DIMORPHOLINETHIURAM DISULFIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C10H16N2O2S4
Molecular Weight	324.506
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of DIMORPHOLINETHIURAM DISULFIDE

Structure Search

SMILES

S=C(SSC(=S)N1CCOCC1)N2CCOCC2

InChI

InChIKey=KKVYOWPPMNSLCP-UHFFFAOYSA-N

InChI=1S/C10H16N2O2S4/c15-9(11-1-5-13-6-2-11)17-18-10(16)12-3-7-14-8-4-12/h1-8H2

HIDE SMILES / InChI

Molecular Formula	C10H16N2O2S4
Molecular Weight	324.506
Charge	0
Count

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

Description
Sources: https://www.google.ru/patents/US4144272 | https://www.ncbi.nlm.nih.gov/pubmed/26483203 | https://www.ncbi.nlm.nih.gov/pubmed/19883085

Dimorpholinethiuram disulfide is a thiuram derivative which was initially used in the vulcanization of rubber. Later it was shown that dimorpholinethiuram disulfide is an inhibitor of monoglycerol lipase and pyruvate dehydrogenase kinase (PDK). The compound suppresses proliferation of A549 lung cancer cell line in vitro and reduces tumor volume of A549 xenografts in mice.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
3-phosphoinositide-dependent protein kinase 1 4 Target ID: O15530 Gene ID: 5170.0 Gene Symbol: PDPK1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/26483203	Inhibitor 8297	49.0 nM [IC50]
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial 1 Target ID: Q15119 Gene ID: 5164.0 Gene Symbol: PDK2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/26483203	Inhibitor 8297	101.0 nM [IC50]
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 3, mitochondrial 1 Target ID: Q15120 Gene ID: 5165.0 Gene Symbol: PDK3 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/26483203	Inhibitor 8297	313.0 nM [IC50]
Monoglyceride lipase 8 Target ID: Q99685 Gene ID: 11343.0 Gene Symbol: MGLL Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/26483203	Inhibitor 8297	6.66 null [pIC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26483203	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Evaluation of selected chemotypes in coupled cellular and molecular target-based screens identifies novel HIV-1 zinc finger inhibitors.	1996 Sep 13	8809151
Inactivation of the human papillomavirus-16 E6 oncoprotein by organic disulfides.	2000 Nov	11092540

Patents

Sample Use Guides

In Vivo Use Guide

The compound was intraperitoneally administered to mice bearing A549 tumor at doses 40 and 80 mg/kg per day. A 21-day continuous treatment of 80 mg/kg dimorpholinethiuram disulfide considerably reduced 67.5% tumor volume compared with the vehicle control.

Route of Administration: Intraperitoneal

In Vitro Use Guide

A549 cells (obtained from ATCC) were seeded into 96-well plate. After attachment, cells were treated with JX06 and CCK8 assay (Life Technologies) was carried out after incubation for 72 hours. Untreated cells served as the indicator of 100% cell viability.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 19:14:25 GMT 2023` Edited by `admin` on `Fri Dec 15 19:14:25 GMT 2023`
Record UNII	72G763P0UO
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DIMORPHOLINETHIURAM DISULFIDE

Common Name

English

DIMORPHOLINETHIURAM DISULPHIDE

Common Name

English

NSC-402538

Code

English

BIS(MORPHOLINOTHIOCARBONYL) DISULFIDE

Systematic Name

English

BIS(4-MORPHOLINOTHIOCARBONYL) DISULFIDE

Systematic Name

English

METHANETHIONE, 1,1'-DITHIOBIS(1-(4-MORPHOLINYL)-

Systematic Name

English

4,4'-(DITHIODICARBONOTHIOYL)DIMORPHOLINE

Systematic Name

English

MORPHOLINE, 4,4'-(DITHIODICARBONOTHIOYL)BIS-

Systematic Name

English

DISULFIDE, BIS(MORPHOLINOTHIOCARBONYL)

Systematic Name

English

THIURAM DISULFIDE, BIS(OXYDI-2,1-ETHANEDIYL)-

Systematic Name

English

4-MORPHOLINETHIOCARBONYL DISULFIDE

Systematic Name

English

Code System Code Type Description

NSC

402538