U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C10H8OS3
Molecular Weight 240.365
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ANETHOLTRITHION

SMILES

COC1=CC=C(C=C1)C2=CC(=S)SS2

InChI

InChIKey=KYLIZBIRMBGUOP-UHFFFAOYSA-N
InChI=1S/C10H8OS3/c1-11-8-4-2-7(3-5-8)9-6-10(12)14-13-9/h2-6H,1H3

HIDE SMILES / InChI

Molecular Formula C10H8OS3
Molecular Weight 240.365
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/19957670

Anethole trithione or anetholtrithione is a drug used in the treatment of dry mouth. Anethole trithione is a bile secretion-stimulating drug that restores salivation. It is listed in the U.S. National Cancer Institute's Dictionary of Cancer Terms as being studied in the treatment of cancer. Anethol has also been identified as a treatment for improving medium and severe dry eye symptoms. The mechanism of action for the chemopreventive and xerostomia properties have not been fully elucidated.

CNS Activity

Curator's Comment: Known to be CNS NON-penetrant in mouse. Human data not available.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Preventing
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Effect of Sialor in treatment of xerostomia in Sjögren's syndrome.
1983 Nov
Chemoprotective effects of two dithiolthiones and of butylhydroxyanisole against carbon tetrachloride and acetaminophen toxicity.
1983 Nov-Dec
A new potent inhibitor of lipid peroxidation in vitro and in vivo, the hepatoprotective drug anisyldithiolthione.
1986 Mar 28
Synergistic effect of sialagogues in management of xerostomia after radiation therapy.
1987 Aug
Systemic therapy of salivary gland hypofunction.
1987 Feb
Effects of chronic anethole trithione and amitriptyline treatment on rat parotid gland signalling.
1992 May 12
Treatment of xerostomia with the bile secretion-stimulating drug anethole trithione: a clinical trial.
1999 Sep
Anethole dithiolethione regulates oxidant-induced tyrosine kinase activation in endothelial cells.
2000 Winter
Lens epithelial cell protection by aminothiol WR-1065 and anetholedithiolethione from ionizing radiation.
2001
Kinetic constraints for the thiolysis of 4-methyl-5-(pyrazin-2-yl)-1,2-dithiole-3-thione (oltipraz) and related dithiole-3-thiones in aqueous solution.
2001 Aug
Enhancement of salivary secretion and neuropeptide (substance P, alpha-calcitonin gene-related peptide) levels in saliva by chronic anethole trithione treatment.
2001 Dec
A randomized phase IIb trial of anethole dithiolethione in smokers with bronchial dysplasia.
2002 Jul 3
The neuroprotective antioxidant alpha-lipoic acid induces detoxication enzymes in cultured astroglial cells.
2002 Jun
Usefulness of basal and pilocarpine-stimulated salivary flow in primary Sjögren's syndrome. Correlation with clinical, immunological and histological features.
2002 Jun
[Radiation protectants of the crystalline lens].
2003 Nov
Seizures in the developing brain.
2004
[Anethole dithiolethione: an antioxidant agent against tenotoxicity induced by fluoroquinolones].
2004 Jul
[A case of pneumatosis cystoides intestinalis developed in a patient with Sjogren syndrome during administration of anetholetrithion].
2005 Jul
The antioxidant anethole dithiolethione inhibits monoamine oxidase-B but not monoamine oxidase A activity in extracts of cultured astrocytes.
2006 May
HPLC determination of anethole trithione and its application to pharmacokinetics in rabbits.
2006 Nov 16
Determination of anethole trithione in human plasma using high performance liquid chromatography coupled with tandem mass spectrometric detection.
2007 Jul 2
Tissue specific increase of the catalytic subunits of the 26S proteasome by indirect antioxidant dithiolethione in mice: enhanced activity for degradation of abnormal protein.
2007 Jun 6
Modulation of angiogenesis by dithiolethione-modified NSAIDs and valproic acid.
2007 May
HPLC determination of 4-hydroxy-anethole trithione in plasma via enzymatic hydrolysis and its application to bioequivalence study.
2008 Jul 15
New sulfurated derivatives of valproic acid with enhanced histone deacetylase inhibitory activity.
2008 Mar 15
Cancer is a preventable disease that requires major lifestyle changes.
2008 Sep
[The clinical therapic efficiency of anethol trithione on dry eye].
2009 Jun
Lipid-based formulations to enhance oral bioavailability of the poorly water-soluble drug anethol trithione: effects of lipid composition and formulation.
2009 Sep 8
Dithiolethione modified valproate and diclofenac increase E-cadherin expression and decrease proliferation of non-small cell lung cancer cells.
2010 May
Patents

Patents

Sample Use Guides

was administered 6 tablets per day
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:04:10 GMT 2023
Edited
by admin
on Fri Dec 15 15:04:10 GMT 2023
Record UNII
QUY32964DJ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ANETHOLTRITHION
JAN  
Common Name English
OP2113
Code English
Anethole trithione [WHO-DD]
Common Name English
ANETHOLE TRITHIONE [MART.]
Common Name English
OP-2113
Code English
ANETHOLE TRITHIONE [MI]
Common Name English
5-(P-METHOXYPHENYL)-3H-1,2-DITHIOLE-3-THIONE
Common Name English
ANETHOLTRITHION [JAN]
Common Name English
ANETHOLE TRITHIONE
MART.   MI   WHO-DD  
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C54630
Created by admin on Fri Dec 15 15:04:10 GMT 2023 , Edited by admin on Fri Dec 15 15:04:10 GMT 2023
WHO-ATC A16AX02
Created by admin on Fri Dec 15 15:04:10 GMT 2023 , Edited by admin on Fri Dec 15 15:04:10 GMT 2023
WHO-VATC QA16AX02
Created by admin on Fri Dec 15 15:04:10 GMT 2023 , Edited by admin on Fri Dec 15 15:04:10 GMT 2023
Code System Code Type Description
PUBCHEM
2194
Created by admin on Fri Dec 15 15:04:10 GMT 2023 , Edited by admin on Fri Dec 15 15:04:10 GMT 2023
PRIMARY
MERCK INDEX
m1907
Created by admin on Fri Dec 15 15:04:10 GMT 2023 , Edited by admin on Fri Dec 15 15:04:10 GMT 2023
PRIMARY Merck Index
ChEMBL
CHEMBL178862
Created by admin on Fri Dec 15 15:04:10 GMT 2023 , Edited by admin on Fri Dec 15 15:04:10 GMT 2023
PRIMARY
SMS_ID
100000077420
Created by admin on Fri Dec 15 15:04:10 GMT 2023 , Edited by admin on Fri Dec 15 15:04:10 GMT 2023
PRIMARY
ECHA (EC/EINECS)
208-528-5
Created by admin on Fri Dec 15 15:04:10 GMT 2023 , Edited by admin on Fri Dec 15 15:04:10 GMT 2023
PRIMARY
WIKIPEDIA
Anethole trithione
Created by admin on Fri Dec 15 15:04:10 GMT 2023 , Edited by admin on Fri Dec 15 15:04:10 GMT 2023
PRIMARY
FDA UNII
QUY32964DJ
Created by admin on Fri Dec 15 15:04:10 GMT 2023 , Edited by admin on Fri Dec 15 15:04:10 GMT 2023
PRIMARY
EPA CompTox
DTXSID9046651
Created by admin on Fri Dec 15 15:04:10 GMT 2023 , Edited by admin on Fri Dec 15 15:04:10 GMT 2023
PRIMARY
CAS
532-11-6
Created by admin on Fri Dec 15 15:04:10 GMT 2023 , Edited by admin on Fri Dec 15 15:04:10 GMT 2023
PRIMARY
DRUG BANK
DB13853
Created by admin on Fri Dec 15 15:04:10 GMT 2023 , Edited by admin on Fri Dec 15 15:04:10 GMT 2023
PRIMARY
MESH
D000781
Created by admin on Fri Dec 15 15:04:10 GMT 2023 , Edited by admin on Fri Dec 15 15:04:10 GMT 2023
PRIMARY
RXCUI
820
Created by admin on Fri Dec 15 15:04:10 GMT 2023 , Edited by admin on Fri Dec 15 15:04:10 GMT 2023
PRIMARY RxNorm
NCI_THESAURUS
C246
Created by admin on Fri Dec 15 15:04:10 GMT 2023 , Edited by admin on Fri Dec 15 15:04:10 GMT 2023
PRIMARY
EVMPD
SUB12902MIG
Created by admin on Fri Dec 15 15:04:10 GMT 2023 , Edited by admin on Fri Dec 15 15:04:10 GMT 2023
PRIMARY
DRUG CENTRAL
218
Created by admin on Fri Dec 15 15:04:10 GMT 2023 , Edited by admin on Fri Dec 15 15:04:10 GMT 2023
PRIMARY
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