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
Thumb
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.

Pharmacology
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Associated Conditions
Associated Therapies
Contraindications & Blackbox Warnings
Contraindications
Contraindications & Blackbox Warnings
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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.

TargetActionsOrganism
ARyanodine receptor 1
modulator
Humans
ARyanodine receptor 2
modulator
Humans
AVoltage-gated sodium channel alpha subunit
blocker
Humans
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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Toxicity

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.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of adverse effects can be increased when Tetracaine is combined with 1,2-Benzodiazepine.
AcetazolamideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Tetracaine.
AcetophenazineThe risk or severity of adverse effects can be increased when Acetophenazine is combined with Tetracaine.
AclidiniumTetracaine 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 Tetracaine.
AlfentanilThe therapeutic efficacy of Tetracaine can be increased when used in combination with Alfentanil.
AlimemazineThe risk or severity of adverse effects can be increased when Alimemazine is combined with Tetracaine.
AlmotriptanThe risk or severity of adverse effects can be increased when Almotriptan is combined with Tetracaine.
AlosetronThe risk or severity of adverse effects can be increased when Alosetron is combined with Tetracaine.
AlprazolamThe risk or severity of adverse effects can be increased when Alprazolam is combined with Tetracaine.
Interactions
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Food Interactions
No interactions found.

Products

Products
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Product Ingredients
IngredientUNIICASInChI Key
Tetracaine hydrochloride5NF5D4OPCI136-47-0PPWHTZKZQNXVAE-UHFFFAOYSA-N
International/Other Brands
Pontocaine HCl
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
AltacaineSolution5 mg/1mLOphthalmicAltaire Pharmaceuticals Inc.2002-02-012019-07-15US flag
Ametop Gel 4%Gel40 mg / gTopicalValeo Pharma Corp.1998-03-16Not applicableCanada flag
NiphanoidInjection, powder, for solution10 mg/1mLSubarachnoidHospira, Inc.1997-06-092015-01-01US flag
PontocainePowder, for solution20 mg / 2 mLIntraspinalHospira Healthcare Ulc2001-07-152018-11-29Canada flag
Pontocaine 5 mg/mlSolution0.5 %OphthalmicHospira Healthcare Ulc2001-06-012018-11-29Canada flag
Pontocaine Dps 0.5%Solution / drops.5 %OphthalmicSanofi1937-12-312001-08-10Canada flag
Pontocaine Pws Inj 20mg/ampPowder, for solution20 mg / ampIntraspinalSanofi1951-12-312001-08-10Canada flag
Supracaine Aerosol 11.6mg/gmAerosol, metered11.6 mg / gOral; TopicalHoechst Roussel Canada Inc.1993-12-312000-07-28Canada flag
TetracaineInjection10 mg/1mLSubarachnoidAkorn, Inc.2010-06-01Not applicableUS flag
Tetracaine HCLInjection10 mg/1mLSubarachnoidBpi Labs Llc2020-06-26Not applicableUS flag
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Blt 3Ointment2 g/100gTopicalCENTURA PHARMACEUTICALS INC2016-10-30Not applicableUS flag
Burn CreamCream10 mg/1mLTopicalBio-Medical & Pharmaceutical Manufacturing Corporation2016-08-19Not applicableUS flag
Burn Solution CreamCream10 mg/1mLTopicalBurn Solution Foundations2021-02-02Not applicableUS flag
Comfortox TetracaineCream20 mg/1000mgTopicalSambria Pharmaceuticals, Inc.2016-09-14Not applicableUS flag
Eclipse Topical Analgesic LLCream20 mg/1000mgTopicalSambria Pharmaceuticals, Inc.2016-02-01Not applicableUS flag
Minims Tetracaine HydrochlorideSolution / drops0.5 % w/vOphthalmicBausch Health, Canada Inc.1995-12-31Not applicableCanada flag
Minims Tetracaine HydrochlorideSolution / drops1 % w/vOphthalmicBausch Health, Canada Inc.1995-12-31Not applicableCanada flag
NeuroMed LACream20 mg/1mLTopicalSambria Pharmaceuticals2015-12-222016-05-23US flag
NeuroMed Topical Analgesic LACream20 mg/1000mgTopicalSambria Pharmaceuticals, Inc.2016-02-01Not applicableUS flag
Numfast Tetracaine GreenCream20 mg/1gTopicalUnit Dose, Ltd.2016-01-20Not applicableUS flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
BLT Skin CreamTetracaine (0.01 g/1g) + Benzocaine (0.2 g/1g) + Lidocaine (0.04 g/1g)CreamTopicalM2B Pharma LLC2020-02-04Not applicableUS flag
Blue Gel AnestheticTetracaine hydrochloride (10 mg/1g) + Epinephrine (1 mg/1g) + Lidocaine hydrochloride (50 mg/1g)GelTopicalDermal Source, Inc.2021-04-01Not applicableUS flag
Blue Gel AnestheticTetracaine hydrochloride (20 mg/1g) + Lidocaine hydrochloride (40 mg/1g)GelTopicalDermal Source, Inc.2004-03-012021-04-02US flag
Cetacaine LiquidTetracaine hydrochloride (2 %) + Benzocaine (14 %) + Butamben (2 %)LiquidTopicalCetylite Industries, Inc.1996-09-19Not applicableCanada flag
Cetacaine SprayTetracaine hydrochloride (2 %) + Benzocaine (14 %) + Butamben (2 %)AerosolTopicalCetylite Industries, Inc.1994-12-31Not applicableCanada flag
CutiecaineTetracaine (20 mg/1g) + Benzocaine (180 mg/1g)CreamTopicalInnovatech Inc2010-08-31Not applicableUS flag
Denti-care Topical Anesthetic GelTetracaine hydrochloride (2 %) + Benzocaine (18 %)GelTopicalAmd Medicom Inc1999-11-29Not applicableCanada flag
Denti-care Topical Anesthetic Liquid SprayTetracaine hydrochloride (2.0 %) + Benzocaine (18.0 %)SprayTopicalAmd Medicom Inc2000-05-012006-08-03Canada flag
Denticare Pro-freezeTetracaine hydrochloride (2 % w/w) + Benzocaine (18 % w/w)GelTopicalAmd Medicom Inc2009-04-162021-01-26Canada flag
Dermacaine-RTetracaine (2 % w/w) + Benzocaine (18 % w/w)CreamTopicalInnovatech IncNot applicableNot applicableCanada flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
AltacaineTetracaine hydrochloride (5 mg/1mL)SolutionOphthalmicAltaire Pharmaceuticals Inc.2002-02-012019-07-15US flag
Benzocaine 20% / Lidocaine 10% / Tetracaine 10%Tetracaine (10 g/100g) + Benzocaine (20 g/100g) + Lidocaine (10 g/100g)CreamTopicalSincerus Florida, LLC2019-05-22Not applicableUS flag
Benzocaine 20% / Lidocaine 10% / Tetracaine 10%Tetracaine (10 g/100g) + Benzocaine (20 g/100g) + Lidocaine (10 g/100g)OintmentTopicalSincerus Florida, LLC2019-05-17Not applicableUS flag
Benzocaine 20% / Lidocaine 10% / Tetracaine 10%Tetracaine (10 g/100g) + Benzocaine (20 g/100g) + Lidocaine (10 g/100g)CreamTopicalSincerus Florida, LLC2019-05-22Not applicableUS flag
Cetacaine AnestheticTetracaine hydrochloride (0.004 g/0.2g) + Benzocaine (0.028 g/0.2g) + Butamben (0.004 g/0.2g)Aerosol, sprayTopicalCetylite Industries, Inc.1958-01-01Not applicableUS flag
Cetacaine AnestheticTetracaine hydrochloride (0.004 g/0.2g) + Benzocaine (0.028 g/0.2g) + Butamben (0.004 g/0.2g)SolutionTopicalCetylite Industries, Inc.1960-01-01Not applicableUS flag
Cetacaine Topical AnestheticTetracaine hydrochloride (0.004 g/0.2g) + Benzocaine (0.028 g/0.2g) + Butamben (0.004 g/0.2g)GelTopicalCetylite Industries, Inc.1960-01-01Not applicableUS flag
Cetacaine Topical AnestheticTetracaine hydrochloride (0.004 g/0.2g) + Benzocaine (0.028 g/0.2g) + Butamben (0.004 g/0.2g)GelTopicalCetylite Industries, Inc.1960-01-01Not applicableUS flag
Denti-Care Denti-Freeze Topical Anesthetic BubblegumTetracaine hydrochloride (0.02 g/1g) + Benzocaine (0.18 g/1g)GelDentalAmd Medicom Inc.2000-02-012021-08-31US flag
Denti-Care Denti-Freeze Topical Anesthetic CherryTetracaine hydrochloride (0.02 g/1g) + Benzocaine (0.18 g/1g)GelDentalAmd Medicom Inc.2000-04-012021-09-30US flag

Categories

ATC Codes
C05AD02 — TetracaineN01BA03 — TetracaineD04AB06 — TetracaineN01BA53 — Tetracaine, combinationsS01HA03 — Tetracaine
Drug Categories
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
KEGG Drug
D00551
KEGG Compound
C07526
PubChem Compound
5411
PubChem Substance
310265012
ChemSpider
5218
BindingDB
50017659
RxNav
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
PhaseStatusPurposeConditionsCount
4CompletedPreventionAnesthesia of Mucous Membrane1
4CompletedSupportive CareArterial Catheterization1
4CompletedSupportive CarePain1
4CompletedTreatmentDermatitis Papillaris Capillitii / Tattooing1
4CompletedTreatmentDisseminated Sclerosis1
4CompletedTreatmentEpicondylitis of the Elbow1
4CompletedTreatmentHealthy Volunteers1
4CompletedTreatmentLacerations / LET / Procedural Pain1
4CompletedTreatmentLET / Skin Lacerations1
4CompletedTreatmentLocal Anesthesia of the Skin1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
GelTopical40 mg / g
OintmentTopical
OintmentTopical2 g/100g
CreamTopical10 mg/1mL
SolutionTopical
AerosolTopical
GelTopical
CreamTopical
GelDental
Solution / dropsBuccal
Aerosol, meteredTopical
Aerosol, sprayTopical
SprayNasal
Solution / dropsOphthalmic0.5 % w/v
Solution / dropsOphthalmic1 % w/v
CreamTopical20 mg/1mL
CreamTopical20 mg/1000mg
Injection, powder, for solutionSubarachnoid10 mg/1mL
CreamTopical20 mg/1g
GelDental; Topical
GelBuccal
Solution / dropsAuricular (otic)
GelOral; Topical
Solution / dropsOphthalmic
CreamTopical2 mg/100mg
Powder, for solutionIntraspinal20 mg / 2 mL
SolutionOphthalmic0.5 %
Solution / dropsOphthalmic.5 %
Powder, for solutionIntraspinal20 mg / amp
PlasterTransdermal
CreamRectal
SuppositoryRectal
CreamCutaneous
KitInfiltration; Topical
LiquidInfiltration; Subcutaneous; Topical
LiquidParenteral; Topical
LiquidInfiltration
LiquidInfiltration; Subcutaneous
Aerosol, meteredDental754 mg / 65 g
Aerosol, meteredOral; Topical11.6 mg / g
PatchCutaneous
PatchTopical
SuppositoryTopical
GelTopical20 mg/1000mL
InjectionSubarachnoid10 mg/1mL
PowderNot applicable1 g/1g
SolutionOphthalmic5 mg/1mL
Solution / dropsOphthalmic5 mg/1mL
CreamTopical2 %
GelTopical20 mg/1g
SprayTopical
LiquidOphthalmic25 mg/5mL
GelTopical2 %
LiquidTopical
AerosolOral
LiquidOphthalmic5 mg/1ml
GelOral
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US6546281No2003-04-082015-07-28US flag
US5658583No1997-08-192015-07-28US flag
US6465006No2002-10-152015-07-28US flag
US6465709No2002-10-152020-07-07US flag
US6780426No2004-08-242015-07-28US flag
US6306431No2001-10-232015-07-28US flag
US5919479No1999-07-062015-07-28US flag
US6528086No2003-03-042019-09-28US flag
US8580282No2013-11-122030-04-02US flag
US6413499No2002-07-022020-03-20US flag
US9308191No2016-04-122030-04-02US flag
US10350180No2019-07-162031-01-14US flag
US10603293No2011-01-142031-01-14US flag
US10751305No2011-01-142031-01-14US flag

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.555 mg/mLALOGPS
logP3.54ALOGPS
logP2.79ChemAxon
logS-2.7ALOGPS
pKa (Strongest Basic)8.42ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area41.57 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity80.17 m3·mol-1ChemAxon
Polarizability31.9 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
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
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-QTOF , positiveLC-MS/MSsplash10-014i-0390000000-0435246ac53e48fff280
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-004i-0900000000-987e041aca4bd931c37e
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-004i-2900000000-8fb0dc9fe24fa06781f9
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00fu-8900000000-13f5e95cf7277be78720
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0603-9500000000-43bdd69ad39be196db4d
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-004i-2910000000-a6e7d7e502323aaae4e8

Targets

Drugtargets
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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
  1. 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]
  2. 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
  1. 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]
  2. 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
  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. 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