PROPOXYCAINE

US Previously Marketed

First approved in 1952

Details

Stereochemistry	ACHIRAL
Molecular Formula	C16H26N2O3
Molecular Weight	294.3892
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCOC1=C(C=CC(N)=C1)C(=O)OCCN(CC)CC

InChI

InChIKey=CAJIGINSTLKQMM-UHFFFAOYSA-N

InChI=1S/C16H26N2O3/c1-4-10-20-15-12-13(17)7-8-14(15)16(19)21-11-9-18(5-2)6-3/h7-8,12H,4-6,9-11,17H2,1-3H3

HIDE SMILES / InChI

Molecular Formula	C16H26N2O3
Molecular Weight	294.3892
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://pubchem.ncbi.nlm.nih.gov/compound/11078

Propoxycaine hydrochloride is a local anesthetic of the ester type that has a rapid onset of action and a longer duration of action than procaine hydrochloride. Propoxycaine Hydrochloride is the hydrochloride salt form of propoxycaine, a para-aminobenzoic acid ester. Propoxycaine binds to and inhibits voltage-gated sodium channels, thereby inhibiting the ionic flux required for the initiation and conduction of impulses. This results in a loss of sensation.

Originator

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 614 Sources: http://jada.ada.org/article/S0002-8177(55)11004-2/abstract	Palliative		Approved 8429	Unknown Approved Use Propoxycaine

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1587	inhibitor 1767	inhibitor 1852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1524 CYP2C19 1478

Drug as perpetrator

Target	Modality	Activity
CYP2C19 1553	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNjIyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDExOTUifX0%3D	no [Activation >10 uM]
CYP2C9 1819	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzk3IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDExOTUifX0%3D	no [Activation >10 uM]
CYP3A4 1925	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMTE5NSJ9fQ%3D%3D	no [Activation >10 uM]
CYP2D6 1891	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyODkiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMTE5NSJ9fQ%3D%3D	yes [Activation 1.99526 uM]
CYP1A2 1692	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzU2IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDExOTUifX0%3D	yes [Activation 12.58925 uM]

Sourcing

Vendor/Aggregator	ID	URL
AK Scientific, Inc. (AKSCI)	Y4376	http://www.aksci.com/item_detail.php?cat=Y4376
Ambinter	Amb22734490	http://www.ambinter.com/reference/22734490
BLD Pharm	BD149274	http://www.bldpharm.com/products/86-43-1.html
BioSynth	J-506353	https://www.biosynth.com/en/products/all-products/products/J-506353.html
ChemMol	99169233	http://www.chemmol.com/chemmol/99169233.html
Matrix Scientific	188763	https://www.matrixscientific.com/188763.html
OChem	30695	http://www.ocheminc.com/index.php?act=psearch&pid=550P834
Renno Tech	RP06763	http://www.rennotech.com/product_show.asp?id=13182
Sigma-Aldrich	CDS021586_ALDRICH	https://www.sigmaaldrich.com/catalog/product/aldrich/cds021586?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule	S588041	https://www.smolecule.com/products/s588041
THE BioTek	bt-374334	https://www.thebiotek.com/product/others/bt-374334
abcr GmbH	AB444846	http://www.abcr.com/shop/en/AB444846
eNovation Chemicals	D205911	https://www.enovationchem.com/ProductDetails.asp?ProductID=D205911

PubMed

Title	Date	PubMed
A comparative study of proxymetacaine-fluorescein and lignocaine-fluorescein use during applanation tonometry.	2001 Apr	11264141
Does instilling proxymetacaine before cyclopentolate significantly reduce stinging? The implications of paediatric cycloplegia.	2001 Feb	11225579
Survival of equine herpesvirus-4, feline herpesvirus-1, and feline calicivirus in multidose ophthalmic solutions.	2002 Dec	12445296
Duration of effect and effect of multiple doses of topical ophthalmic 0.5% proparacaine hydrochloride in clinically normal dogs.	2005 Jan	15691039
Efficacy of topical anesthetics to reduce pain in premature infants during eye examinations for retinopathy of prematurity.	2005 May	15797982
Comparison of corneal thickness after the instillation of topical anesthetics: proparacaine versus oxybuprocaine.	2006 Jan	16331042
Prospective randomized double-masked trial to evaluate perioperative pain profile in different stages of simultaneous bilateral LASIK.	2006 Sep	17102667
[Self-medication with local anaesthetics by glaucoma patients using teletonometry].	2007 Dec	17674006
Effect of proparacaine on central corneal thickness values: an evaluation using noncontact specular microscopy and pentacam.	2007 Jan	17198014
Topical anaesthesia alone versus topical anaesthesia with intracameral lidocaine for phacoemulsification.	2007 Jul 18	17636793
Phacoemulsification complication rates.	2007 Nov	17980754
Anterior sub-Tenon's anesthesia for the treatment of retinopathy of prematurity.	2008 May-Jun	18524202
Patient comfort and surgeon satisfaction during cataract surgery using topical anesthesia with or without dexmedetomidine sedation.	2008 May-Jun	18465717
Topology of a ternary complex (proparacaine-beta-cyclodextrin-liposome) by STD NMR.	2008 Sep	18642398
Prolonged corneal anaesthesia by proxymetacaine hydrochloride detected by a thermal cooling stimulus.	2009 Apr	19181566
Topical proparacaine and episcleral venous pressure in the rabbit.	2009 Jun	19151377
The reuse of ophthalmic minims: an unacceptable cross-infection risk?	2010 Aug	20508657
Ocular blood-flow hemodynamics before and after application of a laser in situ keratomileusis ring.	2010 Feb	20152608
Effect of topical anesthesia and age on pain scores during retinopathy of prematurity screening.	2010 Nov	20237484

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Parenteral

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Sat Dec 16 16:52:37 UTC 2023` Edited by `admin` on `Sat Dec 16 16:52:37 UTC 2023`
Record UNII	EPD1EH7F53
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PROPOXYCAINE

Official Name

English

Propoxycaine [WHO-DD]

Common Name

English

propoxycaine [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C245