TYRPHOSTIN A23

Details

Stereochemistry	ACHIRAL
Molecular Formula	C10H6N2O2
Molecular Weight	186.1668
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC1=CC=C(C=C(C#N)C#N)C=C1O

InChI

InChIKey=VTJXFTPMFYAJJU-UHFFFAOYSA-N

InChI=1S/C10H6N2O2/c11-5-8(6-12)3-7-1-2-9(13)10(14)4-7/h1-4,13-14H

HIDE SMILES / InChI

Molecular Formula	C10H6N2O2
Molecular Weight	186.1668
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/8260363 | https://www.ncbi.nlm.nih.gov/pubmed/21887406 | https://www.ncbi.nlm.nih.gov/pubmed/3263702 | https://www.ncbi.nlm.nih.gov/pubmed/27894844

Tyrphostin A23 belongs to a novel class of low molecular weight proteins that inhibit protein tyrosine kinase and block the EGF-dependent autophosphorylation of the receptor. It has been considered as potential anti-cancer drug. It inhibits pancreatic cancer cell growth in vitro. Inhibition of EGF receptor by tyrphostin A23 was associated with a significantly increased proportion of apoptotic cells in human prostate cancer DU145 cell culture.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Epidermal growth factor receptor 49 Target ID: CHEMBL2363049 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3263702	Inhibitor 8504	10.0 µM [Ki]
PDGFR (rabbit) 1 Target ID: PDGFR (rabbit) Sources: https://www.ncbi.nlm.nih.gov/pubmed/7892601	Inhibitor 8504	25.0 µM [IC50]
p210 (BCR-ABL1) 1 Target ID: p210 (BCR-ABL1) Sources: https://www.ncbi.nlm.nih.gov/pubmed/7892601	Inhibitor 8504	75.0 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Prostate cancer 186 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21887406	Primary		Basic research	Unknown Approved Use Unknown
Pancreatic cancer 98 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8260363	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
The tricarboxylic acid cycle activity in cultured primary astrocytes is strongly accelerated by the protein tyrosine kinase inhibitor tyrphostin 23.	2017-01	27894844
Developmental defects in zebrafish for classification of EGF pathway inhibitors.	2014-01-15	24262764
Growth factor/growth factor receptor loops in autocrine growth regulation of human prostate cancer DU145 cells.	2011	21887406
Interactions of methoxyacetic acid with androgen receptor.	2009-07-15	18486176
Potentiation of the osmosensitive release of taurine and D-aspartate from SH-SY5Y neuroblastoma cells after activation of M3 muscarinic cholinergic receptors.	2004-12	15292461
Monocytic activation of protein tyrosine kinase, protein kinase A and protein kinase C induced by porins isolated from Salmonella enterica serovar Typhimurium.	2003-02	12634073
Inhibition of topoisomerase I activity by tyrphostin derivatives, protein tyrosine kinase blockers: mechanism of action.	1994-10-01	7923131
Inhibition of pancreatic cancer cell growth in vitro by the tyrphostin group of tyrosine kinase inhibitors.	1993-12	8260363
Tyrphostins I: synthesis and biological activity of protein tyrosine kinase inhibitors.	1989-10	2552117

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Both lactate production and glucose consumption were increased in the primary astrocytes by the presence of Tyrphostin A23 (T23) in a concentration-dependent manner. Exposure to 100 uM T23 increased already within the initial 15 min of incubation the extracellular lactate concentration significantly from 0.37±0.01 (control, absence of T23) to 0.91±0.30 uM/mg.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:12:07 GMT 2025` Edited by `admin` on `Mon Mar 31 21:12:07 GMT 2025`
Record UNII	RV0GCD31OJ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

AG 18

Preferred Name

English

TYRPHOSTIN A23

Common Name

English

RG-50810

Code

English

AG-18

Code

English

(3,4-DIHYDROXYBENZYLIDENE)MALONONITRILE

Systematic Name

English

TYRPHOSTIN 23

Common Name

English

((3,4-DIHYDROXYPHENYL)METHYLENE)-PROPENEDINITRILE

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1757