TETRACAINE

US Approved OTC

First marketed in 1932

Details

Stereochemistry	ACHIRAL
Molecular Formula	C15H24N2O2
Molecular Weight	264.3633
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCCNC1=CC=C(C=C1)C(=O)OCCN(C)C

InChI

InChIKey=GKCBAIGFKIBETG-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Molecular Formula	C15H24N2O2
Molecular Weight	264.3633
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/208135s000lbl.pdf
Curator's Comment: description was created based on several sources, including: https://en.wikipedia.org/wiki/Tetracaine http://www.medchemexpress.com/Tetracaine.html

Tetracaine (INN, also known as amethocaine; trade name Pontocaine. Ametop and Dicaine) is a potent local anesthetic of the ester group. It is mainly used topically in ophthalmology and as an antipruritic, and it has been used in spinal anesthesia. Tetracaine blocks sodium ion channels required for the initiation and conduction of neuronal impulses thereby affecting local anesthesia. In biomedical research, tetracaine is used to alter the function of calcium release channels (ryanodine receptors) that control the release of calcium from intracellular stores. Tetracaine is an allosteric blocker of channel function. At low concentrations, tetracaine causes an initial inhibition of spontaneous calcium release events, while at high concentrations, tetracaine blocks release completely.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Sodium channel alpha subunit 76 Target ID: CHEMBL2331043 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/208135s000lbl.pdf	Blocker 537

Conditions

Condition	Modality	Targets	Highest Phase	Product
Rapid and short-acting topical ophthalmic anesthetic 3 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/208135s000lbl.pdf	Primary		Approved 8429	TETRACAINE HYDROCHLORIDE Approved Use is indicated for procedures requiring a rapid and shortacting topical ophthalmic anesthetic Launch Date 2006

C_max

Value	Dose	Co-administered	Analyte	Population
0.24 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22855901/	18 mg single, nasal dose: 18 mg route of administration: Nasal experiment type: SINGLE co-administered: OXYMETAZOLINE	OXYMETAZOLINE	TETRACAINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1.15 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22855901/	36 mg single, nasal dose: 36 mg route of administration: Nasal experiment type: SINGLE co-administered: OXYMETAZOLINE	OXYMETAZOLINE	TETRACAINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
886 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22855901/	36 mg single, nasal dose: 36 mg route of administration: Nasal experiment type: SINGLE co-administered: OXYMETAZOLINE	OXYMETAZOLINE	4-(BUTYLAMINO)BENZOIC ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
492 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22855901/	18 mg single, nasal dose: 18 mg route of administration: Nasal experiment type: SINGLE co-administered: OXYMETAZOLINE	OXYMETAZOLINE	4-(BUTYLAMINO)BENZOIC ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
1773 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22855901/	36 mg single, nasal dose: 36 mg route of administration: Nasal experiment type: SINGLE co-administered: OXYMETAZOLINE	OXYMETAZOLINE	4-(BUTYLAMINO)BENZOIC ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
862 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22855901/	18 mg single, nasal dose: 18 mg route of administration: Nasal experiment type: SINGLE co-administered: OXYMETAZOLINE	OXYMETAZOLINE	4-(BUTYLAMINO)BENZOIC ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
1.01 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22855901/	36 mg single, nasal dose: 36 mg route of administration: Nasal experiment type: SINGLE co-administered: OXYMETAZOLINE	OXYMETAZOLINE	4-(BUTYLAMINO)BENZOIC ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22855901/	18 mg single, nasal dose: 18 mg route of administration: Nasal experiment type: SINGLE co-administered: OXYMETAZOLINE	OXYMETAZOLINE	4-(BUTYLAMINO)BENZOIC ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
0.5 % multiple, oromucosal Dose: 0.5 % Route: oromucosal Route: multiple Dose: 0.5 % Sources: https://pubmed.ncbi.nlm.nih.gov/2721319	unhealthy, 75 years n = 1 Health Status: unhealthy Age Group: 75 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/2721319	Other AEs: Toxic reaction (NOS)... Other AEs: Toxic reaction (NOS) (grade 5) Sources: https://pubmed.ncbi.nlm.nih.gov/2721319

AEs

AE	Significance	Dose	Population
Toxic reaction (NOS)	grade 5	0.5 % multiple, oromucosal Dose: 0.5 % Route: oromucosal Route: multiple Dose: 0.5 % Sources: https://pubmed.ncbi.nlm.nih.gov/2721319	unhealthy, 75 years n = 1 Health Status: unhealthy Age Group: 75 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/2721319

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
			inhibitor 1612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
Nav1.5 97

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
Nav1.5 100	inhibitor 1626 Sources: https://www.nanion.de/images/phocadownloadpap/Application_Notes/Nanion_APP_Note_CE96_PL_384PE_CiPA_CardiacChannels_07001.pdf#page=3 Page: 3.0
hERG 1647	inhibitor 1626 Sources: https://www.nanion.de/images/phocadownloadpap/Application_Notes/Nanion_APP_Note_CE96_PL_384PE_CiPA_CardiacChannels_07001.pdf#page=2 Page: 2.0

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:9468	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:9468
ChemicalBook	CB9775567	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB9775567
MolPort	MolPort-001-783-476	https://www.molport.com/shop/molecule-link/MolPort-001-783-476
ZINC	ZINC000001530811	http://zinc15.docking.org/substances/ZINC000001530811
eMolecules	594825	https://www.emolecules.com/cgi-bin/more?vid=594825

PubMed

Title	Date	PubMed
Nitric oxide synthesis inhibition modifies the cardiotoxicity of tetracaine and lidocaine.	1999 Apr	10195510
Redox properties of local anesthetics: A structural determinant of closed channel blockers in BTX-modified Na+ channels.	2001	11497109
Differential effects of airway anesthesia on ozone-induced pulmonary responses in human subjects.	2001 Apr	11316647
Resident's column: Use of topical anesthetics in children.	2001 Apr	11303440
Local anesthetics potentiate nitric oxide synthase type 2 expression in rat glial cells.	2001 Apr	11294465
Charge movements in intact amphibian skeletal muscle fibres in the presence of cardiac glycosides.	2001 Apr 15	11306668
Inhibition of wild-type and mutant neuronal nicotinic acetylcholine receptors by local anesthetics.	2001 Dec	11723244
Distribution of tetracaine and its metabolite in rabbits after high versus normal spinal anesthesia.	2001 Dec 27	11792502
Topical anesthesia for phacoemulsification and painless subconjunctival antibiotic injection.	2001 Feb	11226781
Local anesthetic-induced microscopic and mesoscopic effects in micelles. A fluorescence, spin label and SAXS study. Single angle X-ray scattering.	2001 Feb 9	11342150
Comparison of HPLC and GC-MS methods for determination of embutramide (a component of Tanax or T-61) in biological specimens.	2001 Jul-Aug	11499885
No more tears: a randomized controlled double-blind trial of Amethocaine gel vs. placebo in the management of procedural pain in neonates.	2001 May	11380714
Simultaneous determination of mepivacaine, tetracaine, and p-butylaminobenzoic acid by high-performance liquid chromatography.	2001 Nov-Dec	12183188
The addition of epinephrine to tetracaine injected intrathecally sustains an increase in glutamate concentrations in the cerebrospinal fluid and worsens neuronal injury.	2001 Oct	11574382
Spinal anesthesia in children: pro.	2001 Sep	11778106
Tetracaine topical anesthesia for myringotomy.	2001 Sep	11568619
Topical anesthesia--a new approach to cataract surgery.	2001 Sep	11565156
Allergic contact dermatitis to proparacaine with subsequent cross-sensitization to tetracaine from ophthalmic preparations.	2001 Sep	11526525
Role of the dorsomedial striatum in behavioral flexibility for response and visual cue discrimination learning.	2002 Feb	11898801
Intercostal nerve block with 5% tetracaine for chronic pain syndromes.	2002 Feb	11880021
Functional properties of ryanodine receptors from rat dorsal root ganglia.	2002 Jan 30	11821055
Principles of office anesthesia: part II. Topical anesthesia.	2002 Jul 1	12126037
Assessment of sarcoplasmic reticulum Ca(2+) flux pathways in cardiomyocytes from rabbits with infarct-induced left-ventricular dysfunction.	2002 Jun	12111244
Bupivacaine, but not tetracaine, protects against the in vitro ischemic insult of rat hippocampal CA1 neurons.	2002 Mar	11900832
Topical anesthesia for minor gynecological procedures: a review.	2002 Mar	11889416
A laser-clinic nurse with allergic contact dermatitis from tetracaine.	2002 May	12084090
Reagent-less detection of a competitive inhibitor of immobilized acetylcholinesterase.	2002 May	11888725
Prophylactic IM small-dose phenylephrine blunts spinal anesthesia-induced hypotensive response during surgical repair of hip fracture in the elderly.	2002 Sep	12198065

Patents

Sample Use Guides

In Vivo Use Guide

One drop topically in the eye(s)

Route of Administration: Topical

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Sat Dec 16 17:16:35 GMT 2023` Edited by `admin` on `Sat Dec 16 17:16:35 GMT 2023`
Record UNII	0619F35CGV
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TETRACAINE

Official Name

English

TETRACAINE [ORANGE BOOK]

Common Name

English

tetracaine [INN]

Common Name

English

Tetracaine [WHO-DD]

Common Name

English

AMETHOCAINE

Common Name

English

TETRACAINE [GREEN BOOK]

Common Name

English

TETRACAINE [USP MONOGRAPH]

Common Name

English

SYNERA COMPONENT TETRACAINE

Common Name

English

TETRACAINE [MART.]

Common Name

English

TETRACAINE [VANDF]

Common Name

English

TETRACAINE COMPONENT OF SYNERA

Common Name

English

TETRACAINE [EP MONOGRAPH]

Common Name

English

TETRACAINE [USP-RS]

Common Name

English

Classification Tree Code System Code

CFR

21 CFR 524.1484C