PIFITHRIN-.BETA.

Details

Stereochemistry	ACHIRAL
Molecular Formula	C16H16N2S
Molecular Weight	268.377
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=CC=C(C=C1)C2=CN3C(SC4=C3CCCC4)=N2

InChI

InChIKey=IMUKUMUNZJILCG-UHFFFAOYSA-N

InChI=1S/C16H16N2S/c1-11-6-8-12(9-7-11)13-10-18-14-4-2-3-5-15(14)19-16(18)17-13/h6-10H,2-5H2,1H3

HIDE SMILES / InChI

Molecular Formula	C16H16N2S
Molecular Weight	268.377
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/24646317
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/21362431 | https://www.ncbi.nlm.nih.gov/pubmed/21324703

Pifithrin-alpha is a small molecule p53 functional inhibitor reported to behave like an antiapoptotic agent in neurodegenerative models. Pifithrin-alpha is a prodrug that under physiological conditions spontaneously undergoes ring closure to yield pifithrin-beta. Pifithrin-beta demonstrated antiproliferative and neuroprotective effects in vitro. Pifithrin-beta is able to activate the aryl hydrocarbon receptor (AhR) in a complete independent way of the p53 inhibition.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Aryl hydrocarbon receptor 26 Target ID: CHEMBL3201 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21362431	Activator 1430
Cellular tumor antigen p53 20 Target ID: CHEMBL4164 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24646317 \| https://www.ncbi.nlm.nih.gov/pubmed/21324703	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Alzheimer’s disease 272 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24646317	Primary		Basic research	Unknown Approved Use Unknown
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21324703	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Imino-tetrahydro-benzothiazole derivatives as p53 inhibitors: discovery of a highly potent in vivo inhibitor and its action mechanism.	2006 Jun 15	16759106
Biological and chemical studies on aryl hydrocarbon receptor induction by the p53 inhibitor pifithrin-α and its condensation product pifithrin-β.	2011 Apr 25	21362431
Synthesis and biological evaluation of imidazolo[2,1-b]benzothiazole derivatives, as potential p53 inhibitors.	2011 Mar 1	21324703
p53 functional inhibitors behaving like pifithrin-β counteract the Alzheimer peptide non-β-amyloid component effects in human SH-SY5Y cells.	2014 May 21	24646317

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

10 μM pifithrin-β prevented apoptosis induced by the fibrillar non-β-amyloid component in human neuroblastoma SH-SY5Y cells

Substance Class	Chemical Created by `admin` on `Sat Dec 16 09:52:46 GMT 2023` Edited by `admin` on `Sat Dec 16 09:52:46 GMT 2023`
Record UNII	45I8QO7K37
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

PIFITHRIN-.BETA.

Common Name

English

IMIDAZO(2,1-B)BENZOTHIAZOLE, 5,6,7,8-TETRAHYDRO-2-(4-METHYLPHENYL)-

Systematic Name

English

CYCLIC PIFITHRIN-.ALPHA.

Common Name

English

5,6,7,8-TETRAHYDRO-2-(4-METHYLPHENYL)IMIDAZO(2,1-B)BENZOTHIAZOLE

Systematic Name

English

PIFITHRIN-.ALPHA. PIFITHRIN-.BETA. [MI]

Common Name

English

Code System Code Type Description

MERCK INDEX

m8803