536-43-6 Usage
Description
Dyclonine hydrochloride is the hydrochloride salt of Dyclonine, an oral anesthetic agent. It is an active ingredient in products like "Sucrets" and some Cepacol sore throat sprays. Dyclonine exerts its effects by reversibly binding to activated sodium channels on neuronal membranes, decreasing sodium permeability, and increasing the excitation threshold. This leads to membrane stabilization, inhibition of depolarization, and suppression of action potential propagation, resulting in a temporary and reversible local anesthetic effect.
Uses
Used in Pharmaceutical Industry:
Dyclonine hydrochloride is used as an oral anesthetic for the temporary relief of occasional mouth and throat symptoms such as pain, minor irritation, sore mouth, and sore throat. It acts as a sodium channel blocker and a HSP90 chaperone protein inhibitor, demonstrating local anesthetic effects in vivo and being orally active.
Used in Medical Procedures:
Dyclonine hydrochloride provides anesthesia of mucous membranes. It can be applied 5 to 10 minutes before a procedure and used b.i.d. to t.i.d. for pain relief. The onset of action occurs within 2 to 10 minutes, and the anesthesia lasts for 30 to 60 minutes.
Used in Neuroprotection:
Dyclonine enhances neuronal mitochondrial function, potentiating respiration and offering protection against neurodegenerative disorders.
Used in Cancer Therapy:
Dyclonine inhibits aldehyde dehydrogenase ALDH3A1, leading to the accumulation of 4-hydroxynonenal. This renders head and neck squamous cell carcinoma cells sensitive to the cystine-glutamate antiporter inhibitor, sulfasalazine.
Used in Rare Disease Treatment:
Dyclonine rescues frataxin deficiency in animal models and buccal cells of patients with Friedreich's Ataxia.
Used in Enhancing Cancer Cell Cytotoxicity:
Dyclonine enhances the cytotoxic effect of proteasome inhibitors like MG-132 and bortezomib in cancer cells.
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.
References
https://en.wikipedia.org/wiki/Dyclonine
https://pubchem.ncbi.nlm.nih.gov/compound/Dyclonine_hydrochloride#section=Top
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
Originator
Dyclone,Dow,US,1956
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.
Therapeutic Function
Local anesthetic
Check Digit Verification of cas no
The CAS Registry Mumber 536-43-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,3 and 6 respectively; the second part has 2 digits, 4 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 536-43:
(5*5)+(4*3)+(3*6)+(2*4)+(1*3)=66
66 % 10 = 6
So 536-43-6 is a valid CAS Registry Number.
InChI:InChI=1/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
