Pramocaine

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Pramocaine
Pramoxine.svg
Systematic (IUPAC) name
4-[3-(4-butoxyphenoxy)propyl]morpholine
Clinical data
AHFS/Drugs.comInternational Drug Names
MedlinePlusa682429
Legal statusOTC (CA) POM (UK) OTC/POM
RoutesTopical, rectal
Identifiers
CAS number140-65-8 N 637-58-1
ATC codeD04AB07 C05AD07
PubChemCID 4886
ChemSpider4717 YesY
UNII068X84E056 YesY
ChEBICHEBI:8357 YesY
ChEMBLCHEMBL1198 YesY
Chemical data
FormulaC17H27NO3 
Mol. mass293.401 g/mol
 N (what is this?)  (verify)
 
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Pramocaine
Pramoxine.svg
Systematic (IUPAC) name
4-[3-(4-butoxyphenoxy)propyl]morpholine
Clinical data
AHFS/Drugs.comInternational Drug Names
MedlinePlusa682429
Legal statusOTC (CA) POM (UK) OTC/POM
RoutesTopical, rectal
Identifiers
CAS number140-65-8 N 637-58-1
ATC codeD04AB07 C05AD07
PubChemCID 4886
ChemSpider4717 YesY
UNII068X84E056 YesY
ChEBICHEBI:8357 YesY
ChEMBLCHEMBL1198 YesY
Chemical data
FormulaC17H27NO3 
Mol. mass293.401 g/mol
 N (what is this?)  (verify)

Pramocaine (INN and BAN, also known as pramoxine or pramoxine HCI) is a topical anesthetic discovered at Abbott Laboratories in 1953[1] and used as an antipruritic. Chemically, it is p-n butoxyphenyl gammamorpholinopropyl ether hydrochloride. During research and development, pramoxine hydrochloride stood out among a series of alkoxy aryl alkamine ethers as an especially good topical local anesthetic agent.[1] Pharmacologic study revealed it to be potent and of low acute and subacute toxicity, well tolerated by most mucous membranes and of a low sensitizing index in man.[1] Like other local anesthetics, paramoxine decreases the permeability of neuronal membranes to sodium ions, blocking both initiation and conduction of nerve impulses. Depolarization and repolarization of excitable neural membranes is thus inhibited, leading to numbness.

The popular itch creams Gold Bond and Calamine Lotion use pramocaine hydrochloride to numb sensitive skin, as does the pain relief variant of Neosporin and some formulations of Sarna. The hydrochloride salt form of pramocaine is water-soluble.

Usage[edit]

Topical anesthetics are used to relieve pain and itching caused by conditions such as sunburn or other minor burns, insect bites or stings, poison ivy, poison oak, poison sumac, and minor cuts and scratches.[2] Pramocaine and dibucaine are also common ingredients in over the counter hemorrhoid preparations.

Notes[edit]

  1. ^ a b c Schmidt JL, Blockus LE, Richards RK. The Pharmacology of Pramoxine Hydrochloride: A New Topical Local Anesthetic. Curr Res Anesth Analg. 1953 Nov-Dec;32(6:1):418-25.
  2. ^ "Pramoxine". MedlinePlus Drug Information. National Library of Medicine. September 25, 2013. Retrieved October 9, 2013. 

See also[edit]