U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C17H27NO3.ClH
Molecular Weight 329.862
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PRAMOXINE HYDROCHLORIDE

SMILES

Cl.CCCCOC1=CC=C(OCCCN2CCOCC2)C=C1

InChI

InChIKey=SYCBXBCPLUFJID-UHFFFAOYSA-N
InChI=1S/C17H27NO3.ClH/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;1H

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

1976
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Screening topical antipruritics: a histamine-induced itch human model.
2002 Jul-Aug
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
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
OTC product: Monistat Soothing Care for vaginial discomfort.
2005 Nov-Dec
Treating itch in psoriasis.
2006 Jun
Evaluation of pramoxine ingestion as reported to poison centers.
2006 May
Contact dermatitis from prilocaine with cross-sensitivity to pramocaine and bupivacaine.
2007 Feb
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 HYDROCHLORIDE
HSDB   MI   ORANGE BOOK   USP   USP-RS   VANDF  
Common Name English
TRONOTHANE
Brand Name English
PRAMOXINE HYDROCHLORIDE [HSDB]
Common Name English
PRAMOXINE HYDROCHLORIDE [USP-RS]
Common Name English
PRAMOXINE HYDROCHLORIDE [USP MONOGRAPH]
Common Name English
PRAMOXINE HCL [INCI]
Common Name English
PRAMOXINE HYDROCHLORIDE COMPONENT OF EPIFOAM
Common Name English
PRAMOSONE COMPONENT PRAMOXINE HYDROCHLORIDE
Common Name English
PROCTOFOAM HC COMPONENT PRAMOXINE HYDROCHLORIDE
Common Name English
PRAMOXINE HYDROCHLORIDE COMPONENT OF PROCTOFOAM HC
Common Name English
PRAMOXINE HCL
INCI  
INCI  
Official Name English
PRAMOXINE HYDROCHLORIDE COMPONENT OF PRAMOSONE
Common Name English
EPIFOAM COMPONENT PRAMOXINE HYDROCHLORIDE
Common Name English
PRAMOXINE HYDROCHLORIDE [VANDF]
Common Name English
PRAMOCAINE HYDROCHLORIDE
MART.   WHO-DD  
Common Name English
PRAMOCAINE HYDROCHLORIDE [MART.]
Common Name English
PRAMOXINE HYDROCHLORIDE [ORANGE BOOK]
Common Name English
PRAMOXINE HYDROCHLORIDE [MI]
Common Name English
4-N-BUTOXYPHENYL.GAMMA.-MORPHOLINOPROPYL ETHER HYDROCHLORIDE
Systematic Name English
NSC-25573
Code English
Pramocaine hydrochloride [WHO-DD]
Common Name English
Classification Tree Code System Code
CFR 21 CFR 346.10
Created by admin on Fri Dec 15 15:35:09 GMT 2023 , Edited by admin on Fri Dec 15 15:35:09 GMT 2023
NCI_THESAURUS C245
Created by admin on Fri Dec 15 15:35:09 GMT 2023 , Edited by admin on Fri Dec 15 15:35:09 GMT 2023
CFR 21 CFR 310.201
Created by admin on Fri Dec 15 15:35:09 GMT 2023 , Edited by admin on Fri Dec 15 15:35:09 GMT 2023
Code System Code Type Description
FDA UNII
88AYB867L5
Created by admin on Fri Dec 15 15:35:09 GMT 2023 , Edited by admin on Fri Dec 15 15:35:09 GMT 2023
PRIMARY
DRUG BANK
DBSALT001353
Created by admin on Fri Dec 15 15:35:09 GMT 2023 , Edited by admin on Fri Dec 15 15:35:09 GMT 2023
PRIMARY
MERCK INDEX
m9099
Created by admin on Fri Dec 15 15:35:09 GMT 2023 , Edited by admin on Fri Dec 15 15:35:09 GMT 2023
PRIMARY Merck Index
SMS_ID
100000078849
Created by admin on Fri Dec 15 15:35:09 GMT 2023 , Edited by admin on Fri Dec 15 15:35:09 GMT 2023
PRIMARY
EPA CompTox
DTXSID2047777
Created by admin on Fri Dec 15 15:35:09 GMT 2023 , Edited by admin on Fri Dec 15 15:35:09 GMT 2023
PRIMARY
ECHA (EC/EINECS)
211-293-1
Created by admin on Fri Dec 15 15:35:09 GMT 2023 , Edited by admin on Fri Dec 15 15:35:09 GMT 2023
PRIMARY
RXCUI
57555
Created by admin on Fri Dec 15 15:35:09 GMT 2023 , Edited by admin on Fri Dec 15 15:35:09 GMT 2023
PRIMARY RxNorm
NSC
25573
Created by admin on Fri Dec 15 15:35:09 GMT 2023 , Edited by admin on Fri Dec 15 15:35:09 GMT 2023
PRIMARY
EVMPD
SUB15004MIG
Created by admin on Fri Dec 15 15:35:09 GMT 2023 , Edited by admin on Fri Dec 15 15:35:09 GMT 2023
PRIMARY
RS_ITEM_NUM
1554002
Created by admin on Fri Dec 15 15:35:09 GMT 2023 , Edited by admin on Fri Dec 15 15:35:09 GMT 2023
PRIMARY
NCI_THESAURUS
C47682
Created by admin on Fri Dec 15 15:35:09 GMT 2023 , Edited by admin on Fri Dec 15 15:35:09 GMT 2023
PRIMARY
PUBCHEM
73957
Created by admin on Fri Dec 15 15:35:09 GMT 2023 , Edited by admin on Fri Dec 15 15:35:09 GMT 2023
PRIMARY
DAILYMED
88AYB867L5
Created by admin on Fri Dec 15 15:35:09 GMT 2023 , Edited by admin on Fri Dec 15 15:35:09 GMT 2023
PRIMARY
ChEMBL
CHEMBL1198
Created by admin on Fri Dec 15 15:35:09 GMT 2023 , Edited by admin on Fri Dec 15 15:35:09 GMT 2023
PRIMARY
HSDB
7220
Created by admin on Fri Dec 15 15:35:09 GMT 2023 , Edited by admin on Fri Dec 15 15:35:09 GMT 2023
PRIMARY
CAS
637-58-1
Created by admin on Fri Dec 15 15:35:09 GMT 2023 , Edited by admin on Fri Dec 15 15:35:09 GMT 2023
PRIMARY