Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C6H10S2 |
| Molecular Weight | 146.274 |
| 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
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 |
|---|---|---|---|
Target ID: map04151 |
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Target ID: P16070|||Q13419|||Q13980|||Q86Z27|||Q9UCB0 Gene ID: 960.0 Gene Symbol: CD44 Target Organism: Homo sapiens (Human) |
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Target ID: P14618|||Q96E76 Gene ID: 5315.0 Gene Symbol: PKM Target Organism: Homo sapiens (Human) |
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Target ID: map04152 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| 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 |
|---|---|---|
| Hepatic metabolism of diallyl disulphide in rat and man. | 2003 Dec |
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| A comparative study of allitin and garlic on lipid turnover in a teleost, Anabas testudineus (Bloch). | 2003 Mar |
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| Photocontact allergy to diallyl disulfide. | 2003 Sep |
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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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| Conjugated docosahexaenoic acid suppresses KPL-1 human breast cancer cell growth in vitro and in vivo: potential mechanisms of action. | 2004 |
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| Inhibition by allyl sulfides and phenethyl isothiocyanate of methyl-n-pentylnitrosamine depentylation by rat esophageal microsomes, human and rat CYP2E1, and Rat CYP2A3. | 2004 |
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| Improvement of scopolamine-induced memory impairment by Z-ajoene in the water maze in mice. | 2004 Aug |
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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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| Garlic metabolites fail to inhibit the activation of the transcription factor NF-kappaB and subsequent expression of the adhesion molecule E-selectin in human endothelial cells. | 2004 Feb |
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| [Diallyl disulfide-induced G2/M arrest of human gastric cancer MGC803 cells involves activation of p38 MAP kinase pathways]. | 2004 Feb |
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| Mechanism and kinetics of synthesis of allicin. | 2004 Jan |
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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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| Enhancement of diallyl disulfide-induced apoptosis by inhibitors of MAPKs in human HepG2 hepatoma cells. | 2004 Jul 15 |
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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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| Biological activity of volatile di-n-propyl disulfide from seeds of neem, Azadirachta indica (Meliaceae), to two species of stored grain pests, Sitophilus oryzae (L.) and Tribolium castaneum (Herbst). | 2004 Jun |
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| [Preventive effect and clinical significance of garlicin injection on mechanical ventilator-associated low respiratory tract deep-seated fungal infection]. | 2004 Jun |
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| Antioxidative and antiglycative effects of six organosulfur compounds in low-density lipoprotein and plasma. | 2004 Jun 2 |
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| Synthesis of radioiodine labeled dibenzyl disulfide for evaluation of tumor cell uptake. | 2004 Mar 1 |
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| [The initiation of G2/M checkpoint by diallyl disulfide requires the activation of p38 MAP kinase in HL-60 cells]. | 2004 May |
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| The effects of allyl sulfides on the induction of phase II detoxification enzymes and liver injury by carbon tetrachloride. | 2004 May |
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| Solid-phase microextraction-gas chromatographic-mass spectrometric analysis of garlic oil obtained by hydrodistillation. | 2004 May 14 |
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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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| Garlic's ability to prevent in vitro Cu2+-induced lipoprotein oxidation in human serum is preserved in heated garlic: effect unrelated to Cu2+-chelation. | 2004 Sep 1 |
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| Diallyl disulfide-induced G2/M arrest of human gastric cancer MGC803 cells involves activation of p38 MAP kinase pathways. | 2004 Sep 15 |
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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
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
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.
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| Classification Tree | Code System | Code | ||
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EPA PESTICIDE CODE |
129087
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NCI_THESAURUS |
C68520
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CFR |
21 CFR 172.515
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JECFA EVALUATION |
ALLYL DISULFIDE
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DTXSID9035206
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C028009
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145
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29228
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16590
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4488
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C68523
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218-548-6
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1223209
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5HI47O6OA7
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2179-57-9
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595
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DIALLYL DISULFIDE
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SUBSTANCE RECORD
