HOMIDIUM BROMIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C21H20N3.Br
Molecular Weight	394.308
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Br-].CC[N+]1=C(C2=CC=CC=C2)C3=C(C=CC(N)=C3)C4=C1C=C(N)C=C4

InChI

InChIKey=ZMMJGEGLRURXTF-UHFFFAOYSA-N

InChI=1S/C21H19N3.BrH/c1-2-24-20-13-16(23)9-11-18(20)17-10-8-15(22)12-19(17)21(24)14-6-4-3-5-7-14;/h3-13,23H,2,22H2,1H3;1H

HIDE SMILES / InChI

Molecular Formula	C21H19N3
Molecular Weight	313.3957
Charge	0
Count

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

Molecular Formula	BrH
Molecular Weight	80.912
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/889813 | https://www.sigmaaldrich.com/content/dam/sigma-aldrich/docs/Sigma/Product_Information_Sheet/e7637pis.pdf

Ethidium is a DNA intercalating agent first discovered as and used as a veterenary trypanocide. A bromide salt is commonly used as a fluorescent tag in molecular biology. The fluorescene of ethidium bromide increased 21 fold upon binding to double-stranded RNA, 25 fold upon binding double stranded DNA. Because of the binding to DNA, ethidium bromide is a powerful inhibitor of DNA polymerase.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DNA 278 Target ID: CHEMBL2366045 Sources: https://www.ncbi.nlm.nih.gov/pubmed/889813	Binding Agent 1064

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bovine trypanosomiasis 3 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21187912	Curative		Preclinical	HOMIDIUM Approved Use Unknown

PubMed

Title	Date	PubMed
Cytochrome P450 2E1 polymorphism and nasopharyngeal carcinoma development in Thailand: a correlative study.	2001	11389775
Formation of viable but non-culturable state (VBNC) of Aeromonas hydrophila and its virulence in goldfish, Carassius auratus.	2001	11372646
[Study of the structural and structure-functional subdomains in the interphase nucleus by photostabilization].	2001	11347467
Atypical Herpes simplex keratitis (HSK) presenting as a perforated corneal ulcer with a large infiltrate in a contact lens wearer: multinucleated giant cells in the Giemsa smear offered a clue to the diagnosis.	2001	11325340
The relationship of the factor V Leiden mutation or the deletion-deletion polymorphism of the angiotensin converting enzyme to postoperative thromboembolic events following total joint arthroplasty.	2001	11311153
Polymorphisms in the Mn-SOD and EC-SOD genes and their relationship to diabetic neuropathy in type 1 diabetes mellitus.	2001	11299047
A tandem repeats database for bacterial genomes: application to the genotyping of Yersinia pestis and Bacillus anthracis.	2001	11299044
Rotational dynamics of curved DNA fragments studied by fluorescence polarization anisotropy.	2001	11288835
Coordinate regulation of RARgamma2, TBP, and TAFII135 by targeted proteolysis during retinoic acid-induced differentiation of F9 embryonal carcinoma cells.	2001	11285139
Effect of graded hypoxia on cerebral cortical genomic DNA fragmentation in newborn piglets.	2001	11275649
Change of dopamine receptor mRNA expression in lymphocyte of schizophrenic patients.	2001	11252158
Maitotoxin-induced membrane blebbing and cell death in bovine aortic endothelial cells.	2001	11231888
Effect of dyskinetoplastic agents on ultrastructure and oxidative phosphorylation in Crithidia fasciculata.	2001 Apr	11387876
Microvascular endothelial cell death and rarefaction in the glucocorticoid-induced hypertensive rat.	2001 Apr	11379792
Sensitivity of Saccharomyces cerevisiae to tannic acid is due to iron deprivation.	2001 Apr	11358167
Precious things come in little packages.	2001 Apr	11321568
Viewing of complex molecules of ethidium bromide and plasmid DNA in solution by atomic force microscopy.	2001 Apr	11310667
Ca2+ signalling and changes of mitochondrial function during low-Mg2+-induced epileptiform activity in organotypic hippocampal slice cultures.	2001 Apr	11298791
Toxicity of natural tear substitutes in a fully defined culture model of human corneal epithelial cells.	2001 Apr	11274071
[Molecular diagnosis of fragile X syndrome with polymerase chain reaction: application of a diagnostic protocol in 50 families from northern Spain].	2001 Apr	11273816
A single carboxyl mutant of the multidrug transporter EmrE is fully functional.	2001 Apr 20	11278804
Ceramide reduces endothelium-dependent vasodilation by increasing superoxide production in small bovine coronary arteries.	2001 Apr 27	11325875
Mechanism of cyclosporin-induced inhibition of intracellular collagen degradation.	2001 Apr 27	11278659
Characterization of P2 receptors in thymic epithelial cells.	2001 Feb	11292255
Detection of deoxyribonuclease I and II activities in Japanese quail oocytes.	2001 Feb	11273029
In vitro antimalarial activity of novel trifluoromethyl- and bis(trifluoromethyl)quinoline derivatives.	2001 Feb	11258047
New Staphylococcus aureus incompatibility group 1 plasmids encoding penicillinase production and resistance to different antibacterial agents.	2001 Feb	11233798
High-throughput conformation-sensitive gel electrophoresis for discovery of SNPs.	2001 Feb	11233602
A limited loss of DNA compaction accompanying the release of cytoplasm from cells of Escherichia coli.	2001 Jan	11356066
DNA endoreplication in the clustered supramedullary neurons of the pufferfish Diodon holacanthus L. (osteichthyes).	2001 Jan	11352402
Hydration changes for DNA intercalation reactions.	2001 Jan 10	11273594
Mdr1b facilitates p53-mediated cell death and p53 is required for Mdr1b upregulation in vivo.	2001 Jan 18	11313959
Binding mode of 4',6-diamidino-2-phenylindole and ethidium to poly(dG).poly(dC).poly(dC)(+) triplex and poly(dG).poly(dC) duplex.	2001 Jan 26	11342102
Placental protein 14 induces apoptosis in T cells but not in monocytes.	2001 Jul 27	11325960
Depletion of mitochondrial DNA alters glucose metabolism in SK-Hep1 cells.	2001 Jun	11350783
Standardised tests in mice and cattle for the detection of drug resistance in tsetse-transmitted trypanosomes of African domestic cattle.	2001 Jun 12	11390069
Reducible cationic lipids for gene transfer.	2001 Jun 15	11389682
Site-specific charge interactions of alpha-conotoxin MI with the nicotinic acetylcholine receptor.	2001 Jun 29	11323431
Factors affecting quantitation of DNA bands in gels using a charge-coupled device imaging system.	2001 Mar	11332753
Counterion-dye staining method for DNA in agarose gels using crystal violet and methyl orange.	2001 Mar	11332752
Protection of ATP-depleted cells by impermeant strychnine derivatives: implications for glycine cytoprotection.	2001 Mar	11238050
Surface-enhanced Raman spectra study of metal complexes of N-D-glucosamine beta-naphthaldehyde and glycine and their interaction with DNA.	2001 Mar 1	11300567
p53 regulates ceramide formation by neutral sphingomyelinase through reactive oxygen species in human glioma cells.	2001 Mar 15	11313880
[Method of the anomalous time dependence of viscosity for registration of changes in conformational state of Escherichia coli cell genome].	2001 Mar-Apr	11357340
Capillary electrophoresis as a method to study DNA reassociation.	2001 Mar-Apr	11312713
Expression of a P2X7 receptor by a subpopulation of human osteoblasts.	2001 May	11341329
Spatial distribution of vital and dead microorganisms in dental biofilms.	2001 May	11286812
Melittin exerts multiple effects on the release of free fatty acids from L1210 cells: lack of selective activation of phospholipase A2 by melittin.	2001 May 1	11370672
Simple, sensitive and accurate method for the quantification of prothrombin mRNA by using competitive PCR.	2001 May 15	11336642
Ethidium bromide and SYBR Green I enhance the genotoxicity of UV-irradiation and chemical mutagens in E. coli.	2001 May 31	11377248

Patents

Sample Use Guides

In Vivo Use Guide

To investigate trypanocide activity, the drug in 1% or 2% aqueous solutions at a dose of 1 mg/kg was injected subcutaneously on the side of the thorax above the elbow, using cattle of the Shorthorn zebu type.

Route of Administration: Other

In Vitro Use Guide

The dye is usually incorporated into the gel and the electrophoresis buffer at 0.5 µg/ml. Note: Electrophoresis mobility of linear double-stranded DNA is reduced by approximately 15% in the presence of the dye. To stain after gel has been run, immerse gel in electrophoresis buffer or water containing EtBr (0.5 µg/ml) for 30-45 minutes at room temperature. Destaining is optional. Detection of very small amounts (<10 ng) of DNA is made easier if the background fluorescence caused by unbound EtBr is reduced by soaking the stained gel in water or 1 mM MgSO4 for 20 minutes at room temperature.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 15:52:45 GMT 2023` Edited by `admin` on `Sat Dec 16 15:52:45 GMT 2023`
Record UNII	059NUO2Z1L
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

HOMIDIUM BROMIDE

Official Name

English

3,8-DIAMINO-5-ETHYL-6-PHENYLPHENANTHRIDINIUM BROMIDE

Systematic Name

English

HOMIDIUM BROMIDE [HSDB]

Common Name

English

homidium bromide [INN]

Common Name

English

ETHIDIUM BROMIDE

Common Name

English

HOMIDIUM BROMIDE [MART.]

Common Name

English

DROMILAC

Brand Name

English

HOMIDIUM BROMIDE [MI]

Common Name

English

2,7-DIAMINO-9-PHENYL-10-ETHYLPHENANTHRIDINIUM BROMIDE

Systematic Name

English

NSC-268986

Code

English

2,7-DIAMINO-10-ETHYL-9-PHENYLPHENANTHRIDINIUM BROMIDE

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C277