Propoxycaine
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Propoxycaine
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CAS No:
86-43-1
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Formula:
C16H26N2O3
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Chemical Name:
Propoxycaine
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Synonyms:
Benzoic acid,4-amino-2-propoxy-,2-(diethylamino)ethyl ester;Blockain;2-Diethylaminoethyl 4-amino-2-propoxybenzoate;2′-Diethylaminoethyl 2-propoxy-4-aminobenzoate;Pravocaine;Ravocaine;Propoxycaine;Ranocaine
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CAS No:
Description
Propoxycaine is a benzoate ester.|Propoxycaine is a local anesthetic of the ester type that has a rapid onset of action and a longer duration of action than procaine hydrochloride. This drug was removed from the US market in 1996. Although no longer available in the United States, this medication was used in combination with procaine to aid in anesthesia during dental procedures. Used in combination with procaine, it was the only dental local anesthetic available in cartridge form.|Propoxycaine is a para-aminobenzoic acid ester with local anesthetic activity. Propoxycaine binds to and inhibits voltage-gated sodium channels, thereby inhibiting the ionic flux required for the initiation and conduction of impulses. This results in a loss of sensation.|A local anesthetic of the ester type that has a rapid onset of action and a longer duration of action than procaine hydrochloride. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1017)
Toxicity
The toxicity of this medication (7-8 times higher than that of procaine), has prevented this medication from being used on its own. Ester-type local anesthetics are much more likely to cause an allergic reaction compared to the amide-group local anesthetics because of the formation of PABA (Para-aminobenzoic acid) during the metabolic process. PABA may cause allergic reactions that range from urticaria to anaphylaxis. PABA is also formed during the metabolism of methylparaben (a common preservative) that is normally found in multi-dose vials including lidocaine (MDV) (amide-type local anesthetic).
Drug Information
Propoxycaine is a local anesthetic medication. It was used beginning in the 1950s during dental procedures. It has been combined with procaine to accelerate its onset of action and provide longer-lasting anesthetic effect. It was produced for use when amide local anesthetics were contraindicated due to allergy or when several amide anesthetics were unsuccessful.
Propoxycaine is a local anesthetic which acts to decrease nerve impulses and therefore pain sensation during dental procedures.
Drugs that block nerve conduction when applied locally to nerve tissue in appropriate concentrations. They act on any part of the nervous system and on every type of nerve fiber. In contact with a nerve trunk, these anesthetics can cause both sensory and motor paralysis in the innervated area. Their action is completely reversible. (From Gilman AG, et. al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 8th ed) Nearly all local anesthetics act by reducing the tendency of voltage-dependent sodium channels to activate. (See all compounds classified as Anesthetics, Local.)
Renal|Via the kidneys, primarily hydrolyzed.
This drug his hydrolyzed in both the plasma and the liver by plasma esterases.
Propoxycaine is a para-aminobenzoic acid ester with local anesthetic activity. Propoxycaine binds to and blocks voltage-gated sodium channels, thereby inhibiting the ionic flux essential for the conduction of nerve impulses. This results in a loss of sensation. In one study, propoxycaine hydrochloride increased annular lipid fluidity in cell lipid bilayers and had a greater fluidizing effect on the inner monolayer than that of the outer monolayer. This may further confirm its role in modulating neural impulses.
Hydrochloride, Propoxycaine
Computed Properties
Molecular Weight:294.39
XLogP3:3.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:10
Exact Mass:294.19434270
Monoisotopic Mass:294.19434270
Topological Polar Surface Area:64.8
Heavy Atom Count:21
Complexity:295
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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