NP-MRD: Showing NP-Card for Escitalopram (NP0334589)

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Record Information

Version

2.0

Created at

2024-09-10 19:02:21 UTC

Updated at

2024-09-10 19:02:22 UTC

NP-MRD ID

NP0334589

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Escitalopram

Description

Escitalopram, also known as esertia or cipralex, 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. Escitalopram is a very strong basic compound (based on its pKa). In humans, escitalopram is involved in escitalopram action pathway. Escitalopram is a potentially toxic compound. Escitalopram was first documented in 2003 (PMID: 14501259). A 1--1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile that has S-configuration at the chiral centre (PMID: 14594439) (PMID: 14708881) (PMID: 15200745) (PMID: 15609164).

Structure

MOL SDF PDB SMILES InChI

1175
  Mrv0541 02231215182D          

 24 26  0  0  1  0            999 V2000
    7.9618    1.5353    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.7701   -1.0638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1681    1.5162    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.3013    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2886   -0.3998    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0351    0.3853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.6513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.4763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2284    0.5582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9569    0.0840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2886   -1.7277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9748    1.3433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.2388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.8888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8721    0.9046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7100   -0.2529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -0.6513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -1.4763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5404    1.3883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3783    0.2308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2935    1.0515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9145    2.3013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6150    0.9041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.8888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 21  1  0  0  0  0
  2  5  1  0  0  0  0
  2 11  1  0  0  0  0
  3 12  1  0  0  0  0
  3 22  1  0  0  0  0
  3 23  1  0  0  0  0
  4 24  3  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  5 10  1  0  0  0  0
  6  9  1  0  0  0  0
  7  8  2  0  0  0  0
  7 13  1  0  0  0  0
  8 11  1  0  0  0  0
  8 14  1  0  0  0  0
  9 12  1  0  0  0  0
 10 15  2  0  0  0  0
 10 16  1  0  0  0  0
 13 17  2  0  0  0  0
 14 18  2  0  0  0  0
 15 19  1  0  0  0  0
 16 20  2  0  0  0  0
 17 18  1  0  0  0  0
 18 24  1  0  0  0  0
 19 21  2  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0334589

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN(C)CCC[C@]1(OCC2=C1C=CC(=C2)C#N)C1=CC=C(F)C=C1

> <INCHI_IDENTIFIER>
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

> <INCHI_KEY>
WSEQXVZVJXJVFP-FQEVSTJZSA-N

> <FORMULA>
C20H21FN2O

> <MOLECULAR_WEIGHT>
324.3919

> <EXACT_MASS>
324.163791509

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
35.20765933974287

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S)-1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile

> <ALOGPS_LOGP>
3.58

> <JCHEM_LOGP>
3.764304206333334

> <ALOGPS_LOGS>
-4.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.784977656720883

> <JCHEM_POLAR_SURFACE_AREA>
36.26

> <JCHEM_REFRACTIVITY>
94.0202

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.88e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
lexapro

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1175                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  F   UNK     0      14.862   2.866   0.000  0.00  0.00           F+0
HETATM    2  O   UNK     0      10.771  -1.986   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       5.914   2.830   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       3.080  -4.296   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       9.872  -0.746   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.399   0.719   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.415  -1.216   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.415  -2.756   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.893   1.042   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.120   0.157   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.872  -3.225   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.420   2.507   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.081  -0.446   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.081  -3.526   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.961   1.689   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.525  -0.472   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.747  -1.216   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.747  -2.756   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.209   2.591   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.773   0.431   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.615   1.963   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.440   4.296   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.881   1.688   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.414  -3.526   0.000  0.00  0.00           C+0
CONECT    1   21                                                            
CONECT    2    5   11                                                       
CONECT    3   12   22   23                                                  
CONECT    4   24                                                            
CONECT    5    2    6    7   10                                             
CONECT    6    5    9                                                       
CONECT    7    5    8   13                                                  
CONECT    8    7   11   14                                                  
CONECT    9    6   12                                                       
CONECT   10    5   15   16                                                  
CONECT   11    2    8                                                       
CONECT   12    3    9                                                       
CONECT   13    7   17                                                       
CONECT   14    8   18                                                       
CONECT   15   10   19                                                       
CONECT   16   10   20                                                       
CONECT   17   13   18                                                       
CONECT   18   14   17   24                                                  
CONECT   19   15   21                                                       
CONECT   20   16   21                                                       
CONECT   21    1   19   20                                                  
CONECT   22    3                                                            
CONECT   23    3                                                            
CONECT   24    4   18                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Value	Source
(+)-Citalopram	ChEBI
(S)-Citalopram	ChEBI
Escitalopramum	ChEBI
Esertia	ChEBI
S(+)-Citalopram	ChEBI
S-(+)-Citalopram	ChEBI
Cipralex	HMDB
Lexapro	HMDB
Cytalopram	HMDB
Citalopram	HMDB
Celexa	HMDB
Citalopram hydrobromide	HMDB
Escitalopram oxalate	HMDB
Seropram	HMDB

Chemical Formula

C₂₀H₂₁FN₂O

Average Mass

324.3919 Da

Monoisotopic Mass

324.16379 Da

IUPAC Name

(1S)-1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile

Traditional Name

lexapro

CAS Registry Number

Not Available

SMILES

CN(C)CCC[C@]1(OCC2=C1C=CC(=C2)C#N)C1=CC=C(F)C=C1

InChI Identifier

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

InChI Key

WSEQXVZVJXJVFP-FQEVSTJZSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylbutylamines

Direct Parent

Phenylbutylamines

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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile (CHEBI:36791 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.58	ALOGPS
logP	3.76	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Basic)	9.78	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	36.26 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	94.02 m³·mol⁻¹	ChemAxon
Polarizability	35.21 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0005028

DrugBank ID

DB01175

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023596

KNApSAcK ID

Not Available

Chemspider ID

129277

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Escitalopram

METLIN ID

Not Available

PubChem Compound

146570

PDB ID

Not Available

ChEBI ID

36791

Good Scents ID

Not Available

References

General References

Sanchez C, Gruca P, Papp M: R-citalopram counteracts the antidepressant-like effect of escitalopram in a rat chronic mild stress model. Behav Pharmacol. 2003 Sep;14(5-6):465-70. doi: 10.1097/01.fbp.0000087733.21047.60. [PubMed:14501259 ]
Croom KF, Plosker GL: Escitalopram: a pharmacoeconomic review of its use in depression. Pharmacoeconomics. 2003;21(16):1185-209. doi: 10.2165/00019053-200321160-00004. [PubMed:14594439 ]
Gutteck U, Rentsch KM: Therapeutic drug monitoring of 13 antidepressant and five neuroleptic drugs in serum with liquid chromatography-electrospray ionization mass spectrometry. Clin Chem Lab Med. 2003 Dec;41(12):1571-9. doi: 10.1515/CCLM.2003.240. [PubMed:14708881 ]
Hemels ME, Kasper S, Walter E, Einarson TR: Cost-effectiveness analysis of escitalopram: a new SSRI in the first-line treatment of major depressive disorder in Austria. Curr Med Res Opin. 2004 Jun;20(6):869-78. doi: 10.1185/030079904125003737. [PubMed:15200745 ]
Francois C, Toumi M, Aakhus AM, Hansen K: A pharmacoeconomic evaluation of escitalopram, a new selective serotonin reuptake inhibitor. Comparison of cost-effectiveness between escitalopram, citalopram, fluoxetine, and venlafaxine for the treatment of depression in Norway. Eur J Health Econ. 2003;4(1):12-9. doi: 10.1007/s10198-002-0139-0. [PubMed:15609164 ]

Showing NP-Card for Escitalopram (NP0334589)

MOL for NP0334589 (Escitalopram)

3D MOL for NP0334589 (Escitalopram)

3D SDF for NP0334589 (Escitalopram)

3D-SDF for NP0334589 (Escitalopram)

PDB for NP0334589 (Escitalopram)

3D PDB for NP0334589 (Escitalopram)

SMILES for NP0334589 (Escitalopram)

INCHI for NP0334589 (Escitalopram)

Structure for NP0334589 (Escitalopram)

3D Structure for NP0334589 (Escitalopram)