Pramocaine

Identification

Summary

Pramocaine is a local anesthetic and antipruritic agent found in various topical preparations.

Brand Names
Analpram HC, Aveeno Anti-itch Reformulated Jun 2007, Caladryl, Caladryl Clear, Cortane-B, Epifoam, Gold Bond Maximum Relief, Itch-X, Neosporin Neo To Go, Neosporin Plus Maximum Strength, Neosporin Plus Maximum Strength Cream, Pramosone, Prax, Preparation H Cream, Procort 1.85/1.15, Proctodan-HC, Proctofoam, Proctofoam-HC, Sarna Sensitive, Triple Antibiotic, Tronolane Anesthetic
Generic Name
Pramocaine
DrugBank Accession Number
DB09345
Background

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.

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 293.407
Monoisotopic: 293.199093733
Chemical Formula
C17H27NO3
Synonyms
  • Pramocaína
  • Pramocaine
  • Pramoxine

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.

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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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 alpha subunit
blocker
Humans
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

Adverse Effects
Adverseeffects
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Toxicity

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

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of adverse effects can be increased when Pramocaine is combined with 1,2-Benzodiazepine.
AcetazolamideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Pramocaine.
AcetophenazineThe risk or severity of adverse effects can be increased when Acetophenazine is combined with Pramocaine.
AclidiniumPramocaine may increase the central nervous system depressant (CNS depressant) activities of Aclidinium.
AgomelatineThe risk or severity of adverse effects can be increased when Agomelatine is combined with Pramocaine.
AlfentanilThe risk or severity of adverse effects can be increased when Alfentanil is combined with Pramocaine.
AlimemazineThe risk or severity of adverse effects can be increased when Alimemazine is combined with Pramocaine.
AlmotriptanThe risk or severity of adverse effects can be increased when Almotriptan is combined with Pramocaine.
AlosetronThe risk or severity of adverse effects can be increased when Alosetron is combined with Pramocaine.
AlprazolamThe risk or severity of adverse effects can be increased when Alprazolam is combined with Pramocaine.
Interactions
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Food Interactions
No interactions found.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Pramoxine hydrochloride88AYB867L5637-58-1SYCBXBCPLUFJID-UHFFFAOYSA-N
Product Images
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
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 flag
Aveeno Restorative Skin Therapy Itch Relief BalmCream5 mg/1gTopicalJohnson & Johnson Consumer Inc.2020-08-01Not applicableUS flag
Bikini Zone MEDICATED After Shave Fresh ScentSpray10 mg/1mLTopicalCCA Industries, Inc.2013-08-012014-04-30US flag
Bikini Zone Medicated After Shave SprayLiquid1 %TopicalCCA Industries, Inc.Not applicableNot applicableCanada flag
Bikini Zone Medicated After-shave Roll-ON ReliefLiquid1 % w/wTopicalCCA Industries, Inc.Not applicableNot applicableCanada flag
CeraVe Developed with Dermatologists Itch Relief MoisturizingLotion1 mg/1mLTopicalL'oreal2017-08-17Not applicableUS flag
CeraVe Developed with Dermatologists Itch Relief MoisturizingCream10 mg/1gTopicalL'Oreal USA Products Inc2017-09-18Not applicableUS flag
CeraVe Itch Relief MoisturizingLotion1 mg/1mLTopicalValeant Pharmaceuticals North America2016-01-18Not applicableUS flag
CeraVe Itch Relief Moisturizing CreamCream10 mg/1gTopicalValeant Pharmaceuticals North America2016-02-01Not applicableUS flag
CocoskinCream1.18 mg/1mLTopicalNet Source, Llc2016-04-01Not applicableUS flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Analpram HCPramoxine hydrochloride (10 mg/1g) + Hydrocortisone acetate (10 mg/1g)CreamTopicalFerndale Laboratories, Inc.1985-12-232016-09-30US flag
Analpram HCPramoxine hydrochloride (10 mg/1g) + Hydrocortisone acetate (10 mg/1g)CreamTopicalSebela Pharmaceuticals Inc.2015-08-05Not applicableUS flag
Analpram HCPramoxine hydrochloride (10 mg/1mL) + Hydrocortisone acetate (25 mg/1mL)LotionTopicalFerndale Laboratories, Inc.1996-01-012016-12-31US flag
Analpram HCPramoxine hydrochloride (10 mg/1mL) + Hydrocortisone acetate (25 mg/1mL)LotionTopicalSebela Pharmaceuticals Inc.2015-08-05Not applicableUS flag
Anesthetic Hemorrhoidal With AloePramoxine hydrochloride (420 mg/42g) + Zinc oxide (5.25 g/42g)OintmentTopicalPersonal Care Products, Inc.2013-07-10Not applicableUS flag
Anodan-plusPramoxine hydrochloride (20 mg) + Zinc sulfate (10 mg)SuppositoryRectalOdan Laboratories LtdNot applicableNot applicableCanada flag
Anodan-plus OintmentPramoxine hydrochloride (1 %) + Zinc sulfate (0.5 %)OintmentRectalOdan Laboratories LtdNot applicableNot applicableCanada flag
Anti Itch Maximum ReliefPramoxine hydrochloride (10 mg/1g) + Levomenthol (10 mg/1g)CreamTopicalNatureplex, LLC2008-01-02Not applicableUS flag
Anti-ItchPramoxine hydrochloride (1 g/100g) + Levomenthol (1 g/100g)CreamTopicalDolgencorp2016-06-30Not applicableUS flag
AntibioticPramoxine hydrochloride (10 mg/1g) + Neomycin sulfate (3.5 mg/1g) + Polymyxin B sulfate (10000 [USP'U]/1g)CreamTopicalKroger2017-05-08Not applicableUS flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Acella Hydrocortisone Acetate - Pramoxine SinglesPramocaine (1 g/100g) + Hydrocortisone acetate (2.5 g/100g)CreamTopicalAcella Pharmaceuticals, LLC2009-04-092017-01-31US flag
Analpram AdvancedPramoxine hydrochloride (10 mg/1g) + Calcium magnesium potassium carbonate chloride hydroxide (30 mg/1) + Diosmin (600 mg/1) + Hydrocortisone acetate (25 mg/1g)KitOral; TopicalSebela Pharmaceuticals Inc.2015-08-072017-02-28US flag
Analpram AdvancedPramoxine hydrochloride (10 mg/1g) + Calcium magnesium potassium carbonate chloride hydroxide (30 mg/1) + Diosmin (600 mg/1) + Hydrocortisone acetate (25 mg/1g)KitTopicalSebela Pharmaceuticals Inc.2015-08-072016-08-31US flag
Analpram AdvancedPramoxine hydrochloride (10 mg/1g) + Hydrocortisone acetate (25 mg/1g)KitTopicalFerndale Laboratories, Inc.2010-10-012016-12-31US flag
Analpram AdvancedPramoxine hydrochloride (10 mg/1g) + Calcium magnesium potassium carbonate chloride hydroxide (30 mg/1) + Diosmin (600 mg/1) + Hydrocortisone acetate (25 mg/1g)KitOral; TopicalSebela Pharmaceuticals Inc.2015-08-072017-02-28US flag
Analpram AdvancedPramoxine hydrochloride (10 mg/1g) + Hydrocortisone acetate (25 mg/1g)KitTopicalFerndale Laboratories, Inc.2010-10-012016-04-30US flag
Analpram AdvancedPramoxine hydrochloride (10 mg/1g) + Hydrocortisone acetate (25 mg/1g)KitTopicalFerndale Laboratories, Inc.2010-08-012016-11-30US flag
Analpram EPramoxine hydrochloride (10 mg/1g) + Pramoxine hydrochloride (10 mg/1g) + Hydrocortisone acetate (25 mg/1g)KitTopicalFerndale Laboratories, Inc.2009-09-012016-05-31US flag
Analpram EPramoxine hydrochloride (10 mg/1g) + Hydrocortisone acetate (25 mg/1g)CreamTopicalFerndale Laboratories, Inc.2009-06-302017-12-31US flag
Analpram EPramoxine hydrochloride (10 mg/1g) + Pramoxine hydrochloride (10 mg/1g) + Hydrocortisone acetate (25 mg/1g)KitTopicalFerndale Laboratories, Inc.2009-09-012016-05-31US flag

Categories

ATC Codes
D04AB07 — PramocaineC05AD07 — Pramocaine
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Alkyl aryl ether / Amine / Aromatic heteromonocyclic compound / Azacycle / Dialkyl ether / Ether / Hydrocarbon derivative / Monocyclic benzene moiety / Morpholine / Organic nitrogen compound
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
aromatic ether, morpholines (CHEBI:8357)
Affected organisms
Not Available

Chemical Identifiers

UNII
068X84E056
CAS number
140-65-8
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

References

General References
  1. Pubchem [Link]
KEGG Compound
C07892
PubChem Compound
4886
PubChem Substance
310265219
ChemSpider
4717
BindingDB
50225493
RxNav
34347
ChEBI
8357
ChEMBL
CHEMBL1198
ZINC
ZINC000019594594
PDBe Ligand
PX9
Wikipedia
Pramocaine
PDB Entries
4y0q / 4y0r / 4y0s

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentDentin Sensitivity / Periodontal Disease (Diagnosis)1
3CompletedTreatmentHypersensitivity Dentin1
3Unknown StatusTreatmentDentine Hypersensitivity1
Not AvailableCompletedNot AvailableHaemorrhoids / Pregnant State1
Not AvailableCompletedOtherHealthy Subjects (HS) / High Blood Pressure (Hypertension)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
KitOral; Topical
KitTopical
SuppositoryRectal
CreamTopical5 mg/1g
Liquid; sprayTopical
LiquidTopical1 %
LiquidTopical1 % w/w
StickTopical
LotionTopical
Aerosol, sprayTopical
CreamTopical10 mg/1g
CreamTopical1.18 mg/1mL
LiquidTopical1 g/100mL
LotionTopical1 g/100g
LotionTopical10 mg/1mL
ClothTopical1 mg/1
SprayTopical
ClothTopical10 mg/1g
LiquidTopical
CreamTopical1 g/57g
SuspensionTopical1 %
OintmentRectal
SprayTopical1 g/100mL
LotionTopical1 g/100mL
OintmentTopical
StickTopical1.0 %
ClothTopical
CreamRectal; Topical
CreamTopical0.01 g/1g
CreamTopical
Solution / dropsAuricular (otic)
KitRectal
OintmentTopical0.5 % w/w
CreamTopical1 % w/w
LotionTopical1 %
LotionTopical10 1/1mL
ClothTopical10 mg/1
ClothTopical10 mg/1000mg
SwabTopical1 %
GelTopical
LiquidAuricular (otic)
LotionTopical1 g
Aerosol, foamRectal150 mg/15g
Aerosol, foamTopical10 mg/1g
SwabTopical10 mg/1g
LotionTopical1 mg/1mg
OintmentRectal; Topical
AerosolRectal
Aerosol, foamRectal
Aerosol, foamTopical
LotionTopical1 mg/1mL
CreamRectal
CreamTopical0.5 % w/w
SolutionTopical1 %
CreamTopical1 %
SuppositoryTopical18 MG
CreamRectal; Topical; Vaginal1 %
SprayTopical10 mg/1mL
GelTopical1 %w/w
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

Targets

Drugtargets2
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Kind
Protein group
Organism
Humans
Pharmacological action
Yes
Actions
Blocker
General Function
Voltage-gated sodium channel activity
Specific Function
Mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a...

Components:
References
  1. Fozzard HA, Sheets MF, Hanck DA: The sodium channel as a target for local anesthetic drugs. Front Pharmacol. 2011 Nov 1;2:68. doi: 10.3389/fphar.2011.00068. eCollection 2011. [Article]
  2. PubChem [Link]

Drug created on November 27, 2015 20:50 / Updated on October 22, 2021 23:18