Procaine
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Basic Info
| Common Name | Procaine(F04765) |
| 2D Structure | |
| Description | Procaine is only found in individuals that have used or taken this drug. It is a local anesthetic of the ester type that has a slow onset and a short duration of action. It is mainly used for infiltration anesthesia, peripheral nerve block, and spinal block. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1016). [PubChem]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. |
| FRCD ID | F04765 |
| CAS Number | 59-46-1 |
| PubChem CID | 4914 |
| Formula | C13H20N2O2 |
| IUPAC Name | 2-(diethylamino)ethyl 4-aminobenzoate |
| InChI Key | MFDFERRIHVXMIY-UHFFFAOYSA-N |
| InChI | InChI=1S/C13H20N2O2/c1-3-15(4-2)9-10-17-13(16)11-5-7-12(14)8-6-11/h5-8H,3-4,9-10,14H2,1-2H3 |
| Canonical SMILES | CCN(CC)CCOC(=O)C1=CC=C(C=C1)N |
| Isomeric SMILES | CCN(CC)CCOC(=O)C1=CC=C(C=C1)N |
| Wikipedia | Procaine |
| Synonyms |
2-(Diethylamino)ethyl 4-aminobenzoate
procaine
59-46-1
Vitamin H3
Novocaine
Spinocaine
Duracaine
Procain
Nissocaine
Novocain
|
| Classifies |
Predicted: Plant Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Benzene and substituted derivatives |
| Subclass | Benzoic acids and derivatives |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Benzoic acid esters |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | Aminobenzoic acid or derivatives - Benzoate ester - Benzoyl - Aniline or substituted anilines - Amino acid or derivatives - Tertiary aliphatic amine - Tertiary amine - Carboxylic acid ester - Carboxylic acid derivative - Monocarboxylic acid or derivatives - Amine - Organonitrogen compound - Organooxygen compound - Primary amine - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 236.315 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 7 |
| Complexity | 222 |
| Monoisotopic Mass | 236.152 |
| Exact Mass | 236.152 |
| XLogP | 1.9 |
| Formal Charge | 0 |
| Heavy Atom Count | 17 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9533 |
| Human Intestinal Absorption | HIA+ | 0.9747 |
| Caco-2 Permeability | Caco2+ | 0.6291 |
| P-glycoprotein Substrate | Substrate | 0.5870 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9492 |
| Non-inhibitor | 0.9884 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.6840 |
| Distribution | ||
| Subcellular localization | Lysosome | 0.6753 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8646 |
| CYP450 2D6 Substrate | Non-substrate | 0.6643 |
| CYP450 3A4 Substrate | Non-substrate | 0.6456 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.6308 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9312 |
| CYP450 2D6 Inhibitor | Inhibitor | 0.8932 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9294 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8308 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.7918 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.8728 |
| Non-inhibitor | 0.6234 | |
| AMES Toxicity | Non AMES toxic | 0.6165 |
| Carcinogens | Non-carcinogens | 0.6462 |
| Fish Toxicity | High FHMT | 0.6525 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.7638 |
| Honey Bee Toxicity | Low HBT | 0.8448 |
| Biodegradation | Not ready biodegradable | 0.9449 |
| Acute Oral Toxicity | III | 0.6873 |
| Carcinogenicity (Three-class) | Non-required | 0.5482 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -1.4623 | LogS |
| Caco-2 Permeability | 1.1877 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.5160 | LD50, mol/kg |
| Fish Toxicity | 1.3134 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.1880 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| A wasp manipulates neuronal activity in the sub-esophageal ganglion to decrease the drive for walking in its cockroach prey. | PLoS One | 2010 Apr 7 | 20383324 |
| DNA methylation and cancer therapy: new developments and expectations. | Curr Opin Oncol | 2005 Jan | 15608514 |
| Benzathine penicillin G and procaine penicillin G in piglets: comparison ofintramuscular and subcutaneous injection. | Vet Res Commun | 2002 Aug | 12241099 |
| Pharmacology of Ca2+ release from red beet microsomes suggests the presence ofryanodine receptor homologs in higher plants. | FEBS Lett | 1996 Oct 14 | 8849685 |
| Dietary antibiotics decrease taurine loss in cats fed a canned heat-processeddiet. | J Nutr | 1996 Feb | 8632225 |
| Effects of essential oil of Croton zehntneri, and of anethole and estragole onskeletal muscles. | J Ethnopharmacol | 1995 Nov 17 | 8786656 |
| Simultaneous multiresidue analysis of beta-lactam antibiotics in bovine milk byliquid chromatography with ultraviolet detection and confirmation by electrospraymass spectrometry. | J AOAC Int | 1994 Sep-Oct | 7950414 |
| Fluid hypersecretion induced by enterotoxin STa in nutritionally deprived rats: jejunal and ileal dynamics in vivo. | Exp Physiol | 1994 Jul | 7946283 |
| An extract of Gymnema sylvestre leaves and purified gymnemic acid inhibits glucose-stimulated gastric inhibitory peptide secretion in rats. | J Nutr | 1992 Dec | 1453221 |
| Effects of cocaine on rat embryo development in vivo and in cultures. | Pediatr Res | 1991 Feb | 2014157 |
| Penicillin therapy of spontaneous streptococcal meningitis in pigs. | Vet Rec | 1987 Oct 10 | 3686793 |
| Apparent inadequacy of sodium requirement in broiler chickens. | Poult Sci | 1977 Jul | 564508 |
Targets
- General Function:
- Monoamine transmembrane transporter activity
- Specific Function:
- Amine transporter. Terminates the action of dopamine by its high affinity sodium-dependent reuptake into presynaptic terminals.
- Gene Name:
- SLC6A3
- Uniprot ID:
- Q01959
- Molecular Weight:
- 68494.255 Da
- Mechanism of Action:
- 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.
References
- Sato T, Kitayama S, Mitsuhata C, Ikeda T, Morita K, Dohi T: Selective inhibition of monoamine neurotransmitter transporters by synthetic local anesthetics. Naunyn Schmiedebergs Arch Pharmacol. 2000 Feb;361(2):214-20. [10685879 ]
- General Function:
- Protein phosphatase 2a binding
- Specific Function:
- NMDA receptor subtype of glutamate-gated ion channels with reduced single-channel conductance, low calcium permeability and low voltage-dependent sensitivity to magnesium. Mediated by glycine. May play a role in the development of dendritic spines. May play a role in PPP2CB-NMDAR mediated signaling mechanism (By similarity).
- Gene Name:
- GRIN3A
- Uniprot ID:
- Q8TCU5
- Molecular Weight:
- 125464.07 Da
- Mechanism of Action:
- 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.
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
- General Function:
- Receptor binding
- Specific Function:
- Ionotropic receptor with a probable role in the modulation of auditory stimuli. Agonist binding may induce an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane. The channel is permeable to a range of divalent cations including calcium, the influx of which may activate a potassium current which hyperpolarizes the cell membrane. In the ear, this may lead to a reduction in basilar membrane motion, altering the activity of auditory nerve fibers and reducing the range of dynamic hearing. This may protect against acoustic trauma.
- Gene Name:
- CHRNA10
- Uniprot ID:
- Q9GZZ6
- Molecular Weight:
- 49704.295 Da
- Mechanism of Action:
- 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.
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
- General Function:
- Voltage-gated sodium channel activity
- Specific Function:
- Tetrodotoxin-resistant channel that mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which sodium ions may pass in accordance with their electrochemical gradient. Plays a role in neuropathic pain mechanisms.
- Gene Name:
- SCN10A
- Uniprot ID:
- Q9Y5Y9
- Molecular Weight:
- 220623.605 Da
- Mechanism of Action:
- 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.
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
References
- Benham CD, Bolton TB, Lang RJ, Takewaki T: The mechanism of action of Ba2+ and TEA on single Ca2+-activated K+ -channels in arterial and intestinal smooth muscle cell membranes. Pflugers Arch. 1985 Feb;403(2):120-7. [2580269 ]
- Uniprot ID:
- P21397; P27338
References
- MacFarlane MD: Procaine HCl (Gerovital H3): a weak, reversible, fully competitive inhibitor of monoamine oxidase. Fed Proc. 1975 Jan;34(1):108-10. [1109354 ]
- General Function:
- Drug binding
- Specific Function:
- After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
- Gene Name:
- CHRNA2
- Uniprot ID:
- Q15822
- Molecular Weight:
- 59764.82 Da
References
- Wang H, Zhang Y, Li ST: The effect of local anesthetics on the inhibition of adult muscle-type nicotinic acetylcholine receptors by nondepolarizing muscle relaxants. Eur J Pharmacol. 2010 Mar 25;630(1-3):29-33. doi: 10.1016/j.ejphar.2009.12.028. Epub 2010 Jan 4. [20045405 ]
- General Function:
- Voltage-gated potassium channel activity
- Specific Function:
- This is one of the several different receptors for 5-hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor is a ligand-gated ion channel, which when activated causes fast, depolarizing responses in neurons. It is a cation-specific, but otherwise relatively nonselective, ion channel.
- Gene Name:
- HTR3A
- Uniprot ID:
- P46098
- Molecular Weight:
- 55279.835 Da
- Mechanism of Action:
- 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.
References
- Fan P, Weight FF: Procaine impairs the function of 5-HT3 receptor-ion channel complex in rat sensory ganglion neurons. Neuropharmacology. 1994 Dec;33(12):1573-9. [7539114 ]