ALLYL DISULFIDE

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

Structure Search

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	146.274
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/29207122 | https://www.ncbi.nlm.nih.gov/pubmed/29329251 | https://www.ncbi.nlm.nih.gov/pubmed/28847761

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
PI3K-Akt signaling pathway 24 Target ID: map04151 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29207122	Inhibitor 8297
CD44 antigen 1 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	Inhibitor 8297
Pyruvate kinase PKM 1 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	Inhibitor 8297
AMPK signaling pathway 5 Target ID: map04152 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29110616	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Esophageal-gastric junction adenocarcinoma 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29207122	Primary	Basic research	Unknown Approved Use Unknown
Emphysema 13 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29329251	Primary	Preclinical	Unknown Approved Use Unknown
Breast cancer 434 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29110616	Primary	Preclinical	Unknown Approved Use Unknown
Acetaminophen-induced hepatotoxicity 3 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28847761	Preventing	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Antimutagenic activity of organosulfur compounds from Allium is associated with phase II enzyme induction.	2001 Aug 22	11448651
In-vitro antimicrobial activity of four diallyl sulphides occurring naturally in garlic and Chinese leek oils.	2001 Jul	11444776
Screening of organosulfur compounds as inhibitors of human CYP2A6.	2001 Jul	11408364
Growth inhibitory effects of diallyl disulfide on human breast cancer cell lines.	2001 Jun	11375895
Effect of diallyl sulfide and diallyl disulfide, the active principles of garlic, on the aflatoxin B(1)-induced DNA damage in primary rat hepatocytes.	2001 May 31	11397556
Modulation of cytochrome P4501-mediated bioactivation of benzo[a]pyrene by volatile allyl sulfides in human hepatoma cells.	2001 Oct	11758911
Anti-tumour-promoting action of Allium constituents.	2002	12484213
Alleviation of cyclophosphamide-induced urotoxicity by naturally occurring sulphur compounds.	2002 Dec	12636097
A model system study of the inhibition of heterocyclic aromatic amine formation by organosulfur compounds.	2002 Dec 18	12475289
Induction of apoptosis by diallyl disulfide through activation of caspase-3 in human leukemia HL-60 cells.	2002 Jan 1	11754872
Differential effects of garlic oil and its three major organosulfur components on the hepatic detoxification system in rats.	2002 Jan 16	11782211
Inhibition of heterocyclic aromatic amine formation in fried ground beef patties by garlic and selected garlic-related sulfur compounds.	2002 Nov	12430700
Effect of garlic on cardiovascular disorders: a review.	2002 Nov 19	12537594
Biofactors in the Mediterranean diet.	2003 Aug	12964804
Inhibition of H-ras as a treatment for experimental brain C6 glioma.	2003 Mar 17	12654504
Diallyl disulfide (DADS) enhances gap-junctional intercellular communication by both direct and indirect mechanisms in rat liver cells.	2004 Jan	14555610
[Preventive effect and clinical significance of garlicin injection on mechanical ventilator-associated low respiratory tract deep-seated fungal infection].	2004 Jun	15250201
Antioxidative and antiglycative effects of six organosulfur compounds in low-density lipoprotein and plasma.	2004 Jun 2	15161248
[The initiation of G2/M checkpoint by diallyl disulfide requires the activation of p38 MAP kinase in HL-60 cells].	2004 May	15182534
Inhibition of the benzo[a]pyrene-induced toxicity by allyl sulfides in human epidermal keratinocytes.	2004 Nov	15604822
Use of gloves in protection from diallyl disulphide allergy.	2004 Nov	15527433
Diallyl disulfide (DADS) induced apoptosis undergo caspase-3 activity in human bladder cancer T24 cells.	2004 Oct	15304301
Diallyldisulfide-induced calcium response of HL-60 human promyelocytes.	2004 Sep-Oct	15587801
Differential effects of organosulfur compounds from garlic oil on nitric oxide and prostaglandin E2 in stimulated macrophages.	2005 Apr	15811776
Diallyl disulfide inhibits N-acetyltransferase activity and gene expression in human esophagus epidermoid carcinoma CE 81T/VGH cells.	2005 Jul	15833378
Allicin and allicin-derived garlic compounds increase breath acetone through allyl methyl sulfide: use in measuring allicin bioavailability.	2005 Mar 23	15769123

Patents

Sample Use Guides

In Vivo Use Guide

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

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 `Fri Dec 15 17:53:29 GMT 2023` Edited by `admin` on `Fri Dec 15 17:53:29 GMT 2023`
Record UNII	5HI47O6OA7
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ALLYL DISULFIDE

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

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