U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C20H21N3O2.ClH
Molecular Weight 371.861
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TUBASTATIN A HYDROCHLORIDE

SMILES

Cl.CN1CCC2=C(C1)C3=CC=CC=C3N2CC4=CC=C(C=C4)C(=O)NO

InChI

InChIKey=LJTSJTWIMOGKRJ-UHFFFAOYSA-N
InChI=1S/C20H21N3O2.ClH/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);1H

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
Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
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

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 15.0 nM [IC50]
Inhibitor
8297
 854.0 nM [IC50]
Inhibitor
8297
 16400.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Basic research
Unknown

Approved Use

Unknown
Primary
Basic research
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
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
Patents

Patents

WO2011011186
2

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 13:25:39 GMT 2023
Edited
by admin
on Sat Dec 16 13:25:39 GMT 2023
Record UNII
UHCM2AYJVX
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TUBASTATIN A HYDROCHLORIDE
Common Name English
TUBASTATIN A HCL
Common Name English
4-((2-METHYL-3,4-DIHYDRO-1H-PYRIDO(4,3-B)INDOL-5-YL)METHYL)BENZENECARBOHYDROXAMIC ACID HYDROCHLORIDE
Systematic Name English
BENZAMIDE, N-HYDROXY-4-((1,2,3,4-TETRAHYDRO-2-METHYL-5H-PYRIDO(4,3-B)INDOL-5-YL)METHYL)-, HYDROCHLORIDE (1:1)
Systematic Name English
Code System Code Type Description
PUBCHEM
57336514
Created by admin on Sat Dec 16 13:25:39 GMT 2023 , Edited by admin on Sat Dec 16 13:25:39 GMT 2023
PRIMARY
CAS
1310693-92-5
Created by admin on Sat Dec 16 13:25:39 GMT 2023 , Edited by admin on Sat Dec 16 13:25:39 GMT 2023
PRIMARY
FDA UNII
UHCM2AYJVX
Created by admin on Sat Dec 16 13:25:39 GMT 2023 , Edited by admin on Sat Dec 16 13:25:39 GMT 2023
PRIMARY
Related Record Type Details
Structure of TUBASTATIN A
PARENT -> SALT/SOLVATE
HISTONE DEACETYLASE 6
TARGET -> INHIBITOR
Tubastatin A HCl is a potent and selective HDAC6 inhibitor in a cell-free assay.
INHIBITOR
IC50
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966