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Details

Stereochemistry ACHIRAL
Molecular Formula C17H27NO3
Molecular Weight 293.4018
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PRAMOXINE

SMILES

CCCCOc1ccc(cc1)OCCCN2CCOCC2

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
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

2.087424E11
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Contact irritant dermatitis and anti-pruritic agents: the need to address the itch.
2003 Apr
Anorectal drug products for over-the-counter human use. Final rule.
2003 Aug 26
Evidence-based veterinary dermatology: a systematic review of the pharmacotherapy of canine atopic dermatitis.
2003 Jun
Childhood shingles. Herpes zoster can occur in healthy children too.
2004 Apr
An evaluation of the moisturizing and anti-itch effects of a lactic acid and pramoxine hydrochloride cream.
2004 Feb
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
Prediction of pharmacological and xenobiotic responses to drugs based on time course gene expression profiles.
2009 Dec 2
Management of side effects associated with sunitinib therapy for patients with renal cell carcinoma.
2009 Feb 18
Psychological interventions in the management of common skin conditions.
2010
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.
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
PRAMOCAINE [WHO-DD]
Common Name English
PRAMOXINE [VANDF]
Common Name English
PRAMOCAINE [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C245
Created by admin on Sat Jun 26 14:03:08 UTC 2021 , Edited by admin on Sat Jun 26 14:03:08 UTC 2021
WHO-ATC C05AD07
Created by admin on Sat Jun 26 14:03:08 UTC 2021 , Edited by admin on Sat Jun 26 14:03:08 UTC 2021
WHO-ATC D04AB07
Created by admin on Sat Jun 26 14:03:08 UTC 2021 , Edited by admin on Sat Jun 26 14:03:08 UTC 2021
WHO-VATC QC05AD07
Created by admin on Sat Jun 26 14:03:08 UTC 2021 , Edited by admin on Sat Jun 26 14:03:08 UTC 2021
WHO-VATC QD04AB07
Created by admin on Sat Jun 26 14:03:08 UTC 2021 , Edited by admin on Sat Jun 26 14:03:08 UTC 2021
Code System Code Type Description
RXCUI
34347
Created by admin on Sat Jun 26 14:03:08 UTC 2021 , Edited by admin on Sat Jun 26 14:03:08 UTC 2021
PRIMARY RxNorm
NCI_THESAURUS
C61903
Created by admin on Sat Jun 26 14:03:08 UTC 2021 , Edited by admin on Sat Jun 26 14:03:08 UTC 2021
PRIMARY
LACTMED
Pramoxine
Created by admin on Sat Jun 26 14:03:08 UTC 2021 , Edited by admin on Sat Jun 26 14:03:08 UTC 2021
PRIMARY
EVMPD
SUB09994MIG
Created by admin on Sat Jun 26 14:03:08 UTC 2021 , Edited by admin on Sat Jun 26 14:03:08 UTC 2021
PRIMARY
EPA CompTox
140-65-8
Created by admin on Sat Jun 26 14:03:08 UTC 2021 , Edited by admin on Sat Jun 26 14:03:08 UTC 2021
PRIMARY
MESH
C005548
Created by admin on Sat Jun 26 14:03:08 UTC 2021 , Edited by admin on Sat Jun 26 14:03:08 UTC 2021
PRIMARY
DRUG CENTRAL
3487
Created by admin on Sat Jun 26 14:03:08 UTC 2021 , Edited by admin on Sat Jun 26 14:03:08 UTC 2021
PRIMARY
DRUG BANK
DB09345
Created by admin on Sat Jun 26 14:03:08 UTC 2021 , Edited by admin on Sat Jun 26 14:03:08 UTC 2021
PRIMARY
ECHA (EC/EINECS)
205-425-7
Created by admin on Sat Jun 26 14:03:08 UTC 2021 , Edited by admin on Sat Jun 26 14:03:08 UTC 2021
PRIMARY
CAS
140-65-8
Created by admin on Sat Jun 26 14:03:08 UTC 2021 , Edited by admin on Sat Jun 26 14:03:08 UTC 2021
PRIMARY
WIKIPEDIA
PRAMOCAINE
Created by admin on Sat Jun 26 14:03:08 UTC 2021 , Edited by admin on Sat Jun 26 14:03:08 UTC 2021
PRIMARY
INN
235
Created by admin on Sat Jun 26 14:03:08 UTC 2021 , Edited by admin on Sat Jun 26 14:03:08 UTC 2021
PRIMARY
MERCK INDEX
M9099
Created by admin on Sat Jun 26 14:03:08 UTC 2021 , Edited by admin on Sat Jun 26 14:03:08 UTC 2021
PRIMARY Merck Index
PUBCHEM
4886
Created by admin on Sat Jun 26 14:03:08 UTC 2021 , Edited by admin on Sat Jun 26 14:03:08 UTC 2021
PRIMARY
FDA UNII
068X84E056
Created by admin on Sat Jun 26 14:03:08 UTC 2021 , Edited by admin on Sat Jun 26 14:03:08 UTC 2021
PRIMARY
ChEMBL
CHEMBL1198
Created by admin on Sat Jun 26 14:03:08 UTC 2021 , Edited by admin on Sat Jun 26 14:03:08 UTC 2021
PRIMARY