3D Mol Similar

Escitalopram oxalate

: Iupac Name：(1S)-1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-3H-2-benzofuran-5-carbonitrile;oxalic acid; CAS No.: 219861-08-2; Molecular Weight：414.433; Modify Date.: 2023-02-13 21:08; Introduction: Escitalopram was launched as Cipralex? in Switzerland, Sweden and UK forthetreatment of depression and panic disorder. It is the S-enantiomer version of theselective serotonin reuptake inhibitor (SSRI) citalopram approved in 1989. It can beobtained from 5cyanophthalide by successive reactions with 4-fluorophenyl magnesiumbromide and 3-(dimethylamino)propyl magnesium chloride. The resulting racemic diol canbe resolved by several routes such as crystallization with a chiral acid. Finally, a two stepcyclisation procedure affords escitalopram. Escitalopram is twice as effective as theracemate and over 100 fold more potent than the R-enantiomer in inhibiting the 5HTreuptake in vivo in rat brain synaptosomes. Moreover, it exhibits higher selectivity for thehuman serotonin transporter relative to the noradrenaline or dopamine transporters thanany other currently available SSRl’s. In the mouse forced swim test, the duration ofimmobility (which reflects antidepressant activity) for escitalopram was comparable tocitalopram and greater than (R)-citalopram. Clinical trials in patients with panic disorders ordepression have shown that escitalopram has a clinically relevant and significant effect.Additionally, it has a faster onset of antidepressant action than citalopram. Escitalopramhas linear pharmacokinetics, with a long half-life (27-32 h). It is extensively metabolized inthe 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 drugmetabolizingenzymes in vitro. Escitalopram is well tolerated with nausea being the mostcommon side effect. View more+

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1. Names and Identifiers

: 1.1 Name; Escitalopram oxalate; 1.2 Synonyms; (1S)-1-[3-(diméthylamino)propyl]-1-(4-fluorophényl)-1,3-dihydro-2-benzofurane-5-carbonitrile oxalate (1S)-1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile ethanedioate (1S)-1-[3-(Dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile ethanedioate (1:1) (1S)-1-[3-(Dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile oxalate (1S)-1-[3-(Dimethylamino)propyl]-1-[4-fluoro(2H4)phenyl]-1,3-dihydro-2-benzofuran-5-carbonitrile ethanedioate (1:1) (S)-CITALOPRAM (S)-Citalopram Oxalate (S)-Citalopram-d6 (S)-Escitalopram Oxalate 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-5-isobenzofuran-carbonitrile oxalate 1S)-1-[3-(Dimethylamino-d6)propyl]-1-(4-fluorophenyl)-1,3-dihydro -5-isobenzofurancarbonitrile 5-Isobenzofurancarbonitrile, 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-, (1S)-, ethanedioate (1:1) 5-Isobenzofurancarbonitrile, 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl-2,3,5,6-d4)-1,3-dihydro-, (1S)-, ethanedioate (1:1) Cipralex Citalopram Impurity 2 ESCIFALOPRAMOXALATE Escitalopram (oxalate) Escitalopram oxalate (USAN) escitalopram oxalic acid Ethandisäure--(1S)-1-[3-(dimethylamino)propyl]-1-(4-fluorphenyl)-1,3-dihydro-2-benzofuran-5-carbonitril(1:1) Lexapro Lexapro (TN) Lu-26-054-0 MFCD06407826 S-(+)-1-3-(dimethyl-amino)propyl-1-(p-fluorophenyl)-5-phthalancarbonitrileoxalate S-(+)-CITAPROLAM OXALATE; View all

1.3 CAS No.: 219861-08-2

1.4 CID: 146571

1.5 EINECS(EC#): 620-544-8

1.6 Molecular Formula: C22H23FN2O5 (isomer)

1.7 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

1.8 InChIkey: KTGRHKOEFSJQNS-BDQAORGHSA-N

1.9 Canonical Smiles: CN(C)CCCC1(C2=C(CO1)C=C(C=C2)C#N)C3=CC=C(C=C3)F.C(=O)(C(=O)O)O

1.10 Isomers Smiles: CN(C)CCC[C@@]1(C2=C(CO1)C=C(C=C2)C#N)C3=CC=C(C=C3)F.C(=O)(C(=O)O)O

2. Properties

2.1 Melting point: 152-153 °C

2.1 Boiling point: 428.3 °C at 760 mmHg

2.1 Flash Point: 212.8 °C

2.1 Precise Quality: 414.15900

2.1 PSA: 110.86000

2.1 logP: 2.96858

2.1 Solubility: DMSO: ≥15mg/mL

2.2 Appearance: white solid

2.3 Storage: -20°C Freezer, Under Inert Atmosphere

2.4 Chemical Properties: White Solid

2.5 Color/Form: Powder

2.6 Water Solubility: DMSO: ≥15mg/mL

2.7 StorageTemp: 2-8°C

3. Use and Manufacturing

3.1 GHS Classification: Signal: Warning
GHS Hazard Statements
Aggregated GHS information provided by 48 companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

H302 (18.75%): Harmful if swallowed [Warning Acute toxicity, oral]
H315 (85.42%): Causes skin irritation [Warning Skin corrosion/irritation]
H319 (83.33%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H335 (83.33%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501; View all

3.2 Usage: An inhibitor of serotonin (5-HT) uptake. Antidepressant

4. Safety and Handling

4.1 Hazard Codes: Xi

4.1 Risk Statements: R36/37/38

4.1 Safety Statements: 26-36

4.1 Hazard Declaration: H302

4.1 RIDADR: NONH for all modes of transport

4.1 Caution Statement: P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501

4.1 WGK Germany: 3

4.1 RTECS: NP6333500

4.1 Safety: Hazard Codes:?Xi
Risk Statements: 36/37/38?
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S36:Wear suitable protective clothing.

4.2 Specification: ?Escitalopram oxalate (CAS NO.219861-08-2) is also named as Cipralex ; Lexapro ; Lu 26-054-0 ; S-(+)-1-(3-(Dimethylamino)propyl)-1-(p-fluorophenyl)-5-phthalancarbonitrile oxalate ; S-(+)-5-Isobenzofurancarbonitrile, 1-(3-
(dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydro-, oxalate ; UNII-5U85DBW7LO?; 5-Isobenzofurancarbonitrile, 1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydro-, (1S)-, ethanedioate (1:1)?.?Escitalopram oxalate (CAS NO.219861-08-2) is white solid. It is soluble in methanol and dimethyl sulfoxide, dissolved in saline, slightly soluble in water and ethanol, slightly soluble in ethyl acetate, insoluble in heptane.

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

no data available

2.2 GHS label elements, including precautionary statements

Pictogram(s)	no data available
Signal word	no data available
Hazard statement(s)	no data available
Precautionary statement(s)
Prevention	no data available
Response	no data available
Storage	no data available
Disposal	no data available

2.3 Other hazards which do not result in classification

no data available

View all

6. Synthesis Route

219861-08-2Total: 12 Synthesis Route

352-13-6 59 Suppliers

219861-08-2 288 Suppliers

Literatures:
US2011/92719 A1, ;
Yield: null

460-00-4 352 Suppliers

219861-08-2 288 Suppliers

Literatures:
US2011/92719 A1, ;
Yield: null

144-62-7 1286 Suppliers

219861-08-2 288 Suppliers

Literatures:
US2007/21499 A1, ; Page/Page column 7-8 ;
Yield: null

View all

7. Precursor and Product

precursor:

1073819-95-0

460-00-4

352-13-6

128196-01-0

917483-01-3

50-00-0

103146-25-4

488787-59-3

5407-04-5

144-62-7

19070-16-7

product :

128196-01-0

8. Other Information

8.0 Merck: 14,2318

8.1 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.; View all

8.2 Chemical Properties: White Solid

8.3 Originator: Lundbeck (Denmark)

8.4 Uses: Escitalopram oxalate may be used as a pharmaceutical primary standard for the quantification of the analyte in pharmaceutical formulations using analytical techniques.

8.5 Collision Cross Section: 178.8 ?2 [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

8.6 Mesh: A structurally and mechanistically diverse group of drugs that are not tricyclics or monoamine oxidase inhibitors. The most clinically important appear to act selectively on serotonergic systems, especially by inhibiting serotonin reuptake. (See all compounds classified as Antidepressive Agents, Second-Generation.)|Compounds that specifically inhibit the reuptake of serotonin in the brain. (See all compounds classified as Serotonin Uptake Inhibitors.)

8.7 Mesh Entry Terms: Celexa

8.8 Use Classification: Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

9. Computational chemical data

Molecular Weight: 414.433g/mol
Molecular Formula: C₂₂H₂₃FN₂O₅
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 414.15910000
Monoisotopic Mass: 414.15910000
Complexity: 537
Rotatable Bond Count: 6
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 8
Topological Polar Surface Area: 111
Heavy Atom Count: 30
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: 2
CACTVS Substructure Key Fingerprint: AAADceB7OQAAAAAAAAAAAAAAAAAAASAAAAAwYAAAAAAAAEgBQAAAHwAACAAADEThmA4yCIMABgCYBiDSCAIiAAAgAAAIiABICIgJpiKAsRiGMAAkwAEJqA+wwPAOwAACAAAQAACAAAQAACAAAAAAAAAAAA==

10. Question & Answer

What are the differences between Escitalopram Oxalate and Sertraline? Jun 27 2023
Escitalopram oxalate and Sertraline are both selective serotonin reuptake inhibitors (SSRIs) that can be used to treat depression, anxiety, and may even be used in combination when monotherapy is ine..
What is the polarity of Escitalopram oxalate (C22H23FN2O5)? Dec 27 2021
It’s a salt (the “oxalate” is a giveaway here). Thus, it will have some polarity due to that. But if you remove the oxalate (in the form of oxalic acid), you get Escitalopram itself (C20H21FN2O), w..

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