Identification

Name
Pramocaine
Accession Number
DB09345
Type
Small Molecule
Groups
Approved
Description

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.

Structure
Thumb
Synonyms
  • Pramoxine
Product Ingredients
IngredientUNIICASInChI Key
Pramoxine hydrochloride88AYB867L5637-58-1SYCBXBCPLUFJID-UHFFFAOYSA-N
Product Images
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Aveeno Active Naturals Skin Relief Medicated Anti Itch TreatmentCream5 mg/1gTopicalJohnson & Johnson Consumer Products Company, Division Of Johnson Consumer Companies, Inc.2011-09-072017-07-01Us
Bikini Zone MEDICATED After Shave Fresh ScentSpray10 mg/1mLTopicalCca Industries, Inc2013-08-01Not applicableUs
Bikini Zone Medicated After Shave SprayLiquid1 %TopicalCca Industries, IncNot applicableNot applicableCanada
Bikini Zone Medicated After-shave Roll-ON ReliefLiquid1 %TopicalCca Industries, IncNot applicableNot applicableCanada
CeraVe Developed with Dermatologists Itch Relief MoisturizingCream10 mg/1gTopicalL'oreal2017-09-18Not applicableUs
CeraVe Developed with Dermatologists Itch Relief MoisturizingLotion1 mg/1mLTopicalL'oreal2017-08-17Not applicableUs
CeraVe Itch Relief MoisturizingLotion1 mg/1mLTopicalValeant Pharmaceuticals North America2016-01-18Not applicableUs
CeraVe Itch Relief Moisturizing CreamCream10 mg/1gTopicalValeant Pharmaceuticals North America2016-02-01Not applicableUs
CocoskinCream1.18 mg/1mLTopicalNet Source, Llc2016-04-01Not applicableUs
CurasoreLiquid1 g/100mLTopicalS.S.S. Company1995-08-31Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Analpram HCPramoxine hydrochloride (10 mg/1mL) + Hydrocortisone acetate (25 mg/1mL)LotionTopicalFerndale Laboratories, Inc.1996-01-012016-12-31Us
Analpram HCPramoxine hydrochloride (10 mg/1g) + Hydrocortisone acetate (10 mg/1g)CreamTopicalSebela Pharmaceuticals Inc.2015-08-05Not applicableUs
Analpram HCPramoxine hydrochloride (10 mg/1g) + Hydrocortisone acetate (10 mg/1g)CreamTopicalFerndale Laboratories, Inc.1985-12-232016-09-30Us
Analpram HCPramoxine hydrochloride (10 mg/1mL) + Hydrocortisone acetate (25 mg/1mL)LotionTopicalSebela Pharmaceuticals Inc.2015-08-05Not applicableUs
Anesthetic Hemorrhoidal With AloePramoxine hydrochloride (420 mg/42g) + Zinc oxide (5.25 g/42g)OintmentTopicalPersonal Care Products2013-07-10Not applicableUs
Anodan-plusPramoxine hydrochloride (20 mg) + Zinc sulfate (10 mg)SuppositoryRectalOdan Laboratories LtdNot applicableNot applicableCanada
Anodan-plus OintmentPramoxine hydrochloride (1 %) + Zinc sulfate (0.5 %)OintmentRectalOdan Laboratories LtdNot applicableNot applicableCanada
Anti Itch Maximum ReliefPramoxine hydrochloride (10 mg/1g) + Menthol (10 mg/1g)CreamTopicalNatureplex, LLC2008-01-02Not applicableUs
Anti-ItchPramoxine hydrochloride (1 g/100g) + Menthol (1 g/100g)CreamTopicalDolgencorp2016-06-30Not applicableUs
AntibioticPramoxine hydrochloride (10 mg/1g) + Neomycin sulfate (3.5 mg/1g) + Polymyxin B Sulfate (10000 [USP'U]/1g)CreamTopicalRite Aid2005-08-042016-05-30Us
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Acella Hydrocortisone Acetate - Pramoxine SinglesPramocaine (1 g/100g) + Hydrocortisone acetate (2.5 g/100g)CreamTopicalAcella Pharmaceuticals, LLC2010-11-082015-05-12Us
Analpram AdvancedPramoxine hydrochloride (10 mg/1g) + Calcium magnesium potassium carbonate chloride hydroxide (30 mg/1) + Diosmin (600 mg/1) + Hydrocortisone acetate (25 mg/1g)KitSebela Pharmaceuticals Inc.2015-08-072017-02-28Us
Analpram AdvancedPramoxine hydrochloride (10 mg/1g) + Hydrocortisone acetate (25 mg/1g)KitFerndale Laboratories, Inc.2010-10-012016-12-31Us
Analpram AdvancedPramoxine hydrochloride (10 mg/1g) + Calcium magnesium potassium carbonate chloride hydroxide (30 mg/1) + Diosmin (600 mg/1) + Hydrocortisone acetate (25 mg/1g)KitOralSebela Pharmaceuticals Inc.2015-08-072016-08-31Us
Analpram AdvancedPramoxine hydrochloride (10 mg/1g) + Calcium magnesium potassium carbonate chloride hydroxide (30 mg/1) + Diosmin (600 mg/1) + Hydrocortisone acetate (25 mg/1g)KitSebela Pharmaceuticals Inc.2015-08-072017-02-28Us
Analpram AdvancedPramoxine hydrochloride (10 mg/1g) + Hydrocortisone acetate (25 mg/1g)KitFerndale Laboratories, Inc.2010-08-012016-11-30Us
Analpram AdvancedPramoxine hydrochloride (10 mg/1g) + Hydrocortisone acetate (25 mg/1g)KitFerndale Laboratories, Inc.2010-10-012016-04-30Us
Analpram EPramoxine hydrochloride (10 mg/1g) + Pramoxine hydrochloride (10 mg/1g) + Hydrocortisone acetate (25 mg/1g)KitFerndale Laboratories, Inc.2009-09-012016-05-31Us
Analpram EPramoxine hydrochloride (10 mg/1g) + Hydrocortisone acetate (25 mg/1g)CreamTopicalFerndale Laboratories, Inc.2009-06-302017-12-31Us
Analpram EPramoxine hydrochloride (10 mg/1g) + Pramoxine hydrochloride (10 mg/1g) + Hydrocortisone acetate (25 mg/1g)KitFerndale Laboratories, Inc.2009-09-012016-05-31Us
Categories
UNII
068X84E056
CAS number
140-65-8
Weight
Average: 293.407
Monoisotopic: 293.199093733
Chemical Formula
C17H27NO3
InChI Key
DQKXQSGTHWVTAD-UHFFFAOYSA-N
InChI
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
IUPAC Name
4-[3-(4-butoxyphenoxy)propyl]morpholine
SMILES
CCCCOC1=CC=C(OCCCN2CCOCC2)C=C1

Pharmacology

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.

Associated Conditions
Pharmacodynamics

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.

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.

TargetActionsOrganism
AVoltage gated sodium channel
antagonist
inhibitor
human
Absorption

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

Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity

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

Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
HyaluronidaseHyaluronidase can cause an increase in the absorption of Pramocaine resulting in an increased serum concentration and potentially a worsening of adverse effects.
Technetium Tc-99m tilmanoceptPramocaine may decrease effectiveness of Technetium Tc-99m tilmanocept as a diagnostic agent.
Food Interactions
Not Available

References

General References
  1. Pubchem [Link]
External Links
KEGG Compound
C07892
PubChem Compound
4886
PubChem Substance
310265219
ChemSpider
4717
ChEBI
8357
ChEMBL
CHEMBL1198
HET
PX9
Wikipedia
Pramocaine
ATC Codes
C05AD07 — PramocaineD04AB07 — Pramocaine
AHFS Codes
  • 84:08.00 — Antipruritics and Local Anesthetics
PDB Entries
4y0q / 4y0r / 4y0s

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedBasic ScienceAtopic Dermatitis (AD)1
1CompletedTreatmentPlasma Cell Myeloma1
3CompletedPreventionFlu caused by Influenza1
3CompletedTreatmentCommunity Acquired Infections / Infections, Gram-Positive Bacterial / Pneumonia, Pneumococcal1
4CompletedBasic ScienceFlu caused by Influenza1
4CompletedDiagnosticColonoscopy1
4CompletedPreventionFlu caused by Influenza1
4CompletedPreventionPostoperative Infections1
4CompletedTreatmentColorectal Cleansing Prior Operation1
4CompletedTreatmentFunctional Dyspepsia / Helicobacter Pylori / Peptic Ulcers1
4CompletedTreatmentHelicobacter Pylori Treatment Failure1
4CompletedTreatmentIndigestion / Peptic Ulcers1
4CompletedTreatmentPruritis1
4CompletedTreatmentPyelonephritis1
4CompletedTreatmentVertebral Osteomyelitis1
4WithdrawnPreventionComplications; Breast Prosthesis, Infection or Inflammation1
Not AvailableCompletedNot AvailableDiverticulitis1
Not AvailableCompletedNot AvailableHealthy Volunteers / High Blood Pressure (Hypertension)1
Not AvailableCompletedNot AvailablePenicillin Allergy1
Not AvailableCompletedPreventionInfection NOS1
Not AvailableCompletedScreeningColorectal Cancers1
Not AvailableCompletedTreatmentDiverticulitis, Colonic1
Not AvailableEnrolling by InvitationTreatmentAppendicitis Acute1
Not AvailableRecruitingTreatmentLiver Cirrhosis / Small Intestinal Bacterial Overgrowth1
Not AvailableWithdrawnNot AvailableCystic Fibrosis (CF)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
KitOral
SuppositoryRectal
CreamTopical5 mg/1g
Liquid; sprayTopical
LiquidTopical1 %
StickTopical
Aerosol, sprayTopical
CreamTopical1.18 mg/1mL
LiquidTopical1 g/100mL
LotionTopical10 mg/1mL
ClothTopical1 mg/1
LiquidTopical
CreamTopical1 g/57g
SuspensionTopical1 %
CreamTopical10 mg/1g
Aerosol, foamTopical
LotionTopical1 g/100mL
StickTopical1.0 %
CreamTopical1 %
ClothTopical
CreamRectal; Topical
CreamTopical0.01 g/1g
CreamTopical
OintmentRectal
Solution / dropsAuricular (otic)
Kit
GelTopical
LotionTopical10 1/1mL
ClothTopical10 mg/1000mg
SwabTopical1 %
LiquidAuricular (otic)
LotionTopical
SprayTopical
Aerosol, foamTopical10 mg/1g
SwabTopical10 mg/1g
LotionTopical1 mg/1mg
OintmentTopical
OintmentRectal; Topical
Aerosol, foamRectal150 mg/15g
AerosolRectal
Aerosol, foamRectal
LotionTopical1 mg/1mL
CreamRectal
CreamTopical0.5 %
SolutionTopical1 %
CreamRectal; Topical; Vaginal1 %
SprayTopical10 mg/1mL
ClothTopical10 mg/1g
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.221 mg/mLALOGPS
logP3.03ALOGPS
logP2.84ChemAxon
logS-3.1ALOGPS
pKa (Strongest Basic)7.06ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area30.93 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity84.82 m3·mol-1ChemAxon
Polarizability35.11 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-0ufu-5900000000-594926332aad338cf632
GC-MS Spectrum - CI-BGC-MSsplash10-0fb9-0920000000-809db2c1fd1e2472e79c
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0006-0090000000-7c9bc5e2393574b551ac
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0006-0290000000-4c336a718a063e0c4bd2
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0udi-0910000000-5d6f0b2eda70998496cd
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0udi-1900000000-6dba3652b26250fc34b5
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0udi-3900000000-cb727bd5218a44669d18
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0udi-6900000000-d132e77318e9757c12bc
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0zmi-9400000000-4e4a238aa95af1cb797e
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0ab9-9100000000-e81d251a19a7e8af2df6
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0a4i-9000000000-3c9f67d2e404ef8d5770

Taxonomy

Description
This compound belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Phenol ethers
Sub Class
Not Available
Direct Parent
Phenol ethers
Alternative Parents
Phenoxy compounds / Alkyl aryl ethers / Morpholines / Trialkylamines / Oxacyclic compounds / Dialkyl ethers / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
Phenoxy compound / Phenol ether / Alkyl aryl ether / Monocyclic benzene moiety / Morpholine / Oxazinane / Tertiary amine / Tertiary aliphatic amine / Dialkyl ether / Ether
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
aromatic ether, morpholines (CHEBI:8357)

Targets

1. Voltage gated sodium channel
Kind
Protein group
Organism
human
Pharmacological action
Yes
Actions
Antagonist
Inhibitor
References
  1. PubChem [Link]

Drug created on November 27, 2015 13:50 / Updated on September 25, 2018 00:40