Identification

Name
Tetracaine
Accession Number
DB09085
Type
Small Molecule
Groups
Approved, Vet approved
Description

Tetracaine is an ester local anaesthetic currently available in combination with lidocaine as a cream and patch.

Structure
Thumb
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 HCl
Product Ingredients
IngredientUNIICASInChI Key
Tetracaine hydrochloride5NF5D4OPCI136-47-0PPWHTZKZQNXVAE-UHFFFAOYSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Ametop Gel 4%Gel40 mgTopicalSmith & Nephew, Inc.1998-03-16Not applicableCanada
PontocainePowder, for solution20 mgIntraspinalHospira, Inc.2001-07-15Not applicableCanada
Pontocaine 5 mg/mlSolution0.5 %OphthalmicHospira, Inc.2001-06-01Not applicableCanada
Pontocaine Dps 0.5%Solution / drops.5 %OphthalmicSanofi1937-12-312001-08-10Canada
Pontocaine Pws Inj 20mg/ampPowder, for solution20 mgIntraspinalSanofi1951-12-312001-08-10Canada
Supracaine Aerosol 11.6mg/gmAerosol, metered11.6 mgOral; TopicalHoechst Roussel Canada Inc.1993-12-312000-07-28Canada
Tetracaine HydrochlorideSolution5 mg/1mLOphthalmicALCON LABORATORIES, INC.2016-10-26Not applicableUs
Tetracaine HydrochlorideSolution5 mg/1mLOphthalmicA-S Medication Solutions1969-03-282017-12-31Us
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Blt 3Ointment2 g/100gTopicalCentura Pharmaceuticals, Inc2016-10-30Not applicableUs
Burn CreamCream10 mg/1mLTopicalBio Medical & Pharmaceutical Manufacturing Corporation2016-08-19Not applicableUs
Burn Solution CreamCream10 mg/1mLTopicalBurn Solution Foundations2016-08-23Not applicableUs
Comfortox TetracaineCream20 mg/1000mgTopicalSambria Pharmaceuticals2016-09-14Not applicableUs
Eclipse Topical Analgesic LLCream20 mg/1000mgTopicalSambria Pharmaceuticals2017-05-01Not applicableUs
Minims Tetracaine Hydrochloride 0.5%Solution / drops0.5 %OphthalmicValeant Canada Lp Valeant Canada S.E.C.1995-12-31Not applicableCanada
Minims Tetracaine Hydrochloride 1%Solution / drops1 %OphthalmicValeant Canada Lp Valeant Canada S.E.C.1995-12-31Not applicableCanada
NeuroMed LACream20 mg/1mLTopicalSambria Pharmaceuticals2015-12-222016-05-23Us
NeuroMed Topical Analgesic LACream20 mg/1000mgTopicalSambria Pharmaceuticals2016-02-01Not applicableUs
Numfast Tetracaine GreenCream20 mg/1gTopicalUnit Dose, Ltd.2016-01-20Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Cetacaine LiquidTetracaine hydrochloride (2 %) + Benzocaine (14 %) + Butamben (2 %)LiquidTopicalCetylite Industries, Inc.1996-09-19Not applicableCanada
Cetacaine SprayTetracaine hydrochloride (2 %) + Benzocaine (14 %) + Butamben (2 %)AerosolTopicalCetylite Industries, Inc.1994-12-31Not applicableCanada
CutiecaineTetracaine (20 mg/1g) + Benzocaine (180 mg/1g)CreamTopicalInnovatech Inc2010-08-31Not applicableUs
Denti-care Denti-freeze Topical Anesthetic GelTetracaine hydrochloride (2 %) + Benzocaine (18 %)GelTopicalAr Medicom Inc.2009-04-16Not applicableCanada
Denti-care Topical Anesthetic GelTetracaine hydrochloride (2 %) + Benzocaine (18 %)GelTopicalAmd Medicom Inc1999-11-29Not applicableCanada
Denti-care Topical Anesthetic Liquid SprayTetracaine hydrochloride (2.0 %) + Benzocaine (18.0 %)SprayTopicalAr Medicom Inc.2000-05-012006-08-03Canada
Dermacaine-RTetracaine (2 %) + Benzocaine (18 %)CreamTopicalInnovatech IncNot applicableNot applicableCanada
EndosprayTetracaine hydrochloride (2 mg) + Benzocaine (18 mg)Aerosol, meteredTopicalAxcan Pharma1998-05-052002-09-26Canada
Henry Schein Topical Anesthetic GelTetracaine hydrochloride (2 %) + Benzocaine (18 %)GelOral; TopicalAbj Custom PackagingNot applicableNot applicableCanada
KovanazeTetracaine hydrochloride (30 mg/1mL) + Oxymetazoline hydrochloride (0.5 mg/1mL)SprayNasalSt. Renatus2016-09-01Not applicableUs
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
AltacaineTetracaine hydrochloride (5 mg/1mL)SolutionOphthalmicAltaire Pharmaceuticals Inc.2002-02-01Not applicableUs
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
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
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
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
Denti-Care Denti-Freeze Topical Anesthetic BubblegumTetracaine hydrochloride (0.02 g/1g) + Benzocaine (0.18 g/1g)GelDentalAr Medicom Inc.2000-02-01Not applicableUs
Denti-Care Denti-Freeze Topical Anesthetic CherryTetracaine hydrochloride (0.02 g/1g) + Benzocaine (0.18 g/1g)GelDentalAr Medicom Inc.2000-04-01Not applicableUs
Denti-Care Denti-Freeze Topical Anesthetic MintTetracaine hydrochloride (0.02 g/1g) + Benzocaine (0.18 g/1g)GelDentalAr Medicom Inc.2000-02-01Not applicableUs
Denti-Care Denti-Freeze Topical Anesthetic RaspberryTetracaine hydrochloride (0.02 g/1g) + Benzocaine (0.18 g/1g)GelDentalAr Medicom Inc.2005-04-01Not applicableUs
Denti-Care Denti-Freeze Topical Anesthetic StrawberryTetracaine hydrochloride (0.02 g/1g) + Benzocaine (0.18 g/1g)GelDentalAr Medicom Inc.2000-02-01Not applicableUs
International/Other Brands
Pontocaine / Pontocaine HCl
Categories
UNII
0619F35CGV
CAS number
94-24-6
Weight
Average: 264.369
Monoisotopic: 264.183778021
Chemical Formula
C15H24N2O2
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

Pharmacology

Indication

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.

Associated Therapies
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
Human
ARyanodine receptor 2
modulator
Human
AVoltage gated sodium channel
antagonist
human
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.

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.

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.

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 Tetracaine resulting in an increased serum concentration and potentially a worsening of adverse effects.
Technetium Tc-99m tilmanoceptTetracaine may decrease effectiveness of Technetium Tc-99m tilmanocept as a diagnostic agent.
Food Interactions
Not Available

References

General References
Not Available
External Links
KEGG Drug
D00551
KEGG Compound
C07526
PubChem Compound
5411
PubChem Substance
310265012
ChemSpider
5218
BindingDB
50017659
ChEBI
9468
ChEMBL
CHEMBL698
PharmGKB
PA451638
HET
TE4
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Tetracaine
ATC Codes
D04AB06 — TetracaineN01BA03 — TetracaineS01HA03 — TetracaineC05AD02 — Tetracaine
AHFS Codes
  • 84:08.00 — Antipruritics and Local Anesthetics
  • 34:00.00 — Dental Agents
  • 28:04.00 — General Anesthetics
  • 52:16.00 — Local Anesthetics
PDB Entries
4omw / 4y0p
FDA label
Download (3.51 MB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedSupportive CareCutaneous Abscess / Pain NOS1
0WithdrawnPreventionHemodynamics Instability1
1CompletedBasic ScienceAnaesthesia therapy1
1CompletedBasic ScienceHealthy Volunteers2
1CompletedHealth Services ResearchPain NOS1
1, 2CompletedTreatmentKnee Osteoarthritis (Knee OA)1
2CompletedPreventionAnaesthesia therapy1
2CompletedPreventionNo Disease State or Condition1
2CompletedSupportive CareAnaesthesia therapy1
2CompletedSupportive CareNeedle Phobia / Pain NOS1
2CompletedTreatmentAnaesthesia therapy3
2CompletedTreatmentAnesthetics, Local / Pain NOS / Venipuncture1
2CompletedTreatmentCarpal Tunnel Syndrome (CTS)1
2CompletedTreatmentMyofascial Pain Syndromes1
2CompletedTreatmentPain NOS1
2CompletedTreatmentPain NOS / Palliative Care / Phlebotomy1
2CompletedTreatmentPatellar Tendinopathy1
2CompletedTreatmentPostherpetic Neuralgia1
2CompletedTreatmentShoulder Impingement Syndrome1
2Unknown StatusTreatmentShoulder Pain1
2, 3Not Yet RecruitingTreatmentCorneal Abrasions1
3CompletedSupportive CareProcedural Pain Relief1
3CompletedTreatmentAnaesthesia therapy3
3CompletedTreatmentCataracts1
3CompletedTreatmentNewborn Infants / Pain NOS1
3CompletedTreatmentPain NOS6
3TerminatedTreatmentAnaesthesia therapy1
4CompletedPreventionAnesthesia of Mucous Membrane1
4CompletedSupportive CareArterial Catheterization1
4CompletedSupportive CarePain NOS1
4CompletedTreatmentDermatitis Papillaris Capillitii / Tattooing1
4CompletedTreatmentDisseminated Sclerosis1
4CompletedTreatmentEpicondylitis of the Elbow1
4CompletedTreatmentHealthy Volunteers1
4CompletedTreatmentLocal Anesthesia of the Skin1
4CompletedTreatmentPain Associated With Epidural Needle Insertion1
4CompletedTreatmentPain NOS1
4Not Yet RecruitingOtherLocal Anesthetic Drug Adverse Reaction / Local Infiltration / Pulp Disease, Dental1
4SuspendedBasic SciencePain NOS1
4TerminatedSupportive CarePain NOS1
4TerminatedTreatmentLabour Pain1
4TerminatedTreatmentNasolabial Folds1
4WithdrawnNot AvailableFeeling Anxious / Pain NOS1
4WithdrawnTreatmentAnaesthesia therapy / Healthy Volunteers1
4WithdrawnTreatmentAnesthesia, Dental / Endodontic Disease / Inflammations, Endodontic / Local Anesthesia1
Not AvailableActive Not RecruitingPreventionArterial Hypotension1
Not AvailableCompletedNot AvailableAdverse Drug Events1
Not AvailableCompletedPreventionPain NOS1
Not AvailableCompletedPreventionPharyngitis1
Not AvailableCompletedSupportive CareCataracts1
Not AvailableCompletedTreatmentAge-Related Macular Degeneration (AMD)1
Not AvailableCompletedTreatmentHysteroscopy1
Not AvailableUnknown StatusPreventionPain NOS1
Not AvailableUnknown StatusTreatmentMacular Degeneration1
Not AvailableWithdrawnTreatmentPain NOS1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
GelTopical40 mg
OintmentTopical2 g/100g
CreamTopical10 mg/1mL
SolutionTopical
AerosolTopical
GelDental
Aerosol, meteredTopical
Aerosol, sprayTopical
SprayNasal
Solution / dropsOphthalmic0.5 %
Solution / dropsOphthalmic1 %
CreamTopical20 mg/1mL
Injection, powder, for solutionSubarachnoid10 mg/1mL
CreamTopical20 mg/1g
GelDental; Topical
GelBuccal
CreamTopical20 mg/1000mg
GelOral; Topical
CreamTopical
CreamTopical2 mg/100mg
SolutionOphthalmic0.5 %
Solution / dropsOphthalmic.5 %
Powder, for solutionIntraspinal20 mg
KitInfiltration; Topical
LiquidInfiltration; Subcutaneous; Topical
LiquidParenteral; Topical
LiquidInfiltration
LiquidInfiltration; Subcutaneous
Aerosol, meteredDental754 mg
Aerosol, meteredOral; Topical11.6 mg
PatchCutaneous
PatchTopical
Kit
GelTopical20 mg/1000mL
InjectionSubarachnoid10 mg/1mL
SolutionOphthalmic5 mg/1mL
CreamTopical2 %
GelTopical20 mg/1g
LiquidOphthalmic25 mg/5mL
LiquidOphthalmic3 mg/ 0.6mL
GelTopical2 %
LiquidTopical
GelTopical
SprayTopical
AerosolOral
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US6546281No2003-04-082015-07-28Us
US5658583No1997-08-192015-07-28Us
US6465006No2002-10-152015-07-28Us
US6465709No2002-10-152020-07-07Us
US6780426No2004-08-242015-07-28Us
US6306431No2001-10-232015-07-28Us
US5919479No1999-07-062015-07-28Us
US6528086No2003-03-042019-09-28Us
US8580282No2013-11-122030-04-02Us
US6413499No2002-07-022020-03-20Us
US9308191No2016-04-122030-04-02Us

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

Taxonomy

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
Aminobenzoic acid or derivatives / Benzoate ester / Benzoyl / Aniline or substituted anilines / Phenylalkylamine / Secondary aliphatic/aromatic amine / Carboxylic acid ester / Amino acid or derivatives / Tertiary aliphatic amine / Tertiary amine
show 12 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
tertiary amino compound, benzoate ester (CHEBI:9468)

Targets

Kind
Protein
Organism
Human
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. [PubMed:21624373]
  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. [PubMed:20961976]
Kind
Protein
Organism
Human
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. [PubMed:21624373]
  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. [PubMed:20961976]
3. Voltage gated sodium channel
Kind
Protein group
Organism
human
Pharmacological action
Yes
Actions
Antagonist
References
  1. 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. [PubMed:23888118]

Drug created on September 15, 2015 14:08 / Updated on November 18, 2018 13:32