CITIOLONE

Details

Stereochemistry	RACEMIC
Molecular Formula	C6H9NO2S
Molecular Weight	159.206
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(=O)NC1CCSC1=O

InChI

InChIKey=NRFJZTXWLKPZAV-UHFFFAOYSA-N

InChI=1S/C6H9NO2S/c1-4(8)7-5-2-3-10-6(5)9/h5H,2-3H2,1H3,(H,7,8)

HIDE SMILES / InChI

Description
Sources: http://egypt-drug-index.blogspot.ru/2013/07/reducdyn-citiolonel-cysteine-for-acute.html

Citiolone (N-acetylhomocysteine thiolactone) is an antioxidant drug used in the treatment of liver diseases.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Oxidative Stress 162 Target ID: WP408 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9827694 \| https://www.ncbi.nlm.nih.gov/pubmed/1864487	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Liver diseases 15 Sources: https://www.ncbi.nlm.nih.gov/pubmed/917333 https://www.ncbi.nlm.nih.gov/pubmed/846658 https://www.ncbi.nlm.nih.gov/pubmed/5137693	Primary		Approved 8583	REDUCDYN Approved Use Reducdyn (Citiolone + L-Cysteine) is used for acute hepatitis, infections and toxic liver diseases, intoxications, side effects of irradiation, Allergic dermatoses, pruritis.

Overview

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

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP19A1 429 OATP1B1 1079 OATP1B3 961 CYP2C19 2057 CYP1A2 2153 P-gp 1741	P-gp 2052

Drug as perpetrator

Target	Modality	Activity
P-gp 1932	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/14520#section=Biological-Test-Results Page: 5.0	inconclusive
CYP19A1 430	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/14520#section=Biological-Test-Results Page: 42.0	no
CYP1A2 2333	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/14520#section=Biological-Test-Results Page: 104.0	no
CYP2C19 2141	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/14520#section=Biological-Test-Results Page: 104.0	no
CYP2C9 2497	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/14520#section=Biological-Test-Results Page: 95.0	no
CYP2D6 2546	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/14520#section=Biological-Test-Results Page: 95.0	no
CYP3A4 2633	inducer 1966 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/14520#section=Biological-Test-Results Page: 92.0	no
CYP3A4 2633	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/14520#section=Biological-Test-Results Page: 94.0	no
OATP1B1 1095	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNjk3NjY4IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDIxMDQ0NTcifX0=	yes [Inhibition 10 uM]
OATP1B3 970	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNzQzMTIxIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDIxMDQ0NTcifX0=	yes [Inhibition 10 uM]

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 2052	substrate 4014 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/14520#section=Biological-Test-Results Page: 70 \| 72	no

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/14520#section=Biological-Test-Results Page: 105.0

PubMed

Title	Date	PubMed
Organelle specific enzyme markers as indicators of methylmercury neurotoxicity and antidotal efficacy in mice.	2003-06	12572686
Macrophages and antioxidant status in the NOD mouse pancreas.	1998-12-15	9827694
Acetyl-homocysteine thiolactone protects against some neurotoxic effects of thallium.	1989	2616067
Methylmercury chloride-induced and antagonist-reverted succinic dehydrogenase changes in the brain and trigeminal ganglia of the rat.	1987-06	3034565

Patents

Sample Use Guides

In Vivo Use Guide

Reducdyn (Citiolone 50mg/tab. + L-Cysteine 50mg/tab): 3 tablets 3 times daily, to be swallowed whole with some liquid during or immediately after meals.

Route of Administration: Oral

In Vitro Use Guide

Human skin fibroblasts were irradiated following incubation with N-acetyl-homocysteine-thiolactone (citiolone (CIT), 1 mM). Treatments with CIT resulted in a significant rise in glutathione levels compared with control cells, with protection against UVA radiation.

Name

Type

Language

CITIOLONE

Official Name

English

NSC-22878

Preferred Name

English

CITIOLONE [MI]

Common Name

English

CITIOLONE [MART.]

Common Name

English

Citiolone [WHO-DD]

Common Name

English

citiolone [INN]

Common Name

English

N-(TETRAHYDRO-2-OXO-3-THIENYL)ACETAMIDE

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29767