added, and absorption at 490 nm was determined using a SoftMax Pro plate reader.

Name

Type

Language

TILORONE HYDROCHLORIDE

Official Name

English

TILORONE DIHYDROCHLORIDE [MI]

Common Name

English

TILORONE HYDROCHLORIDE [MART.]

Common Name

English

2,7-Bis[2-(diethylamino)ethoxy]fluoren-9-one dihydrochloride

Systematic Name

English

NSC-143969

Code

English

TILORONE DIHYDROCHLORIDE

Common Name

English

TILORONE HYDROCHLORIDE [USAN]

Common Name

English

Tilorone Hydrochloride [WHO-DD]

Common Name

English

9H-FLUOREN-9-ONE, 2,7-BIS(2-(DIETHYLAMINO)ETHOXY)-, DIHYDROCHLORIDE

Common Name

English

TILORONE HCL

Common Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

624717