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Importing Wikidata short description: "Chemical compound" (Shortdesc helper)
 
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{{Short description|Chemical compound}}
{{Drugbox
{{Drugbox
| Verifiedfields = changed
| IUPAC_name = (''RS'' or ''S'')-1-[3-aminopropyl]-1-<br/>(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile
| Watchedfields = changed
| imagename = Didesmethylescitalopram
| verifiedrevid = 451228130
| image = Didesmethylescitalopram skeletal.svg
| IUPAC_name = (''RS'' or ''S'')-1-[3-aminopropyl]-1-<br/>(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile
| width =
| CAS_number =
| image = Didesmethylescitalopram skeletal.svg
| ATC_prefix = none
| width =
<!-- Clinical data -->
| ATC_suffix =
| PubChem =
| tradename =
| DrugBank =
| pregnancy_category =
| ChemSpiderID =
| legal_status = uncontrolled
| routes_of_administration =
| C=18|H=17|F=1|N=2|O=1
<!-- Pharmacokinetic data -->
| molecular_weight = 296.338783 g/mol
| bioavailability =
| bioavailability =
| protein_bound =
| protein_bound =
| metabolism =
| metabolism =
| elimination_half-life =
| elimination_half-life = 100 h
| excretion =
| excretion =
<!-- Identifiers -->
| pregnancy_category=
| CAS_number_Ref = {{cascite|correct|CAS}}
| legal_status = uncontrolled
| CAS_number = 62498-69-5
| routes_of_administration =
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = ZE9YVI4ZEE
| ATC_prefix = none
| ATC_suffix =
| PubChem =
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank =
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 23935928
| smiles = c1cc(ccc1[C@]2(c3ccc(cc3CO2)C#N)CCCN)F
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C18H17FN2O/c19-16-5-3-15(4-6-16)18(8-1-9-20)17-7-2-13(11-21)10-14(17)12-22-18/h2-7,10H,1,8-9,12,20H2/t18-/m0/s1
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = RKUKMUWCRLRPEJ-SFHVURJKSA-N
<!-- Chemical data -->
| C=18 | H= 17 | F= 1 | N= 2 | O= 1
}}
}}
'''Didesmethylcitalopram''' is an [[active metabolite]] of the [[antidepressant]] [[drug]] [[citalopram]] ([[racemic]]).<ref name="pmid2365786">{{cite journal | vauthors = Rop PP, Durand A, Viala A, Jørgensen A | title = Simultaneous determination of citalopram, monodesmethylcitalopram and didesmethylcitalopram in plasma by high-performance liquid chromatography after column extraction | journal = Journal of Chromatography | volume = 527 | issue = 1 | pages = 226–32 | date = April 1990 | pmid = 2365786 | doi = 10.1016/s0378-4347(00)82105-2 }}</ref> '''Didesmethyl''es''citalopram''' is an active metabolite of the antidepressant [[escitalopram]], the ''S''-[[enantiomer]] of citalopram. Like citalopram and escitalopram, didesmethyl(es)citalopram functions as a [[selective serotonin reuptake inhibitor]] (SSRI), and is responsible for some of its parents' [[therapeutic benefit]]s.

'''Didesmethylcitalopram''' is an [[activity (chemistry)|active]] [[metabolite]] of the [[antidepressant]] [[drug]] [[citalopram]] ([[racemic]]). '''Didesmethyl''es''citalopram''' is an active metabolite of the antidepressant [[escitalopram]], the ''S''-[[enantiomer]] of citalopram. Like citalopram and escitalopram, didesmethyl(es)citalopram functions as a [[selective serotonin reuptake inhibitor]] (SSRI), and is responsible for some of its parents' [[therapeutic benefit]]s.


== See also ==
== See also ==
{{div col|colwidth=30em}}
<div style="-moz-column-count:2; column-count:2; -webkit-column-count:2;">
* [[Desmethylcitalopram]]
* [[Desmethylcitalopram]]
* [[Desmethylsertraline]]
* [[Desmethylsertraline]]
* [[Desmethylvenlafaxine]]
* [[Desmethylvenlafaxine]]
* [[Norfluoxetine]]
* [[Norfluoxetine]]
{{div col end}}
</div>


== References ==
== References ==
{{Reflist|2}}
{{Reflist}}



{{Antidepressants}}
{{Antidepressants}}
{{Serotonergics}}
{{Serotonergics}}


[[Category:Isobenzofurans]]
[[Category:Nitriles]]
[[Category:Fluoroarenes]]
[[Category:Human drug metabolites]]


{{nervous-system-drug-stub}}
{{nervous-system-drug-stub}}

Latest revision as of 09:57, 23 April 2022

Didesmethylcitalopram
Clinical data
ATC code
  • none
Legal status
Legal status
  • In general: uncontrolled
Pharmacokinetic data
Elimination half-life100 h
Identifiers
  • (RS or S)-1-[3-aminopropyl]-1-
    (4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile
CAS Number
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC18H17FN2O
Molar mass296.345 g·mol−1
3D model (JSmol)
  • c1cc(ccc1[C@]2(c3ccc(cc3CO2)C#N)CCCN)F
  • InChI=1S/C18H17FN2O/c19-16-5-3-15(4-6-16)18(8-1-9-20)17-7-2-13(11-21)10-14(17)12-22-18/h2-7,10H,1,8-9,12,20H2/t18-/m0/s1 ☒N
  • Key:RKUKMUWCRLRPEJ-SFHVURJKSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Didesmethylcitalopram is an active metabolite of the antidepressant drug citalopram (racemic).[1] Didesmethylescitalopram is an active metabolite of the antidepressant escitalopram, the S-enantiomer of citalopram. Like citalopram and escitalopram, didesmethyl(es)citalopram functions as a selective serotonin reuptake inhibitor (SSRI), and is responsible for some of its parents' therapeutic benefits.

See also

References

  1. ^ Rop PP, Durand A, Viala A, Jørgensen A (April 1990). "Simultaneous determination of citalopram, monodesmethylcitalopram and didesmethylcitalopram in plasma by high-performance liquid chromatography after column extraction". Journal of Chromatography. 527 (1): 226–32. doi:10.1016/s0378-4347(00)82105-2. PMID 2365786.