Pramocaine

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Pramocaine
Clinical data
AHFS/Drugs.comInternational Drug Names
MedlinePlusa682429
Routes of
administration
Topical, rectal, Vaginal
ATC code
Legal status
Legal status
  • CA: OTC
  • UK: POM (Prescription only)
  • OTC/POM
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
ChEMBL
E number{{#property:P628}}
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Chemical and physical data
FormulaC17H27NO3
Molar mass293.401 g/mol
3D model (JSmol)
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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

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

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.

Synthesis

Pramoxine synthesis:[3]

See also

Notes

  1. 1.0 1.1 1.2 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.
  3. Template:Cite doi


Template:Vasoprotectives Template:Antipruritics