TILORONE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C25H34N2O3
Molecular Weight	410.5491
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=MPMFCABZENCRHV-UHFFFAOYSA-N

InChI=1S/C25H34N2O3/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

HIDE SMILES / InChI

Molecular Formula	C25H34N2O3
Molecular Weight	410.5491
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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 1447

Conditions

Condition	Modality	Highest Phase	Product
Hepatitis A 2 Sources: https://www.rlsnet.ru/mnn_index_id_2731.htm	Primary	Approved 8583	Amixin Approved Use Unknown
Hepatitis B 59 Sources: https://www.rlsnet.ru/mnn_index_id_2731.htm	Primary	Approved 8583	Amixin Approved Use Unknown
Hepatitis C 42 Sources: https://www.rlsnet.ru/mnn_index_id_2731.htm	Primary	Approved 8583	Amixin Approved Use Unknown
Cytomegalovirus infection 6 Sources: https://www.rlsnet.ru/mnn_index_id_2731.htm	Primary	Approved 8583	Amixin Approved Use Unknown

F_unbound

Value	Dose	Co-administered	Analyte	Population
48% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29133569/			TILORONE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
8.1 mg/kg 3 times / day multiple, oral Studied dose Dose: 8.1 mg/kg, 3 times / day Route: oral Route: multiple Dose: 8.1 mg/kg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/7446671/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/7446671/	Disc. AE: Retinopathy... AEs leading to discontinuation/dose reduction: Retinopathy Sources: https://pubmed.ncbi.nlm.nih.gov/7446671/
8.4 mg/kg 1 times / day multiple, oral Studied dose Dose: 8.4 mg/kg, 1 times / day Route: oral Route: multiple Dose: 8.4 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6243446/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/6243446/	Disc. AE: Keratopathy... AEs leading to discontinuation/dose reduction: Keratopathy Sources: https://pubmed.ncbi.nlm.nih.gov/6243446/

AEs

AE	Significance	Dose	Population
Retinopathy	Disc. AE	8.1 mg/kg 3 times / day multiple, oral Studied dose Dose: 8.1 mg/kg, 3 times / day Route: oral Route: multiple Dose: 8.1 mg/kg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/7446671/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/7446671/
Keratopathy	Disc. AE	8.4 mg/kg 1 times / day multiple, oral Studied dose Dose: 8.4 mg/kg, 1 times / day Route: oral Route: multiple Dose: 8.4 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6243446/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/6243446/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252 activator 150 inducer 1087	inhibitor 2438	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
MRP4 290 OCT1 620 MRP3 246 BSEP 550 MRP2 499 MATE1 415 OCT2 779 CYP2C19 2057 CYP1A2 2153 CYP19A1 429	P-gp 2052

Drug as perpetrator

Target	Modality	Activity
CYP1A2 2333	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/5475#section=BioAssay-Results Page: 36.0	inconclusive [IC50 36.2576 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/5475#section=BioAssay-Results Page: 11.0	inconclusive [IC50 8.709 uM]
MATE1 416	inhibitor 4027 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9006906/	moderate [IC50 52.9 uM]
CYP19A1 430	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/5475#section=BioAssay-Results Page: 9.0	no [IC50 5.9557 uM]
CYP2C19 2141	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/5475#section=BioAssay-Results Page: 10.0	no [IC50 7.7619 uM]
BSEP 554	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw2MDIwIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDQ3Mjk4In19	no [IC50 >133 uM]
MRP2 625	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1NzQ4IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDQ3Mjk4In19	no [IC50 >133 uM]
MRP3 326	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1OTE4IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDQ3Mjk4In19	no [IC50 >133 uM]
MRP4 345	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNzQzMTI4IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDQ3Mjk4In19	no [IC50 >133 uM]
CYP2C9 2497	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/5475#section=BioAssay-Results Page: 189.0	no
CYP3A4 2633	activator 342 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/5475#section=BioAssay-Results Page: 40.0	no
CYP3A4 2633	inducer 1966 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/5475#section=BioAssay-Results Page: 168.0	no
CYP3A4 2633	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/5475#section=BioAssay-Results Page: 41.0	no
OCT2 782	inhibitor 4027 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9006906/	yes [IC50 1.11 uM]
OCT1 656	inhibitor 4027 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9006906/	yes [IC50 8.4 uM]

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 2052	substrate 4014 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/5475#section=BioAssay-Results Page: 27 \| 169	inconclusive [Activation 23.1093 uM]

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/5475#section=BioAssay-Results Page: 82.0

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 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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:15:46 GMT 2025` Edited by `admin` on `Mon Mar 31 18:15:46 GMT 2025`
Record UNII	O6W7VEW6KS
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TILORONE

Official Name

English

TILORONE [MI]

Preferred Name

English

Tilorone [WHO-DD]

Common Name

English

tilorone [INN]

Common Name

English

Classification Tree Code System Code

EU-Orphan Drug

EU/3/18/2069