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

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	MOL RATIO 1 MOL RATIO (average)

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

Description

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	Inhibitor 8,297
CD44 antigen 1	Inhibitor 8,297
Pyruvate kinase PKM 1	Inhibitor 8,297
AMPK signaling pathway 5	Inhibitor 8,297

Conditions

Condition	Modality	Highest Phase	Product
Esophageal-gastric junction adenocarcinoma 1	Primary	Basic research	Unknown
Emphysema 13	Primary	Preclinical	Unknown
Breast cancer 434	Primary	Preclinical	Unknown
Acetaminophen-induced hepatotoxicity 3	Preventing	Preclinical	Unknown

PubMed

Show entries

Title	Date	PubMed
Effects of diallyl disulfide and other donors of sulfane sulfur on the proliferation of human hepatoma cell line (HepG2).	2001	11712684
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	11470743
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

Showing 1 to 5 of 35 entries

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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.