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Substance Name: Citalopram [USP:INN:BAN]
RN: 59729-33-8
UNII: 0DHU5B8D6V
InChIKey: WSEQXVZVJXJVFP-UHFFFAOYSA-N

Note

  • A furancarbonitrile that is one of the SEROTONIN UPTAKE INHIBITORS used as an antidepressant. The drug is also effective in reducing ethanol uptake in alcoholics and is used in depressed patients who also suffer from tardive dyskinesia in preference to tricyclic antidepressants, which aggravate this condition.

Molecular Formula

  • C20-H21-F-N2-O

Molecular Weight

  • 324.3969
 

Classification Codes

  • Antidepressive Agents
  • Antidepressive Agents, Second-Generation
  • Central Nervous System Agents
  • Drug / Therapeutic Agent
  • Human Data
  • Membrane Transport Modulators
  • Neurotransmitter Agents
  • Neurotransmitter Uptake Inhibitors
  • Psychotropic Drugs
  • Serotonin Agents
  • Serotonin Uptake Inhibitors

Names and Synonyms

Name of Substance

  • Citalopram
  • Citalopram [USP:INN:BAN]

MeSH Heading

  • Citalopram

Synonyms

  • 1,3-Dihydro-1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-5-isobenzofurancarbonitrile
  • 1-(3-(Dimethylamino)propyl)-1-(p-fluorophenyl)-5-phthalancarbonitrile
  • Cipram
  • Citalopram
  • Citalopramum
  • Citalopramum [INN-Latin]
  • EINECS 261-891-1
  • Lu 10-171
  • Nitalapram
  • Perrigo citalopram
  • UNII-0DHU5B8D6V

Systematic Names

  • 1-(3-(Dimethylamino)propyl)-1-(p-fluorophenyl)-5-phthalancarbonitrile
  • 5-Isobenzofurancarbonitrile, 1,3-dihydro-1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-
  • 5-Isobenzofurancarbonitrile, 1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydro-
  • Citalopram

Registry Numbers

CAS Registry Number

  • 59729-33-8

FDA UNII

  • 0DHU5B8D6V

System Generated Number

  • 0059729338

Structure Descriptors

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

InChIKey

WSEQXVZVJXJVFP-UHFFFAOYSA-N

Smiles

c12[C@@](c3ccc(F)cc3)(OCc1cc(C#N)cc2)CCCN(C)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
human TDLo oral 4571ug/kg/8D- (4.571mg/kg) BEHAVIORAL: SLEEP

BEHAVIORAL: HEADACHE

GASTROINTESTINAL: NAUSEA OR VOMITING
Human Psychopharmacology. Vol. 12, Pg. 119, 1997.
man LDLo oral 56mg/kg (56mg/kg) CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION) Lancet. Vol. 348, Pg. 339, 1996.
mouse LD50 intraperitoneal 179mg/kg (179mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Journal of Pharmacy and Pharmacology. Vol. 49, Pg. 1019, 1997.

Physical Properties

Physical Property Value Units Temp (deg C) Source
log P (octanol-water) 3.740 (none)   EST
Atmospheric OH Rate Constant 9.21E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.