TUBASTATIN A

Details

Stereochemistry	ACHIRAL
Molecular Formula	C20H21N3O2
Molecular Weight	335.3996
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN1CCC2=C(C1)C3=C(C=CC=C3)N2CC4=CC=C(C=C4)C(=O)NO

InChI

InChIKey=GOVYBPLHWIEHEJ-UHFFFAOYSA-N

InChI=1S/C20H21N3O2/c1-22-11-10-19-17(13-22)16-4-2-3-5-18(16)23(19)12-14-6-8-15(9-7-14)20(24)21-25/h2-9,25H,10-13H2,1H3,(H,21,24)

HIDE SMILES / InChI

Molecular Formula	C20H21N3O2
Molecular Weight	335.3996
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/20614936
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/26086931 | https://www.ncbi.nlm.nih.gov/pubmed/25637120 | https://www.ncbi.nlm.nih.gov/pubmed/23964961 | https://www.ncbi.nlm.nih.gov/pubmed/20614936 | https://www.ncbi.nlm.nih.gov/pubmed/28131906

Tubastatin A is a potent and selective HDAC6 inhibitor with IC50 of 15 nM in a cell-free assay. Tubastatin A is a very selective HDAC6 inhibitor with 100 to over 1000-fold selectivity for HDAC6 over other HDAC classes. Tubastatin A increases the total numbers of mitochondria and restores the number of moving mitochondria in DRG neurons. It reverses the axonal loss in peripheral neurons in the mouse model of Charcot-Marie-Tooth disease. Tubastatin A inhibits the deacetylation of α-tubulin in murine myoblasts.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Histone deacetylase 6 27 Target ID: CHEMBL1865 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23964961	Inhibitor 8297	15.0 nM [IC50]
Histone deacetylase 8 17 Target ID: CHEMBL3192 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23964961	Inhibitor 8297	854.0 nM [IC50]
Histone deacetylase 1 51 Target ID: CHEMBL325 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23964961	Inhibitor 8297	16400.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Alzheimer’s disease 272 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24576665	Primary		Basic research	Unknown Approved Use Unknown
Cancer 592 Sources: https://www.google.com/patents/WO2011011186A2	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
A novel HDAC6 inhibitor Tubastatin A: Controls HDAC6-p97/VCP-mediated ubiquitination-autophagy turnover and reverses Temozolomide-induced ER stress-tolerance in GBM cells.	2017 Apr 10	28131906

Patents

Sample Use Guides

In Vivo Use Guide

rTg4510 mice were used for activity evaluation. Tubastatin A was administered using daily intraperitoneal injections into rTg4510 mice and nontransgenic littermates from 5 to 7 months of age. Each group consisted of six animals per genotype. Mice were weighed, and injected with tubastatin (25 mg/kg) or 0.9% normal saline solution (vehicle).

Route of Administration: Intraperitoneal

In Vitro Use Guide

TUB (Tubastatin A) enhanced TMZ (Temozolomide)-induced cytotoxicity in different TMZ-resistant cell lines (A172, U118, U251, U87). Cells were pre-incubated with TUB (1-32 mkM) for 12 h and then co-treated with 34mkM of TMZ for 24 h. Cell viability rates were determined by a CCK-8 assay.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 13:58:55 GMT 2023` Edited by `admin` on `Sat Dec 16 13:58:55 GMT 2023`
Record UNII	2XTSOX1NF8
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TUBASTATIN A

Common Name

English

N-HYDROXY-4-((1,2,3,4-TETRAHYDRO-2-METHYL-5H-PYRIDO(4,3-B)INDOL-5-YL)METHYL)BENZAMIDE

Systematic Name

English

BENZAMIDE, N-HYDROXY-4-((1,2,3,4-TETRAHYDRO-2-METHYL-5H-PYRIDO(4,3-B)INDOL-5-YL)METHYL)-

Systematic Name

English

Code System Code Type Description

EPA CompTox

DTXSID701318079