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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
Structure of ALLYL DISULFIDE

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

HIDE SMILES / InChI

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P16070|||Q13419|||Q13980|||Q86Z27|||Q9UCB0
Gene ID: 960.0
Gene Symbol: CD44
Target Organism: Homo sapiens (Human)
Target ID: P14618|||Q96E76
Gene ID: 5315.0
Gene Symbol: PKM
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Preventing
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
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
Screening of organosulfur compounds as inhibitors of human CYP2A6.
2001 Jul
Growth inhibitory effects of diallyl disulfide on human breast cancer cell lines.
2001 Jun
Effects of organosulfur compounds from garlic oil on the antioxidation system in rat liver and red blood cells.
2001 Jun
Anti-tumour-promoting action of Allium constituents.
2002
Diallyl disulfide (DADS) induces the antitumorigenic NSAID-activated gene (NAG-1) by a p53-dependent mechanism in human colorectal HCT 116 cells.
2002 Apr
Nonenzymatic antioxidant activity of four organosulfur compounds derived from garlic.
2002 Oct 9
Biofactors in the Mediterranean diet.
2003 Aug
Hepatic metabolism of diallyl disulphide in rat and man.
2003 Dec
Diallyl disulfide ameliorates gentamicin-induced oxidative stress and nephropathy in rats.
2003 Jul 18
Chemoprotective effect of diallyl trisulfide from garlic against carbon tetrachloride-induced acute liver injury of rats.
2004
Anticarcinogenic properties of garlic: a review.
2004
Inhibition of cyclooxygenase-2 by diallyl sulfides (DAS) in HEK 293T cells.
2004
[The experimental study of garlicin in treating Pneumocystis carinii pneumonia in rats].
2004 Dec
Repetitive treatments of colon HT-29 cells with diallyl disulfide induce a prolonged hyperacetylation of histone H3 K14.
2004 Dec
Differential effects of allyl sulfides from garlic essential oil on cell cycle regulation in human liver tumor cells.
2004 Dec
Influence of organosulphur compounds from garlic on the secretion of matrix metalloproteinases and their inhibitor TIMP-1 by cultured HUVEC cells.
2004 Jul
Diallyl disulfide (DADS) increases histone acetylation and p21(waf1/cip1) expression in human colon tumor cell lines.
2004 Jul
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
Selective expression of glutathione S-transferase genes in the murine gastrointestinal tract in response to dietary organosulfur compounds.
2004 Mar
Synthesis of radioiodine labeled dibenzyl disulfide for evaluation of tumor cell uptake.
2004 Mar 1
Inhibition of the benzo[a]pyrene-induced toxicity by allyl sulfides in human epidermal keratinocytes.
2004 Nov
Use of gloves in protection from diallyl disulphide allergy.
2004 Nov
Diallyl disulfide, a chemopreventive agent in garlic, induces multidrug resistance-associated protein 2 expression.
2004 Nov 12
Induction of detoxifying enzymes by garlic organosulfur compounds through transcription factor Nrf2: effect of chemical structure and stress signals.
2004 Nov 15
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
Diallyl disulfide (DADS) induced apoptosis undergo caspase-3 activity in human bladder cancer T24 cells.
2004 Oct
Antioxidant effects of sulfur-containing amino acids.
2004 Oct 31
Post-initiation modulating effects of allyl sulfides in rat hepatocarcinogenesis.
2004 Sep
Diallyldisulfide-induced calcium response of HL-60 human promyelocytes.
2004 Sep-Oct
Inhibition by allyl sulfides and crushed garlic of O6-methylguanine formation in liver DNA of dimethylnitrosamine-treated rats.
2005
Differential effects of organosulfur compounds from garlic oil on nitric oxide and prostaglandin E2 in stimulated macrophages.
2005 Apr
Growth suppressing effect of garlic compound diallyl disulfide on prostate cancer cell line (PC-3) in vitro.
2005 Apr
Analytical method for appreciation of garlic therapeutic potential and for validation of a new formulation.
2005 Apr 29
Modulation of cytokine secretion by garlic oil derivatives is associated with suppressed nitric oxide production in stimulated macrophages.
2005 Apr 6
Protective effect of diallyl disulfide on oxidative stress-injured neuronally differentiated PC12 cells.
2005 Feb 18
Diallyl disulfide inhibits N-acetyltransferase activity and gene expression in human esophagus epidermoid carcinoma CE 81T/VGH cells.
2005 Jul
Differential effects of diallyl disulfide on neuronal cells depend on its concentration.
2005 Jul 1
A case-control study in Shanghai of fruit and vegetable intake and endometrial cancer.
2005 Jun 6
Garlic-fingered chefs.
2005 Mar
Allicin and allicin-derived garlic compounds increase breath acetone through allyl methyl sulfide: use in measuring allicin bioavailability.
2005 Mar 23
Allyl disulfide as donor and cyanide as acceptor of sulfane sulfur in the mouse tissues.
2005 Mar-Apr
Garlic arrests MDA-MB-435 cancer cells in mitosis, phosphorylates the proapoptotic BH3-only protein BimEL and induces apoptosis.
2005 May 9
Patents

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.
Substance Class Chemical
Created
by admin
on Sat Jun 26 05:58:18 UTC 2021
Edited
by admin
on Sat Jun 26 05:58:18 UTC 2021
Record UNII
5HI47O6OA7
Record Status Validated (UNII)
Record Version
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Name Type Language
ALLYL DISULFIDE
FHFI   USP-RS  
Systematic Name English
ALLYL DISULPHIDE
Systematic Name English
NSC-29228
Code English
ALLYL DISULFIDE [FHFI]
Common Name English
DIALLYL DISULPHIDE
Systematic Name English
2-PROPENYL DISULFIDE
Systematic Name English
FEMA NO. 2028
Code English
DIALLYL DISULFIDE [HSDB]
Common Name English
ALLYL DISULFIDE [USP-RS]
Common Name English
DIALLYL DISULFIDE
HSDB  
Systematic Name English
DIALLYLDISULFIDE
Systematic Name English
2-PROPENYL DISULPHIDE
Systematic Name English
DISULFIDE, DI-2-PROPENYL
Systematic Name English
Classification Tree Code System Code
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
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
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
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
Code System Code Type Description
EPA CompTox
2179-57-9
Created by admin on Sat Jun 26 05:58:18 UTC 2021 , Edited by admin on Sat Jun 26 05:58:18 UTC 2021
PRIMARY
MESH
C028009
Created by admin on Sat Jun 26 05:58:18 UTC 2021 , Edited by admin on Sat Jun 26 05:58:18 UTC 2021
PRIMARY
USP_CATALOG
1223209
Created by admin on Sat Jun 26 05:58:18 UTC 2021 , Edited by admin on Sat Jun 26 05:58:18 UTC 2021
PRIMARY USP-RS
PUBCHEM
16590
Created by admin on Sat Jun 26 05:58:18 UTC 2021 , Edited by admin on Sat Jun 26 05:58:18 UTC 2021
PRIMARY
NCI_THESAURUS
C68523
Created by admin on Sat Jun 26 05:58:18 UTC 2021 , Edited by admin on Sat Jun 26 05:58:18 UTC 2021
PRIMARY
ECHA (EC/EINECS)
218-548-6
Created by admin on Sat Jun 26 05:58:18 UTC 2021 , Edited by admin on Sat Jun 26 05:58:18 UTC 2021
PRIMARY
FDA UNII
5HI47O6OA7
Created by admin on Sat Jun 26 05:58:18 UTC 2021 , Edited by admin on Sat Jun 26 05:58:18 UTC 2021
PRIMARY
CAS
2179-57-9
Created by admin on Sat Jun 26 05:58:18 UTC 2021 , Edited by admin on Sat Jun 26 05:58:18 UTC 2021
PRIMARY
HSDB
595
Created by admin on Sat Jun 26 05:58:18 UTC 2021 , Edited by admin on Sat Jun 26 05:58:18 UTC 2021
PRIMARY
WIKIPEDIA
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
PRIMARY
Related Record Type Details
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METABOLIC ENZYME -> INHIBITOR