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 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
Structure for Pramocaine (DB09345)
- 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.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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.
Target Actions Organism AVoltage-gated sodium channel alpha subunit blockerHumans - 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- 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.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when Pramocaine is combined with 1,2-Benzodiazepine. Abemaciclib The risk or severity of methemoglobinemia can be increased when Abemaciclib is combined with Pramocaine. Abiraterone The risk or severity of methemoglobinemia can be increased when Abiraterone is combined with Pramocaine. Acetaminophen The risk or severity of methemoglobinemia can be increased when Acetaminophen is combined with Pramocaine. Acetazolamide The risk or severity of methemoglobinemia can be increased when Acetazolamide is combined with Pramocaine. Acetic acid The risk or severity of methemoglobinemia can be increased when Acetic acid is combined with Pramocaine. Acetophenazine The risk or severity of CNS depression can be increased when Acetophenazine is combined with Pramocaine. Acetyl sulfisoxazole The risk or severity of methemoglobinemia can be increased when Acetyl sulfisoxazole is combined with Pramocaine. Adagrasib The risk or severity of methemoglobinemia can be increased when Adagrasib is combined with Pramocaine. Afatinib The risk or severity of methemoglobinemia can be increased when Afatinib is combined with Pramocaine. 
Identify potential medication risksEasily compare up to 40 drugs with our drug interaction checker.Get severity rating, description, and management advice.Learn more - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Pramoxine hydrochloride 88AYB867L5 637-58-1 SYCBXBCPLUFJID-UHFFFAOYSA-N - Product Images
- Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Anti Itch Soothing 1 Pramoxine Hydrochloride Spray 10 mg/1mL Topical The Honey Pot Company LLC 2022-03-01 Not applicable US 
Anti-Itch Soothing Wipes 1 Pramoxine Hydrochloride Cloth 10 mg/1mL Topical The Honey Pot Company LLC 2022-03-01 Not applicable US Anti-Itch Wipes Cloth 1 g/100g Topical Diamond Wipes International 2022-07-06 Not applicable US Aveeno Active Naturals Skin Relief Medicated Anti Itch Treatment Cream 5 mg/1g Topical Johnson & Johnson Consumer Products Company, Division Of Johnson Consumer Companies, Inc. 2011-09-07 2017-07-01 US Aveeno Calm Plus Restore Itch Relief Balm Cream 5 mg/1g Topical Johnson & Johnson Consumer Inc. 2023-07-03 Not applicable US Aveeno Restorative Skin Therapy Itch Relief Balm Cream 5 mg/1g Topical Johnson & Johnson Consumer Inc. 2020-08-01 Not applicable US Bikini Zone MEDICATED After Shave Fresh Scent Spray 10 mg/1mL Topical CCA Industries, Inc. 2013-08-01 2014-04-30 US Bikini Zone Medicated After Shave Spray Liquid 1 % Topical CCA Industries, Inc. Not applicable Not applicable Canada 
Bikini Zone Medicated After-shave Roll-ON Relief Liquid 1 % w/w Topical CCA Industries, Inc. Not applicable Not applicable Canada CeraVe Developed with Dermatologists Itch Relief Moisturizing Lotion 1 mg/1mL Topical L'Oreal USA Products Inc 2017-08-17 Not applicable US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Analpram HC Pramoxine hydrochloride (10 mg/1g) + Hydrocortisone acetate (10 mg/1g) Cream Topical Sebela Pharmaceuticals Inc. 2015-08-05 Not applicable US Analpram HC Pramoxine hydrochloride (10 mg/1mL) + Hydrocortisone acetate (25 mg/1mL) Lotion Topical Sebela Pharmaceuticals Inc. 2015-08-05 Not applicable US Analpram HC Pramoxine hydrochloride (10 mg/1g) + Hydrocortisone acetate (10 mg/1g) Cream Topical Ferndale Laboratories, Inc. 1985-12-23 2016-09-30 US Analpram HC Pramoxine hydrochloride (10 mg/1mL) + Hydrocortisone acetate (25 mg/1mL) Lotion Topical Ferndale Laboratories, Inc. 1996-01-01 2016-12-31 US Anesthetic Hemorrhoidal With Aloe Pramoxine hydrochloride (420 mg/42g) + Zinc oxide (5.25 g/42g) Ointment Topical Personal Care Products, Inc. 2013-07-10 Not applicable US Anodan-plus Pramoxine hydrochloride (20 mg) + Zinc sulfate (10 mg) Suppository Rectal Odan Laboratories Ltd Not applicable Not applicable Canada Anodan-plus Ointment Pramoxine hydrochloride (1 %) + Zinc sulfate (0.5 %) Ointment Rectal Odan Laboratories Ltd Not applicable Not applicable Canada Anti Itch Maximum Relief Pramoxine hydrochloride (10 mg/1g) + Menthol (10 mg/1g) Cream Topical Natureplex LLC 2008-01-02 Not applicable US Anti-Itch Pramoxine hydrochloride (1 g/100g) + Menthol (1 g/100g) Cream Topical Dolgencorp, Inc. 2016-06-30 Not applicable US Antibiotic Pramoxine hydrochloride (10 mg/1g) + Neomycin sulfate (3.5 mg/1g) + Polymyxin B sulfate (10000 [USP'U]/1g) Cream Topical Kroger 2017-05-08 Not applicable US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Acella Hydrocortisone Acetate - Pramoxine Singles Pramocaine (1 g/100g) + Hydrocortisone acetate (2.5 g/100g) Cream Topical Acella Pharmaceuticals, LLC 2009-04-09 2017-01-31 US Analpram Advanced Pramoxine hydrochloride (10 mg/1g) + Hydrocortisone acetate (25 mg/1g) Kit Topical Ferndale Laboratories, Inc. 2010-10-01 2016-12-31 US Analpram Advanced Pramoxine hydrochloride (10 mg/1g) + Calcium magnesium potassium carbonate chloride hydroxide (30 mg/1) + Diosmin (600 mg/1) + Hydrocortisone acetate (25 mg/1g) Kit Oral; Topical Sebela Pharmaceuticals Inc. 2015-08-07 2017-02-28 US Analpram Advanced Pramoxine hydrochloride (10 mg/1g) + Hydrocortisone acetate (25 mg/1g) Kit Topical Ferndale Laboratories, Inc. 2010-10-01 2016-04-30 US Analpram Advanced Pramoxine hydrochloride (10 mg/1g) + Calcium magnesium potassium carbonate chloride hydroxide (30 mg/1) + Diosmin (600 mg/1) + Hydrocortisone acetate (25 mg/1g) Kit Oral; Topical Sebela Pharmaceuticals Inc. 2015-08-07 2017-02-28 US Analpram Advanced Pramoxine hydrochloride (10 mg/1g) + Hydrocortisone acetate (25 mg/1g) Kit Topical Ferndale Laboratories, Inc. 2010-08-01 2016-11-30 US Analpram Advanced Pramoxine hydrochloride (10 mg/1g) + Calcium magnesium potassium carbonate chloride hydroxide (30 mg/1) + Diosmin (600 mg/1) + Hydrocortisone acetate (25 mg/1g) Kit Topical Sebela Pharmaceuticals Inc. 2015-08-07 2016-08-31 US Analpram E Pramoxine hydrochloride (10 mg/1g) + Pramoxine hydrochloride (10 mg/1g) + Hydrocortisone acetate (25 mg/1g) Kit Topical Ferndale Laboratories, Inc. 2009-09-01 2016-05-31 US Analpram E Pramoxine hydrochloride (10 mg/1g) + Pramoxine hydrochloride (10 mg/1g) + Hydrocortisone acetate (25 mg/1g) Kit Topical Ferndale Laboratories, Inc. 2009-09-01 2016-05-31 US Analpram E Pramoxine hydrochloride (10 mg/1g) + Pramoxine hydrochloride (10 mg/1g) + Hydrocortisone acetate (25 mg/1g) Kit Topical Ferndale Laboratories, Inc. 2009-09-01 2016-05-31 US
Categories
- ATC Codes
- D04AB07 — Pramocaine
- D04AB — Anesthetics for topical use
- D04A — ANTIPRURITICS, INCL. ANTIHISTAMINES, ANESTHETICS, ETC.
- D04 — ANTIPRURITICS, INCL. ANTIHISTAMINES, ANESTHETICS, ETC.
- D — DERMATOLOGICALS
- Drug Categories
- Agents for Treatment of Hemorrhoids and Anal Fissures for Topical Use
- Anesthetics
- Anesthetics for Topical Use
- Anesthetics, Local
- Antipruritics and Local Anesthetics
- Antipruritics, Incl. Antihistamines, Anesthetics, Etc.
- Central Nervous System Agents
- Central Nervous System Depressants
- Dermatologicals
- Oxazines
- Peripheral Nervous System Agents
- Sensory System Agents
- Vasoprotectives
- 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
- Pubchem [Link]
- External Links
- KEGG Compound
- C07892
- PubChem Compound
- 4886
- PubChem Substance
- 310265219
- ChemSpider
- 4717
- BindingDB
- 50225493
- 34347
- ChEBI
- 8357
- ChEMBL
- CHEMBL1198
- ZINC
- ZINC000019594594
- PDBe Ligand
- PX9
- Wikipedia
- Pramocaine
- PDB Entries
- 4y0q / 4y0r / 4y0s / 7z9z / 7za0 / 7zcd
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Treatment Dentin Sensitivity / Periodontal Disease 1 3 Completed Treatment Hypersensitivity Dentin 1 3 Unknown Status Treatment Dentine Hypersensitivity 1 Not Available Completed Not Available Haemorrhoids / Pregnancy 1 Not Available Completed Other Healthy Subjects (HS) / Hypertension 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Kit Oral; Topical Kit Topical Cloth Topical 10 mg/1mL Cloth Topical 1 g/100g Suppository Rectal Cream Topical 5 mg/1g Liquid; spray Topical Liquid Topical 1 % Liquid Topical 1 % w/w Stick Topical Lotion Topical Aerosol, spray Topical Cream Topical 10 mg/1g Cream Topical 1.18 mg/1mL Liquid Topical 1 g/100mL Lotion Topical 1 g/100g Lotion Topical 10 mg/1mL Cloth Topical 1 mg/1 Spray Topical Cloth Topical 10 mg/1g Liquid Topical Cream Topical 1 g/57g Suspension Topical 1 % Ointment Rectal Spray Topical 1 g/100mL Lotion Topical 1 g/100mL Ointment Topical Stick Topical 1.0 % Cream Topical 1 % Cloth Topical Cream Rectal; Topical Cream Topical 0.01 g/1g Cream Topical Liquid Topical 10 mg/1mL Solution / drops Auricular (otic) Kit Rectal Ointment Topical 0.5 % w/w Cream Topical 1 % w/w Lotion Topical 1 % Lotion Topical 10 1/1mL Cream; kit; tablet, film coated Oral; Topical Cloth Topical 10 mg/1 Cloth Topical 10 mg/1000mg Kit; ointment Topical Swab Topical 1 % Gel Topical Liquid Auricular (otic) Lotion Topical 1 g Aerosol, foam Rectal 150 mg/15g Aerosol, foam Topical 10 mg/1g Cream Topical 1 g/100g Swab Topical 10 mg/1g Lotion Topical 1 mg/1mg Ointment Rectal; Topical Aerosol Rectal Aerosol, foam Rectal Aerosol, foam Topical Lotion Topical 0.9 g/90mL Lotion Topical 1 mg/1mL Cream Rectal Cream Topical 0.5 % w/w Solution Topical 1 % Suppository Topical 18 MG Cream Rectal; Topical; Vaginal 1 % Spray Topical 10 mg/1mL Gel Topical 1 %w/w - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.221 mg/mL ALOGPS logP 3.03 ALOGPS logP 2.84 Chemaxon logS -3.1 ALOGPS pKa (Strongest Basic) 7.06 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 30.93 Å2 Chemaxon Rotatable Bond Count 9 Chemaxon Refractivity 84.82 m3·mol-1 Chemaxon Polarizability 35.11 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Targets
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
- 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
Drug created at November 27, 2015 20:50 / Updated at December 01, 2023 08:05