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Pramoxine

Pramoxine structure

CAS No:
140-65-8
Formula:
C17H27NO3
Chemical Name:
Pramoxine
Synonyms:
Morpholine,4-[3-(4-butoxyphenoxy)propyl]-;Morpholine,4-[3-(p-butoxyphenoxy)propyl]-;Pramoxine;4-[3-(4-Butoxyphenoxy)propyl]morpholine;4-[3-(p-Butoxyphenoxy)propyl]morpholine;p-Butoxyphenyl γ-morpholinopropyl ether;γ-Morpholinopropyl 4-n-butoxyphenyl ether;Pramocaine;Tronopthane;Pallisan;Pramocain;Pramoxin;Tronotene;Proxazocain;4-[3-(4-Butoxyphenoxy)propyl]-morpholine
Categories:
Pharmaceutical Intermediates > Bulk Drug Intermediates

Description

Pramocaine is a member of the class of morpholines that is morpholine substituted at the nitrogen atom by a 3-(4-butoxyphenoxy)propyl group. It has a role as a local anaesthetic. It is a member of morpholines and an aromatic ether.|Pramocaine (also known as pramoxine or pramoxine HCI) is a topical anesthetic and antipruritic. It is used for many dermatological and anorectal/anogenital conditions including minor cuts/burns, insect bites, hives/rashes due to poison ivy exposure, hemorrhoids and other anorectal/anogenital disorders. Pramocaine is available by itself and in combination with other medications in various topical preparations. It works by preventing ionic fluctuations needed for neuron membrane depolarization and action potential propagation.|Pramocaine is a morpholine derivative with local anesthetic property. Pramocaine decreases the permeability of the neuronal membrane to sodium ions by reversibly binding to and inhibiting voltage-gated sodium channels. This results in stabilization of the membrane and, thereby inhibiting the ionic fluxes required for membrane depolarization, hence resulting in the failure to initiate a propagated action potential and subsequent conduction blockade.

Pramoxine Basic Attributes

Molecular Weight：

293.40100

Exact Mass：

293.40

EC Number：

205-425-7

UNII：

068X84E056

DSSTox ID：

DTXSID8040692

NCI Thesaurus Code：

C61903

ATC Code：

C - Cardiovascular system|D - Dermatologicals

HScode：

2934999090

Characteristics

PSA：

30.93000

XLogP3：

2.90450

Density：

1.031g/cm3

Boiling Point：

196 °C

Flash Point：

123.5ºC

Refractive Index：

1.505

Vapor Pressure：

1.7E-07mmHg at 25°C

Toxicity

Toxicity Summary：

LD50 Mouse ip 300 mg/kg, LD50 Mouse sc 750 mg/kg

Drug Information

Drug Indication：

It is indicated for temporary relief of pain and pruritus from minor lip and skin irritations as well as for temporary relief from pain, burning, itching and discomfort associated with hemorrhoids and other anorectal/anogenital disorders.

Pharmacology：

Pramocaine temporarily relieves pain, pruritis, burning and discomfort associated with minor lip and skin irritations and hemorrhoid's by inhibiting voltage gated sodium channels on neurons.

MeSH：

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.)

Absorption：

There is minimal absorption after topical administration and it is not given orally.

Mechanism of Action：

Pramocaine reversibly binds and inhibits voltage gated sodium channels on neurons decreasing sodium permeability into the cell. This stabilizes the membrane and prevents ionic fluctuations needed for depolarization stopping any action potential propagation.

MeSH Entry Terms：

4-(3-(4-butoxyphenoxy)propyl)morpholine

Pramoxine Use and Manufacturing

Use Classification：

Pharmaceuticals

Computed Properties

Molecular Weight:293.4
XLogP3:3.1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:9
Exact Mass:293.19909372
Monoisotopic Mass:293.19909372
Topological Polar Surface Area:30.9
Heavy Atom Count:21
Complexity:248
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes