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
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
DescriptionCurator's Comment:: description was created based on several sources, including:
https://en.wikipedia.org/wiki/Tetracaine
http://www.medchemexpress.com/Tetracaine.html
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
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2331043 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | TETRACAINE HYDROCHLORIDE Approved Useis indicated for procedures requiring a rapid and shortacting topical ophthalmic anesthetic Launch Date1.16294405E12 |
Cmax
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 |
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 |
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 |
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 |
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 |
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 |
4-(BUTYLAMINO)BENZOIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
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 |
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 |
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: |
unhealthy, 75 years n = 1 Health Status: unhealthy Age Group: 75 years Sex: M Population Size: 1 Sources: |
Other AEs: Toxic reaction (NOS)... |
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: |
unhealthy, 75 years n = 1 Health Status: unhealthy Age Group: 75 years Sex: M Population Size: 1 Sources: |
PubMed
Title | Date | PubMed |
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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 |
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Topical anesthetics update: EMLA and beyond. | 2001 Dec |
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Allergic contact dermatitis from local anaesthetic on peristomal skin. | 2001 Dec |
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An integrative, in situ approach to examining K+ flux in resting skeletal muscle. | 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 |
|
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 |
|
EMLA or Ametop, and for how long? | 2001 Oct |
|
The addition of epinephrine to tetracaine injected intrathecally sustains an increase in glutamate concentrations in the cerebrospinal fluid and worsens neuronal injury. | 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 |
|
Direct neurotoxicity of tetracaine on growth cones and neurites of growing neurons in vitro. | 2001 Sep |
|
Topical anesthesia--a new approach to cataract surgery. | 2001 Sep |
|
Role of airway receptors in altitude-induced dyspnea. | 2001 Sep |
|
Phospholipase A(2) in rabbit tears: a host defense against Staphylococcus aureus. | 2001 Sep |
|
Radial artery cannulation: topical amethocaine gel versus lidocaine infiltration. | 2002 Apr |
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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 |
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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 |
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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 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 |
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Principles of office anesthesia: part II. Topical anesthesia. | 2002 Jul 1 |
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Allosterically linked noncompetitive antagonist binding sites in the resting nicotinic acetylcholine receptor ion channel. | 2002 Jul 1 |
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Assessment of sarcoplasmic reticulum Ca(2+) flux pathways in cardiomyocytes from rabbits with infarct-induced left-ventricular dysfunction. | 2002 Jun |
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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 |
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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 |
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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 |
Sample Use Guides
In Vitro Use Guide
Sources: http://www.ncbi.nlm.nih.gov/pubmed/410897
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
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Classification Tree | Code System | Code | ||
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CFR |
21 CFR 524.1484C
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WHO-ATC |
C05AD02
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WHO-ATC |
D04AB06
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WHO-VATC |
QN01BA03
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WHO-VATC |
QD04AB06
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WHO-ESSENTIAL MEDICINES LIST |
21.3
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NDF-RT |
N0000175976
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WHO-ATC |
N01BA53
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WHO-ATC |
S01HA03
Created by
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CFR |
21 CFR 524.1484F
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NDF-RT |
N0000175683
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WHO-VATC |
QC05AD02
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WHO-VATC |
QS01HA03
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NDF-RT |
N0000166743
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CFR |
21 CFR 524.1484B
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CFR |
21 CFR 524.1484D
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CFR |
21 CFR 346.10
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WHO-ATC |
N01BA03
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NCI_THESAURUS |
C245
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94-24-6
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2610
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C66590
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0619F35CGV
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CHEMBL698
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94-24-6
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DB09085
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SUB10940MIG
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10391
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431
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1649991
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5411
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TETRACAINE
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D013748
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202-316-6
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Tetracaine
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)