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Details

Stereochemistry ACHIRAL
Molecular Formula C10H20N2O2
Molecular Weight 200.278
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of HEXAMETHYLENE BISACETAMIDE

SMILES

CC(=O)NCCCCCCNC(C)=O

InChI

InChIKey=BNQSTAOJRULKNX-UHFFFAOYSA-N
InChI=1S/C10H20N2O2/c1-9(13)11-7-5-3-4-6-8-12-10(2)14/h3-8H2,1-2H3,(H,11,13)(H,12,14)

HIDE SMILES / InChI

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
670.0 nM [IC50]
PubMed

PubMed

TitleDatePubMed
Localization and altered expression of nucleophosmin in the nuclear matrix during the differentiation of human hepatocarcinoma SMMC-7721 cells induced by HMBA.
2010-12
Antagonistic roles of the ERK and p38 MAPK signalling pathways in globin expression, haem biosynthesis and iron uptake.
2010-11-15
Occupational exposure to HDI: progress and challenges in biomarker analysis.
2010-10-01
Sequential changes in chromatin structure during transcriptional activation in the beta globin LCR and its target gene.
2010-09
HMBA depolymerizes microtubules, activates mitotic checkpoints and induces mitotic block in MCF-7 cells by binding at the colchicine site in tubulin.
2010-07-01
Aberrant expression of nuclear matrix proteins during HMBA-induced differentiation of gastric cancer cells.
2010-05-07
Molecular control of HIV-1 postintegration latency: implications for the development of new therapeutic strategies.
2009-12-04
Wnt pathway reprogramming during human embryonal carcinoma differentiation and potential for therapeutic targeting.
2009-10-29
P-TEFb- the final frontier.
2009-09-02
Properties of virion transactivator proteins encoded by primate cytomegaloviruses.
2009-05-27
Gene therapy: the end of the rainbow?
2009-03-30
De novo synthesis of VP16 coordinates the exit from HSV latency in vivo.
2009-03
Hexamethylene bisacetamide can convert nonpermissive human cells to a permissive state for expressing the major immediate-early genes of human cytomegalovirus by up-regulating NF-kappaB activity.
2009-01-20
Control of stochastic gene expression by host factors at the HIV promoter.
2009-01
Discordant varicella-zoster virus glycoprotein C expression and localization between cultured cells and human skin vesicles.
2008-12-20
Hexamethylene bisacetamide (HMBA) simultaneously targets AKT and MAPK pathway and represses NF kappaB activity: implications for cancer therapy.
2008-12
Multi-stage Friend murine erythroleukemia: molecular insights into oncogenic cooperation.
2008-11-04
[Molecular mechanism underlying differentiation of HL-60 cells induced by hexamethylene bisacetamide].
2008-10
HEXIM1 regulates 17beta-estradiol/estrogen receptor-alpha-mediated expression of cyclin D1 in mammary cells via modulation of P-TEFb.
2008-09-01
[Expression and localization of hnRNP A2/B1 during differentiation of human osteosarcoma MG-63 cells induced by HMBA].
2008-07
PP2B and PP1alpha cooperatively disrupt 7SK snRNP to release P-TEFb for transcription in response to Ca2+ signaling.
2008-05-15
Hexamethylene bisacetamide as a treatment for T-cell leukemia (T-ALL).
2008-05
Hexamethylene bisacetamide inhibits malignant phenotype in T-ALL cell lines.
2008-05
Hexamethylbisacetamide and disruption of human immunodeficiency virus type 1 latency in CD4(+) T cells.
2008-04-15
Non-random subcellular distribution of variant EKLF in erythroid cells.
2008-04-15
Detailed characterization of the mouse embryonic stem cell transcriptome reveals novel genes and intergenic splicing associated with pluripotency.
2008-04-09
[Localization of prohibitin in nuclear matrix and its expressive alteration during the differentiation of human osteosarcoma MG-63 cells induced by HMBA].
2008-02
Hexamethylene bisacetamide leads to reduced helper virus-free HSV-1 amplicon expression titers via suppression of ICP0.
2008-02
Effect of hexamethylene bisacetamide (HMBA) on the microtubular system of Tetrahymena pyriformis.
2008-02
Overexpression of CDC2/CyclinB1 in gliomas, and CDC2 depletion inhibits proliferation of human glioma cells in vitro and in vivo.
2008-01-29
Histone modifications associated with herpes simplex virus type 1 genomes during quiescence and following ICP0-mediated de-repression.
2008-01
Relationship between the induction of leukemia cell differentiation and the enhancement of reporter gene expression in 3T3 Swiss cells.
2008-01
PU.1 is dispensable to block erythroid differentiation in Friend erythroleukemia cells.
2008-01
HMBA releases P-TEFb from HEXIM1 and 7SK snRNA via PI3K/Akt and activates HIV transcription.
2007-10-12
Cellular mRNA activates transcription elongation by displacing 7SK RNA.
2007-10-10
HEXIM1 and the control of transcription elongation: from cancer and inflammation to AIDS and cardiac hypertrophy.
2007-08-01
Alteration of nuclear matrix-intermediate filament system and differential expression of nuclear matrix proteins during human hepatocarcinoma cell differentiation.
2007-05-28
Down-regulation of CD44 contributes to the differentiation of HL-60 cells induced by ATRA or HMBA.
2007-02
Proteomic analysis of erythroid differentiation induced by hexamethylene bisacetamide in murine erythroleukemia cells.
2007-02
Temporal variation in the expression of the p53 protein in proliferating and differentiating murine erythroleukaemia cells.
2007-01
Delayed biosynthesis of varicella-zoster virus glycoprotein C: upregulation by hexamethylene bisacetamide and retinoic acid treatment of infected cells.
2006-10
Enhancement of antitumor activity of herpes simplex virus gamma(1)34.5-deficient mutant for oral squamous cell carcinoma cells by hexamethylene bisacetamide.
2006-08
Growth inhibition and differentiation of human breast cancer cells by the PAFR antagonist WEB-2086.
2006-06-05
The carbonic anhydrase I locus contains a c-Myb target promoter and modulates differentiation of murine erythroleukemia cells.
2006-05-04
[Changes of nuclear matrix proteins during differentiation of human osteosarcoma MG-63 cells induced by HMBA].
2006-04
Following the differentiation of human pluripotent stem cells by proteomic identification of biomarkers.
2006-04
Changes of nuclear matrix proteins following the differentiation of human osteosarcoma MG-63 cells.
2006-02
1,6-Diaminohexane contributes to the hexamethylene bisacetamide-induced erythroid differentiation pathway by stimulating Ca2+ release from inositol 1,4,5-trisphosphate-sensitive stores and promoting Ca2+ influx.
2006-01-01
Differentiation-inducing therapy for solid tumors.
2006
Interplay between 7SK snRNA and oppositely charged regions in HEXIM1 direct the inhibition of P-TEFb.
2005-12-21
Patents
Name Type Language
HEXAMETHYLENE BISACETAMIDE
Systematic Name English
NSC-95580
Preferred Name English
HMBA
Common Name English
N,N'-HEXAMETHYLENE BIS(ACETAMIDE)
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C292
Created by admin on Mon Mar 31 19:38:29 GMT 2025 , Edited by admin on Mon Mar 31 19:38:29 GMT 2025
NCI_THESAURUS C1934
Created by admin on Mon Mar 31 19:38:29 GMT 2025 , Edited by admin on Mon Mar 31 19:38:29 GMT 2025
Code System Code Type Description
EPA CompTox
DTXSID2041044
Created by admin on Mon Mar 31 19:38:29 GMT 2025 , Edited by admin on Mon Mar 31 19:38:29 GMT 2025
PRIMARY
FDA UNII
LA133J59VU
Created by admin on Mon Mar 31 19:38:29 GMT 2025 , Edited by admin on Mon Mar 31 19:38:29 GMT 2025
PRIMARY
MESH
C014026
Created by admin on Mon Mar 31 19:38:29 GMT 2025 , Edited by admin on Mon Mar 31 19:38:29 GMT 2025
PRIMARY
NCI_THESAURUS
C1125
Created by admin on Mon Mar 31 19:38:29 GMT 2025 , Edited by admin on Mon Mar 31 19:38:29 GMT 2025
PRIMARY
CAS
3073-59-4
Created by admin on Mon Mar 31 19:38:29 GMT 2025 , Edited by admin on Mon Mar 31 19:38:29 GMT 2025
PRIMARY
PUBCHEM
3616
Created by admin on Mon Mar 31 19:38:29 GMT 2025 , Edited by admin on Mon Mar 31 19:38:29 GMT 2025
PRIMARY
NSC
95580
Created by admin on Mon Mar 31 19:38:29 GMT 2025 , Edited by admin on Mon Mar 31 19:38:29 GMT 2025
PRIMARY