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Details

Stereochemistry ACHIRAL
Molecular Formula C13H19N3O3
Molecular Weight 265.3083
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PYROXAMIDE

SMILES

ONC(=O)CCCCCCC(=O)NC1=CC=CN=C1

InChI

InChIKey=PTJGLFIIZFVFJV-UHFFFAOYSA-N
InChI=1S/C13H19N3O3/c17-12(15-11-6-5-9-14-10-11)7-3-1-2-4-8-13(18)16-19/h5-6,9-10,19H,1-4,7-8H2,(H,15,17)(H,16,18)

HIDE SMILES / InChI

Molecular Formula C13H19N3O3
Molecular Weight 265.3083
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: The description was created based on several sources, including https://www.drugbank.ca/drugs/DB12847 | https://www.ncbi.nlm.nih.gov/pubmed/11831887 | https://www.ncbi.nlm.nih.gov/pubmed/20139990 | https://clinicaltrials.gov/ct2/show/record/NCT00042900

Pyroxamide is a potent histone deacetylase (HDAC) inhibitor. Pyroxamide induced terminal differentiation in murine erythroleukemia (MEL) cells and inhibited the growth by cell cycle arrest or apoptosis in a variety of tumor cells. An accumulation of acetylated histones and increased levels of p21/WAF1 expression were detected in cancer cells and in prostate xenografts treated with Pyroxamide.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
8.0 nM [Ki]
2.7 nM [Ki]
4.8 nM [Ki]
200.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Patents

Patents

Sample Use Guides

Patients receive pyroxamide IV continuously over 5-7 days. Courses repeat every 21 days in the absence of disease progression or unacceptable toxicity.
Route of Administration: Intravenous
HCT116 cells were used for activity evaluation. Cells were plated in 96-well plates at initial densities of between 1000 and 3000 cells/well and incubated. After 24 h, test compound 7c (Pyroxamide) were added to test wells, vehicle added to vehicle control (VC) wells and initial growth control wells (IGC) received 10 µL 3-(4,5-dimethylthiazol-2-yl)-5-(3- carboxymethoxyphenyl)-2-(4-sulfophenyl)-2H-tetrazolium, inner salt (MTS) mixture (prepared on day of use at a ratio of 10 µL of a 0.92 mg/mL solution of phenazine methosulfate (PMS) to a 190 µL of a 2 mg/mL solution of MTS), the plate was incubated for 4 h and the OD490 of IGC wells was measured on a Molecular Devices Thermomax at 490 nm using the Softmax program to determine initial cell density values. The plates were incubated for 72 h, 10 µL/well of MTS mixture was added to the test and VC wells and the OD490 was measured.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:54:06 GMT 2023
Edited
by admin
on Fri Dec 15 15:54:06 GMT 2023
Record UNII
12N86DSS23
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PYROXAMIDE
Common Name English
N-HYDROXY-N'-(3-PYRIDYL)-1,8-OCTANEDIAMIDE
Systematic Name English
SUBEROYL-3-AMINOPYRIDINEAMIDE HYDROXAMIC ACID
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1946
Created by admin on Fri Dec 15 15:54:07 GMT 2023 , Edited by admin on Fri Dec 15 15:54:07 GMT 2023
Code System Code Type Description
PUBCHEM
4996
Created by admin on Fri Dec 15 15:54:07 GMT 2023 , Edited by admin on Fri Dec 15 15:54:07 GMT 2023
PRIMARY
CAS
382180-17-8
Created by admin on Fri Dec 15 15:54:07 GMT 2023 , Edited by admin on Fri Dec 15 15:54:07 GMT 2023
PRIMARY
NCI_THESAURUS
C2801
Created by admin on Fri Dec 15 15:54:07 GMT 2023 , Edited by admin on Fri Dec 15 15:54:07 GMT 2023
PRIMARY
EPA CompTox
DTXSID70191595
Created by admin on Fri Dec 15 15:54:07 GMT 2023 , Edited by admin on Fri Dec 15 15:54:07 GMT 2023
PRIMARY
DRUG BANK
DB12847
Created by admin on Fri Dec 15 15:54:07 GMT 2023 , Edited by admin on Fri Dec 15 15:54:07 GMT 2023
PRIMARY
FDA UNII
12N86DSS23
Created by admin on Fri Dec 15 15:54:07 GMT 2023 , Edited by admin on Fri Dec 15 15:54:07 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY