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
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 |
|---|---|---|
| The incidence of systemic side-effects following subconjunctival Mydricaine no. 1 injection. | 1999 Dec |
|
| Minimal blocking concentrations of bupivacaine and procaine in an exclusively nociceptive system in humans. | 1999 Jul-Aug |
|
| Spinal procaine with and without epinephrine and its relation to transient radicular irritation. | 1999 Sep |
|
| 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 |
|
| Swelling of capillary endothelial cells and cardiomyocytes in the ischaemic myocardium of artificially arrested canine hearts. | 2001 |
|
| [Prognosis and criteria of recovered motility of one of the vocal cords in the middle position as a result cordectomy]. | 2001 |
|
| [Potentiation of local anesthesia in endonasal surgery]. | 2001 |
|
| Local anesthetics noncompetitively inhibit function of four distinct nicotinic acetylcholine receptor subtypes. | 2001 Dec |
|
| [Rheologic infusion therapy, neurotransmitter administration and lidocaine injection in tinnitus. A staged therapeutic concept]. | 2001 Feb |
|
| Ionomycin and 2,5'-di(tertbutyl)-1,4,-benzohydroquinone elicit Ca2+-induced Ca2+ release from intracellular pools in Physarum polycephalum. | 2001 Feb |
|
| Role of inferior olive and thoracic IML neurons in nonshivering thermogenesis in rats. | 2001 Feb |
|
| Comparison of paracervical block techniques during first trimester pregnancy termination. | 2001 Feb |
|
| Mechanical stress stimulates phospholipase C activity and intracellular calcium ion levels in neonatal rat cardiomyocytes. | 2001 Feb |
|
| 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 |
|
| 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 |
|
| Hospital discharge after ambulatory knee arthroscopy: A comparison of epidural 2-chloroprocaine versus lidocaine. | 2001 Jan-Feb |
|
| [Preservation of hepatocytes in UW and HTK solutions with added fluorocarbons]. | 2001 Jan-Mar |
|
| 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 |
|
| 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 |
|
| Effects of L-carnitine-hydrochloride in the cold ischemic preservation of fatty liver grafts. | 2001 Jun |
|
| Retention behaviour and fluorimetric detection of procaine hydrochloride using carboxymethyl-beta-cyclodextrin as an additive in reversed-phase liquid chromatography. | 2001 Jun 15 |
|
| Interaction of local anaesthetic agents with the endogenous norepinephrine transporter in SH-SY5Y human neuroblastoma cells. | 2001 Jun 15 |
|
| [Cochlear hearing loss following Mycoplasma pneumoniae infection]. | 2001 Mar |
|
| Limbic responsiveness to procaine in cocaine-addicted subjects. | 2001 Mar |
|
| Periorbital allergic contact dermatitis from oxybuprocaine. | 2001 Mar |
|
| Neurotoxicity of spinal procaine--a caution. | 2001 May-Jun |
|
| Update: Interim recommendations for antimicrobial prophylaxis for children and breastfeeding mothers and treatment of children with anthrax. | 2001 Nov 16 |
|
| [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 |
|
| [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 |
|
| [Allergic alteration of leukocytes in patients with drug intolerance]. | 2001 Sep-Oct |
|
| Intrapericardial procaine affects volume expansion-induced fos immunoreactivity in unanesthetized rats. | 2002 Apr |
|
| Effect of cholesterol liposomes on calcium mobilization in muscle cells from the rabbit sphincter of Oddi. | 2002 Feb |
|
| The inhibition of the N-methyl-D-aspartate receptor channel by local anesthetics in mouse CA1 pyramidal neurons. | 2002 Feb |
|
| 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 |
|
| 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 |
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
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| Code System | Code | Type | Description | ||
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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
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PRIMARY | |||
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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
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NON-SPECIFIC STOICHIOMETRY | |||
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4846-79-1
Created by
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PRIMARY | |||
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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
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PRIMARY |
PARENT (SALT/SOLVATE)
PARENT (SALT/SOLVATE)
SUBSTANCE RECORD
