PROPOXYCAINE HYDROCHLORIDE

US Previously Marketed

First approved in 1952

Details

Stereochemistry	ACHIRAL
Molecular Formula	C16H26N2O3.ClH
Molecular Weight	330.85
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=GITPCGSPKUQZTE-UHFFFAOYSA-N

InChI=1S/C16H26N2O3.ClH/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;1H

HIDE SMILES / InChI

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
Local anaesthesia for vitreoretinal surgery: an audit of patient and surgical experience.	2001 Oct-Dec	11820309
Allergic contact dermatitis to proparacaine with subsequent cross-sensitization to tetracaine from ophthalmic preparations.	2001 Sep	11526525
In vivo transscleral iontophoresis of amikacin to rabbit eyes.	2002 Dec	12537681
Survival of equine herpesvirus-4, feline herpesvirus-1, and feline calicivirus in multidose ophthalmic solutions.	2002 Dec	12445296
Epithelial activity of hexokinase and glucose-6-phosphate dehydrogenase in cultured bovine lenses recovering from pharmaceutical-induced optical damage.	2003 Nov 3	14627957
[A subjective evaluation of epibulbar and etrobulbar anesthesia in cataract phacoemulsification].	2005 Jan-Feb	15759841
Efficacy of sucrose to reduce pain in premature infants during eye examinations for retinopathy of prematurity.	2005 Jun	15855243
Randomised controlled trial of sub-Tenon's block versus topical anaesthesia for cataract surgery: a comparison of patient satisfaction.	2005 Mar	15722306
Flap suturing with proparacaine for recurrent epithelial ingrowth following laser in situ keratomileusis surgery.	2005 May	15975456
Efficacy of topical anesthetics to reduce pain in premature infants during eye examinations for retinopathy of prematurity.	2005 May	15797982
Patient pain during stretching of small pupils in phacoemulsification performed using topical anesthesia.	2005 Sep	16246780
Contamination of single-use Minims eye drops by multiple use in clinics.	2006 Feb	16289460
Duration of corneal anesthesia following topical administration of 0.5% proparacaine hydrochloride solution in clinically normal cats.	2006 Oct	17014333
Prospective randomized double-masked trial to evaluate perioperative pain profile in different stages of simultaneous bilateral LASIK.	2006 Sep	17102667
Assisted local anaesthesia for endoscopic dacryocystorhinostomy.	2007 Apr	17430513
Topical anaesthesia alone versus topical anaesthesia with intracameral lidocaine for phacoemulsification.	2007 Jul 18	17636793
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 Mar	17324205
Assessment of bacterial contamination of three multidose ophthalmic solutions.	2007 Mar-Apr	17324162
Phacoemulsification in vitrectomized eyes under topical anesthesia.	2007 May-Jun	17534813
Cataract surgery complication rates.	2008 Aug	18675698
Protein kinase C-delta mediates neuronal apoptosis in the retinas of diabetic rats via the Akt signaling pathway.	2008 Aug	18443201
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 Dec	19046014
Adjustable suture strabismus surgery in infants and children.	2008 Dec	18848481
The effect of propoxycaine.HCl on the physical properties of neuronal membranes.	2008 Jul	18407836
Patient comfort and surgeon satisfaction during cataract surgery using topical anesthesia with or without dexmedetomidine sedation.	2008 May-Jun	18465717
A lacrimal sac abscess incision and drainage technique.	2008 Sep	18779495
Topology of a ternary complex (proparacaine-beta-cyclodextrin-liposome) by STD NMR.	2008 Sep	18642398
Neuroprotective effect of intravitreal triamcinolone acetonide against photoreceptor apoptosis in a rabbit model of subretinal hemorrhage.	2008 Sep	18421081
Intraoperative adjustable suture strabismus surgery under topical and subconjunctival anesthesia.	2008 Sep-Oct	18831418
Prolonged corneal anaesthesia by proxymetacaine hydrochloride detected by a thermal cooling stimulus.	2009 Apr	19181566
Ring keratitis associated with topical abuse of a dilute anesthetic after refractive surgery.	2009 Dec	20040463
Liquid nitrogen cryotherapy of superior limbic keratoconjunctivitis.	2009 Feb	18835475
An atypical presentation of acanthamoeba keratitis in a patient with keratoconus treated briefly with topical anesthetic.	2009 Jan	19125047
Antibacterial activity of preservative-free topical anesthetic drops in current use in ophthalmology departments.	2009 Jan	19092407
Comparative study of analgesic effectiveness using three different anesthetic techniques for intravitreal injection of bevacizumab.	2009 Jan-Feb	19205490
Topical proparacaine and episcleral venous pressure in the rabbit.	2009 Jun	19151377
Intrathecal oxybuprocaine and proxymetacaine produced potent and long-lasting spinal anesthesia in rats.	2009 May 1	19429093
Proparacaine complexation with beta-cyclodextrin and p-sulfonic acid calix[6]arene, as evaluated by varied (1)H-NMR approaches.	2009 Sep	19557725
The reuse of ophthalmic minims: an unacceptable cross-infection risk?	2010 Aug	20508657
Light sensitivity and pain sensation during cataract surgery. A comparative study of two modes of anaesthesia.	2010 Dec	20107867
Ocular blood-flow hemodynamics before and after application of a laser in situ keratomileusis ring.	2010 Feb	20152608
The reuse of opthalmic Minims: an unacceptable cross-infection risk?	2010 Jan	19247391
The systemic toxicity of equipotent proxymetacaine, oxybuprocaine, and bupivacaine during continuous intravenous infusion in rats.	2010 Jan 1	19897799
Pain management during eye examinations for retinopathy of prematurity in preterm infants: a systematic review.	2010 Mar	19958293
Effect of topical anesthesia and age on pain scores during retinopathy of prematurity screening.	2010 Nov	20237484
Dilute proparacaine for the management of acute corneal injuries in the emergency department.	2010 Sep	20880433

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Parenteral

In Vitro Use Guide

Unknown

Name

Type

Language

PROPOXYCAINE HYDROCHLORIDE

Common Name

English

PROPOXYCAINE HYDROCHLORIDE [ORANGE BOOK]

Common Name

English

PROPOXYCAINE HCL

Common Name

English

2-(Diethylamino)ethyl 4-amino-2-propoxybenzoate monohydrochloride

Systematic Name

English

PROPOXYCAINE HYDROCHLORIDE [MI]

Common Name

English

PROPOXYCAINE HYDROCHLORIDE [MART.]

Common Name

English

Propoxycaine hydrochloride [WHO-DD]

Common Name

English

PROPOXYCAINE HYDROCHLORIDE [USP IMPURITY]

Common Name

English

NSC-760044

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C245