Tetracaine

Tetracaine
Clinical data
Trade names	Pontocaine, Ametop, Dicaine, others
AHFS/Drugs.com	Monograph
MedlinePlus	a682640
License data	US DailyMed: Tetracaine;
Pregnancy; category	AU: B2;
Routes of; administration	Topical
ATC code	C05AD02 (WHO) D04AB06 (WHO) N01BA03 (WHO) S01HA03 (WHO);
Legal status
Legal status	AU: S4 (Prescription only) / S2; BR: Class C1 (Other controlled substances); US: ℞-only; In general: ℞ (Prescription only);
Pharmacokinetic data
Protein binding	75.6
Identifiers
	IUPAC name 2-(Dimethylamino)ethyl 4-(butylamino)benzoate;
CAS Number	94-24-6 ; as HCl: 136-47-0 ;
PubChem CID	5411;
DrugBank	DB09085 ;
ChemSpider	5218 ;
UNII	0619F35CGV; as HCl: 5NF5D4OPCI ;
KEGG	D00551 ; as HCl: D00741 ;
ChEBI	CHEBI:9468 ;
ChEMBL	ChEMBL698 ;
PDB ligand	TE4 (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID1043883 ;
ECHA InfoCard	100.002.106
Chemical and physical data
Formula	C15H24N2O2
Molar mass	264.369 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(OCCN(C)C)c1ccc(NCCCC)cc1;
	InChI 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 ; Key:GKCBAIGFKIBETG-UHFFFAOYSA-N ;
	(verify)

Tetracaine, also known as amethocaine, is an ester local anesthetic used to numb the eyes, nose, or throat.^[2] It may also be applied to the skin before starting intravenous therapy to decrease pain from the procedure.^[3] Typically it is applied as a liquid to the area.^[2] Onset of effects when used in the eyes is within 30 seconds and last for less than 15 minutes.^[2]

Common side effects include a brief period of burning at the site of use.^[2] Allergic reactions may uncommonly occur.^[4] Long-term use is generally not recommended as it may slow healing of the eye.^[2] It is unclear if use during pregnancy is safe for the baby.^[2] Tetracaine is in the ester-type local anesthetic family of medications.^[4] It works by blocking the sending of nerve impulses.^[2]

Tetracaine was patented in 1930 and came into medical use in 1941.^[5] It is on the World Health Organization's List of Essential Medicines^[6]

^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
^ ^a ^b ^c ^d ^e ^f ^g "Tetracaine". The American Society of Health-System Pharmacists. Archived from the original on 28 December 2016. Retrieved 8 December 2016.
^ British national formulary : BNF 69 (69 ed.). British Medical Association. 2015. pp. 769, 897. ISBN 9780857111562.
^ ^a ^b World Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.). WHO Model Formulary 2008. World Health Organization. p. 437. hdl:10665/44053. ISBN 9789241547659.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 475. ISBN 9783527607495. Archived from the original on 2016-12-29.
^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.

[1] Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.

[AHFS2016-2] ^ ^a ^b ^c ^d ^e ^f ^g "Tetracaine". The American Society of Health-System Pharmacists. Archived from the original on 28 December 2016. Retrieved 8 December 2016.

[BNF69-3] British national formulary : BNF 69 (69 ed.). British Medical Association. 2015. pp. 769, 897. ISBN 9780857111562.

[WHO2008-4] World Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.). WHO Model Formulary 2008. World Health Organization. p. 437. hdl:10665/44053. ISBN 9789241547659.

[Fis2006-5] Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 475. ISBN 9783527607495. Archived from the original on 2016-12-29.

[WHO21st-6] World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.

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