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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

CNS Non-penetrant
1040
Curator's Comment: Known to be CNS NON-penetrant in mouse. Human data not available.

Approval Year

Unknown
149124
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Basic research
Unknown

Approved Use

Unknown
Primary
Basic research
Unknown

Approved Use

Unknown
Preventing
Phase III
665
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
0.96 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/17586125/
75 mg single, oral
dose: 75 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ANETHOLTRITHION plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
0.98 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/17586125/
75 mg single, oral
dose: 75 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ANETHOLTRITHION plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
279.6 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/20980118/
75 mg single, oral
dose: 75 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ANETHOLTRITHION plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
1035.2 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/20980118/
75 mg single, oral
dose: 75 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ANETHOLTRITHION plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
4.03 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/17586125/
75 mg single, oral
dose: 75 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ANETHOLTRITHION plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
3.78 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/17586125/
75 mg single, oral
dose: 75 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ANETHOLTRITHION plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
4.5 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/20980118/
75 mg single, oral
dose: 75 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ANETHOLTRITHION plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
25 mg 3 times / day multiple, oral
Recommended
Dose: 25 mg, 3 times / day
Route: oral
Route: multiple
Dose: 25 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/9272401/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/9272401/
Sources:
https://pubmed.ncbi.nlm.nih.gov/9272401/
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
inhibitor
2252

inducer
1087

substrate
1946
inhibitor
2438

substrate
1193
inhibitor
2507

substrate
1388
inhibitor
2217

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP2C19
2057

CYP1A2
2153

CYP19A1
429
P-gp
2052

CYP1A2
1197

CYP1A1
389

CYP1B1
104

CYP2A6
626

CYP2C19
1119

FMO3
77

CYP2E1
729

FMO1
25
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP2D6
2546
 inconclusive [IC50 10.964 uM]
CYP3A4
2633
 inconclusive [IC50 10.964 uM]
CYP19A1
430
 inconclusive [IC50 5.308 uM]
CYP3A4
2633
 no
CYP1A2
2333
 yes [IC50 0.9107 uM]
CYP2C9
2497
 yes [IC50 10.964 uM]
CYP2C19
2141
 yes [IC50 9.7717 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
P-gp
2052
 inconclusive
CYP2A6
626
 likely
FMO3
77
 likely
CYP1A1
389
 major
CYP1A2
1197
 major
CYP1B1
104
 major
CYP2C19
1119
 major
CYP2C9
1193
 yes
CYP2D6
1388
 yes
CYP2E1
729
 yes
CYP3A4
1946
 yes
FMO1
25
 yes
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
2263
PubMed

PubMed

TitleDatePubMed
Design, synthesis, and pharmacological evaluation of the aqueous prodrugs of desmethyl anethole trithione with hepatoprotective activity.
2010-07
Modulation of thiol homeostasis induced by H2S-releasing aspirin.
2010-05-01
Dithiolethione modified valproate and diclofenac increase E-cadherin expression and decrease proliferation of non-small cell lung cancer cells.
2010-05
Quantitative morphometry of respiratory tract epithelial cells as a tool for testing chemopreventive agent efficacy.
2010-03
Lipid-based formulations to enhance oral bioavailability of the poorly water-soluble drug anethol trithione: effects of lipid composition and formulation.
2009-09-08
[The clinical therapic efficiency of anethol trithione on dry eye].
2009-06
Cancer is a preventable disease that requires major lifestyle changes.
2008-09
HPLC determination of 4-hydroxy-anethole trithione in plasma via enzymatic hydrolysis and its application to bioequivalence study.
2008-07-15
New sulfurated derivatives of valproic acid with enhanced histone deacetylase inhibitory activity.
2008-03-15
Determination of anethole trithione in human plasma using high performance liquid chromatography coupled with tandem mass spectrometric detection.
2007-07-02
Tissue specific increase of the catalytic subunits of the 26S proteasome by indirect antioxidant dithiolethione in mice: enhanced activity for degradation of abnormal protein.
2007-06-06
Modulation of angiogenesis by dithiolethione-modified NSAIDs and valproic acid.
2007-05
HPLC determination of anethole trithione and its application to pharmacokinetics in rabbits.
2006-11-16
The antioxidant anethole dithiolethione inhibits monoamine oxidase-B but not monoamine oxidase A activity in extracts of cultured astrocytes.
2006-05
[A case of pneumatosis cystoides intestinalis developed in a patient with Sjogren syndrome during administration of anetholetrithion].
2005-07
[Anethole dithiolethione: an antioxidant agent against tenotoxicity induced by fluoroquinolones].
2004-07
Seizures in the developing brain.
2004
[Radiation protectants of the crystalline lens].
2003-11
A randomized phase IIb trial of anethole dithiolethione in smokers with bronchial dysplasia.
2002-07-03
The neuroprotective antioxidant alpha-lipoic acid induces detoxication enzymes in cultured astroglial cells.
2002-06
Usefulness of basal and pilocarpine-stimulated salivary flow in primary Sjögren's syndrome. Correlation with clinical, immunological and histological features.
2002-06
Enhancement of salivary secretion and neuropeptide (substance P, alpha-calcitonin gene-related peptide) levels in saliva by chronic anethole trithione treatment.
2001-12
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.
2001-08
Lens epithelial cell protection by aminothiol WR-1065 and anetholedithiolethione from ionizing radiation.
2001
Anethole dithiolethione regulates oxidant-induced tyrosine kinase activation in endothelial cells.
2000
Treatment of xerostomia with the bile secretion-stimulating drug anethole trithione: a clinical trial.
1999-09
Protective effects of anethole dithiolethione against oxidative stress-induced cytotoxicity in human Jurkat T cells.
1998-07-01
Chemopreventive efficacy of anethole trithione, N-acetyl-L-cysteine, miconazole and phenethylisothiocyanate in the DMBA-induced rat mammary cancer model.
1997-07-03
Assessment of the role of glutathione conjugation in the protection afforded by anethol dithiolthione against hexachloro-1,3-butadiene-induced nephrotoxicity.
1996-07
Inhibition of NF-kappa B activation in human T-cell lines by anetholdithiolthione.
1996-01-05
Chemoprevention of colon carcinogenesis by organosulfur compounds.
1993-08-01
Effects of chronic anethole trithione and amitriptyline treatment on rat parotid gland signalling.
1992-05-12
Pharmacological studies on anethole trithione.
1988-10
Synergistic effect of sialagogues in management of xerostomia after radiation therapy.
1987-08
Systemic therapy of salivary gland hypofunction.
1987-02
[Protective effect of malotilate (diisopropyl 1,3-dithiol-2-ylidenemalonate) on chemical-induced hepatotoxicity].
1986-08
A new potent inhibitor of lipid peroxidation in vitro and in vivo, the hepatoprotective drug anisyldithiolthione.
1986-03-28
Effects of anethole dithiolthione and 2(3)-tert-butyl-4-hydroxyanisole on schistosome granuloma formation.
1985-11
Chemoprotective effects of two dithiolthiones and of butylhydroxyanisole against carbon tetrachloride and acetaminophen toxicity.
1983-11-01
Effect of Sialor in treatment of xerostomia in Sjögren's syndrome.
1983-11
Patents

Patents

JPS05883037A
1

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 Mon Mar 31 17:45:17 GMT 2025
Edited
by admin
on Mon Mar 31 17:45:17 GMT 2025
Record UNII
QUY32964DJ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ANETHOLTRITHION
JAN  
Common Name English
ANETHOLE TRITHIONE
MART.   MI   WHO-DD  
Preferred 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
Classification Tree Code System Code
NCI_THESAURUS C54630
Created by admin on Mon Mar 31 17:45:17 GMT 2025 , Edited by admin on Mon Mar 31 17:45:17 GMT 2025
WHO-ATC A16AX02
Created by admin on Mon Mar 31 17:45:17 GMT 2025 , Edited by admin on Mon Mar 31 17:45:17 GMT 2025
WHO-VATC QA16AX02
Created by admin on Mon Mar 31 17:45:17 GMT 2025 , Edited by admin on Mon Mar 31 17:45:17 GMT 2025
Code System Code Type Description
PUBCHEM
2194
Created by admin on Mon Mar 31 17:45:17 GMT 2025 , Edited by admin on Mon Mar 31 17:45:17 GMT 2025
PRIMARY
MERCK INDEX
m1907
Created by admin on Mon Mar 31 17:45:17 GMT 2025 , Edited by admin on Mon Mar 31 17:45:17 GMT 2025
PRIMARY Merck Index
ChEMBL
CHEMBL178862
Created by admin on Mon Mar 31 17:45:17 GMT 2025 , Edited by admin on Mon Mar 31 17:45:17 GMT 2025
PRIMARY
SMS_ID
100000077420
Created by admin on Mon Mar 31 17:45:17 GMT 2025 , Edited by admin on Mon Mar 31 17:45:17 GMT 2025
PRIMARY
ECHA (EC/EINECS)
208-528-5
Created by admin on Mon Mar 31 17:45:17 GMT 2025 , Edited by admin on Mon Mar 31 17:45:17 GMT 2025
PRIMARY
WIKIPEDIA
Anethole trithione
Created by admin on Mon Mar 31 17:45:17 GMT 2025 , Edited by admin on Mon Mar 31 17:45:17 GMT 2025
PRIMARY
FDA UNII
QUY32964DJ
Created by admin on Mon Mar 31 17:45:17 GMT 2025 , Edited by admin on Mon Mar 31 17:45:17 GMT 2025
PRIMARY
EPA CompTox
DTXSID9046651
Created by admin on Mon Mar 31 17:45:17 GMT 2025 , Edited by admin on Mon Mar 31 17:45:17 GMT 2025
PRIMARY
CAS
532-11-6
Created by admin on Mon Mar 31 17:45:17 GMT 2025 , Edited by admin on Mon Mar 31 17:45:17 GMT 2025
PRIMARY
DRUG BANK
DB13853
Created by admin on Mon Mar 31 17:45:17 GMT 2025 , Edited by admin on Mon Mar 31 17:45:17 GMT 2025
PRIMARY
MESH
D000781
Created by admin on Mon Mar 31 17:45:17 GMT 2025 , Edited by admin on Mon Mar 31 17:45:17 GMT 2025
PRIMARY
RXCUI
820
Created by admin on Mon Mar 31 17:45:17 GMT 2025 , Edited by admin on Mon Mar 31 17:45:17 GMT 2025
PRIMARY RxNorm
NCI_THESAURUS
C246
Created by admin on Mon Mar 31 17:45:17 GMT 2025 , Edited by admin on Mon Mar 31 17:45:17 GMT 2025
PRIMARY
EVMPD
SUB12902MIG
Created by admin on Mon Mar 31 17:45:17 GMT 2025 , Edited by admin on Mon Mar 31 17:45:17 GMT 2025
PRIMARY
DRUG CENTRAL
218
Created by admin on Mon Mar 31 17:45:17 GMT 2025 , Edited by admin on Mon Mar 31 17:45:17 GMT 2025
PRIMARY
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MAJOR
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ACTIVE MOIETY
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