Tetracaine
Identification
- Summary
Tetracaine is a local anaesthetic agent used to induce local analgesia in the eyes and skin during medical procedures.
- Brand Names
- Ametop, Cetacaine, Denticare Denti Freeze Gel, Denticare Denti Freeze Ointment, Kovanaze, One Touch Reformulated Apr 2009, Pliaglis, Synera, Zap
- Generic Name
- Tetracaine
- DrugBank Accession Number
- DB09085
- Background
Tetracaine is an ester local anaesthetic currently available in combination with lidocaine as a cream and patch.
- Type
- Small Molecule
- Groups
- Approved, Vet approved
- Structure
Structure for Tetracaine (DB09085)
- Weight
- Average: 264.369
Monoisotopic: 264.183778021 - Chemical Formula
- C15H24N2O2
- Synonyms
- 2-(dimethylamino)ethyl 4-(butylamino)benzoate
- 2-(Dimethylamino)ethyl p-(butylamino)benzoate
- Amethocaine
- Amethocaine HCl
- Diäthylaminoäthanol ester der p-butylaminobenzösäure
- Dicaine
- Medihaler-Tetracaine
- Metraspray
- p-(butylamino)benzoic acid β-(dimethylamino)ethyl ester
- p-Butylaminobenzoyl-2-dimethylaminoethanol
- Tetracaína
- Tétracaïne
- Tetracaine
- Tetracaine HCl
Pharmacology
- Indication
Ophthalmic tetracaine is indicated for the for procedures requiring a rapid and short- acting topical ophthalmic anesthetic.
The combination lidocaine and tetracaine patch is indicated for local dermal analgesia for superficial dermatological procedures and superficial venous access. The combination lidocaine and tetracaine cream is intended to provide topical local analgesia for superficial dermatological procedures.
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- Associated Therapies
- Contraindications & Blackbox Warnings
Contraindications & Blackbox WarningsWith our commercial data, access important information on dangerous risks, contraindications, and adverse effects.Our Blackbox Warnings cover Risks, Contraindications, and Adverse Effects- Pharmacodynamics
Not Available
- Mechanism of action
Tetracaine is an ester-type anesthetic and produces local anesthesia by blocking the sodium ion channels involved in initiation and conduction of neuronal impulses.
Target Actions Organism ARyanodine receptor 1 modulatorHumans ARyanodine receptor 2 modulatorHumans AVoltage-gated sodium channel alpha subunit blockerHumans - Absorption
Systemic absorption of anaesthetic from the combination cream is directly related to the duration and surface area of application. Although peak plasma concentrations for lidocaine were measured, plasma levels for tetracaine could not be determined due to low levels (<0.9 ng/mL)
- Volume of distribution
Tetracaine is rapidly hydrolyzed in the plasma; therefore, volume of distribution could not be determined.
- Protein binding
Tetracaine is rapidly hydrolyzed in the plasma; therefore, protein binding could not be determined.
- Metabolism
Tetracaine is rapidly hydrolyzed by plasma esterases to the following primary metabolites: para-aminobenzoic acid and diethylaminoethanol. The activity of both metabolites is unspecified.
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- Route of elimination
Not Available
- Half-life
Tetracaine is hydrolyzed rapidly in the plasma; therefore, half-life has not been determined.
- Clearance
Tetracaine is hydrolyzed rapidly in the plasma; therefore, clearance has not been determined.
- Adverse Effects
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The most common adverse effects with the combination cream are localized reactions such as: erythema (47%), skin discoloration (16%), and edema (14%). Systemic adverse events were less common, occurring at a rate of <1% and included vomiting, headache, dizziness, and fever. Similar to other amide and ester anesthetics, CNS excitation and/or depression may occur. It is not well known at which plasma concentration systemic toxicity occurs with tetracaine; however, the threshold is thought to be much lower than that of lidocaine which is 1000 ng/mL.
- 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 adverse effects can be increased when Tetracaine is combined with 1,2-Benzodiazepine. Acetazolamide The risk or severity of adverse effects can be increased when Acetazolamide is combined with Tetracaine. Acetophenazine The risk or severity of adverse effects can be increased when Acetophenazine is combined with Tetracaine. Aclidinium Tetracaine may increase the central nervous system depressant (CNS depressant) activities of Aclidinium. Agomelatine The risk or severity of adverse effects can be increased when Agomelatine is combined with Tetracaine. Alfentanil The therapeutic efficacy of Tetracaine can be increased when used in combination with Alfentanil. Alimemazine The risk or severity of adverse effects can be increased when Alimemazine is combined with Tetracaine. Almotriptan The risk or severity of adverse effects can be increased when Almotriptan is combined with Tetracaine. Alosetron The risk or severity of adverse effects can be increased when Alosetron is combined with Tetracaine. Alprazolam The risk or severity of adverse effects can be increased when Alprazolam is combined with Tetracaine. 
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- No interactions found.
Products
Comprehensive & structured drug product infoFrom application numbers to product codes, connect different identifiers through our commercial datasets.Easily connect various identifiers back to our datasets- Product Ingredients
Ingredient UNII CAS InChI Key Tetracaine hydrochloride 5NF5D4OPCI 136-47-0 PPWHTZKZQNXVAE-UHFFFAOYSA-N - International/Other Brands
- Pontocaine HCl
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Altacaine Solution 5 mg/1mL Ophthalmic Altaire Pharmaceuticals Inc. 2002-02-01 2019-07-15 US 
Ametop Gel 4% Gel 40 mg / g Topical Valeo Pharma Corp. 1998-03-16 Not applicable Canada 
Niphanoid Injection, powder, for solution 10 mg/1mL Subarachnoid Hospira, Inc. 1997-06-09 2015-01-01 US Pontocaine Powder, for solution 20 mg / 2 mL Intraspinal Hospira Healthcare Ulc 2001-07-15 2018-11-29 Canada Pontocaine 5 mg/ml Solution 0.5 % Ophthalmic Hospira Healthcare Ulc 2001-06-01 2018-11-29 Canada Pontocaine Dps 0.5% Solution / drops .5 % Ophthalmic Sanofi 1937-12-31 2001-08-10 Canada Pontocaine Pws Inj 20mg/amp Powder, for solution 20 mg / amp Intraspinal Sanofi 1951-12-31 2001-08-10 Canada Supracaine Aerosol 11.6mg/gm Aerosol, metered 11.6 mg / g Oral; Topical Hoechst Roussel Canada Inc. 1993-12-31 2000-07-28 Canada Tetracaine Injection 10 mg/1mL Subarachnoid Akorn, Inc. 2010-06-01 Not applicable US Tetracaine HCL Injection 10 mg/1mL Subarachnoid Bpi Labs Llc 2020-06-26 Not applicable US - Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Blt 3 Ointment 2 g/100g Topical CENTURA PHARMACEUTICALS INC 2016-10-30 Not applicable US Burn Cream Cream 10 mg/1mL Topical Bio-Medical & Pharmaceutical Manufacturing Corporation 2016-08-19 Not applicable US Burn Solution Cream Cream 10 mg/1mL Topical Burn Solution Foundations 2021-02-02 Not applicable US Comfortox Tetracaine Cream 20 mg/1000mg Topical Sambria Pharmaceuticals, Inc. 2016-09-14 Not applicable US Eclipse Topical Analgesic LL Cream 20 mg/1000mg Topical Sambria Pharmaceuticals, Inc. 2016-02-01 Not applicable US Minims Tetracaine Hydrochloride Solution / drops 0.5 % w/v Ophthalmic Bausch Health, Canada Inc. 1995-12-31 Not applicable Canada Minims Tetracaine Hydrochloride Solution / drops 1 % w/v Ophthalmic Bausch Health, Canada Inc. 1995-12-31 Not applicable Canada NeuroMed LA Cream 20 mg/1mL Topical Sambria Pharmaceuticals 2015-12-22 2016-05-23 US NeuroMed Topical Analgesic LA Cream 20 mg/1000mg Topical Sambria Pharmaceuticals, Inc. 2016-02-01 Not applicable US Numfast Tetracaine Green Cream 20 mg/1g Topical Unit Dose, Ltd. 2016-01-20 Not applicable US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image BLT Skin Cream Tetracaine (0.01 g/1g) + Benzocaine (0.2 g/1g) + Lidocaine (0.04 g/1g) Cream Topical M2B Pharma LLC 2020-02-04 Not applicable US Blue Gel Anesthetic Tetracaine hydrochloride (10 mg/1g) + Epinephrine (1 mg/1g) + Lidocaine hydrochloride (50 mg/1g) Gel Topical Dermal Source, Inc. 2021-04-01 Not applicable US Blue Gel Anesthetic Tetracaine hydrochloride (20 mg/1g) + Lidocaine hydrochloride (40 mg/1g) Gel Topical Dermal Source, Inc. 2004-03-01 2021-04-02 US Cetacaine Liquid Tetracaine hydrochloride (2 %) + Benzocaine (14 %) + Butamben (2 %) Liquid Topical Cetylite Industries, Inc. 1996-09-19 Not applicable Canada Cetacaine Spray Tetracaine hydrochloride (2 %) + Benzocaine (14 %) + Butamben (2 %) Aerosol Topical Cetylite Industries, Inc. 1994-12-31 Not applicable Canada Cutiecaine Tetracaine (20 mg/1g) + Benzocaine (180 mg/1g) Cream Topical Innovatech Inc 2010-08-31 Not applicable US Denti-care Topical Anesthetic Gel Tetracaine hydrochloride (2 %) + Benzocaine (18 %) Gel Topical Amd Medicom Inc 1999-11-29 Not applicable Canada Denti-care Topical Anesthetic Liquid Spray Tetracaine hydrochloride (2.0 %) + Benzocaine (18.0 %) Spray Topical Amd Medicom Inc 2000-05-01 2006-08-03 Canada Denticare Pro-freeze Tetracaine hydrochloride (2 % w/w) + Benzocaine (18 % w/w) Gel Topical Amd Medicom Inc 2009-04-16 2021-01-26 Canada Dermacaine-R Tetracaine (2 % w/w) + Benzocaine (18 % w/w) Cream Topical Innovatech Inc Not applicable Not applicable Canada - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Altacaine Tetracaine hydrochloride (5 mg/1mL) Solution Ophthalmic Altaire Pharmaceuticals Inc. 2002-02-01 2019-07-15 US Benzocaine 20% / Lidocaine 10% / Tetracaine 10% Tetracaine (10 g/100g) + Benzocaine (20 g/100g) + Lidocaine (10 g/100g) Cream Topical Sincerus Florida, LLC 2019-05-22 Not applicable US Benzocaine 20% / Lidocaine 10% / Tetracaine 10% Tetracaine (10 g/100g) + Benzocaine (20 g/100g) + Lidocaine (10 g/100g) Ointment Topical Sincerus Florida, LLC 2019-05-17 Not applicable US Benzocaine 20% / Lidocaine 10% / Tetracaine 10% Tetracaine (10 g/100g) + Benzocaine (20 g/100g) + Lidocaine (10 g/100g) Cream Topical Sincerus Florida, LLC 2019-05-22 Not applicable US Cetacaine Anesthetic Tetracaine hydrochloride (0.004 g/0.2g) + Benzocaine (0.028 g/0.2g) + Butamben (0.004 g/0.2g) Aerosol, spray Topical Cetylite Industries, Inc. 1958-01-01 Not applicable US Cetacaine Anesthetic Tetracaine hydrochloride (0.004 g/0.2g) + Benzocaine (0.028 g/0.2g) + Butamben (0.004 g/0.2g) Solution Topical Cetylite Industries, Inc. 1960-01-01 Not applicable US Cetacaine Topical Anesthetic Tetracaine hydrochloride (0.004 g/0.2g) + Benzocaine (0.028 g/0.2g) + Butamben (0.004 g/0.2g) Gel Topical Cetylite Industries, Inc. 1960-01-01 Not applicable US Cetacaine Topical Anesthetic Tetracaine hydrochloride (0.004 g/0.2g) + Benzocaine (0.028 g/0.2g) + Butamben (0.004 g/0.2g) Gel Topical Cetylite Industries, Inc. 1960-01-01 Not applicable US Denti-Care Denti-Freeze Topical Anesthetic Bubblegum Tetracaine hydrochloride (0.02 g/1g) + Benzocaine (0.18 g/1g) Gel Dental Amd Medicom Inc. 2000-02-01 2021-08-31 US Denti-Care Denti-Freeze Topical Anesthetic Cherry Tetracaine hydrochloride (0.02 g/1g) + Benzocaine (0.18 g/1g) Gel Dental Amd Medicom Inc. 2000-04-01 2021-09-30 US
Categories
- ATC Codes
- C05AD02 — Tetracaine
- C05AD — Local anesthetics
- C05A — AGENTS FOR TREATMENT OF HEMORRHOIDS AND ANAL FISSURES FOR TOPICAL USE
- C05 — VASOPROTECTIVES
- C — CARDIOVASCULAR SYSTEM
- D04AB — Anesthetics for topical use
- D04A — ANTIPRURITICS, INCL. ANTIHISTAMINES, ANESTHETICS, ETC.
- D04 — ANTIPRURITICS, INCL. ANTIHISTAMINES, ANESTHETICS, ETC.
- D — DERMATOLOGICALS
- Drug Categories
- Acids, Carbocyclic
- Agents for Treatment of Hemorrhoids and Anal Fissures for Topical Use
- Aminobenzoates
- Anesthetics
- Anesthetics for Topical Use
- Anesthetics, General
- Anesthetics, Local
- Antipruritics and Local Anesthetics
- Antipruritics, Incl. Antihistamines, Anesthetics, Etc.
- Benzene Derivatives
- Benzoates
- Central Nervous System Agents
- Central Nervous System Depressants
- Dental Agents
- Dermatologicals
- Esters of Aminobenzoic Acid
- Local Anesthesia
- Local Anesthetics (Ester)
- Methemoglobinemia Associated Agents
- Nervous System
- Ophthalmologicals
- para-Aminobenzoates
- Peripheral Nervous System Agents
- Sensory Organs
- Sensory System Agents
- Vasoprotectives
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Benzoic acids and derivatives
- Direct Parent
- Benzoic acid esters
- Alternative Parents
- Aminobenzoic acids and derivatives / Phenylalkylamines / Benzoyl derivatives / Aniline and substituted anilines / Secondary alkylarylamines / Trialkylamines / Carboxylic acid esters / Amino acids and derivatives / Monocarboxylic acids and derivatives / Organopnictogen compounds show 3 more
- Substituents
- Amine / Amino acid or derivatives / Aminobenzoic acid or derivatives / Aniline or substituted anilines / Aromatic homomonocyclic compound / Benzoate ester / Benzoyl / Carboxylic acid derivative / Carboxylic acid ester / Hydrocarbon derivative show 12 more
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- tertiary amino compound, benzoate ester (CHEBI:9468)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 0619F35CGV
- CAS number
- 94-24-6
- InChI Key
- GKCBAIGFKIBETG-UHFFFAOYSA-N
- InChI
- InChI=1S/C15H24N2O2/c1-4-5-10-16-14-8-6-13(7-9-14)15(18)19-12-11-17(2)3/h6-9,16H,4-5,10-12H2,1-3H3
- IUPAC Name
- 2-(dimethylamino)ethyl 4-(butylamino)benzoate
- SMILES
- CCCCNC1=CC=C(C=C1)C(=O)OCCN(C)C
References
- General References
- Not Available
- External Links
- KEGG Drug
- D00551
- KEGG Compound
- C07526
- PubChem Compound
- 5411
- PubChem Substance
- 310265012
- ChemSpider
- 5218
- BindingDB
- 50017659
- 10391
- ChEBI
- 9468
- ChEMBL
- CHEMBL698
- ZINC
- ZINC000001530811
- PharmGKB
- PA451638
- PDBe Ligand
- TE4
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Tetracaine
- PDB Entries
- 4omw / 4y0p / 6yqg / 7bf7 / 7bf8 / 7bf9
- FDA label
- Download (3.51 MB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Prevention Anesthesia of Mucous Membrane 1 4 Completed Supportive Care Arterial Catheterization 1 4 Completed Supportive Care Pain 1 4 Completed Treatment Dermatitis Papillaris Capillitii / Tattooing 1 4 Completed Treatment Disseminated Sclerosis 1 4 Completed Treatment Epicondylitis of the Elbow 1 4 Completed Treatment Healthy Volunteers 1 4 Completed Treatment Lacerations / LET / Procedural Pain 1 4 Completed Treatment LET / Skin Lacerations 1 4 Completed Treatment Local Anesthesia of the Skin 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Gel Topical 40 mg / g Ointment Topical Ointment Topical 2 g/100g Cream Topical 10 mg/1mL Solution Topical Aerosol Topical Gel Topical Cream Topical Gel Dental Solution / drops Buccal Aerosol, metered Topical Aerosol, spray Topical Spray Nasal Solution / drops Ophthalmic 0.5 % w/v Solution / drops Ophthalmic 1 % w/v Cream Topical 20 mg/1mL Cream Topical 20 mg/1000mg Injection, powder, for solution Subarachnoid 10 mg/1mL Cream Topical 20 mg/1g Gel Dental; Topical Gel Buccal Solution / drops Auricular (otic) Gel Oral; Topical Solution / drops Ophthalmic Cream Topical 2 mg/100mg Powder, for solution Intraspinal 20 mg / 2 mL Solution Ophthalmic 0.5 % Solution / drops Ophthalmic .5 % Powder, for solution Intraspinal 20 mg / amp Plaster Transdermal Cream Rectal Suppository Rectal Cream Cutaneous Kit Infiltration; Topical Liquid Infiltration; Subcutaneous; Topical Liquid Parenteral; Topical Liquid Infiltration Liquid Infiltration; Subcutaneous Aerosol, metered Dental 754 mg / 65 g Aerosol, metered Oral; Topical 11.6 mg / g Patch Cutaneous Patch Topical Suppository Topical Gel Topical 20 mg/1000mL Injection Subarachnoid 10 mg/1mL Powder Not applicable 1 g/1g Solution Ophthalmic 5 mg/1mL Solution / drops Ophthalmic 5 mg/1mL Cream Topical 2 % Gel Topical 20 mg/1g Spray Topical Liquid Ophthalmic 25 mg/5mL Gel Topical 2 % Liquid Topical Aerosol Oral Liquid Ophthalmic 5 mg/1ml Gel Oral - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US6546281 No 2003-04-08 2015-07-28 US US5658583 No 1997-08-19 2015-07-28 US US6465006 No 2002-10-15 2015-07-28 US US6465709 No 2002-10-15 2020-07-07 US US6780426 No 2004-08-24 2015-07-28 US US6306431 No 2001-10-23 2015-07-28 US US5919479 No 1999-07-06 2015-07-28 US US6528086 No 2003-03-04 2019-09-28 US US8580282 No 2013-11-12 2030-04-02 US US6413499 No 2002-07-02 2020-03-20 US US9308191 No 2016-04-12 2030-04-02 US US10350180 No 2019-07-16 2031-01-14 US US10603293 No 2011-01-14 2031-01-14 US US10751305 No 2011-01-14 2031-01-14 US
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.555 mg/mL ALOGPS logP 3.54 ALOGPS logP 2.79 ChemAxon logS -2.7 ALOGPS pKa (Strongest Basic) 8.42 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 3 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 41.57 Å2 ChemAxon Rotatable Bond Count 9 ChemAxon Refractivity 80.17 m3·mol-1 ChemAxon Polarizability 31.9 Å3 ChemAxon Number of Rings 1 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Modulator
- General Function
- Voltage-gated calcium channel activity
- Specific Function
- Calcium channel that mediates the release of Ca(2+) from the sarcoplasmic reticulum into the cytoplasm and thereby plays a key role in triggering muscle contraction following depolarization of T-tu...
- Gene Name
- RYR1
- Uniprot ID
- P21817
- Uniprot Name
- Ryanodine receptor 1
- Molecular Weight
- 565170.715 Da
References
- Laver DR, van Helden DF: Three independent mechanisms contribute to tetracaine inhibition of cardiac calcium release channels. J Mol Cell Cardiol. 2011 Sep;51(3):357-69. doi: 10.1016/j.yjmcc.2011.05.009. Epub 2011 May 19. [Article]
- Lanner JT, Georgiou DK, Joshi AD, Hamilton SL: Ryanodine receptors: structure, expression, molecular details, and function in calcium release. Cold Spring Harb Perspect Biol. 2010 Nov;2(11):a003996. doi: 10.1101/cshperspect.a003996. Epub 2010 Oct 20. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Modulator
- General Function
- Suramin binding
- Specific Function
- Calcium channel that mediates the release of Ca(2+) from the sarcoplasmic reticulum into the cytoplasm and thereby plays a key role in triggering cardiac muscle contraction. Aberrant channel activa...
- Gene Name
- RYR2
- Uniprot ID
- Q92736
- Uniprot Name
- Ryanodine receptor 2
- Molecular Weight
- 564562.71 Da
References
- Laver DR, van Helden DF: Three independent mechanisms contribute to tetracaine inhibition of cardiac calcium release channels. J Mol Cell Cardiol. 2011 Sep;51(3):357-69. doi: 10.1016/j.yjmcc.2011.05.009. Epub 2011 May 19. [Article]
- Lanner JT, Georgiou DK, Joshi AD, Hamilton SL: Ryanodine receptors: structure, expression, molecular details, and function in calcium release. Cold Spring Harb Perspect Biol. 2010 Nov;2(11):a003996. doi: 10.1101/cshperspect.a003996. Epub 2010 Oct 20. [Article]
- 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
- 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]
- Gammaitoni AR, Goitz HT, Marsh S, Marriott TB, Galer BS: Heated lidocaine/tetracaine patch for treatment of patellar tendinopathy pain. J Pain Res. 2013 Jul 19;6:565-70. doi: 10.2147/JPR.S46239. Print 2013. [Article]
Drug created on September 15, 2015 20:08 / Updated on July 23, 2021 16:03