Skip to content
Vinony
English
EnglishEspañolFrançaisNederlandsPolskiPortuguêsTiếng Việtالعربية中文日本語
pramoxine

Structure via PubChem · Public domain (PubChem)

EntityQ1240076· pop 14· linked from 63 articles

pramoxine

Sign in to save

Also known as p-butoxyphenyl gamma-morpholinopropyl ether, gamma-morpholinopropyl 4-n-butoxyphenyl ether, proxazocain, pramocaine

Pramocaine (INN and BAN, also known as pramoxine or pramoxine HCl) is a topical anesthetic discovered at Abbott Laboratories in 1953 and used as an antipruritic. During research and development, pramocaine hydrochloride stood out among a series of alkoxy aryl alkamine ethers as an especially good topical local anesthetic agent. 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 humans. Like other local anesthetics, pramocaine decreases the permeability of neuronal membranes to sodium ion

Chemical data

Formula
C17H27NO3
Molecular weight
293.4 g/mol
IUPAC name
4-[3-(4-butoxyphenoxy)propyl]morpholine
SMILES
CCCCOC1=CC=C(C=C1)OCCCN2CCOCC2
InChIKey
DQKXQSGTHWVTAD-UHFFFAOYSA-N
XLogP
3.1
Polar surface area
30.9 Ų
H-bond donors
0
H-bond acceptors
4
Formal charge
0

via PubChem

Drug data · ChEMBL

Max clinical phase
Approved
Molecule type
Small molecule
First approval
1976
Admin. routes
topical
Indications
Pruritus, hemorrhoid

via ChEMBL · EBI

Research

75 papers

via PubMed

Wikidata facts

Subclass of
chemical compound
Mass
293.199
Show 4 more facts
medical condition treated
hemorrhoid
chemical formula
C₁₇H₂₇NO₃
canonical SMILES
CCCCOC1=CC=C(C=C1)OCCCN2CCOCC2
subject has role
local anesthetic
Sources (2)

via Wikidata · CC0

~2 min read

Encyclopedic overview

4 sections
Contents
  • Use
  • Synthesis
  • See also
  • References

Pramocaine (INN and BAN, also known as pramoxine or pramoxine HCl) is a topical anesthetic discovered at Abbott Laboratories in 1953 and used as an antipruritic. During research and development, pramocaine hydrochloride stood out among a series of alkoxy aryl alkamine ethers as an especially good topical local anesthetic agent. 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 humans. Like other local anesthetics, pramocaine 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. Notably, pramocaine is chemically distinct from other local anesthetics, being neither an amino amide nor an amino ester.

== Use ==

Excerpted from Wikipedia’s “pramoxine” article, available under the CC BY-SA 4.0 licence.

Gallery (2)

Available in 14 languages

via Wikidata sitelinks · CC0