PROCAINE PHOSPHATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C13H20N2O2.H3O4P
Molecular Weight	334.3053
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OP(O)(O)=O.CCN(CC)CCOC(=O)C1=CC=C(N)C=C1

InChI

InChIKey=NPBISBZNYVWJOL-UHFFFAOYSA-N

InChI=1S/C13H20N2O2.H3O4P/c1-3-15(4-2)9-10-17-13(16)11-5-7-12(14)8-6-11;1-5(2,3)4/h5-8H,3-4,9-10,14H2,1-2H3;(H3,1,2,3,4)

HIDE SMILES / InChI

Molecular Formula	H3O4P
Molecular Weight	97.9952
Charge	0
Count

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

Molecular Formula	C13H20N2O2
Molecular Weight	236.3101
Charge	0
Count

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

Description
Sources: https://www.drugs.com/monograph/procaine-hydrochloride.html | https://www.drugbank.ca/drugs/DB00721

Procaine is an anesthetic agent indicated for production of local or regional anesthesia, particularly for oral surgery. Procaine (like cocaine) has the advantage of constricting blood vessels which reduces bleeding, unlike other local anesthetics like lidocaine. Procaine is an ester anesthetic. It is metabolized in the plasma by the enzyme pseudocholinesterase through hydrolysis into para-aminobenzoic acid (PABA), which is then excreted by the kidneys into the urine. Procaine acts mainly by inhibiting sodium influx through voltage gated sodium channels in the neuronal cell membrane of peripheral nerves. When the influx of sodium is interrupted, an action potential cannot arise and signal conduction is thus inhibited. The receptor site is thought to be located at the cytoplasmic (inner) portion of the sodium channel. Procaine has also been shown to bind or antagonize the function of N-methyl-D-aspartate (NMDA) receptors as well as nicotinic acetylcholine receptors and the serotonin receptor-ion channel complex.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Sodium channel alpha subunit 76 Target ID: CHEMBL2331043 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2167458 \| https://www.ncbi.nlm.nih.gov/pubmed/9768788 \| https://www.drugbank.ca/drugs/DB00721 \| http://www.genome.jp/dbget-bin/www_bget?dr:D00732 \| https://www.ncbi.nlm.nih.gov/pubmed/8981487	Blocker 537	60.0 nM [IC50]
Muscle-type nicotinic acetylcholine receptor 65 Target ID: CHEMBL2362997 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8531111	Antagonist 2778	50.0 µM [IC50]
Glutamate [NMDA] receptor subunit 3A 21 Target ID: CHEMBL4787 Sources: https://www.drugbank.ca/drugs/DB00721 \| https://www.ncbi.nlm.nih.gov/pubmed/16299047	Antagonist 2778
Serotonin 3a (5-HT3a) receptor 46 Target ID: CHEMBL2411 Sources: https://www.drugbank.ca/drugs/DB00721 \| https://www.ncbi.nlm.nih.gov/pubmed/7539114	Antagonist 2778	1.7 µM [Kd]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 614 Sources: https://www.drugs.com/answers/what-are-the-indications-contraindictions-and-84645.html	Primary		Approved 8429	Procaine Approved Use Procaine is a local anesthetic. Procaine causes loss of feeling (numbness) of skin and mucous membranes. Procaine is used as an injection during surgery and other medical and dental procedures. Launch Date 1972

C_max

Value	Dose	Co-administered	Analyte	Population
12 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/573562/	60 mg/kg single, intravenous dose: 60 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:		PROCAINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
12.5 μg × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/573562/	60 mg/kg single, intravenous dose: 60 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:		PROCAINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
8.3 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/573562/	60 mg/kg single, intravenous dose: 60 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:		PROCAINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
50 mg 1 times / day multiple, oral Studied dose Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6362368 Page: p.304	healthy, 72.8 n = 119 Health Status: healthy Condition: Age-related decline Age Group: 72.8 Sex: M+F Population Size: 119 Sources: https://pubmed.ncbi.nlm.nih.gov/6362368 Page: p.304	Disc. AE: Systemic lupus erythematosus synd... AEs leading to discontinuation/dose reduction: Systemic lupus erythematosus synd (0.84%) Sources: https://pubmed.ncbi.nlm.nih.gov/6362368 Page: p.304

AEs

AE	Significance	Dose	Population
Systemic lupus erythematosus synd	0.84% Disc. AE	50 mg 1 times / day multiple, oral Studied dose Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6362368 Page: p.304	healthy, 72.8 n = 119 Health Status: healthy Condition: Age-related decline Age Group: 72.8 Sex: M+F Population Size: 119 Sources: https://pubmed.ncbi.nlm.nih.gov/6362368 Page: p.304

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
			inhibitor 1612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1647	inhibitor 1626 Sources: https://www.sciencedirect.com/science/article/pii/S1347861319302804

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:8430	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:8430
ChemicalBook	CB34796982	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB34796982
ChemicalBook	CB9296712	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB9296712
ChemicalBook	CB94796979	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB94796979
MolPort	MolPort-000-889-177	https://www.molport.com/shop/molecule-link/MolPort-000-889-177
ZINC	ZINC000001530757	http://zinc15.docking.org/substances/ZINC000001530757
eMolecules	739616	https://www.emolecules.com/cgi-bin/more?vid=739616

PubMed

Title	Date	PubMed
Spinal procaine with and without epinephrine and its relation to transient radicular irritation.	1999 Sep	10490152
Effects of anticonvulsants on local anaesthetic-induced neurotoxicity in rats.	2000 Feb	10728915
Changes in seizure susceptibility to local anesthetics by repeated administration of cocaine and nomifensine but not GBR12935: possible involvement of noradrenergic system.	2000 Jul	10952077
Subtle differences in the discriminative stimulus effects of cocaine and GBR-12909.	2001 Apr	11371002
From cocaine to ropivacaine: the history of local anesthetic drugs.	2001 Aug	11895133
Supraventricular ectopics and supraventricular tachycardia following injection of subconjunctival Mydricaine No. 2.	2001 Aug	11767035
Calcification in the planula and polyp of the hydroid Hydractinia symbiolongicarpus (Cnidaria, Hydrozoa).	2001 Aug	11533115
Effect of sub-Tenon's and peribulbar anesthesia on intraocular pressure and ocular pulse amplitude.	2001 Aug	11524193
Ionomycin and 2,5'-di(tertbutyl)-1,4,-benzohydroquinone elicit Ca2+-induced Ca2+ release from intracellular pools in Physarum polycephalum.	2001 Feb	11223389
Role of inferior olive and thoracic IML neurons in nonshivering thermogenesis in rats.	2001 Feb	11208585
Comparison of paracervical block techniques during first trimester pregnancy termination.	2001 Feb	11166751
Fistulation of the auditory tube diverticulum (guttural pouch) with a neodymium:yttrium-aluminum-garnet laser for treatment of chronic empyema in two horses.	2001 Feb 1	11201568
Time-dependent influence of procaine hydrochloride on cisplatin antitumor activity in P388 tumor bearing mice.	2001 Jan-Feb	11299784
Penicillin concentrations in serum, milk, and urine following intramuscular and subcutaneous administration of increasing doses of procaine penicillin G in lactating dairy cows.	2001 Jul	11480523
A comprehensive review of epinephrine in the finger: to do or not to do.	2001 Jul	11420511
Functional overlap of IP(3)- and cADP-ribose-sensitive calcium stores in guinea pig myenteric neurons.	2001 Jul	11408274
Clinical impact of histidine-ketoglutarate-tryptophan (HTK) cardioplegic solution on the perioperative period in open heart surgery patients.	2001 Jul-Aug	11440787
Retention behaviour and fluorimetric detection of procaine hydrochloride using carboxymethyl-beta-cyclodextrin as an additive in reversed-phase liquid chromatography.	2001 Jun 15	11442038
Interaction of local anaesthetic agents with the endogenous norepinephrine transporter in SH-SY5Y human neuroblastoma cells.	2001 Jun 15	11403930
Seventy cases of external humeral epicondylitis treated by local blocking and massotherapy.	2001 Mar	11360542
High epidural block with chloroprocaine in a parturient with low pseudocholinesterase activity.	2001 Mar	11305839
Periorbital allergic contact dermatitis from oxybuprocaine.	2001 Mar	11218008
Limiting transient radicular irritation.	2001 Mar-Apr	11251145
Bronchoconstrictive and relaxant effects of lidocaine on the airway in dogs.	2001 May	11378619
Neurotoxicity of spinal procaine--a caution.	2001 May-Jun	11359235
Santayana's prophecy fulfilled.	2001 Nov-Dec	11707796
[Interactions of histamine and glucocorticoids with nerve structures of respiration passages].	2001 Oct	11767456
Chloroprocaine is less painful than lidocaine for skin infiltration anesthesia.	2002 Feb	11812697
Ligand-dependent activation of the melanocortin 5 receptor: cAMP production and ryanodine receptor-dependent elevations of [Ca(2+)](I).	2002 Jan 18	11785979
Non-surgical management of rectal tears in two mares.	2002 Mar	12019697

Patents

Sample Use Guides

In Vivo Use Guide

Adults Local or Regional Anesthesia Local Infiltration Usually, 350–600 mg, administered as diluted solution (i.e., 140–240 mL of a 0.25% solution or 70–120 mL of a 0.5% solution) Peripheral Nerve Block Up to 1 g, administered undiluted (i.e., 100 mL of a 1% injection) or as diluted solution (i.e., 200 mL of a 0.5% solution). For local infiltration or peripheral nerve block, inject slowly and avoid rapid injection of large volumes; when feasible, administer in fractional (incremental) doses. For subarachnoid (spinal) block, use 2-mL single-dose ampuls containing procaine hydrochloride 10% only.c d Position patient properly prior to spinal anesthesia.

Route of Administration: Other

In Vitro Use Guide

Procaine 0.2 mM reduced the maximal NMDA-induced currents without affecting the 50% effective concentration values for NMDA in mouse CA1 pyramidal neurons..

Substance Class	Chemical Created by `admin` on `Sat Dec 16 01:37:31 GMT 2023` Edited by `admin` on `Sat Dec 16 01:37:31 GMT 2023`
Record UNII	A18LHT9ZXJ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PROCAINE PHOSPHATE

Common Name

English

NSC-30375

Code

English

Procaine phosphate [WHO-DD]

Common Name

English

Code System Code Type Description

ECHA (EC/EINECS)

259-358-3