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=CC(N)=CC=C1C(=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 619 Sources: http://jada.ada.org/article/S0002-8177(55)11004-2/abstract	Palliative		Approved 8583	Unknown Approved Use Propoxycaine

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252	inhibitor 2438	inhibitor 2507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 CYP2C19 2057

Drug as perpetrator

Target	Modality	Activity
CYP2C19 2141	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNjIyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDExOTUifX0%3D	no [Activation >10 uM]
CYP2C9 2497	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzk3IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDExOTUifX0%3D	no [Activation >10 uM]
CYP3A4 2633	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMTE5NSJ9fQ%3D%3D	no [Activation >10 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyODkiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMTE5NSJ9fQ%3D%3D	yes [Activation 1.99526 uM]
CYP1A2 2333	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzU2IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDExOTUifX0%3D	yes [Activation 12.58925 uM]

Sourcing

Vendor/Aggregator	ID	URL
abcr GmbH	AB444846	http://www.abcr.com/shop/en/AB444846
AK Scientific, Inc. (AKSCI)	Y4376	http://www.aksci.com/item_detail.php?cat=Y4376
Ambinter	Amb22734490	http://www.ambinter.com/reference/22734490
BioSynth	J-506353	https://www.biosynth.com/en/products/all-products/products/J-506353.html
BLD Pharm	BD149274	http://www.bldpharm.com/products/86-43-1.html
ChemMol	99169233	http://www.chemmol.com/chemmol/99169233.html
eNovation Chemicals	D205911	https://www.enovationchem.com/ProductDetails.asp?ProductID=D205911
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

PubMed

Title	Date	PubMed
Light sensitivity and pain sensation during cataract surgery. A comparative study of two modes of anaesthesia.	2010-12	20107867
Effect of topical anesthesia and age on pain scores during retinopathy of prematurity screening.	2010-11	20237484
Dilute proparacaine for the management of acute corneal injuries in the emergency department.	2010-09	20880433
The reuse of ophthalmic minims: an unacceptable cross-infection risk?	2010-08	20508657
Pain management during eye examinations for retinopathy of prematurity in preterm infants: a systematic review.	2010-03	19958293
Ocular blood-flow hemodynamics before and after application of a laser in situ keratomileusis ring.	2010-02	20152608
The systemic toxicity of equipotent proxymetacaine, oxybuprocaine, and bupivacaine during continuous intravenous infusion in rats.	2010-01-01	19897799
The reuse of opthalmic Minims: an unacceptable cross-infection risk?	2010-01	19247391
Ring keratitis associated with topical abuse of a dilute anesthetic after refractive surgery.	2009-12	20040463
Proparacaine complexation with beta-cyclodextrin and p-sulfonic acid calix[6]arene, as evaluated by varied (1)H-NMR approaches.	2009-09	19557725
Topical proparacaine and episcleral venous pressure in the rabbit.	2009-06	19151377
Intrathecal oxybuprocaine and proxymetacaine produced potent and long-lasting spinal anesthesia in rats.	2009-05-01	19429093
Prolonged corneal anaesthesia by proxymetacaine hydrochloride detected by a thermal cooling stimulus.	2009-04	19181566
Comparative study of analgesic effectiveness using three different anesthetic techniques for intravitreal injection of bevacizumab.	2009-02-12	19205490
Liquid nitrogen cryotherapy of superior limbic keratoconjunctivitis.	2009-02	18835475
An atypical presentation of acanthamoeba keratitis in a patient with keratoconus treated briefly with topical anesthetic.	2009-01	19125047
Antibacterial activity of preservative-free topical anesthetic drops in current use in ophthalmology departments.	2009-01	19092407
Evaluation of duration of corneal anesthesia induced with ophthalmic 0.5% proparacaine hydrochloride by use of a Cochet-Bonnet aesthesiometer in clinically normal horses.	2008-12	19046014
Adjustable suture strabismus surgery in infants and children.	2008-12	18848481
Intraoperative adjustable suture strabismus surgery under topical and subconjunctival anesthesia.	2008-10-04	18831418
A lacrimal sac abscess incision and drainage technique.	2008-09	18779495
Topology of a ternary complex (proparacaine-beta-cyclodextrin-liposome) by STD NMR.	2008-09	18642398
Neuroprotective effect of intravitreal triamcinolone acetonide against photoreceptor apoptosis in a rabbit model of subretinal hemorrhage.	2008-09	18421081
Cataract surgery complication rates.	2008-08	18675698
Protein kinase C-delta mediates neuronal apoptosis in the retinas of diabetic rats via the Akt signaling pathway.	2008-08	18443201
The effect of propoxycaine.HCl on the physical properties of neuronal membranes.	2008-07	18407836
Anterior sub-Tenon's anesthesia for the treatment of retinopathy of prematurity.	2008-06-06	18524202
Patient comfort and surgeon satisfaction during cataract surgery using topical anesthesia with or without dexmedetomidine sedation.	2008-05-10	18465717
[Self-medication with local anaesthetics by glaucoma patients using teletonometry].	2007-12	17674006
Phacoemulsification complication rates.	2007-11	17980754
Topical anaesthesia alone versus topical anaesthesia with intracameral lidocaine for phacoemulsification.	2007-07-18	17636793
Phacoemulsification in vitrectomized eyes under topical anesthesia.	2007-05-31	17534813
Does prior instillation of a topical anaesthetic alter the pupillary mydriasis produced by tropicamide (0.5%)?	2007-05	17470245
Analgesic efficacy of single-dose parecoxib for corneal suturing in children.	2007-05	17087840
Assisted local anaesthesia for endoscopic dacryocystorhinostomy.	2007-04	17430513
Posterior vitrectomy under topical anesthesia.	2007-04	17392852
An assessment of the discomfort associated with the use of rose bengal 1% eyedrops on the normal human eye: a comparison with saline 0.9% and a topical ocular anaesthetic.	2007-03	17324205
Assessment of bacterial contamination of three multidose ophthalmic solutions.	2007-02-28	17324162
Effect of proparacaine on central corneal thickness values: an evaluation using noncontact specular microscopy and pentacam.	2007-01	17198014
Topical anesthesia in transconjunctival sutureless 25-gauge vitrectomy for macular-based disorders.	2007	17183205
Duration of corneal anesthesia following topical administration of 0.5% proparacaine hydrochloride solution in clinically normal cats.	2006-10	17014333
Prospective randomized double-masked trial to evaluate perioperative pain profile in different stages of simultaneous bilateral LASIK.	2006-09	17102667
Pupil dilation using a pledget sponge: a randomized controlled trial.	2006-08	16925701
Non-antiepileptic drugs for trigeminal neuralgia.	2006-07-19	16856027
Anaesthetic abuse keratopathy as a manifestation of ocular Munchausen's syndrome.	2006-02-03	16451265
Contamination of single-use Minims eye drops by multiple use in clinics.	2006-02	16289460
Comparison of corneal thickness after the instillation of topical anesthetics: proparacaine versus oxybuprocaine.	2006-01	16331042
Subtenon lidocaine vs topical proparacaine in adult strabismus surgery.	2006	17416954
Patient pain during stretching of small pupils in phacoemulsification performed using topical anesthesia.	2005-09	16246780
Flap suturing with proparacaine for recurrent epithelial ingrowth following laser in situ keratomileusis surgery.	2005-05	15975456

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 `Wed Apr 02 08:29:05 GMT 2025` Edited by `admin` on `Wed Apr 02 08:29:05 GMT 2025`
Record UNII	EPD1EH7F53
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PROPOXYCAINE

Official Name

English

Propoxycaine [WHO-DD]

Preferred Name

English

propoxycaine [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C245