Escitalopram oxalateProduct ingredient for Escitalopram

Name
Escitalopram oxalate
Drug Entry
Escitalopram

Escitalopram is a selective serotonin re-uptake inhibitor (SSRI) and the S-enantiomer of racemic citalopram.11 It is used to restore serotonergic function in the treatment of depression and anxiety.18,19,20 Escitalopram is approximately 150 times more potent than citalopram’s R-enantiomer and is responsible for the vast majority of citalopram’s clinical activity, with some evidence suggesting that the R-enantiomer of racemic citalopram actively dampens the activity of escitalopram rather than existing simply as an inactive enantiomer.6,14 Amongst SSRIs, escitalopram exerts the highest degree of selectivity for the serotonin transporter (SERT) relative to other off-targets which may explain its lower rates of adverse effects as compared to other agents in this class.13 Escitalopram also differentiates itself from other SSRIs via allosteric action on its target - this may be the mechanism responsible for its observed superior efficacy and faster onset compared to other SSRIs.16,13,15

Accession Number
DBSALT002455
Structure
Thumb
Synonyms
Not Available
External IDs
LU 26-054-0 / LU-26-054-0 / LU-26-054-O
UNII
5U85DBW7LO
CAS Number
219861-08-2
Weight
Average: 414.433
Monoisotopic: 414.159100012
Chemical Formula
C22H23FN2O5
InChI Key
KTGRHKOEFSJQNS-BDQAORGHSA-N
InChI
InChI=1S/C20H21FN2O.C2H2O4/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;3-1(4)2(5)6/h4-9,12H,3,10-11,14H2,1-2H3;(H,3,4)(H,5,6)/t20-;/m0./s1
IUPAC Name
(1S)-1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile; oxalic acid
SMILES
OC(=O)C(O)=O.CN(C)CCC[C@]1(OCC2=C1C=CC(=C2)C#N)C1=CC=C(F)C=C1
External Links
ChemSpider
129278
ChEMBL
CHEMBL1200322
Wikipedia
Escitalopram
Predicted Properties
PropertyValueSource
Water Solubility0.00588 mg/mLALOGPS
logP3.58ALOGPS
logP3.76ChemAxon
logS-4.7ALOGPS
pKa (Strongest Basic)9.78ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area36.26 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity94.02 m3·mol-1ChemAxon
Polarizability35.21 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon