TETRACAINE

US Approved OTC

First marketed in 1932

Details

Stereochemistry	ACHIRAL
Molecular Formula	C15H24N2O2
Molecular Weight	264.3638
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCCNc1ccc(cc1)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

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 69 Target ID: CHEMBL2331043 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/208135s000lbl.pdf	Blocker 511

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 8043	TETRACAINE HYDROCHLORIDE Approved Use is indicated for procedures requiring a rapid and shortacting topical ophthalmic anesthetic Launch Date 1.16294405E12

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 1475

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
Nav1.5 93

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
Nav1.5 96	inhibitor 1489 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 1507	inhibitor 1489 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
From cocaine to ropivacaine: the history of local anesthetic drugs.	2001 Aug	11895133
Topical anesthetics in children: agents and techniques that equally comfort patients, parents, and clinicians.	2001 Aug	11717557
Topical anesthetics update: EMLA and beyond.	2001 Dec	11849263
Allergic contact dermatitis from local anaesthetic on peristomal skin.	2001 Dec	11846754
An integrative, in situ approach to examining K+ flux in resting skeletal muscle.	2001 Dec	11824943
[An electrophysiological study of ropivacaine on excised cervical vagus nerves of rabbit].	2001 Dec	11797357
Pharmacological regulation of gastric acid secretion in the apical membrane of parietal cells; a new target for antisecretory drugs.	2001 Dec	11787764
High-concentration tetracaine for the management of trigeminal neuralgia: quantitative assessment of sensory function after peripheral nerve block.	2001 Dec	11783812
Histamine-induced Ca2+ release in bovine adrenal chromaffin cells.	2001 Dec	11770005
Role of the bandage soft contact lens in the postoperative laser in situ keratomileusis patient.	2001 Dec	11738907
Inhibition of wild-type and mutant neuronal nicotinic acetylcholine receptors by local anesthetics.	2001 Dec	11723244
Local anesthetics noncompetitively inhibit function of four distinct nicotinic acetylcholine receptor subtypes.	2001 Dec	11714893
Spark- and ember-like elementary Ca2+ release events in skinned fibres of adult mammalian skeletal muscle.	2001 Dec 1	11731572
Distribution of tetracaine and its metabolite in rabbits after high versus normal spinal anesthesia.	2001 Dec 27	11792502
Ouabain stimulates unidirectional and net potassium efflux in resting mammalian skeletal muscle.	2001 Nov	11760095
Cauda equina syndrome after spinal tetracaine: electromyographic evaluation--20 years follow-up.	2001 Nov	11685003
Simultaneous determination of mepivacaine, tetracaine, and p-butylaminobenzoic acid by high-performance liquid chromatography.	2001 Nov-Dec	12183188
[Low dose intrathecal morphine and postoperative pain relief in elderly patients].	2001 Oct	11712341
Spinal anesthesia in children: pro.	2001 Sep	11778106
Role of the dopamine transporter and the sodium channel in the cocaine-like discriminative stimulus effects of local anesthetics in rats.	2001 Sep	11605081
Radial artery cannulation: topical amethocaine gel versus lidocaine infiltration.	2002 Apr	12066736
Lidocaine-prilocaine cream versus tetracaine gel for procedural pain in children.	2002 Apr	11918521
Tetramethylpyrazine attenuates spinal cord ischemic injury due to aortic cross-clamping in rabbits.	2002 Apr 17	11960559
Amphiphilic effects of local anesthetics on rotational mobility in neuronal and model membranes.	2002 Aug 19	12101004
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
Lidocaine inhibits secretion of IL-8 and IL-1beta and stimulates secretion of IL-1 receptor antagonist by epithelial cells.	2002 Feb	11876744
The inhibition of the N-methyl-D-aspartate receptor channel by local anesthetics in mouse CA1 pyramidal neurons.	2002 Feb	11812692
A novel Ca2+-induced Ca2+ release mechanism mediated by neither inositol trisphosphate nor ryanodine receptors.	2002 Feb 1	11802790
The feasibility of office-based laser-assisted tympanic membrane fenestration with tympanostomy tube insertion: the duPont Hospital experience.	2002 Jan 11	11738691
Functional properties of ryanodine receptors from rat dorsal root ganglia.	2002 Jan 30	11821055
Ciguatoxin-induced oscillations in membrane potential and action potential firing in rat parasympathetic neurons.	2002 Jul	12169106
The inhibitory effect of local anesthetics on bradykinin-induced phospholipase D activation in rat pheochromocytoma PC12 cells.	2002 Jul	12088949
Principles of office anesthesia: part II. Topical anesthesia.	2002 Jul 1	12126037
Allosterically linked noncompetitive antagonist binding sites in the resting nicotinic acetylcholine receptor ion channel.	2002 Jul 1	12061809
Assessment of sarcoplasmic reticulum Ca(2+) flux pathways in cardiomyocytes from rabbits with infarct-induced left-ventricular dysfunction.	2002 Jun	12111244
Interaction of monosulfonate tetraphenyl porphyrin, a competitive inhibitor, with acetylcholinesterase.	2002 Jun	11959466
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
Spinal anesthesia in 62 premature, former-premature or young infants--technical aspects and pitfalls.	2002 Mar	11861344
Buprenorphine added to the local anesthetic for axillary brachial plexus block prolongs postoperative analgesia.	2002 Mar-Apr	11915063
A laser-clinic nurse with allergic contact dermatitis from tetracaine.	2002 May	12084090
The effect of baricity of intrathecal morphine in children receiving tetracaine spinal anaesthesia for cardiac surgery: a preliminary report.	2002 May	11982840
Involvement of the mitogen-activated protein kinase family in tetracaine-induced PC12 cell death.	2002 May	11981161
Reagent-less detection of a competitive inhibitor of immobilized acetylcholinesterase.	2002 May	11888725
Agonist-induced phasic and tonic responses in smooth muscle are mediated by InsP(3).	2002 May 15	11973361
Managing patients with local anesthetic complications using alternative methods.	2002 May-Jun	12174527
Amethocaine-lidocaine cream, a new topical formulation for preventing venopuncture-induced pain in children.	2002 May-Jun	12016603
Calcium-induced calcium release and cyclic ADP-ribose-mediated signaling in the myocytes from small coronary arteries.	2002 Sep	12204658
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

Name

Type

Language

TETRACAINE

Official Name

English

TETRACAINE [ORANGE BOOK]

Common Name

English

TETRACAINE [INN]

Common Name

English

AMETHOCAINE

Common Name

English

TETRACAINE [GREEN BOOK]

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]

Common Name

English

TETRACAINE [USP-RS]

Common Name

English

TETRACAINE [WHO-DD]

Common Name

English

Classification Tree Code System Code

CFR

21 CFR 524.1484C