Dyclonine hydrochloride Chemical Properties

Melting point:

175-176°C

storage temp. 

Inert atmosphere,2-8°C

solubility 

Soluble in DMSO (20 mg/ml); Water (25 mg/ml)

form 

solid

color 

White

Water Solubility 

Partly soluble in water. Soluble in chloroform, ethanol, acetone and methanol.

Merck 

14,3473

Stability:

Stable for 2 years from date of purchase as supplied. Solutions in DMSO or distilled water may be stored at -20°C for up to 2 months.

InChI

InChI=1S/C18H27NO2.ClH/c1-2-3-15-21-17-9-7-16(8-10-17)18(20)11-14-19-12-5-4-6-13-19;/h7-10H,2-6,11-15H2,1H3;1H

InChIKey

KNZADIMHVBBPOA-UHFFFAOYSA-N

SMILES

C1(C(=O)CCN2CCCCC2)C=CC(OCCCC)=CC=1.Cl

CAS DataBase Reference

536-43-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-37/38-41

Safety Statements 

26-36

RIDADR 

3249

WGK Germany 

3

RTECS 

UG8750000

HazardClass 

6.1(b)

PackingGroup 

III

HS Code 

2933399090

MSDS

• Language:English Provider:SigmaAldrich

Dyclonine hydrochloride Usage And Synthesis

Description

Dyclonine hydrochloride is the hydrochloride salt of Dyclonine. Dyclonine belongs to a kind of oral anaesthetic. It is contained in the “Sucrets” as well as some kinds of Cepacol sore throat spray as an active ingredient. Dyclonine takes effect through reversibly binding to the activated sodium channels located on the neuronal membrane. This decreases the permeability of sodium across the neuronal membrane, further increasing the threshold for excitation. Overall, Dyclonine stabilizes the membrane and inhibits depolarization, resulting in the failure of a propagated action potential and further suppressing the subsequent conduction. This causes a transient and reversible anaesthetic effect in a local area of the body.

Chemical Properties

Dyclonine hydrochloride is a white crystalline powder possessing topical anesthetic properties characterized by rapid onset of effect, lack of systemic toxicity and a low index of sensitization.

Indications

Dyclonine hydrochloride is a ketone derivative without an ester or amide linkage that may be used in patients who are allergic to the common anesthetics. Dyclonine offers advantages over other topical anesthetic agents.Extensive experience with the topical preparation has shown it to be effective and safe. As a topical anesthetic, dyclonine hydrochloride is available by prescription, and to patients it is available over-the-counter in Sucrets lozenges.
Classification: Ketone.
Available concentration: Formulated for use in dentistry as a 0.5% or 1% solution.
Onset of action: Slow; may take up to 10 minutes to become effective. Duration: Average duration of 30 minutes; however, effects may last up to 1 hour.
Maximum recommended dose: 200 mg (40 mL of 0.5% solution or 20 mL of a 1% solution).
Metabolism/excretion: No information is available on the metabolism and excretion of dyclonine hydrochloride.
Pregnancy/lactation: FDA Category C/Caution is recommended during lactation.

Uses

Dyclonine hydrochloride is used for the temporary relief of the following occasional mouth and throat symptoms: pain, minor irritation, sore mouth and sore throat. It is a sodium channel blocker and a HSP90 chaperone protein inhibitor. It shows local anesthetic effects in vivo and is orally active.

References

https://en.wikipedia.org/wiki/Dyclonine
https://pubchem.ncbi.nlm.nih.gov/compound/Dyclonine_hydrochloride#section=Top

Description

Dyclonine (536-43-6) is a? topical anesthetic which has been used for oral and throat analgesia.1 Enhances neuronal mitochondrial function, potentiating respiration and providing protection against insults associated with neurodegenerative disorders.2 Inhibits aldehyde dehydrogenase ALDH3A1 resulting in accumulation of 4-hydroxynonenal, which renders head and neck squamous cell carcinoma cells sensitive to the cystine-glutamate antiporter inhibitor, sulfasalazine.3 Rescues frataxin deficiency in animal models as well as in buccal cells of patients with Friedreich’s Ataxia.4 Enhances the cytotoxic effect of proteasome inhibitors MG-1325 and bortezomib6 in cancer cells.

Chemical Properties

White Crystalline Solid

Originator

Dyclone,Dow,US,1956

Uses

Provides anesthesia of mucous membranes. Apply 5 to 10 minutes before a procedure; apply b.i.d. to t.i.d. for pain relief. Onset of action is within 2 to 10 minutes. Anesthesia lasts 30 to 60 minutes.

Uses

anesthetic (topical)

Uses

Used as a local anesthetic

Uses

Dyclonine hydrochloride is used for the temporary relief of the following occasional mouth and throat symptoms: pain, minor irritation, sore mouth and sore throat. It is a sodium channel blocker and a HSP90 chaperone protein inhibitor. It shows local anesthetic effects in vivo and is orally active.

Definition

ChEBI: The hydrochloride salt of dyclonine.

Manufacturing Process

A mixture of 17.6 grams of p-n-butoxyacetophenone, 12.1 grams of piperidine hydrochloride, 4.5 grams paraformaldehyde, 0.25 cc concentrated hydrochloric acid, 52.5 cc nitroethane, 7.5 cc of 95% ethanol, and 15 cc of toluene was boiled under reflux for one hour, removing water formed in the reaction by means of a condensate trap. The mixture was then cooled. The crystals which formed were collected by filtration, washed with anhydrous ether and recrystallized from methyl ethyl ketone. The crystals thus obtained, which melted at 174-175°C, were shown by analysis to be 4-n-butoxy-β- piperidinopropiophenone hydrochloride.

brand name

Dyclone (AstraZeneca).

Therapeutic Function

Local anesthetic

References

Groeben et al. (2001), Airway anesthesia alone does not explain attenuation of histamine-induced bronchospasm by local anesthetics: a comparison of lidocaine, ropivacaine, and dyclonine; Anesthesiology, 94 423 Boglarka et al. (2020), High-Throughput Small Molecule Screen Identifies Modulators of Mitochondrial Function in Neurons; iScience, 23 100931 Okazaki et al. (2018), Synthetic lethality of the ALDH3A1 inhibitor dyclonine and xCT inhibitors in glutathione deficiency-resistant cancer cells; Oncotarget, 9 33832 Sahdeo et al. (2014), Dyclonine rescues frataxin deficiency in animal models and buccal cells of patients with Friedriech’s ataxia; Hum. Mol. Genet., 23 6848 Ju et al. (2009), Dyclonine and alverine citrate enhance the cytotoxic effects of proteasome inhibitor MG132 on breast cancer cells; J. Mol. Med., 23 205 Ju et al. (2014), Dyclonine enhances the cytotoxic effect of proteasome inhibitor bortezomib in multiple myeloma cells; Mol. Med. Rep., 10 2609

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