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Details

Stereochemistry ACHIRAL
Molecular Formula C17H27NO3
Molecular Weight 293.4012
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PRAMOXINE

SMILES

CCCCOC1=CC=C(OCCCN2CCOCC2)C=C1

InChI

InChIKey=DQKXQSGTHWVTAD-UHFFFAOYSA-N
InChI=1S/C17H27NO3/c1-2-3-12-20-16-5-7-17(8-6-16)21-13-4-9-18-10-14-19-15-11-18/h5-8H,2-4,9-15H2,1H3

HIDE SMILES / InChI

Molecular Formula C17H27NO3
Molecular Weight 293.4012
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Pramoxine (also known as pramocaine or pramoxine HCI) is a topical anesthetic and antipruritic. Pramoxine is used to temporarily relieve itching and pain caused by minor skin irritation such as minor burns/cuts/scrapes, sunburn, eczema, insect bites, cold sores, or rashes from poison ivy, poison oak, or poison sumac. Some products containing pramoxine are also used to temporarily relieve the itching and discomfort from hemorrhoids and certain other problems of the genital/anal area (such as anal fissures, itching around the vagina/rectum). 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. Pramoxine 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.

CNS Activity

Curator's Comment: If significant quantities of topical anesthetics are absorbed, actions on the central nervous system (CNS) may lead to CNS stimulation and/or CNS depression.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
PRAMOSONE

Approved Use

Use for the temporary relief of pain and itching associated with minor lip or skin irritations (e.g., dermatoses, insect bites, minor burns or sunburns, minor cuts or scrapes, cold sores, hives, rashes due to poison ivy, poison oak, or poison sumac)

Launch Date

1976
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Childhood shingles. Herpes zoster can occur in healthy children too.
2004 Apr
Uncovering tinea incognito. Topical corticosteroids can mask typical features of ringworm.
2004 Jul
Lack of burning and stinging from a novel first-aid formulation applied to experimental wounds.
2004 Mar-Apr
Decreased efficacy of topical anesthetic creams in presence of benzoyl peroxide.
2005 Nov
Treating itch in psoriasis.
2006 Jun
Evaluation of pramoxine ingestion as reported to poison centers.
2006 May
Perioral dermatitis.
2008
A pramoxine-based anti-itch lotion is more effective than a control lotion for the treatment of uremic pruritus in adult hemodialysis patients.
2009
Patents

Sample Use Guides

Adults Dermatologic Conditions Topical As self-medication: Apply gel, lotion, ointment, or solution to the affected area up to 3 or 4 times daily. Fixed combination with hydrocortisone: Apply cream, lotion, or ointment to the affected area as a thin film 3 or 4 times daily.
Route of Administration: Topical
In Vitro Use Guide
Pramoxine (1.36 x 10(-5) M) caused attenuation of the response to substance P, the responses to acetylcholine, histamine and barium chloride in guinea-pig ileum.
Substance Class Chemical
Created
by admin
on Sat Dec 16 17:05:23 GMT 2023
Edited
by admin
on Sat Dec 16 17:05:23 GMT 2023
Record UNII
068X84E056
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PRAMOXINE
MI   VANDF  
Common Name English
PRAMOXINE [MI]
Common Name English
PRAMOCAINE
INN   WHO-DD  
INN  
Official Name English
4-(3-(P-BUTOXYPHENOXY)PROPYL)MORPHOLINE
Common Name English
PRAMOXINE [VANDF]
Common Name English
pramocaine [INN]
Common Name English
Pramocaine [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C245
Created by admin on Sat Dec 16 17:05:23 GMT 2023 , Edited by admin on Sat Dec 16 17:05:23 GMT 2023
WHO-ATC C05AD07
Created by admin on Sat Dec 16 17:05:23 GMT 2023 , Edited by admin on Sat Dec 16 17:05:23 GMT 2023
WHO-ATC D04AB07
Created by admin on Sat Dec 16 17:05:23 GMT 2023 , Edited by admin on Sat Dec 16 17:05:23 GMT 2023
WHO-VATC QC05AD07
Created by admin on Sat Dec 16 17:05:23 GMT 2023 , Edited by admin on Sat Dec 16 17:05:23 GMT 2023
WHO-VATC QD04AB07
Created by admin on Sat Dec 16 17:05:23 GMT 2023 , Edited by admin on Sat Dec 16 17:05:23 GMT 2023
Code System Code Type Description
RXCUI
34347
Created by admin on Sat Dec 16 17:05:23 GMT 2023 , Edited by admin on Sat Dec 16 17:05:23 GMT 2023
PRIMARY RxNorm
NCI_THESAURUS
C61903
Created by admin on Sat Dec 16 17:05:23 GMT 2023 , Edited by admin on Sat Dec 16 17:05:23 GMT 2023
PRIMARY
LACTMED
Pramoxine
Created by admin on Sat Dec 16 17:05:23 GMT 2023 , Edited by admin on Sat Dec 16 17:05:23 GMT 2023
PRIMARY
SMS_ID
100000081415
Created by admin on Sat Dec 16 17:05:23 GMT 2023 , Edited by admin on Sat Dec 16 17:05:23 GMT 2023
PRIMARY
EVMPD
SUB09994MIG
Created by admin on Sat Dec 16 17:05:23 GMT 2023 , Edited by admin on Sat Dec 16 17:05:23 GMT 2023
PRIMARY
DAILYMED
068X84E056
Created by admin on Sat Dec 16 17:05:23 GMT 2023 , Edited by admin on Sat Dec 16 17:05:23 GMT 2023
PRIMARY
EPA CompTox
DTXSID8040692
Created by admin on Sat Dec 16 17:05:23 GMT 2023 , Edited by admin on Sat Dec 16 17:05:23 GMT 2023
PRIMARY
MESH
C005548
Created by admin on Sat Dec 16 17:05:23 GMT 2023 , Edited by admin on Sat Dec 16 17:05:23 GMT 2023
PRIMARY
DRUG CENTRAL
3487
Created by admin on Sat Dec 16 17:05:23 GMT 2023 , Edited by admin on Sat Dec 16 17:05:23 GMT 2023
PRIMARY
DRUG BANK
DB09345
Created by admin on Sat Dec 16 17:05:23 GMT 2023 , Edited by admin on Sat Dec 16 17:05:23 GMT 2023
PRIMARY
CHEBI
8357
Created by admin on Sat Dec 16 17:05:23 GMT 2023 , Edited by admin on Sat Dec 16 17:05:23 GMT 2023
PRIMARY
ECHA (EC/EINECS)
205-425-7
Created by admin on Sat Dec 16 17:05:23 GMT 2023 , Edited by admin on Sat Dec 16 17:05:23 GMT 2023
PRIMARY
CAS
140-65-8
Created by admin on Sat Dec 16 17:05:23 GMT 2023 , Edited by admin on Sat Dec 16 17:05:23 GMT 2023
PRIMARY
WIKIPEDIA
PRAMOCAINE
Created by admin on Sat Dec 16 17:05:23 GMT 2023 , Edited by admin on Sat Dec 16 17:05:23 GMT 2023
PRIMARY
INN
235
Created by admin on Sat Dec 16 17:05:23 GMT 2023 , Edited by admin on Sat Dec 16 17:05:23 GMT 2023
PRIMARY
MERCK INDEX
m9099
Created by admin on Sat Dec 16 17:05:23 GMT 2023 , Edited by admin on Sat Dec 16 17:05:23 GMT 2023
PRIMARY Merck Index
PUBCHEM
4886
Created by admin on Sat Dec 16 17:05:23 GMT 2023 , Edited by admin on Sat Dec 16 17:05:23 GMT 2023
PRIMARY
FDA UNII
068X84E056
Created by admin on Sat Dec 16 17:05:23 GMT 2023 , Edited by admin on Sat Dec 16 17:05:23 GMT 2023
PRIMARY
ChEMBL
CHEMBL1198
Created by admin on Sat Dec 16 17:05:23 GMT 2023 , Edited by admin on Sat Dec 16 17:05:23 GMT 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY