Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C13H20N2O2.C6H8O6 |
| Molecular Weight | 412.4342 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]1(OC(=O)C(O)=C1O)[C@@H](O)CO.CCN(CC)CCOC(=O)C2=CC=C(N)C=C2
InChI
InChIKey=VBLCUGWJTRVXLE-MGMRMFRLSA-N
InChI=1S/C13H20N2O2.C6H8O6/c1-3-15(4-2)9-10-17-13(16)11-5-7-12(14)8-6-11;7-1-2(8)5-3(9)4(10)6(11)12-5/h5-8H,3-4,9-10,14H2,1-2H3;2,5,7-10H,1H2/t;2-,5+/m.0/s1
| Molecular Formula | C6H8O6 |
| Molecular Weight | 176.1241 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
| 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 |
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.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
| 60.0 nM [IC50] | |||
Target ID: CHEMBL2362997 |
50.0 µM [IC50] | ||
Target ID: CHEMBL2411 |
1.7 µM [Kd] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Procaine Approved UseProcaine 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 Date1972 |
Cmax
| 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 |
T1/2
| 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: 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
| 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: 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 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Spinal procaine with and without epinephrine and its relation to transient radicular irritation. | 1999 Sep |
|
| Swelling of capillary endothelial cells and cardiomyocytes in the ischaemic myocardium of artificially arrested canine hearts. | 2001 |
|
| [Potentiation of local anesthesia in endonasal surgery]. | 2001 |
|
| From cocaine to ropivacaine: the history of local anesthetic drugs. | 2001 Aug |
|
| Effect of sub-Tenon's and peribulbar anesthesia on intraocular pressure and ocular pulse amplitude. | 2001 Aug |
|
| The insular but not the perirhinal cortex is involved in the expression of fully-kindled amygdaloid seizures in rats. | 2001 Aug |
|
| Local anesthetics noncompetitively inhibit function of four distinct nicotinic acetylcholine receptor subtypes. | 2001 Dec |
|
| Mechanical stress stimulates phospholipase C activity and intracellular calcium ion levels in neonatal rat cardiomyocytes. | 2001 Feb |
|
| The mechanism of maitotoxin-induced elevation of the cytosolic free calcium level in rat cerebrocortical synaptosomes. | 2001 Jan |
|
| Establishment of a simple method for measurement of chronic blood flow in uterine artery of pregnant cows. | 2001 Jul |
|
| A comprehensive review of epinephrine in the finger: to do or not to do. | 2001 Jul |
|
| Functional overlap of IP(3)- and cADP-ribose-sensitive calcium stores in guinea pig myenteric neurons. | 2001 Jul |
|
| Common solvent toxicity: autoxidation of respiratory redox-cyclers enforced by membrane derangement. | 2001 Jul-Aug |
|
| Subconjunctival anesthesia in contact diode laser cyclophotocoagulation. | 2001 Jul-Aug |
|
| Clinical impact of histidine-ketoglutarate-tryptophan (HTK) cardioplegic solution on the perioperative period in open heart surgery patients. | 2001 Jul-Aug |
|
| [Hoigne syndrome as an acute non-allergic reaction to different drugs: case reports]. | 2001 Jun |
|
| High epidural block with chloroprocaine in a parturient with low pseudocholinesterase activity. | 2001 Mar |
|
| Spinal anesthesia: a comparison of procaine and lidocaine. | 2001 May |
|
| Intrathecal fentanyl does not modify the duration of spinal procaine block. | 2001 May |
|
| Bronchoconstrictive and relaxant effects of lidocaine on the airway in dogs. | 2001 May |
|
| Determination of the hydrophobicity of local anesthetic agents. | 2001 May 1 |
|
| Local anaesthetic activity of beta-caryophyllene. | 2001 May-Jul |
|
| Release of non-neuronal acetylcholine from the isolated human placenta is mediated by organic cation transporters. | 2001 Nov |
|
| [Increase in brain activity of the carp Cyprinus carpio during visual deafferentation]. | 2001 Nov-Dec |
|
| [Investigation on the mechanisms of leukocyte alteration in patients with intolerance to some drugs (with novocaine as a model)]. | 2001 Nov-Dec |
|
| Santayana's prophecy fulfilled. | 2001 Nov-Dec |
|
| [Interactions of histamine and glucocorticoids with nerve structures of respiration passages]. | 2001 Oct |
|
| Optimisation and validation of a capillary electrophoresis method for the simultaneous determination of diazepam and otilonium bromide. | 2001 Oct |
|
| [Myasthenia gravis]. | 2001 Oct |
|
| Properties of Ca(2+) release induced by clofibric acid from the sarcoplasmic reticulum of mouse skeletal muscle fibres. | 2001 Oct |
|
| [Treatment of animals with acute and/or chronic complaints by electric stimulation therapy]. | 2001 Oct 15 |
|
| Role of the dopamine transporter and the sodium channel in the cocaine-like discriminative stimulus effects of local anesthetics in rats. | 2001 Sep |
|
| Evidence that spinal segmental nitric oxide mediates tachyphylaxis to peripheral local anesthetic nerve block. | 2001 Sep |
|
| Topical anesthesia with or without propofol sedation versus retrobulbar/peribulbar anesthesia for cataract extraction: prospective randomized trial. | 2001 Sep |
|
| Cembranoid and long-chain alkanol sites on the nicotinic acetylcholine receptor and their allosteric interaction. | 2001 Sep 18 |
|
| Clinical issues in the prophylaxis, diagnosis, and treatment of anthrax. | 2002 Feb |
|
| Ionic basis of the resting membrane potential and action potential in the pharyngeal muscle of Caenorhabditis elegans. | 2002 Feb |
|
| Recurrent corneal ulceration as late complication of toxic keratitis. | 2002 Feb |
|
| Chloroprocaine is less painful than lidocaine for skin infiltration anesthesia. | 2002 Feb |
|
| The inhibition of the N-methyl-D-aspartate receptor channel by local anesthetics in mouse CA1 pyramidal neurons. | 2002 Feb |
|
| Improved right heart function after myocardial preservation with 2,3-butanedione 2-monoxime in a porcine model of allogenic heart transplantation. | 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 |
|
| Interaction of monosulfonate tetraphenyl porphyrin, a competitive inhibitor, with acetylcholinesterase. | 2002 Jun |
|
| Non-surgical management of rectal tears in two mares. | 2002 Mar |
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
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:05:49 GMT 2023
by
admin
on
Fri Dec 15 15:05:49 GMT 2023
|
| Record UNII |
RM32BO3NX4
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English |
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
137331850
Created by
admin on Fri Dec 15 15:05:49 GMT 2023 , Edited by admin on Fri Dec 15 15:05:49 GMT 2023
|
PRIMARY | |||
|
10248-51-8
Created by
admin on Fri Dec 15 15:05:49 GMT 2023 , Edited by admin on Fri Dec 15 15:05:49 GMT 2023
|
NON-SPECIFIC STOICHIOMETRY | |||
|
4846-79-1
Created by
admin on Fri Dec 15 15:05:49 GMT 2023 , Edited by admin on Fri Dec 15 15:05:49 GMT 2023
|
PRIMARY | |||
|
RM32BO3NX4
Created by
admin on Fri Dec 15 15:05:49 GMT 2023 , Edited by admin on Fri Dec 15 15:05:49 GMT 2023
|
PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
PARENT -> SALT/SOLVATE | |||
|
|
PARENT -> SALT/SOLVATE |
