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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 of TETRACAINE

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
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.

Originator

Curator's Comment:: Tetracaine was first synthesized in Germany in 1928 by Otto Eisleb (1887-1948), a chemist working for IG Farben

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
TETRACAINE HYDROCHLORIDE

Approved Use

is indicated for procedures requiring a rapid and shortacting topical ophthalmic anesthetic

Launch Date

1.16294405E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
0.24 ng/mL
18 mg single, nasal
dose: 18 mg
route of administration: Nasal
experiment type: SINGLE
co-administered: OXYMETAZOLINE
TETRACAINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
1.15 ng/mL
36 mg single, nasal
dose: 36 mg
route of administration: Nasal
experiment type: SINGLE
co-administered: OXYMETAZOLINE
TETRACAINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
886 ng/mL
36 mg single, nasal
dose: 36 mg
route of administration: Nasal
experiment type: SINGLE
co-administered: OXYMETAZOLINE
4-(BUTYLAMINO)BENZOIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
492 ng/mL
18 mg single, nasal
dose: 18 mg
route of administration: Nasal
experiment type: SINGLE
co-administered: OXYMETAZOLINE
4-(BUTYLAMINO)BENZOIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
1773 ng × h/mL
36 mg single, nasal
dose: 36 mg
route of administration: Nasal
experiment type: SINGLE
co-administered: OXYMETAZOLINE
4-(BUTYLAMINO)BENZOIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
862 ng × h/mL
18 mg single, nasal
dose: 18 mg
route of administration: Nasal
experiment type: SINGLE
co-administered: OXYMETAZOLINE
4-(BUTYLAMINO)BENZOIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
1.01 h
36 mg single, nasal
dose: 36 mg
route of administration: Nasal
experiment type: SINGLE
co-administered: OXYMETAZOLINE
4-(BUTYLAMINO)BENZOIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
1 h
18 mg single, nasal
dose: 18 mg
route of administration: Nasal
experiment type: SINGLE
co-administered: OXYMETAZOLINE
4-(BUTYLAMINO)BENZOIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
0.5 % multiple, oromucosal
Dose: 0.5 %
Route: oromucosal
Route: multiple
Dose: 0.5 %
Sources:
unhealthy, 75 years
n = 1
Health Status: unhealthy
Age Group: 75 years
Sex: M
Population Size: 1
Sources:
Other AEs: Toxic reaction (NOS)...
Other AEs:
Toxic reaction (NOS) (grade 5)
Sources:
AEs

AEs

AESignificanceDosePopulation
Toxic reaction (NOS) grade 5
0.5 % multiple, oromucosal
Dose: 0.5 %
Route: oromucosal
Route: multiple
Dose: 0.5 %
Sources:
unhealthy, 75 years
n = 1
Health Status: unhealthy
Age Group: 75 years
Sex: M
Population Size: 1
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Tox targets
PubMed

PubMed

TitleDatePubMed
From cocaine to ropivacaine: the history of local anesthetic drugs.
2001 Aug
Topical anesthetics in children: agents and techniques that equally comfort patients, parents, and clinicians.
2001 Aug
Topical anesthetics update: EMLA and beyond.
2001 Dec
Allergic contact dermatitis from local anaesthetic on peristomal skin.
2001 Dec
An integrative, in situ approach to examining K+ flux in resting skeletal muscle.
2001 Dec
[An electrophysiological study of ropivacaine on excised cervical vagus nerves of rabbit].
2001 Dec
Pharmacological regulation of gastric acid secretion in the apical membrane of parietal cells; a new target for antisecretory drugs.
2001 Dec
High-concentration tetracaine for the management of trigeminal neuralgia: quantitative assessment of sensory function after peripheral nerve block.
2001 Dec
Histamine-induced Ca2+ release in bovine adrenal chromaffin cells.
2001 Dec
Role of the bandage soft contact lens in the postoperative laser in situ keratomileusis patient.
2001 Dec
Inhibition of wild-type and mutant neuronal nicotinic acetylcholine receptors by local anesthetics.
2001 Dec
Local anesthetics noncompetitively inhibit function of four distinct nicotinic acetylcholine receptor subtypes.
2001 Dec
Spark- and ember-like elementary Ca2+ release events in skinned fibres of adult mammalian skeletal muscle.
2001 Dec 1
Distribution of tetracaine and its metabolite in rabbits after high versus normal spinal anesthesia.
2001 Dec 27
Ouabain stimulates unidirectional and net potassium efflux in resting mammalian skeletal muscle.
2001 Nov
Cauda equina syndrome after spinal tetracaine: electromyographic evaluation--20 years follow-up.
2001 Nov
Simultaneous determination of mepivacaine, tetracaine, and p-butylaminobenzoic acid by high-performance liquid chromatography.
2001 Nov-Dec
[Low dose intrathecal morphine and postoperative pain relief in elderly patients].
2001 Oct
Spinal anesthesia in children: pro.
2001 Sep
Role of the dopamine transporter and the sodium channel in the cocaine-like discriminative stimulus effects of local anesthetics in rats.
2001 Sep
Radial artery cannulation: topical amethocaine gel versus lidocaine infiltration.
2002 Apr
Lidocaine-prilocaine cream versus tetracaine gel for procedural pain in children.
2002 Apr
Tetramethylpyrazine attenuates spinal cord ischemic injury due to aortic cross-clamping in rabbits.
2002 Apr 17
Amphiphilic effects of local anesthetics on rotational mobility in neuronal and model membranes.
2002 Aug 19
Role of the dorsomedial striatum in behavioral flexibility for response and visual cue discrimination learning.
2002 Feb
Intercostal nerve block with 5% tetracaine for chronic pain syndromes.
2002 Feb
Lidocaine inhibits secretion of IL-8 and IL-1beta and stimulates secretion of IL-1 receptor antagonist by epithelial cells.
2002 Feb
The inhibition of the N-methyl-D-aspartate receptor channel by local anesthetics in mouse CA1 pyramidal neurons.
2002 Feb
A novel Ca2+-induced Ca2+ release mechanism mediated by neither inositol trisphosphate nor ryanodine receptors.
2002 Feb 1
The feasibility of office-based laser-assisted tympanic membrane fenestration with tympanostomy tube insertion: the duPont Hospital experience.
2002 Jan 11
Functional properties of ryanodine receptors from rat dorsal root ganglia.
2002 Jan 30
Ciguatoxin-induced oscillations in membrane potential and action potential firing in rat parasympathetic neurons.
2002 Jul
The inhibitory effect of local anesthetics on bradykinin-induced phospholipase D activation in rat pheochromocytoma PC12 cells.
2002 Jul
Principles of office anesthesia: part II. Topical anesthesia.
2002 Jul 1
Allosterically linked noncompetitive antagonist binding sites in the resting nicotinic acetylcholine receptor ion channel.
2002 Jul 1
Assessment of sarcoplasmic reticulum Ca(2+) flux pathways in cardiomyocytes from rabbits with infarct-induced left-ventricular dysfunction.
2002 Jun
Interaction of monosulfonate tetraphenyl porphyrin, a competitive inhibitor, with acetylcholinesterase.
2002 Jun
Bupivacaine, but not tetracaine, protects against the in vitro ischemic insult of rat hippocampal CA1 neurons.
2002 Mar
Topical anesthesia for minor gynecological procedures: a review.
2002 Mar
Spinal anesthesia in 62 premature, former-premature or young infants--technical aspects and pitfalls.
2002 Mar
Buprenorphine added to the local anesthetic for axillary brachial plexus block prolongs postoperative analgesia.
2002 Mar-Apr
A laser-clinic nurse with allergic contact dermatitis from tetracaine.
2002 May
The effect of baricity of intrathecal morphine in children receiving tetracaine spinal anaesthesia for cardiac surgery: a preliminary report.
2002 May
Involvement of the mitogen-activated protein kinase family in tetracaine-induced PC12 cell death.
2002 May
Reagent-less detection of a competitive inhibitor of immobilized acetylcholinesterase.
2002 May
Agonist-induced phasic and tonic responses in smooth muscle are mediated by InsP(3).
2002 May 15
Managing patients with local anesthetic complications using alternative methods.
2002 May-Jun
Amethocaine-lidocaine cream, a new topical formulation for preventing venopuncture-induced pain in children.
2002 May-Jun
Calcium-induced calcium release and cyclic ADP-ribose-mediated signaling in the myocytes from small coronary arteries.
2002 Sep
Prophylactic IM small-dose phenylephrine blunts spinal anesthesia-induced hypotensive response during surgical repair of hip fracture in the elderly.
2002 Sep
Patents

Sample Use Guides

One drop topically in the eye(s)
Route of Administration: Topical
In Vitro Use Guide
Curator's Comment:: The action of tetracaine hydrochloride in vitro on Pseudomonas aeruginosa was investigates. The inhibitory and bactericidal action of tetracaine hydrochloride in vitro was adversely affected by magnesium ions. Observation of cellular lysis, leakage of intracellular materials, dehydrogenase activity, and a higher sensitivity of spheroplasts than of whole cells to tetracaine led to the conclusion that tetracaine acts by damaging the cell membrane.
Unknown
Name Type Language
TETRACAINE
GREEN BOOK   INN   MART.   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD  
INN  
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
Created by admin on Fri Jun 25 21:07:00 UTC 2021 , Edited by admin on Fri Jun 25 21:07:00 UTC 2021
WHO-ATC C05AD02
Created by admin on Fri Jun 25 21:07:00 UTC 2021 , Edited by admin on Fri Jun 25 21:07:00 UTC 2021
WHO-ATC D04AB06
Created by admin on Fri Jun 25 21:07:00 UTC 2021 , Edited by admin on Fri Jun 25 21:07:00 UTC 2021
WHO-VATC QN01BA03
Created by admin on Fri Jun 25 21:07:00 UTC 2021 , Edited by admin on Fri Jun 25 21:07:00 UTC 2021
WHO-VATC QD04AB06
Created by admin on Fri Jun 25 21:07:00 UTC 2021 , Edited by admin on Fri Jun 25 21:07:00 UTC 2021
WHO-ESSENTIAL MEDICINES LIST 21.3
Created by admin on Fri Jun 25 21:07:00 UTC 2021 , Edited by admin on Fri Jun 25 21:07:00 UTC 2021
NDF-RT N0000175976
Created by admin on Fri Jun 25 21:07:00 UTC 2021 , Edited by admin on Fri Jun 25 21:07:00 UTC 2021
WHO-ATC N01BA53
Created by admin on Fri Jun 25 21:07:00 UTC 2021 , Edited by admin on Fri Jun 25 21:07:00 UTC 2021
WHO-ATC S01HA03
Created by admin on Fri Jun 25 21:07:00 UTC 2021 , Edited by admin on Fri Jun 25 21:07:00 UTC 2021
CFR 21 CFR 524.1484F
Created by admin on Fri Jun 25 21:07:00 UTC 2021 , Edited by admin on Fri Jun 25 21:07:00 UTC 2021
NDF-RT N0000175683
Created by admin on Fri Jun 25 21:07:00 UTC 2021 , Edited by admin on Fri Jun 25 21:07:00 UTC 2021
WHO-VATC QC05AD02
Created by admin on Fri Jun 25 21:07:00 UTC 2021 , Edited by admin on Fri Jun 25 21:07:00 UTC 2021
WHO-VATC QS01HA03
Created by admin on Fri Jun 25 21:07:00 UTC 2021 , Edited by admin on Fri Jun 25 21:07:00 UTC 2021
NDF-RT N0000166743
Created by admin on Fri Jun 25 21:07:00 UTC 2021 , Edited by admin on Fri Jun 25 21:07:00 UTC 2021
CFR 21 CFR 524.1484B
Created by admin on Fri Jun 25 21:07:00 UTC 2021 , Edited by admin on Fri Jun 25 21:07:00 UTC 2021
CFR 21 CFR 524.1484D
Created by admin on Fri Jun 25 21:07:00 UTC 2021 , Edited by admin on Fri Jun 25 21:07:00 UTC 2021
CFR 21 CFR 346.10
Created by admin on Fri Jun 25 21:07:00 UTC 2021 , Edited by admin on Fri Jun 25 21:07:00 UTC 2021
WHO-ATC N01BA03
Created by admin on Fri Jun 25 21:07:00 UTC 2021 , Edited by admin on Fri Jun 25 21:07:00 UTC 2021
NCI_THESAURUS C245
Created by admin on Fri Jun 25 21:07:00 UTC 2021 , Edited by admin on Fri Jun 25 21:07:00 UTC 2021
Code System Code Type Description
CAS
94-24-6
Created by admin on Fri Jun 25 21:07:00 UTC 2021 , Edited by admin on Fri Jun 25 21:07:00 UTC 2021
PRIMARY
DRUG CENTRAL
2610
Created by admin on Fri Jun 25 21:07:00 UTC 2021 , Edited by admin on Fri Jun 25 21:07:00 UTC 2021
PRIMARY
NCI_THESAURUS
C66590
Created by admin on Fri Jun 25 21:07:00 UTC 2021 , Edited by admin on Fri Jun 25 21:07:00 UTC 2021
PRIMARY
FDA UNII
0619F35CGV
Created by admin on Fri Jun 25 21:07:00 UTC 2021 , Edited by admin on Fri Jun 25 21:07:00 UTC 2021
PRIMARY
ChEMBL
CHEMBL698
Created by admin on Fri Jun 25 21:07:00 UTC 2021 , Edited by admin on Fri Jun 25 21:07:00 UTC 2021
PRIMARY
EPA CompTox
94-24-6
Created by admin on Fri Jun 25 21:07:00 UTC 2021 , Edited by admin on Fri Jun 25 21:07:00 UTC 2021
PRIMARY
DRUG BANK
DB09085
Created by admin on Fri Jun 25 21:07:00 UTC 2021 , Edited by admin on Fri Jun 25 21:07:00 UTC 2021
PRIMARY
EVMPD
SUB10940MIG
Created by admin on Fri Jun 25 21:07:00 UTC 2021 , Edited by admin on Fri Jun 25 21:07:00 UTC 2021
PRIMARY
RXCUI
10391
Created by admin on Fri Jun 25 21:07:00 UTC 2021 , Edited by admin on Fri Jun 25 21:07:00 UTC 2021
PRIMARY RxNorm
INN
431
Created by admin on Fri Jun 25 21:07:00 UTC 2021 , Edited by admin on Fri Jun 25 21:07:00 UTC 2021
PRIMARY
USP_CATALOG
1649991
Created by admin on Fri Jun 25 21:07:00 UTC 2021 , Edited by admin on Fri Jun 25 21:07:00 UTC 2021
PRIMARY USP-RS
PUBCHEM
5411
Created by admin on Fri Jun 25 21:07:00 UTC 2021 , Edited by admin on Fri Jun 25 21:07:00 UTC 2021
PRIMARY
WIKIPEDIA
TETRACAINE
Created by admin on Fri Jun 25 21:07:00 UTC 2021 , Edited by admin on Fri Jun 25 21:07:00 UTC 2021
PRIMARY
MESH
D013748
Created by admin on Fri Jun 25 21:07:00 UTC 2021 , Edited by admin on Fri Jun 25 21:07:00 UTC 2021
PRIMARY
ECHA (EC/EINECS)
202-316-6
Created by admin on Fri Jun 25 21:07:00 UTC 2021 , Edited by admin on Fri Jun 25 21:07:00 UTC 2021
PRIMARY
LACTMED
Tetracaine
Created by admin on Fri Jun 25 21:07:00 UTC 2021 , Edited by admin on Fri Jun 25 21:07:00 UTC 2021
PRIMARY