ANETHOLTRITHION

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 Search

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
Sources: http://www.ncbi.nlm.nih.gov/pubmed/1327842
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

Approval Year

Conditions

Condition	Modality	Highest Phase	Product
Dry eye syndrome 21 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19957670	Primary	Basic research	Unknown Approved Use Unknown
Drug-induced xerostomia 1 Sources: http://www.ncbi.nlm.nih.gov/pubmed/1327842	Primary	Basic research	Unknown Approved Use Unknown
Lung cancer 67 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12096085	Preventing	Phase III 651	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Effect of Sialor in treatment of xerostomia in Sjögren's syndrome.	1983 Nov	6358997
Chemoprotective effects of two dithiolthiones and of butylhydroxyanisole against carbon tetrachloride and acetaminophen toxicity.	1983 Nov-Dec	6629324
Effects of anethole dithiolthione and 2(3)-tert-butyl-4-hydroxyanisole on schistosome granuloma formation.	1985 Nov	3005948
[Protective effect of malotilate (diisopropyl 1,3-dithiol-2-ylidenemalonate) on chemical-induced hepatotoxicity].	1986 Aug	3795300
A new potent inhibitor of lipid peroxidation in vitro and in vivo, the hepatoprotective drug anisyldithiolthione.	1986 Mar 28	3964266
Synergistic effect of sialagogues in management of xerostomia after radiation therapy.	1987 Aug	3306552
Systemic therapy of salivary gland hypofunction.	1987 Feb	3476633
Pharmacological studies on anethole trithione.	1988 Oct	3196385
Effects of chronic anethole trithione and amitriptyline treatment on rat parotid gland signalling.	1992 May 12	1327842
Chemoprevention of colon carcinogenesis by organosulfur compounds.	1993 Aug 1	8339252
Inhibition of NF-kappa B activation in human T-cell lines by anetholdithiolthione.	1996 Jan 5	8573121
Assessment of the role of glutathione conjugation in the protection afforded by anethol dithiolthione against hexachloro-1,3-butadiene-induced nephrotoxicity.	1996 Jul	8685901
Chemopreventive efficacy of anethole trithione, N-acetyl-L-cysteine, miconazole and phenethylisothiocyanate in the DMBA-induced rat mammary cancer model.	1997 Jul 3	9212229
Protective effects of anethole dithiolethione against oxidative stress-induced cytotoxicity in human Jurkat T cells.	1998 Jul 1	9698089
Treatment of xerostomia with the bile secretion-stimulating drug anethole trithione: a clinical trial.	1999 Sep	10487404
Anethole dithiolethione regulates oxidant-induced tyrosine kinase activation in endothelial cells.	2000 Winter	11213483
Lens epithelial cell protection by aminothiol WR-1065 and anetholedithiolethione from ionizing radiation.	2001	11992383
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	11511166
Enhancement of salivary secretion and neuropeptide (substance P, alpha-calcitonin gene-related peptide) levels in saliva by chronic anethole trithione treatment.	2001 Dec	11804400
A randomized phase IIb trial of anethole dithiolethione in smokers with bronchial dysplasia.	2002 Jul 3	12096085
The neuroprotective antioxidant alpha-lipoic acid induces detoxication enzymes in cultured astroglial cells.	2002 Jun	12180195
Usefulness of basal and pilocarpine-stimulated salivary flow in primary Sjögren's syndrome. Correlation with clinical, immunological and histological features.	2002 Jun	12048294
[Radiation protectants of the crystalline lens].	2003 Nov	15124544
Seizures in the developing brain.	2004	15610187
[Anethole dithiolethione: an antioxidant agent against tenotoxicity induced by fluoroquinolones].	2004 Jul	15261372
[A case of pneumatosis cystoides intestinalis developed in a patient with Sjogren syndrome during administration of anetholetrithion].	2005 Jul	16038437
The antioxidant anethole dithiolethione inhibits monoamine oxidase-B but not monoamine oxidase A activity in extracts of cultured astrocytes.	2006 May	16252076
HPLC determination of anethole trithione and its application to pharmacokinetics in rabbits.	2006 Nov 16	16824723
Determination of anethole trithione in human plasma using high performance liquid chromatography coupled with tandem mass spectrometric detection.	2007 Jul 2	17586125
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	17521679
Modulation of angiogenesis by dithiolethione-modified NSAIDs and valproic acid.	2007 May	17351657
HPLC determination of 4-hydroxy-anethole trithione in plasma via enzymatic hydrolysis and its application to bioequivalence study.	2008 Jul 15	18353592
New sulfurated derivatives of valproic acid with enhanced histone deacetylase inhibitory activity.	2008 Mar 15	18294844
Cancer is a preventable disease that requires major lifestyle changes.	2008 Sep	18626751
[The clinical therapic efficiency of anethol trithione on dry eye].	2009 Jun	19957670
Lipid-based formulations to enhance oral bioavailability of the poorly water-soluble drug anethol trithione: effects of lipid composition and formulation.	2009 Sep 8	19508887
Design, synthesis, and pharmacological evaluation of the aqueous prodrugs of desmethyl anethole trithione with hepatoprotective activity.	2010 Jul	20392547
Quantitative morphometry of respiratory tract epithelial cells as a tool for testing chemopreventive agent efficacy.	2010 Mar	20392991
Dithiolethione modified valproate and diclofenac increase E-cadherin expression and decrease proliferation of non-small cell lung cancer cells.	2010 May	19628293
Modulation of thiol homeostasis induced by H2S-releasing aspirin.	2010 May 1	20171274

Patents

Sample Use Guides

In Vivo Use Guide

was administered 6 tablets per day

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Fri Dec 16 16:04:25 UTC 2022` Edited by `admin` on `Fri Dec 16 16:04:25 UTC 2022`
Record UNII	QUY32964DJ
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

ANETHOLTRITHION

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

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C54630