Domiphen Bromide | CAS#538-71-6 | Antifungal

MedKoo Cat#: 531017 | Name: Domiphen Bromide

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Domiphen bromide is a quaternary antiseptic used as an antifungal agent. Domiphen bromide has potent activity on blockade of human ether-a-go-go related gene (HERG) channels. Domiphen bromide inhibited HERG channel currents in a dose-dependent manner with IC50 values of 9nM. Block of HERG channel by domiphen bromide was voltage-dependent and use-dependent. Domiphen bromide caused substantial negative shift of the activation curves, accelerated activated process, but had no effects on the deactivation and reactivation processes.

Chemical Structure

Domiphen Bromide

CAS#538-71-6 (bromide)

Theoretical Analysis

MedKoo Cat#: 531017

Name: Domiphen Bromide

CAS#: 538-71-6 (bromide)

Chemical Formula: C22H40BrNO

Exact Mass: 0.0000

Molecular Weight: 414.47

Elemental Analysis: C, 63.75; H, 9.73; Br, 19.28; N, 3.38; O, 3.86

Price and Availability

Size	Price	Availability	Quantity
10g	USD 250.00	2 weeks
25g	USD 450.00	2 weeks

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Related CAS #

538-71-6 (bromide) 13900-14-6 (cation)

Synonym

Domiphen; Domiphen Br; Domiphen bromide; Bradasol; Fungitex; Oradol; PDDB; NSC 39415; NSC39415; NSC-39415

IUPAC/Chemical Name

N,N-dimethyl-N-(2-phenoxyethyl)dodecan-1-aminium bromide

InChi Key

OJIYIVCMRYCWSE-UHFFFAOYSA-M

InChi Code

InChI=1S/C22H40NO.BrH/c1-4-5-6-7-8-9-10-11-12-16-19-23(2,3)20-21-24-22-17-14-13-15-18-22;/h13-15,17-18H,4-12,16,19-21H2,1-3H3;1H/q+1;/p-1

SMILES Code

CCCCCCCCCCCC[N+](C)(C)CCOC1=CC=CC=C1.[Br-]

Appearance

White to off-white crystalline powder.

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Domiphen bromide is a chemical antiseptic and a quaternary ammonium compound, used as a cationic surfactant.

In vitro activity:

This study characterized the antiplasmodial activity of domiphen bromide (DB), another MEP pathway inhibitor with a rapid mode of action that arrests the in vitro growth of Plasmodium falciparum at the early trophozoite stage. Reference: Pharmaceutics. 2022 Jun 22;14(7):1320. https://pubmed.ncbi.nlm.nih.gov/35890216/

In vivo activity:

Moreover, in vivo rabbit ECG data demonstrated that 12.85 mg/kg BZT and 3.85 mg/kg DMP (domiphen bromide) evoked QTc prolongation, noncomplex arrhythmias and ventricular tachycardias. These findings support the cardiac safety of 0.01 μM BZT/DMP in vitro and the intravenous infusion of 3.85 mg/kg BZT and 1.28 mg/kg DMP in vivo, whereas higher concentrations of both compounds cause mild to moderate cardiotoxicity that should not be neglected during medical and industrial applications. Reference: Toxicol Appl Pharmacol. 2021 Nov 15;431:115731. https://pubmed.ncbi.nlm.nih.gov/34592322/

	Solvent	mg/mL	mM
Solubility
	DMSO	91.5	220.76
	Ethanol	83.0	200.25
	Water	91.5	220.76

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 414.47 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Biosca A, Ramírez M, Gomez-Gomez A, Lafuente A, Iglesias V, Pozo OJ, Imperial S, Fernàndez-Busquets X. Characterization of Domiphen Bromide as a New Fast-Acting Antiplasmodial Agent Inhibiting the Apicoplastidic Methyl Erythritol Phosphate Pathway. Pharmaceutics. 2022 Jun 22;14(7):1320. doi: 10.3390/pharmaceutics14071320. PMID: 35890216; PMCID: PMC9319574. 2. Biosca A, Dirscherl L, Moles E, Imperial S, Fernàndez-Busquets X. An ImmunoPEGliposome for Targeted Antimalarial Combination Therapy at the Nanoscale. Pharmaceutics. 2019 Jul 16;11(7):341. doi: 10.3390/pharmaceutics11070341. PMID: 31315185; PMCID: PMC6680488. 3. Long Y, Hou J, Tang F, Lin Z, Huang X, Li W, Chen Y, Li Z, Wu Z. Proarrhythmic effects induced by benzethonium chloride and domiphen bromide in vitro and in vivo. Toxicol Appl Pharmacol. 2021 Nov 15;431:115731. doi: 10.1016/j.taap.2021.115731. Epub 2021 Sep 27. PMID: 34592322.

In vitro protocol:

In vivo protocol:

1. Long Y, Hou J, Tang F, Lin Z, Huang X, Li W, Chen Y, Li Z, Wu Z. Proarrhythmic effects induced by benzethonium chloride and domiphen bromide in vitro and in vivo. Toxicol Appl Pharmacol. 2021 Nov 15;431:115731. doi: 10.1016/j.taap.2021.115731. Epub 2021 Sep 27. PMID: 34592322.

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