THIOLUTIN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C8H8N2O2S2
Molecular Weight	228.291
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN1C(=O)C(NC(C)=O)=C2SSC=C12

InChI

InChIKey=MHMRAFONCSQAIA-UHFFFAOYSA-N

InChI=1S/C8H8N2O2S2/c1-4(11)9-6-7-5(3-13-14-7)10(2)8(6)12/h3H,1-2H3,(H,9,11)

HIDE SMILES / InChI

Molecular Formula	C8H8N2O2S2
Molecular Weight	228.291
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/11433393 | https://www.ncbi.nlm.nih.gov/pubmed/17914747

Thiolutin is a naturally occurring bicyclic dithiole that was first isolated from Streptomyces luteorectiuli based on its antibiotic activities. Thiolutin inhibits the growth of Saccharomyces cerevisiae and several gram-positive and -negative bacteria by inhibiting DNA-dependent RNA polymerases. It also inhibits the adhesion of endothelial cells, including adhesion of human umbilical vein endothelial cells (HUVECs) to vitronectin, and restricts tumor cell-induced angiogenesis.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial DNA-directed RNA polymerase 11 Target ID: CHEMBL2364672 Sources: https://www.ncbi.nlm.nih.gov/pubmed/4597739	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
RNA polymerase inhibitors with activity against rifampin-resistant mutants of Staphylococcus aureus.	2000 Nov	11036042
Thiolutin, an inhibitor of HUVEC adhesion to vitronectin, reduces paxillin in HUVECs and suppresses tumor cell-induced angiogenesis.	2001 Aug 1	11433393
New dithiolopyrrolone antibiotics from Saccharothrix sp. SA 233. I. Taxonomy, fermentation, isolation and biological activities.	2002 Aug	12374382
The transcriptional inhibitor thiolutin blocks mRNA degradation in yeast.	2008 Feb	17914747

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

At concentrations as low as 2 mug/ml, the thiolutin inhibited ribonucleic acid (RNA) and protein synthesis in whole cells and spheroplasts. At these low concentrations, protein synthesis continued for a short period of time after RNA synthesis was completely stopped. With higher drug concentrations (greater than 20 mug/ml) protein synthesis was inhibited; concentrations of thiolutin up to 100 mug/ml did not affect translocation or peptide bond formation in cell-free protein-synthesizing systems from yeast. The effect of thiolutin on the activity of partially purified deoxyribonucleic acid-dependent RNA polymerases was examined, and the drug was found to be a potent inhibitor of RNA synthesis in vitro

Substance Class	Chemical Created by `admin` on `Sat Dec 16 02:08:39 GMT 2023` Edited by `admin` on `Sat Dec 16 02:08:39 GMT 2023`
Record UNII	02C005Q20B
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

THIOLUTIN

Common Name

English

1,2-DITHIOLO(4,3-B)PYRROL-5(4H)-ONE, 6-ACETAMIDO-4-METHYL-

Systematic Name

English

THIOLUTIN [MI]

Common Name

English

NSC-3927

Code

English

N-(4,5-DIHYDRO-4-METHYL-5-OXO-1,2-DITHIOLO(4,3-B)PYRROL-6-YL)ACETAMIDE

Systematic Name

English

ACETOPYRROTHINE

Common Name

English

3-ACETAMIDO-5-METHYLPYRROLIN-4-ONE(4,3-D)-1,2-DITHIOLE

Common Name

English

6-(ACETAMIDO)-4-METHYL-1,2-DITHIOLO(4,3-B)PYRROL-5(4H)-ONE

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C258