TETRACAINE HYDROCHLORIDE

US Approved OTC

First marketed in 1932

Details

Stereochemistry	ACHIRAL
Molecular Formula	C15H24N2O2.ClH
Molecular Weight	300.824
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=PPWHTZKZQNXVAE-UHFFFAOYSA-N

InChI=1S/C15H24N2O2.ClH/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;1H

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 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
Unexpected recurrent seizures following repeated spinal injections of tetracaine--a case report.	2000 Jun	11000675
Redox properties of local anesthetics: A structural determinant of closed channel blockers in BTX-modified Na+ channels.	2001	11497109
From cocaine to ropivacaine: the history of local anesthetic drugs.	2001 Aug	11895133
Dynamic regulation of sarcoplasmic reticulum Ca(2+) content and release by luminal Ca(2+)-sensitive leak in rat ventricular myocytes.	2001 Aug	11463625
Topical anesthetics update: EMLA and beyond.	2001 Dec	11849263
[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
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
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
Local anesthetic effects on priming and activation of human neutrophils.	2001 Jul	11465548
Interactions between 3-(Trifluoromethyl)-3-(m-[(125)I]iodophenyl)diazirine and tetracaine, phencyclidine, or histrionicotoxin in the Torpedo series nicotinic acetylcholine receptor ion channel.	2001 Jun	11353813
Corneal sensation after topical anesthesia.	2001 Mar	11248828
Endoscopic carbon dioxide laser turbinoplasty.	2001 Mar	11244523
LET versus EMLA for pretreating lacerations: a randomized trial.	2001 Mar	11229943
Effect of tetracaine chlorhydrate on the mechanical properties of the erythrocyte membrane.	2001 Mar-Apr	11259160
Ouabain stimulates unidirectional and net potassium efflux in resting mammalian skeletal muscle.	2001 Nov	11760095
EMLA or Ametop, and for how long?	2001 Oct	11576145
Spinal anesthesia in children: pro.	2001 Sep	11778106
Tetracaine topical anesthesia for myringotomy.	2001 Sep	11568619
Tetramethylpyrazine attenuates spinal cord ischemic injury due to aortic cross-clamping in rabbits.	2002 Apr 17	11960559
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
A novel Ca2+-induced Ca2+ release mechanism mediated by neither inositol trisphosphate nor ryanodine receptors.	2002 Feb 1	11802790
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
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
Agonist-induced phasic and tonic responses in smooth muscle are mediated by InsP(3).	2002 May 15	11973361
Calcium-induced calcium release and cyclic ADP-ribose-mediated signaling in the myocytes from small coronary arteries.	2002 Sep	12204658

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 HYDROCHLORIDE

Common Name

English

NSC-757337

Code

English

MENONASAL

Common Name

English

TETRACAINE HYDROCHLORIDE [EP MONOGRAPH]

Common Name

English

2-(DIMETHYLAMINO)ETHYL P-(BUTYLAMINO)BENZOATE MONOHYDROCHLORIDE

Common Name

English

TETOCAINE

Common Name

English

TETRACAINE HYDROCHLORIDE COMPONENT OF KOVANAZE

Brand Name

English

TETRACAINE HYDROCHLORIDE [MART.]

Common Name

English

TETRACAINI HYDROCHLORIDUM [WHO-IP LATIN]

Common Name

English

BUTETHANOL

Common Name

English

TETRACAINE HYDROCHLORIDE [USP-RS]

Common Name

English

PANTOCAINE

Common Name

English

CURTACAIN

Common Name

English

BENZOIC ACID, 4-(BUTYLAMINO)-, 2-(DIMETHYLAMINO)ETHYL ESTER, MONOHYDROCHLORIDE

Common Name

English

DICAINUM [WHO-IP]

Common Name

English

TETRACAINE HCL

Common Name

English

TETRACAINE HYDROCHLORIDE [JAN]

Common Name

English

TETRACA

Brand Name

English

TETRACAINE HYDROCHLORIDE [GREEN BOOK]

Common Name

English

TETRACAINE HYDROCHLORIDE [USP MONOGRAPH]

Common Name

English

Tetracaine hydrochloride [WHO-DD]

Common Name

English

TETRACAINE HYDROCHLORIDE [WHO-IP]

Common Name

English

AMETHOCAINE HYDROCHLORIDE [WHO-IP]

Common Name

English

TETRACAINE HYDROCHLORIDE [MI]

Common Name

English

TETRACAINE HYDROCHLORIDE [ORANGE BOOK]

Common Name

English

KOVANAZE COMPONENT TETRACAINE HYDROCHLORIDE

Brand Name

English

ANETHAINE

Common Name

English

TETRACAINE HYDROCHLORIDE [VANDF]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C245