HEXAMETHYLENE BISACETAMIDE

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 Search

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

Molecular Formula	C10H20N2O2
Molecular Weight	200.278
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Tubulin 69 Target ID: CHEMBL2095182 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12852768	Inhibitor 8504		670.0 nM [IC50]

PubMed

Title	Date	PubMed
Localization and altered expression of nucleophosmin in the nuclear matrix during the differentiation of human hepatocarcinoma SMMC-7721 cells induced by HMBA.	2010-12	20690796
Antagonistic roles of the ERK and p38 MAPK signalling pathways in globin expression, haem biosynthesis and iron uptake.	2010-11-15	20738258
Occupational exposure to HDI: progress and challenges in biomarker analysis.	2010-10-01	20176515
Sequential changes in chromatin structure during transcriptional activation in the beta globin LCR and its target gene.	2010-09	20561915
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	20302847
Aberrant expression of nuclear matrix proteins during HMBA-induced differentiation of gastric cancer cells.	2010-05-07	20440860
Molecular control of HIV-1 postintegration latency: implications for the development of new therapeutic strategies.	2009-12-04	19961595
Wnt pathway reprogramming during human embryonal carcinoma differentiation and potential for therapeutic targeting.	2009-10-29	19874621
P-TEFb- the final frontier.	2009-09-02	19723344
Properties of virion transactivator proteins encoded by primate cytomegaloviruses.	2009-05-27	19473490
Gene therapy: the end of the rainbow?	2009-03-30	19331651
De novo synthesis of VP16 coordinates the exit from HSV latency in vivo.	2009-03	19325890
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	19027925
Control of stochastic gene expression by host factors at the HIV promoter.	2009-01	19132086
Discordant varicella-zoster virus glycoprotein C expression and localization between cultured cells and human skin vesicles.	2008-12-20	18954885
Hexamethylene bisacetamide (HMBA) simultaneously targets AKT and MAPK pathway and represses NF kappaB activity: implications for cancer therapy.	2008-12	19029824
Multi-stage Friend murine erythroleukemia: molecular insights into oncogenic cooperation.	2008-11-04	18983647
[Molecular mechanism underlying differentiation of HL-60 cells induced by hexamethylene bisacetamide].	2008-10	18928589
HEXIM1 regulates 17beta-estradiol/estrogen receptor-alpha-mediated expression of cyclin D1 in mammary cells via modulation of P-TEFb.	2008-09-01	18757415
[Expression and localization of hnRNP A2/B1 during differentiation of human osteosarcoma MG-63 cells induced by HMBA].	2008-07	18606058
PP2B and PP1alpha cooperatively disrupt 7SK snRNP to release P-TEFb for transcription in response to Ca2+ signaling.	2008-05-15	18483222
Hexamethylene bisacetamide as a treatment for T-cell leukemia (T-ALL).	2008-05	18164760
Hexamethylene bisacetamide inhibits malignant phenotype in T-ALL cell lines.	2008-05	17964649
Hexamethylbisacetamide and disruption of human immunodeficiency virus type 1 latency in CD4(+) T cells.	2008-04-15	18419522
Non-random subcellular distribution of variant EKLF in erythroid cells.	2008-04-15	18329016
Detailed characterization of the mouse embryonic stem cell transcriptome reveals novel genes and intergenic splicing associated with pluripotency.	2008-04-09	18400104
[Localization of prohibitin in nuclear matrix and its expressive alteration during the differentiation of human osteosarcoma MG-63 cells induced by HMBA].	2008-02	18464584
Hexamethylene bisacetamide leads to reduced helper virus-free HSV-1 amplicon expression titers via suppression of ICP0.	2008-02	18058952
Effect of hexamethylene bisacetamide (HMBA) on the microtubular system of Tetrahymena pyriformis.	2008-02	17945523
Overexpression of CDC2/CyclinB1 in gliomas, and CDC2 depletion inhibits proliferation of human glioma cells in vitro and in vivo.	2008-01-29	18230152
Histone modifications associated with herpes simplex virus type 1 genomes during quiescence and following ICP0-mediated de-repression.	2008-01	18089730
Relationship between the induction of leukemia cell differentiation and the enhancement of reporter gene expression in 3T3 Swiss cells.	2008-01	17617452
PU.1 is dispensable to block erythroid differentiation in Friend erythroleukemia cells.	2008-01	17586044
HMBA releases P-TEFb from HEXIM1 and 7SK snRNA via PI3K/Akt and activates HIV transcription.	2007-10-12	17937499
Cellular mRNA activates transcription elongation by displacing 7SK RNA.	2007-10-10	17925858
HEXIM1 and the control of transcription elongation: from cancer and inflammation to AIDS and cardiac hypertrophy.	2007-08-01	17671421
Alteration of nuclear matrix-intermediate filament system and differential expression of nuclear matrix proteins during human hepatocarcinoma cell differentiation.	2007-05-28	17569113
Down-regulation of CD44 contributes to the differentiation of HL-60 cells induced by ATRA or HMBA.	2007-02	17349212
Proteomic analysis of erythroid differentiation induced by hexamethylene bisacetamide in murine erythroleukemia cells.	2007-02	17258068
Temporal variation in the expression of the p53 protein in proliferating and differentiating murine erythroleukaemia cells.	2007-01	16896537
Delayed biosynthesis of varicella-zoster virus glycoprotein C: upregulation by hexamethylene bisacetamide and retinoic acid treatment of infected cells.	2006-10	16973558
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	16645620
Growth inhibition and differentiation of human breast cancer cells by the PAFR antagonist WEB-2086.	2006-06-05	16721373
The carbonic anhydrase I locus contains a c-Myb target promoter and modulates differentiation of murine erythroleukemia cells.	2006-05-04	16407849
[Changes of nuclear matrix proteins during differentiation of human osteosarcoma MG-63 cells induced by HMBA].	2006-04	16944589
Following the differentiation of human pluripotent stem cells by proteomic identification of biomarkers.	2006-04	16646668
Changes of nuclear matrix proteins following the differentiation of human osteosarcoma MG-63 cells.	2006-02	16689697
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	16343414
Differentiation-inducing therapy for solid tumors.	2006	16454751
Interplay between 7SK snRNA and oppositely charged regions in HEXIM1 direct the inhibition of P-TEFb.	2005-12-21	16362050

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:38:29 GMT 2025` Edited by `admin` on `Mon Mar 31 19:38:29 GMT 2025`
Record UNII	LA133J59VU
Record Status	`Validated (UNII)`
Record Version

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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