Escitalopram (CHEM002365)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (15)XML
Record Information
Version1.0
Creation Date2009-07-21 20:28:32 UTC
Update Date2026-05-14 16:58:29 UTC
Accession NumberCHEM002365
Identification
Common NameEscitalopram
ClassSmall Molecule
DescriptionEscitalopram, the S-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 D2 or histamine H1 receptors. During acute use, SSRIs block serotonin reuptake and increase serotonin stimulation of somatodendritic 5-HT1A and terminal autoreceptors. Chronic use leads to desensitization of somatodendritic 5-HT1A 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.
Contaminant Sources
  • FooDB Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
Contaminant Type
  • Amine
  • Antidepressant, Second-Generation
  • Antidepressive Agent, Second-Generation
  • Drug
  • Ether
  • Food Toxin
  • Human Neurotoxin
  • Metabolite
  • Nitrile
  • Organic Compound
  • Organofluoride
  • Serotonin Uptake Inhibitor
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(+)-CitalopramChEBI
(S)-CitalopramChEBI
EscitalopramumChEBI
EsertiaChEBI
S(+)-CitalopramChEBI
S-(+)-CitalopramChEBI
CipralexHMDB
LexaproHMDB
CytalopramHMDB
CitalopramHMDB
CelexaHMDB
Citalopram hydrobromideHMDB
Escitalopram oxalateHMDB
SeropramHMDB
Chemical FormulaC20H21FN2O
Average Molecular Mass324.392 g/mol
Monoisotopic Mass324.164 g/mol
CAS Registry Number128196-01-0
IUPAC Name(1S)-1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile
Traditional Namelexapro
SMILESCN(C)CCC[C@]1(OCC2=C1C=CC(=C2)C#N)C1=CC=C(F)C=C1
InChI IdentifierInChI=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
InChI KeyWSEQXVZVJXJVFP-FQEVSTJZSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenylbutylamines. Phenylbutylamines are compounds containing a phenylbutylamine moiety, which consists of a phenyl group substituted at the fourth carbon by an butan-1-amine.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylbutylamines
Direct ParentPhenylbutylamines
Alternative Parents
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
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
  • 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile (CHEBI:36791 )
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical Roles
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0059 g/LALOGPS
logP3.58ALOGPS
logP3.76ChemAxon
logS-4.7ALOGPS
pKa (Strongest Basic)9.78ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area36.26 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity94.02 m³·mol⁻¹ChemAxon
Polarizability35.21 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-6190000000-9c092c583199a2a486efSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-004i-1497000000-a840cd3176ff240d74f6Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0bt9-0692000000-dbd03d31621a5efaba54Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-1029000000-b0f10b0f7897ca083ed5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-003r-2294000000-5935fccdd160458bb836Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9740000000-7a3a98de78c385feae56Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0019000000-84c6ddc8fad411d8541fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-1029000000-d4716f92fec4a098ef2cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0005-5290000000-45334fd57d41c1fadf1aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0009000000-5baf9d241e4712801e87Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-3079000000-3efd9cf0f4fddbeed2c9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-1950000000-69ba9b80f8bec9cbe874Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0009000000-23521c8b9dc4834c9328Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0091000000-bdb51930294423bb3315Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-1590000000-b821092ee64991ad4390Spectrum
Toxicity Profile
Route of ExposureThe absolute bioavailability of citalopram is about 80% relative to an intravenous dose.
Mechanism of ToxicityThe 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 5HT1A autoreceptors. SSRIs bind with significantly less affinity to histamine, acetylcholine, and norepinephrine receptors than tricyclic antidepressant drugs.
MetabolismMainly hepatic. Escitalopram undergoes N-demethylation to S-demethylcitalopram (S-DCT) and S-didemethylcitalopram (S-DDCT). CYP3A4 and CYP2C19 are the enzymes responsible for this N-demethylation reaction. Route of Elimination: Following oral administrations of escitalopram, the fraction of drug recovered in the urine as escitalopram and S-demethylcitalopram (S-DCT) is about 8% and 10%, respectively. The oral clearance of escitalopram is 600 mL/min, with approximately 7% of that due to renal clearance. Escitalopram is metabolized to S-DCT and S-didemethylcitalopram (S-DDCT). Half Life: 27-32 hours
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesLabeled indications include major depressive disorder (MDD) and generalized anxiety disorder (GAD). Unlabeled indications include treatment of mild dementia-associated agitation in nonpsychotic patients.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsSigns of overdose include convulsions, coma, dizziness, hypotension, insomnia, nausea, vomiting, sinus tachycardia, somnolence, and ECG changes (including QT prolongation).
TreatmentEstablish and maintain an airway to ensure adequate ventilation and oxygenation. Gastric evacuation by lavage and use of activated charcoal should be considered. Careful observation and cardiac and vital sign monitoring are recommended, along with general symptomatic and supportive care. Due to the large volume of distribution of escitalopram, forced diuresis, dialysis, hemoperfusion, and exchange transfusion are unlikely to be of benefit. There are no specific antidotes for Escitalopram. (7)
Concentrations
Not Available
DrugBank IDDB01175
HMDB IDHMDB0005028
FooDB IDFDB023596
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkEscitalopram
Chemspider ID129277
ChEBI ID36791
PubChem Compound ID146570
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Robert Dancer, “Escitalopram hydrobromide and a method for the preparation thereof.” U.S. Patent US20040167209, issued August 26, 2004.

MSDSNot Available
General References
1. Dall'asta, Leone; Casazza, Umberto; Petersen, Hans. Method for the preparation of citalopram. PCT Int. Appl. (2000), 26 pp. CODEN: PIXXD2 WO 2000023431 A1 20000427 CAN 132:308238 AN 2000:277969
2. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043.
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=14501259
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=14594439
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=14708881
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=15200745
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=15609164
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=16266205
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=16421462
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=16937393
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=16953656
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=18789789
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=19710642
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=20825390
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=24172161
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=24176515
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=24289655
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=24424469
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=24469525
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=24528284