Tetracaine

Tetracaine
Systematic (IUPAC) name
2-(dimethylamino)ethyl 4-(butylamino)benzoate
Clinical data
AHFS/Drugs.com monograph
MedlinePlus a682640
Pregnancy cat.  ?
Legal status Rx Only
Routes Topical, Epidural, Spinal
Pharmacokinetic data
Protein binding 75.6
Identifiers
CAS number 94-24-6 Y
136-47-0 (hydrochloride)
ATC code C05AD02 D04AB06 N01BA03 S01HA03
PubChem CID 5411
ChemSpider 5218 Y
UNII 0619F35CGV Y
KEGG D00551 Y
ChEBI CHEBI:9468 N
ChEMBL CHEMBL698 Y
Chemical data
Formula C15H24N2O2 
Mol. mass 264.363 g/mol
SMILES eMolecules & PubChem
 N(what is this?)  (verify)

Tetracaine (INN, also known as amethocaine; trade name Pontocaine 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.

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[1].

Chemistry

Tetracaine is synthesized from 4-butylaminobenzoic acid. The ethyl ester is formed through an acid-catalyzed esterification reaction. Base-catalyzed transesterification is achieved by boiling the ethyl ester of 4-butylaminobenzoic acid with excess 2-dimethylaminoethanol in the presence of a small amount of sodium ethoxide.[2]

References

  1. ^ Györke, S; Lukyanenko, V et al. (1997). Dual effects of tetracaine on spontaneous sodium release in rat ventricular myocytes. 500. J Physiol. pp. 297–309. 
  2. ^ Winthrop Chemical Company, Inc. U.S. Patent 1,889,645, 1932.

Further reading

Antihemorrhoidals for topical use
Antivaricose therapy
Capillary stabilising agents

M: VAS

anat(a:h/u/t/a/l,v:h/u/t/a/l)/phys/devp/cell/prot

noco/syva/cong/lyvd/tumr, sysi/epon, injr

proc, drug(C2s+n/3/4/5/7/8/9)
Antihistamines for topical use
Anesthetics for topical use

M: INT, SF, LCT

anat/phys/devp

noco(i/b/d/q/u/r/p/m/k/v/f)/cong/tumr(n/e/d), sysi/epon

proc, drug (D2/3/4/5/8/11)
Esters
Amylocaine • Benzocaine • Butacaine • Butamben • Chloroprocaine • Dimethocaine • Meprylcaine • Metabutoxycaine • Orthocaine • Propoxycaine • Procaine (Novocaine) • Proxymetacaine • Risocaine • Tetracaine
Esters of benzoic acid
Amides
Combinations

M: PNS

anat(h/r/t/c/b/l/s/a)/phys(r)/devp/prot/nttr/nttm/ntrp

noco/auto/cong/tumr, sysi/epon, injr

proc, drug(N1B)