Details
Stereochemistry | ACHIRAL |
Molecular Formula | C6H10S2 |
Molecular Weight | 146.276 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
C=CCSSCC=C
InChI
InChIKey=PFRGXCVKLLPLIP-UHFFFAOYSA-N
InChI=1S/C6H10S2/c1-3-5-7-8-6-4-2/h3-4H,1-2,5-6H2
Molecular Formula | C6H10S2 |
Molecular Weight | 146.276 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Diallyl disulfide (DADS) or allyl disulfide is the main organosulfur ingredient in garlic, with known antioxidant and anti-inflammatory activities. It has been shown to have multi-targeted antitumor activities in a variety of cancer cells Experiments in vitro have revealed, that diallyl disulfide inhibits the metastasis of type Ⅱ esophageal-gastric junction adenocarcinoma cells via NF-κB and PI3K/AKT signaling pathways. At the same time, was shown the drug suppresses cell stemness, proliferation, metastasis and glucose metabolism in breast cancer stem cells partly through the inhibition of CD44/PKM2/AMPK. Besides diallyl disulfide can be a promising agent for the treatment of emphysema, this was discovered in experiments on rats. And also drug shows protective effects against acetaminophen (AAP)-induced acute hepatotoxicity.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: map04151 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29207122 |
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Target ID: P16070|||Q13419|||Q13980|||Q86Z27|||Q9UCB0 Gene ID: 960.0 Gene Symbol: CD44 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/29110616 |
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Target ID: P14618|||Q96E76 Gene ID: 5315.0 Gene Symbol: PKM Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/29110616 |
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Target ID: map04152 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29110616 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Preventing | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Effects of the garlic compound diallyl disulfide on the metabolism, adherence and cell cycle of HT-29 colon carcinoma cells: evidence of sensitive and resistant sub-populations. | 2001 Aug |
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Screening of organosulfur compounds as inhibitors of human CYP2A6. | 2001 Jul |
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Growth inhibitory effects of diallyl disulfide on human breast cancer cell lines. | 2001 Jun |
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Effects of organosulfur compounds from garlic oil on the antioxidation system in rat liver and red blood cells. | 2001 Jun |
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Anti-tumour-promoting action of Allium constituents. | 2002 |
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Diallyl disulfide (DADS) induces the antitumorigenic NSAID-activated gene (NAG-1) by a p53-dependent mechanism in human colorectal HCT 116 cells. | 2002 Apr |
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Nonenzymatic antioxidant activity of four organosulfur compounds derived from garlic. | 2002 Oct 9 |
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Biofactors in the Mediterranean diet. | 2003 Aug |
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Hepatic metabolism of diallyl disulphide in rat and man. | 2003 Dec |
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Diallyl disulfide ameliorates gentamicin-induced oxidative stress and nephropathy in rats. | 2003 Jul 18 |
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Chemoprotective effect of diallyl trisulfide from garlic against carbon tetrachloride-induced acute liver injury of rats. | 2004 |
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Anticarcinogenic properties of garlic: a review. | 2004 |
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Inhibition of cyclooxygenase-2 by diallyl sulfides (DAS) in HEK 293T cells. | 2004 |
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[The experimental study of garlicin in treating Pneumocystis carinii pneumonia in rats]. | 2004 Dec |
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Repetitive treatments of colon HT-29 cells with diallyl disulfide induce a prolonged hyperacetylation of histone H3 K14. | 2004 Dec |
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Differential effects of allyl sulfides from garlic essential oil on cell cycle regulation in human liver tumor cells. | 2004 Dec |
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Influence of organosulphur compounds from garlic on the secretion of matrix metalloproteinases and their inhibitor TIMP-1 by cultured HUVEC cells. | 2004 Jul |
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Diallyl disulfide (DADS) increases histone acetylation and p21(waf1/cip1) expression in human colon tumor cell lines. | 2004 Jul |
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Diallyl trisulfide-induced apoptosis in human prostate cancer cells involves c-Jun N-terminal kinase and extracellular-signal regulated kinase-mediated phosphorylation of Bcl-2. | 2004 Jul 22 |
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Selective expression of glutathione S-transferase genes in the murine gastrointestinal tract in response to dietary organosulfur compounds. | 2004 Mar |
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Synthesis of radioiodine labeled dibenzyl disulfide for evaluation of tumor cell uptake. | 2004 Mar 1 |
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Inhibition of the benzo[a]pyrene-induced toxicity by allyl sulfides in human epidermal keratinocytes. | 2004 Nov |
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Use of gloves in protection from diallyl disulphide allergy. | 2004 Nov |
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Diallyl disulfide, a chemopreventive agent in garlic, induces multidrug resistance-associated protein 2 expression. | 2004 Nov 12 |
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Induction of detoxifying enzymes by garlic organosulfur compounds through transcription factor Nrf2: effect of chemical structure and stress signals. | 2004 Nov 15 |
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Signal transduction pathways leading to cell cycle arrest and apoptosis induction in cancer cells by Allium vegetable-derived organosulfur compounds: a review. | 2004 Nov 2 |
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Diallyl disulfide (DADS) induced apoptosis undergo caspase-3 activity in human bladder cancer T24 cells. | 2004 Oct |
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Antioxidant effects of sulfur-containing amino acids. | 2004 Oct 31 |
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Post-initiation modulating effects of allyl sulfides in rat hepatocarcinogenesis. | 2004 Sep |
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Diallyldisulfide-induced calcium response of HL-60 human promyelocytes. | 2004 Sep-Oct |
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Inhibition by allyl sulfides and crushed garlic of O6-methylguanine formation in liver DNA of dimethylnitrosamine-treated rats. | 2005 |
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Differential effects of organosulfur compounds from garlic oil on nitric oxide and prostaglandin E2 in stimulated macrophages. | 2005 Apr |
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Growth suppressing effect of garlic compound diallyl disulfide on prostate cancer cell line (PC-3) in vitro. | 2005 Apr |
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Analytical method for appreciation of garlic therapeutic potential and for validation of a new formulation. | 2005 Apr 29 |
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Modulation of cytokine secretion by garlic oil derivatives is associated with suppressed nitric oxide production in stimulated macrophages. | 2005 Apr 6 |
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Protective effect of diallyl disulfide on oxidative stress-injured neuronally differentiated PC12 cells. | 2005 Feb 18 |
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Diallyl disulfide inhibits N-acetyltransferase activity and gene expression in human esophagus epidermoid carcinoma CE 81T/VGH cells. | 2005 Jul |
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Differential effects of diallyl disulfide on neuronal cells depend on its concentration. | 2005 Jul 1 |
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A case-control study in Shanghai of fruit and vegetable intake and endometrial cancer. | 2005 Jun 6 |
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Garlic-fingered chefs. | 2005 Mar |
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Allicin and allicin-derived garlic compounds increase breath acetone through allyl methyl sulfide: use in measuring allicin bioavailability. | 2005 Mar 23 |
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Allyl disulfide as donor and cyanide as acceptor of sulfane sulfur in the mouse tissues. | 2005 Mar-Apr |
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Garlic arrests MDA-MB-435 cancer cells in mitosis, phosphorylates the proapoptotic BH3-only protein BimEL and induces apoptosis. | 2005 May 9 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/29329251
Rat emphysema model: the rat emphysema model was established by intraperitoneal injection of cigarette smoke extract (CSE). Each rat in the CSE group was intraperitoneally injected with 1mL CSE-PBS solution on days 1, 8, and 15. Rats in the diallyl disulfide (DADS) and budesonide groups were intraperitoneally injected with 1 mL of CSE on Days 1, 8, and 15 along with the daily injection of DADS or budesonide. The doss of test groups were as follows: 100 and 10 mg/kg/day for DADS and budesonide, respectively.
Route of Administration:
Intraperitoneal
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/29207122
Diallyl disulfide (DADS) inhibited cell viability of OE19 cells with low cytotoxicity to healthy hepatocytes, L02 cells, in vitro. Non-toxic doses of DADS were ≤10 µg/ml for a 24-h treatment. These non-toxic doses of DADS were found to block the metastasis of OE19 cells by suppressing MMPs, increasing u-PA and TIMPs, as well as altering the balance of MMPs/TIMPs, which at least in part resulted from the suppression of NF-κB and PI3K/AKT signaling pathways.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Jun 26 05:58:18 UTC 2021
by
admin
on
Sat Jun 26 05:58:18 UTC 2021
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Record UNII |
5HI47O6OA7
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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EPA PESTICIDE CODE |
129087
Created by
admin on Sat Jun 26 05:58:18 UTC 2021 , Edited by admin on Sat Jun 26 05:58:18 UTC 2021
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NCI_THESAURUS |
C68520
Created by
admin on Sat Jun 26 05:58:18 UTC 2021 , Edited by admin on Sat Jun 26 05:58:18 UTC 2021
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CFR |
21 CFR 172.515
Created by
admin on Sat Jun 26 05:58:18 UTC 2021 , Edited by admin on Sat Jun 26 05:58:18 UTC 2021
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JECFA EVALUATION |
ALLYL DISULFIDE
Created by
admin on Sat Jun 26 05:58:18 UTC 2021 , Edited by admin on Sat Jun 26 05:58:18 UTC 2021
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Code System | Code | Type | Description | ||
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2179-57-9
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C028009
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1223209
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16590
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C68523
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218-548-6
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5HI47O6OA7
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2179-57-9
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595
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DIALLYL DISULFIDE
Created by
admin on Sat Jun 26 05:58:18 UTC 2021 , Edited by admin on Sat Jun 26 05:58:18 UTC 2021
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Related Record | Type | Details | ||
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PARENT -> POSSIBLE ACTIVE CONSTITUENT ALWAYS PRESENT | |||
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METABOLIC ENZYME -> INHIBITOR |