Escitalopram
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Basic Info
Common Name | Escitalopram(F04786) |
2D Structure | |
Description | Escitalopram, the <i>S</i>-enantiomer of citalopram, belongs to a class of antidepressant agents known as selective serotonin-reuptake inhibitors (SSRIs). Despite distinct structural differences between compounds in this class, SSRIs possess similar pharmacological activity. As with other antidepressant agents, several weeks of therapy may be required before a clinical effect is seen. SSRIs are potent inhibitors of neuronal serotonin reuptake. They have little to no effect on norepinephrine or dopamine reuptake and do not antagonize α- or β-adrenergic, dopamine D<sub>2</sub> or histamine H<sub>1</sub> receptors. During acute use, SSRIs block serotonin reuptake and increase serotonin stimulation of somatodendritic 5-HT<sub>1A</sub> and terminal autoreceptors. Chronic use leads to desensitization of somatodendritic 5-HT<sub>1A</sub> and terminal autoreceptors. The overall clinical effect of increased mood and decreased anxiety is thought to be due to adaptive changes in neuronal function that leads to enhanced serotonergic neurotransmission. Side effects include dry mouth, nausea, dizziness, drowsiness, sexual dysfunction and headache. Side effects generally occur within the first two weeks of therapy and are usually less severe and frequent than those observed with tricyclic antidepressants. Escitalopram may be used to treat major depressive disorder (MDD) and generalized anxiety disorder (GAD). Escitalopram is a furancarbonitrile that is one of the Serotonin uptake inhibitors used as an antidepressant. The drug is also effective in reducing ethanol uptake in alcoholics and is used in depressed patients who also suffer from tardive dyskinesia in preference to tricyclic antidepressants, which aggravate this condition; Escitalopram (Cipralex) is a medication developed by the Danish pharmaceutical company Lundbeck, that acts as a selective serotonin reuptake inhibitor (SSRI). It is typically used as an antidepressant to treat depression associated with mood disorders, although it also may be used in the treatment of body dysmorphic disorder and anxiety, including OCD. In the United States, the drug is marketed under the name Lexapro by Forest Laboratories, Inc; Escitalopram is a medication that acts as a selective serotonin reuptake inhibitor (SSRI). It is typically used as an antidepressant to treat depression associated with mood disorders, although it also may be used in the treatment of body dysmorphic disorder and anxiety, including OCD; Discontinuation from antidepressants, especially abruptly, has been known to cause certain withdrawal symptoms. One possible discontinuation symptom from Escitalopram is a type of spontaneous nerve pulse known as paresthesia or 'electric shock sensations', described by some patients as a feeling of small electric shocks, which may be accompanied by dizziness. These pulses may be short in duration, only milliseconds long, may affect any region of the body, and recur up to several times a minute, throughout all waking hours. They can be increased by physical activity, but are not solely linked to muscular activity. Other discontinuation symptoms include extreme sensitivity to loud sounds and bright lights, chills, hot flushes, cold sweats, reddening of the face, abdominal pain, weight gain and extreme mental fatigue. |
FRCD ID | F04786 |
CAS Number | 128196-01-0 |
PubChem CID | 146570 |
Formula | C20H21FN2O |
IUPAC Name | (1S)-1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-3H-2-benzofuran-5-carbonitrile |
InChI Key | WSEQXVZVJXJVFP-FQEVSTJZSA-N |
InChI | InChI=1S/C20H21FN2O/c1-23(2)11-3-10-20(17-5-7-18(21)8-6-17)19-9-4-15(13-22)12-16(19)14-24-20/h4-9,12H,3,10-11,14H2,1-2H3/t20-/m0/s1 |
Canonical SMILES | CN(C)CCCC1(C2=C(CO1)C=C(C=C2)C#N)C3=CC=C(C=C3)F |
Isomeric SMILES | CN(C)CCC[C@@]1(C2=C(CO1)C=C(C=C2)C#N)C3=CC=C(C=C3)F |
Wikipedia | Escitalopram |
Synonyms | Escitalopram [INN] Escitalopram (S)-Citalopram S(+)-Citalopram 128196-01-0 (+)-Citalopram Seroplex S-(+)-Citalopram Lexapro escitalopramum |
Classifies | Predicted: Pesticide |
Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
Kingdom | Organic compounds |
Superclass | Benzenoids |
Class | Benzene and substituted derivatives |
Subclass | Phenylbutylamines |
Intermediate Tree Nodes | Not available |
Direct Parent | Phenylbutylamines |
Alternative Parents | |
Molecular Framework | Aromatic heteropolycyclic compounds |
Substituents | Phenylbutylamine - Isocoumaran - Fluorobenzene - Halobenzene - Aralkylamine - Aryl halide - Aryl fluoride - Tertiary amine - Tertiary aliphatic amine - Oxacycle - Dialkyl ether - Ether - Carbonitrile - Nitrile - Organoheterocyclic compound - Organic oxygen compound - Organopnictogen compound - Amine - Organohalogen compound - Organofluoride - Organonitrogen compound - Organooxygen compound - Organic nitrogen compound - Hydrocarbon derivative - Aromatic heteropolycyclic compound |
Description | This compound belongs to the class of organic compounds known as phenylbutylamines. These are compounds containing a phenylbutylamine moiety, which consists of a phenyl group substituted at the fourth carbon by an butan-1-amine. |
Properties
Property Name | Property Value |
---|---|
Molecular Weight | 324.399 |
Hydrogen Bond Donor Count | 0 |
Hydrogen Bond Acceptor Count | 4 |
Rotatable Bond Count | 5 |
Complexity | 466 |
Monoisotopic Mass | 324.164 |
Exact Mass | 324.164 |
XLogP | 3.2 |
Formal Charge | 0 |
Heavy Atom Count | 24 |
Defined Atom Stereocenter Count | 1 |
Undefined Atom Stereocenter Count | 0 |
Defined Bond Stereocenter Count | 0 |
Undefined Bond Stereocenter Count | 0 |
Isotope Atom Count | 0 |
Covalently-Bonded Unit Count | 1 |
References
Title | Journal | Date | Pubmed ID |
---|---|---|---|
QCM-4, a 5-HT₃ receptor antagonist ameliorates plasma HPA axis hyperactivity,leptin resistance and brain oxidative stress in depression and anxiety-likebehavior in obese mice. | Biochem Biophys Res Commun | 2015 Jan 2 | 25446100 |
Changed Synaptic Plasticity in Neural Circuits of Depressive-Like andEscitalopram-Treated Rats. | Int J Neuropsychopharmacol | 2015 Apr 21 | 25899067 |
Inhibitory control deficits in rats with ventral hippocampal lesions. | Cereb Cortex | 2013 Jun | 22615141 |
Proteomic investigation of the ventral rat hippocampus links DRP-2 toescitalopram treatment resistance and SNAP to stress resilience in the chronicmild stress model of depression. | J Mol Neurosci | 2007 | 17873297 |
Effects of desipramine and escitalopram on postprandial symptoms induced by thenutrient drink test in healthy volunteers: a randomized, double-blind,placebo-controlled study. | Digestion | 2005 | 16172545 |
Targets
- General Function:
- Protein heterodimerization activity
- Specific Function:
- This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) proteins. Nuclear ADRA1A-ADRA1B heterooligomers regulate phenylephrine(PE)-stimulated ERK signaling in cardiac myocytes.
- Gene Name:
- ADRA1A
- Uniprot ID:
- P35348
- Molecular Weight:
- 51486.005 Da
References
- Bareggi SR, Mundo E, Dell'Osso B, Altamura AC: The use of escitalopram beyond major depression: pharmacological aspects, efficacy and tolerability in anxiety disorders. Expert Opin Drug Metab Toxicol. 2007 Oct;3(5):741-53. [17916059 ]
- General Function:
- Histamine receptor activity
- Specific Function:
- In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system.
- Gene Name:
- HRH1
- Uniprot ID:
- P35367
- Molecular Weight:
- 55783.61 Da
References
- Bareggi SR, Mundo E, Dell'Osso B, Altamura AC: The use of escitalopram beyond major depression: pharmacological aspects, efficacy and tolerability in anxiety disorders. Expert Opin Drug Metab Toxicol. 2007 Oct;3(5):741-53. [17916059 ]
- 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
References
- Bareggi SR, Mundo E, Dell'Osso B, Altamura AC: The use of escitalopram beyond major depression: pharmacological aspects, efficacy and tolerability in anxiety disorders. Expert Opin Drug Metab Toxicol. 2007 Oct;3(5):741-53. [17916059 ]
- General Function:
- Norepinephrine:sodium symporter activity
- Specific Function:
- Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
- Gene Name:
- SLC6A2
- Uniprot ID:
- P23975
- Molecular Weight:
- 69331.42 Da
References
- Bareggi SR, Mundo E, Dell'Osso B, Altamura AC: The use of escitalopram beyond major depression: pharmacological aspects, efficacy and tolerability in anxiety disorders. Expert Opin Drug Metab Toxicol. 2007 Oct;3(5):741-53. [17916059 ]
- General Function:
- Serotonin:sodium symporter activity
- Specific Function:
- Serotonin transporter whose primary function in the central nervous system involves the regulation of serotonergic signaling via transport of serotonin molecules from the synaptic cleft back into the pre-synaptic terminal for re-utilization. Plays a key role in mediating regulation of the availability of serotonin to other receptors of serotonergic systems. Terminates the action of serotonin and recycles it in a sodium-dependent manner.
- Gene Name:
- SLC6A4
- Uniprot ID:
- P31645
- Molecular Weight:
- 70324.165 Da
- Mechanism of Action:
- The antidepressant, antiobsessive-compulsive, and antibulimic actions of escitalopram are presumed to be linked to its inhibition of CNS neuronal uptake of serotonin. Escitalopram blocks the reuptake of serotonin at the serotonin reuptake pump of the neuronal membrane, enhancing the actions of serotonin on 5HT<sub>1A</sub> autoreceptors. SSRIs bind with significantly less affinity to histamine, acetylcholine, and norepinephrine receptors than tricyclic antidepressant drugs.
References
- Owens MJ, Knight DL, Nemeroff CB: Second-generation SSRIs: human monoamine transporter binding profile of escitalopram and R-fluoxetine. Biol Psychiatry. 2001 Sep 1;50(5):345-50. [11543737 ]
- General Function:
- Phosphatidylinositol phospholipase c activity
- Specific Function:
- The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover.
- Gene Name:
- CHRM1
- Uniprot ID:
- P11229
- Molecular Weight:
- 51420.375 Da
References
- Bareggi SR, Mundo E, Dell'Osso B, Altamura AC: The use of escitalopram beyond major depression: pharmacological aspects, efficacy and tolerability in anxiety disorders. Expert Opin Drug Metab Toxicol. 2007 Oct;3(5):741-53. [17916059 ]