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Details

Stereochemistry ABSOLUTE
Molecular Formula C13H14N2O4S2
Molecular Weight 326.391
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GLIOTOXIN

SMILES

[H][C@@]12[C@@H](O)C=CC=C1C[C@@]34SS[C@@](CO)(N(C)C3=O)C(=O)N24

InChI

InChIKey=FIVPIPIDMRVLAY-RBJBARPLSA-N
InChI=1S/C13H14N2O4S2/c1-14-10(18)12-5-7-3-2-4-8(17)9(7)15(12)11(19)13(14,6-16)21-20-12/h2-4,8-9,16-17H,5-6H2,1H3/t8-,9-,12+,13+/m0/s1

HIDE SMILES / InChI

Molecular Formula C13H14N2O4S2
Molecular Weight 326.391
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Gliotoxin is a potent crystalline antibiotic substance produced during the growth of the imperfect fungus Gliocladium jimbriatum. It is a natural mycotoxin with immunosuppressive and antimicrobial activity. Gliotoxin acts as NOTCH2 transactivation inhibitor in human neoplasias. It induced growth inhibition and apoptosis in multiple colorectal cancer cell lines with mutations of the Wnt signaling pathway. Gliotoxin stimulates the apoptosis of human and rat hepatic stellate cells and enhances the resolution of liver fibrosis in rats. Gliotoxin is a dual inhibitor of farnesyltransferase and geranylgeranyltransferase I with pronounced antitumor activity and favorable toxicity profile against breast cancer in vitro and in vivo.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
80.0 µM [IC50]
17.0 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
Unknown
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
Rat: 3 mg/kg body wt
Route of Administration: Intraperitoneal
In Vitro Use Guide
Culture-activated (14-day) rat Hepatic stellate cells (HSCs) and Culture-activated (24-day) human (H2) HSCs cells were treated for 4 hours with 1.5 umol/L gliotoxin. Rat and human HSCs resulted in striking morphologic alterations within 1 hour as judged by light microscopy. HSCs changed from a flattened fibroblastic phenotype with distinct cell-cell interfaces to a substratum-detached, rounded, and blebbed morphology.
Substance Class Chemical
Record UNII
5L648PH06K
Record Status Validated (UNII)
Record Version