Prilocaine

Prilocaine, which is equal in potency to lidocaine, has a longer duration of action. It is metabolized to o-toluidine, which in toxic doses may cause methemoglobinemia. 

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Prilocaine hydrochloride [1786-81-8] is also similar in profile to Hdocaine, although prilocaine has significantly less vasodilator activity. Prilocaine is the least toxic of the amino amide local anesthetics. However, its tendency to cause methemoglobinemia, especially in newborns, has eliminated its use in obstetric surgery. 

Appllca.tlons. Various A/-derivatives of amino acids (qv) are resolvable on BSA columns. These /V-amino acid derivatives include ben2enesulfonyl-, phthalimido-, S-dimethylarnino-l-naphthalenesulfonyl- (DANSYL-), 2,4-dinitrophenyl- (DNP-), and 2,3,6-trinitrophenyl- (TNP-) derivatives (30). Amines such as Prilocain, ( )-2-(prop5lamino)-(9-propiono-toluidide, a local anesthetic (Astra Pharm. Co.), are also resolved on BSA. The aromatic amino acids DL-tryptophan, 5-hydroxy-DL-tryptophan, DL-kynurenine [343-65-7] C qH 2N 2 3 3-hydroxy-DT.-kynurenine [484-78-6] and dmgs... 

Acylation of ortho-toluidine with 2-bromopropionyl bromide Ifords the haloamide (73). Displacement of the halogen by ii uns of butylamine affords prilocaine (74). ... 

Prilocaine 1, 17 Primaquine 1, 346 Primidolol 29 Primidone j, 276 Prizidilol 151 Probarbital 268... 

Prilocaine local anesthetic. S(-r)-isomer slowly hydrolyzed by amidase... 

Another topical anesthetic, similar to benzocaine, is lidocaine, which is used to relieve the pain of shingles (herpes zoster) infections. Lidocaine is called an amide anesthetic, because it is not an ester (the alcohol is replaced by an amide, the nitrogen group). Amide anesthetics are metabolized by the liver, and are less prone to cause allergic reactions. If an anesthetic has the letter i in the prefix (lidocaine, prilocaine, bupivacaine), it is an amide anesthetic. 

Some other anesthetics with similar structures are prilocaine, tetracaine, ropivacaine, bupivacaine, chloroprocaine, and mepivacaine ... 

CijHisBrO, 92905-04-9) see Domiodol 2-bromo-lV-(2-methylphenyl)propanamide (C nH 2BrNO 19397-79-6) see Prilocaine... 

C7H4Br20 563-76-8) see Prilocaine Propyramazine bromide Tiopronin Tocainide... 

C Hi N I07-W-H) see Carticaine Cropropamide Etidocaine Prilocaine Propafenone propyl benzenesulfonate (CjHijOjS KO-42-2) see Propoxycaine propyl bromide... 

Since TCA in higher concentrations tends to produce increased scarring and hypopigmenta-tion, 70% glycolic acid solution was applied to the entire face of patients and diluted with water after 2 min. This was followed by the sequential application of EMLA cream (lidocaine 2.5% and prilocaine 2.5%) or ELA-Max cream (lidocaine 4%) to selected areas on the face for 30 min without occlusion. These agents were then removed and 35% TCA was applied to the entire face [10]. 

Local Anesthetics. Local anesthetics used in anesthesiology are currently amide derivatives (lidocaine, mepivacaine, prilocaine, bupivacaine, levobupivacaine. 

Benzocaine, cetacaine, EMLA cream, lidocaine, prilocaine, and... 

Procaine Amethocaine Lidocaine Prilocaine Bupivicaine Ropivicaine Mepivicaine... 

Schmidt SH, Anniko M, Hellstrom S. 1990. Electrophysiological effects of the clinically used local anesthetics lidocaine, lidocaine-prilocaine and phenol on the rat s inner ear. Eur Arch Otorhinolaryngol 248 87-94. 

Prilocaine (4.138), a chiral local anesthetic, was hydrolyzed stereoselec-tively at its amide bond. Indeed, the plasma concentrations of the (-)-(/ )-enantiomer were lower than those of the (+)-(5 )-enantiomer after i.v. administration in the cat. In vitro studies of liver preparations from various mammals confirmed that the (R)-isomer was hydrolyzed at much higher rates than the (.S )-form [84],... 

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