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Details

Stereochemistry ABSOLUTE
Molecular Formula C13H20N2O2.C5H7NO3
Molecular Weight 365.4241
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PROCAINE PIDOLATE

SMILES

OC(=O)[C@@H]1CCC(=O)N1.CCN(CC)CCOC(=O)C2=CC=C(N)C=C2

InChI

InChIKey=CTURZEPMXLXYMZ-HVDRVSQOSA-N
InChI=1S/C13H20N2O2.C5H7NO3/c1-3-15(4-2)9-10-17-13(16)11-5-7-12(14)8-6-11;7-4-2-1-3(6-4)5(8)9/h5-8H,3-4,9-10,14H2,1-2H3;3H,1-2H2,(H,6,7)(H,8,9)/t;3-/m.0/s1

HIDE SMILES / InChI

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

Molecular Formula C5H7NO3
Molecular Weight 129.114
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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

8.5363196E10
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
12 μg/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
12.5 μg × min/mL
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
8.3 min
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

Doses

DosePopulationAdverse 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: 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: Page: p.304
Disc. AE: Systemic lupus erythematosus synd...
AEs leading to
discontinuation/dose reduction:
Systemic lupus erythematosus synd (0.84%)
Sources: Page: p.304
AEs

AEs

AESignificanceDosePopulation
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: 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: Page: p.304
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Effects of anticonvulsants on local anaesthetic-induced neurotoxicity in rats.
2000 Feb
Changes in seizure susceptibility to local anesthetics by repeated administration of cocaine and nomifensine but not GBR12935: possible involvement of noradrenergic system.
2000 Jul
[Drug allergy among patients suffering from nasal polyps].
2001
Supraventricular ectopics and supraventricular tachycardia following injection of subconjunctival Mydricaine No. 2.
2001 Aug
Calcification in the planula and polyp of the hydroid Hydractinia symbiolongicarpus (Cnidaria, Hydrozoa).
2001 Aug
Role of inferior olive and thoracic IML neurons in nonshivering thermogenesis in rats.
2001 Feb
Mechanical stress stimulates phospholipase C activity and intracellular calcium ion levels in neonatal rat cardiomyocytes.
2001 Feb
The effects of intracellular pH changes on resting cytosolic calcium in voltage-clamped snail neurones.
2001 Feb 1
Ion-transfer voltammetry of local anesthetics at an organic solvent/water interface and pharmacological activity vs. ion partition coefficient relationship.
2001 Jan
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
Common solvent toxicity: autoxidation of respiratory redox-cyclers enforced by membrane derangement.
2001 Jul-Aug
Effects of L-carnitine-hydrochloride in the cold ischemic preservation of fatty liver grafts.
2001 Jun
Local anaesthetic activity of beta-caryophyllene.
2001 May-Jul
[Interactions of histamine and glucocorticoids with nerve structures of respiration passages].
2001 Oct
Cembranoid and long-chain alkanol sites on the nicotinic acetylcholine receptor and their allosteric interaction.
2001 Sep 18
Intrapericardial procaine affects volume expansion-induced fos immunoreactivity in unanesthetized rats.
2002 Apr
Improved right heart function after myocardial preservation with 2,3-butanedione 2-monoxime in a porcine model of allogenic heart transplantation.
2002 Jan
Short-acting peribulbar anesthesia with 2-chloroprocaine.
2002 Jan
Ligand-dependent activation of the melanocortin 5 receptor: cAMP production and ryanodine receptor-dependent elevations of [Ca(2+)](I).
2002 Jan 18
Liver preservation with HTK: salutary effect of hypothermic aerobiosis by either gaseous oxygen or machine perfusion.
2002 Jun
Non-surgical management of rectal tears in two mares.
2002 Mar
Biochemical and morphological changes in pancreas stored under hypothermic conditions.
2002 Mar
[Magnetically-guided anesthetics based on highly dispersed iron powders coated by polyacrylamide].
2002 Mar-Apr
Patents

Sample Use Guides

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
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 Wed Jul 05 22:37:49 UTC 2023
Edited
by admin
on Wed Jul 05 22:37:49 UTC 2023
Record UNII
W84930057W
Record Status Validated (UNII)
Record Version
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Name Type Language
PROCAINE PIDOLATE
Common Name English
PROCAINE PYROGLUTAMATE
Common Name English
L-PROLINE, 5-OXO-, COMPD. WITH 2-(DIETHYLAMINO)ETHYL 4-AMINOBENZOATE
Common Name English
PROLINE, 5-OXO-, COMPD. WITH 2-(DIETHYLAMINO)ETHYL 4-AMINOBENZOATE (1:1)
Systematic Name English
BENZOIC ACID, 4-AMINO-, 2-(DIETHYLAMINO)ETHYL ESTER, COMPD. WITH 5-OXOPROLINE (1:1)
Systematic Name English
BENZOIC ACID, P-AMINO-, 2-(DIETHYLAMINO)ETHYL ESTER, COMPD. WITH 5-OXOPROLINE (1:1)
Systematic Name English
Code System Code Type Description
EPA CompTox
DTXSID00274784
Created by admin on Wed Jul 05 22:37:49 UTC 2023 , Edited by admin on Wed Jul 05 22:37:49 UTC 2023
PRIMARY
PUBCHEM
44148136
Created by admin on Wed Jul 05 22:37:49 UTC 2023 , Edited by admin on Wed Jul 05 22:37:49 UTC 2023
PRIMARY
ECHA (EC/EINECS)
241-201-5
Created by admin on Wed Jul 05 22:37:49 UTC 2023 , Edited by admin on Wed Jul 05 22:37:49 UTC 2023
PRIMARY
CAS
10248-52-9
Created by admin on Wed Jul 05 22:37:49 UTC 2023 , Edited by admin on Wed Jul 05 22:37:49 UTC 2023
NON-SPECIFIC STOICHIOMETRY
FDA UNII
W84930057W
Created by admin on Wed Jul 05 22:37:49 UTC 2023 , Edited by admin on Wed Jul 05 22:37:49 UTC 2023
PRIMARY
CAS
17140-49-7
Created by admin on Wed Jul 05 22:37:49 UTC 2023 , Edited by admin on Wed Jul 05 22:37:49 UTC 2023
PRIMARY
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