| Identification | More | [Name]
Escitalopram oxalate | [CAS]
219861-08-2 | [Synonyms]
1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-5-isobenzofuran-carbonitrile oxalate
ESCITALOPRAM
ESCITALOPRAM OXALATE
(S)-CITALOPRAM
S-(+)-CITAPROLAM OXALATE
S-(+)-1-3-(dimethyl-amino)propyl-1-(p-fluorophenyl)-5-phthalancarbonitrileoxalate
ESCIFALOPRAMOXALATE
(1S)-1-[3-(Dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-5-isobenzofurancarbonitrile Ethanedioate
Cipralex
(S)-Citalopram-d6
1S)-1-[3-(Dimethylamino-d6)propyl]-1-(4-fluorophenyl)-1,3-dihydro-5-isobenzofurancarbonitrile
(S)-Citalopram-d6 Oxalate
1S)-1-[3-(Dimethylamino-d6)propyl]-1-(4-fluorophenyl)-1,3-dihydro-5-isobenzofurancarbonitrile Oxalate | [EINECS(EC#)]
620-544-8 | [Molecular Formula]
C22H23FN2O5 | [MDL Number]
MFCD06407826 | [Molecular Weight]
414.43 | [MOL File]
219861-08-2.mol |
| Chemical Properties | Back Directory | [Appearance]
White Solid | [Melting point ]
152-153°C | [alpha ]
D +12.31° (c = 1 in methanol) | [storage temp. ]
2-8°C | [solubility ]
DMSO: ≥15mg/mL | [form ]
powder | [color ]
white to tan | [Usage]
A labelled inhibitor of serotonin (5-HT) uptake. Antidepressant | [Merck ]
14,2318 | [BCS Class]
1 | [Stability:]
Hygroscopic | [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) | [InChIKey]
KTGRHKOEFSJQNS-UHFFFAOYSA-N | [SMILES]
C1(CCCN(C)C)(C2=CC=C(F)C=C2)C2=C(C=C(C#N)C=C2)CO1.C(O)(=O)C(O)=O | [CAS DataBase Reference]
219861-08-2(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3 | [RTECS ]
NP6333500 | [HS Code ]
29322090 |
| Hazard Information | Back Directory | [Description]
Escitalopram was launched as Cipralex? in Switzerland, Sweden and UK for
the
treatment of depression and panic disorder. It is the S-enantiomer version of the
selective serotonin reuptake inhibitor (SSRI) citalopram approved in 1989. It can be
obtained from 5cyanophthalide by successive reactions with 4-fluorophenyl magnesium
bromide and 3-(dimethylamino)propyl magnesium chloride. The resulting racemic diol can
be resolved by several routes such as crystallization with a chiral acid. Finally, a two step
cyclisation procedure affords escitalopram. Escitalopram is twice as effective as the
racemate and over 100 fold more potent than the R-enantiomer in inhibiting the 5HT
reuptake in vivo in rat brain synaptosomes. Moreover, it exhibits higher selectivity for the
human serotonin transporter relative to the noradrenaline or dopamine transporters than
any other currently available SSRl’s. In the mouse forced swim test, the duration of
immobility (which reflects antidepressant activity) for escitalopram was comparable to
citalopram and greater than (R)-citalopram. Clinical trials in patients with panic disorders or
depression have shown that escitalopram has a clinically relevant and significant effect.
Additionally, it has a faster onset of antidepressant action than citalopram. Escitalopram
has linear pharmacokinetics, with a long half-life (27-32 h). It is extensively metabolized in
the liver via cytochromes P450 to S(+)-desmethyl and S(+)-didesmethyl citalopram.
However, it has been shown to be a weak or negligible inhibitor of CYP450 drugmetabolizing
enzymes in vitro. Escitalopram is well tolerated with nausea being the most
common side effect. | [Chemical Properties]
White Solid | [Originator]
Lundbeck (Denmark) | [Uses]
A labelled inhibitor of serotonin (5-HT) uptake. Antidepressant | [Uses]
An inhibitor of serotonin (5-HT) uptake. Antidepressant | [Uses]
antineoplastic | [Brand name]
Lexapro (Forest). | [General Description]
Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.
Escitalopram Oxalate, a highly selective serotonin re-uptake inhibitor antidepressant, is a pure S-enantiomer of the racemic, bicyclic pthalates derivatives of citalopram. It is mainly developed for the treatment of depression and anxiety disorders. | [Biochem/physiol Actions]
Escitalopram is a selective serotonin reuptake inhibitor (SSRI), the S-enantiomer and eutomer of citalopram. | [Mechanism of action]
Escitalopram is the S-enantiomer of citalopram and is the most selective of SSRIs. SSRIs' mechanism of action is exerted by binding to the sodium-dependant serotonin transporter protein (SERT) located in the presynaptic neuron. SERT works by re-uptaking serotonin from the synaptic cleft to the presynaptic neuron. When SERT is inactivated by escitalopram, this increases the amount of serotonin in the synaptic cleft.
| [Side effects]
The main side effect of escitalopram include: Nausea, dry mouth, trouble sleeping, constipation, tiredness, drowsiness, dizziness, and increased sweating may occur. | [Synthesis]
The synthesis of escitalopram was carried out in several
different routes [30-33]. 5-Cyanophthalide (72) was treated
with Grignard reagent 73 at 0??C to provide intermediate 75
which was reacted in situ with another Grignard reagent 76
to afford the diol in a one-pot process. Racemic diol 77 was
resolved using (+)-p-toluoyltartaric acid to afford desired S
isomer 78 in 55% yield. The ring closure reaction was
carried out at 0??C using methanesulfonyl chloride in toluene
to furnish escitalopram (7) in 60% yield.
| [storage]
+4°C | [References]
[1] sánchez c1, bergqvist pb, brennum lt, gupta s, hogg s, larsen a, wiborg o. escitalopram, the s-(+)-enantiomer of citalopram, is a selective serotonin reuptake inhibitor with potent effects in animal models predictive of antidepressant and anxiolytic activities. psychopharmacology (berl). 2003 jun;167(4):353-62. epub 2003 apr 26. |
|
|