File:Citalopram_racemic.svg · Wikimedia Commons · See Wikimedia Commons
(RS)-citalopram
Sign in to saveAlso known as citalopram
Citalopram, sold under the brand name Celexa among others, is an antidepressant of the selective serotonin reuptake inhibitor (SSRI) class. It is used to treat major depressive disorder, obsessive compulsive disorder, panic disorder, and social phobia. The antidepressant effects may take one to four weeks to occur. It is typically taken orally (swallowed by mouth). In some European countries, it is sometimes given intravenously (injected into a vein) to initiate treatment, before switching to the oral route of administration for continuation of treatment. It has also been used intravenously in
OverviewAI-generated
(RS)-citalopram is a chemical compound with the formula C₂₀H₂₁FN₂O. Its IUPAC name is 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-3H-2-benzofuran-5-carbonitrile. The molecule has a mass of 324.163792 and a weight of 324.4. It carries a charge of 0 and features a defined daily dose of 20.
Physicochemical properties include an xlogp of 3.2 and a topological polar surface area of 36.3. The structure contains 0 hydrogen bond donors and 4 hydrogen bond acceptors. A stylized name for the compound is CeleXA. The substance is referenced by 886 other encyclopedia articles.
Synthesized by Vinony from 19 facts across 4 sources: Wikidata, PubMed, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.
Chemical data
- Formula
- C20H21FN2O
- Molecular weight
- 324.4 g/mol
- IUPAC name
- 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-3H-2-benzofuran-5-carbonitrile
- SMILES
- CN(C)CCCC1(C2=C(CO1)C=C(C=C2)C#N)C3=CC=C(C=C3)F
- InChIKey
- WSEQXVZVJXJVFP-UHFFFAOYSA-N
- XLogP
- 3.2
- Polar surface area
- 36.3 Ų
- H-bond donors
- 0
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Research
9 papers- Escitalopram : a review of its use in the management of major depressive and anxiety disorders.CNS drugs · 2003
- Escitalopram: a review of its use in the management of major depressive disorder.Drugs · 2005
- Escitalopram: a pharmacoeconomic review of its use in depression.PharmacoEconomics · 2003
- R-citalopram functionally antagonises escitalopram in vivo and in vitro: evidence for kinetic interaction at the serotonin transporter.British journal of pharmacology · 2004
- Escitalopram block of hERG potassium channels.Naunyn-Schmiedeberg's archives of pharmacology · 2014
via PubMed
Wikidata facts
- Mass
- 324.163792
Show 10 more facts
- significant drug interaction
- fluoxetine
- Commons category
- Citalopram
- chemical formula
- C₂₀H₂₁FN₂O
- medical condition treated
- anxiety disorder
- World Health Organisation international non-proprietary name
- citalopram
- canonical SMILES
- CN(C)CCCC1(C2=C(CO1)C=C(C=C2)C#N)C3=CC=C(C=C3)F
- physically interacts with
- solute carrier family 6 member 4
- stylized name
- CeleXA
- defined daily dose
- 20
- legal status (medicine)
- boxed warning
via Wikidata · CC0
~13 min read
Encyclopedic overview
28 sectionsContents
- Medical uses
- Depression
- Panic disorder
- Other
- Administration
- Adverse effects
- Sexual dysfunction
- Abnormal heart rhythm
- Endocrine effects
- Exposure in pregnancy
- Overdose
- Suicidality
- Discontinuation syndrome
- Interactions
- Serotonin syndrome
- Other interactions
- Pharmacology
- Pharmacodynamics
- Pharmacokinetics
- Stereochemistry
- Metabolism
- History
- Society and culture
- Brand names
- European Commission fine
- Other uses
- See also
- References
Citalopram, sold under the brand name Celexa among others, is an antidepressant of the selective serotonin reuptake inhibitor (SSRI) class. It is used to treat major depressive disorder, obsessive compulsive disorder, panic disorder, and social phobia. The antidepressant effects may take one to four weeks to occur. It is typically taken orally (swallowed by mouth). In some European countries, it is sometimes given intravenously (injected into a vein) to initiate treatment, before switching to the oral route of administration for continuation of treatment. It has also been used intravenously in other parts of the world in some other circumstances.
Common side effects include nausea, trouble sleeping, sexual problems, shakiness, feeling tired, and sweating. Serious side effects include an increased risk of suicide in those under the age of 25, serotonin syndrome, glaucoma, and QT prolongation. It should not be used in persons who take or have recently taken an MAO inhibitor. There are concerns that use during pregnancy may harm the fetus.
Excerpted from Wikipedia’s “(RS)-citalopram” article, available under the CC BY-SA 4.0 licence.