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Chemistry

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Also known as: 59729-33-8, Nitalapram, Celexa, Cipram, Bonitrile, Citadur
Molecular Formula
C20H21FN2O
Molecular Weight
324.4  g/mol
InChI Key
WSEQXVZVJXJVFP-UHFFFAOYSA-N
FDA UNII
0DHU5B8D6V

Citalopram
A furancarbonitrile that is one of the SELECTIVE SEROTONIN REUPTAKE 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 dyskinesia.
Citalopram is a Serotonin Reuptake Inhibitor. The mechanism of action of citalopram is as a Serotonin Uptake Inhibitor.
1 2D Structure

Citalopram

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-3H-2-benzofuran-5-carbonitrile
2.1.2 InChI
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
2.1.3 InChI Key
WSEQXVZVJXJVFP-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CN(C)CCCC1(C2=C(CO1)C=C(C=C2)C#N)C3=CC=C(C=C3)F
2.2 Other Identifiers
2.2.1 UNII
0DHU5B8D6V
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Celexa

2. Citalopram Hydrobromide

3. Cytalopram

4. Lu-10-171

5. Lu10171

6. Seropram

2.3.2 Depositor-Supplied Synonyms

1. 59729-33-8

2. Nitalapram

3. Celexa

4. Cipram

5. Bonitrile

6. Citadur

7. 1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile

8. [3h]citalopram

9. 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile

10. Lu-10-171

11. Chembl549

12. 1-(3-(dimethylamino)propyl)-1-(p-fluorophenyl)-5-phthalancarbonitrile

13. 0dhu5b8d6v

14. 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-3h-2-benzofuran-5-carbonitrile

15. Chebi:77397

16. [3h]-citalopram

17. Citalopramum [inn-latin]

18. Citalopramum

19. 5-isobenzofurancarbonitrile, 1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydro-

20. 5-isobenzofurancarbonitrile, 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-

21. 5-isobenzofurancarbonitrile,1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-

22. Perrigo Citalopram

23. 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-5-isobenzofurancarbonitrile

24. Smr000465669

25. Citadur (tn)

26. Citalopram (usp/inn)

27. Einecs 261-891-1

28. Unii-0dhu5b8d6v

29. Citalopram [usp:inn:ban]

30. 1-[3-(dimethylamino)propyl]-1-(p-fluorophenyl)-5-phthalancarbonitrile

31. [3h]cytalopram

32. 1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydro-5-isobenzofurancarbonitrile

33. [3h]escitalopram

34. Citalopram-[d4]

35. Citalopram-[d6]

36. [3h]lexapro

37. 1,3-dihydro-1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-5-isobenzofurancarbonitrile

38. Citalopram-d4 Oxalate

39. Escitalopram Impurity A

40. Citalopram [mi]

41. Citalopram [inn]

42. Prestwick3_000692

43. Schembl946

44. Citalopram [vandf]

45. Citalopram [mart.]

46. Citalopram [who-dd]

47. Lopac0_000258

48. Bspbio_000843

49. Mls000028578

50. Mls006011858

51. Bpbio1_000929

52. Gtpl4621

53. Gtpl7547

54. Dtxsid8022826

55. Bdbm25870

56. Hsdb 7042

57. Wseqxvzvjxjvfp-uhfffaoysa-

58. Citalopram [usp Impurity]

59. Hms2090o09

60. Hms2093a14

61. Hms3259b10

62. Act02666

63. Bbl029066

64. Lu-10171b

65. Stl058639

66. Akos005711003

67. Ac-8894

68. Ccg-204353

69. Db00215

70. Nc00711

71. Sdccgsbi-0050246.p003

72. 1-(3-dimethylaminopropyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile

73. 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carb Onitrile

74. 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-3h-isobenzofuran-5-carbonitrile

75. 5-isobenzofurancarbonitrile, 1,3-dihydro-1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-

76. Mrf-0000302

77. Ncgc00015267-04

78. Ncgc00015267-05

79. Ncgc00015267-07

80. Ncgc00015267-09

81. Ncgc00015267-11

82. Ncgc00015267-12

83. Ncgc00015267-20

84. Ncgc00025160-02

85. As-76503

86. Sbi-0050246.p002

87. Hy-121203

88. Ab00513896

89. Cs-0081223

90. Ft-0657967

91. Ft-0660873

92. C07572

93. D07704

94. Ab00513896-09

95. Ab00513896-11

96. Ab00513896_12

97. Ab00513896_13

98. 729c338

99. A832440

100. L001223

101. Q409672

102. Sr-01000003129-8

103. Brd-a47598013-004-02-0

104. Brd-a47598013-004-06-1

105. 1-(3'-dimethylaminopropyl)-1-(4'-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile

106. 1-(3-(dimethylamino)propyl)-1-(4'-fluorophenyl)-1,3-dihydroisobenzofuran-5-carbonitrile

107. 1-(3-dimethylamino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile

108. 1-[3-(dimethylamino) Propyl]-1-(4-fluorophenyl)-1,3-dihydro-5-isobenzofuran Carbonitrile

109. 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-5-isobenzo[b]furancarbonitrile

110. 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro[3,4]benzofuran-5-carbonitrile

111. 5-cyano-1-(4-fluorophenyl)-1-(3-dimethylaminopropyl)-1,3-dihydro-isobenzofuran

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 324.4 g/mol
Molecular Formula C20H21FN2O
XLogP33.2
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count4
Rotatable Bond Count5
Exact Mass324.16379146 g/mol
Monoisotopic Mass324.16379146 g/mol
Topological Polar Surface Area36.3 Ų
Heavy Atom Count24
Formal Charge0
Complexity466
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameCelexa
PubMed HealthCitalopram (By mouth)
Drug ClassesAntidepressant
Active IngredientCitalopram hydrobromide
Dosage FormTablet
RouteOral
Strengtheq 40mg base; eq 20mg base; eq 10mg base
Market StatusPrescription
CompanyForest Labs

2 of 2  
Drug NameCelexa
PubMed HealthCitalopram (By mouth)
Drug ClassesAntidepressant
Active IngredientCitalopram hydrobromide
Dosage FormTablet
RouteOral
Strengtheq 40mg base; eq 20mg base; eq 10mg base
Market StatusPrescription
CompanyForest Labs

4.2 Therapeutic Uses

Serotonin Uptake Inhibitors; Antidepressive Agents, Second-Generation

National Library of Medicine's Medical Subject Headings. Citalopram. Online file (MeSH, 2018). Available from, as of February 2, 2018: https://meshb.nlm.nih.gov/search


/CLINICAL TRIALS/ ClinicalTrials.gov is a registry and results database of publicly and privately supported clinical studies of human participants conducted around the world. The Web site is maintained by the National Library of Medicine (NLM) and the National Institutes of Health (NIH). Each ClinicalTrials.gov record presents summary information about a study protocol and includes the following: Disease or condition; Intervention (for example, the medical product, behavior, or procedure being studied); Title, description, and design of the study; Requirements for participation (eligibility criteria); Locations where the study is being conducted; Contact information for the study locations; and Links to relevant information on other health Web sites, such as NLM's MedlinePlus for patient health information and PubMed for citations and abstracts for scholarly articles in the field of medicine. Citalopram is included in the database.

NIH/NLM; ClinicalTrials.Gov. Available from, as of February 2, 2018: https://clinicaltrials.gov/


Citalopram tablets are indicated for the treatment of depression. /Included in US product label/

NIH; DailyMed. Current Medication Information Citalopram Tablet, Film Coated (Updated: June 14, 2017). Available from, as of February 9, 2018: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=6daeb45c-451d-b135-bf8f-2d6dff4b6b01


Citalopram has been used in the treatment of obsessive-compulsive disorder. /NOT included in US product label/

American Society of Health-System Pharmacists 2017; Drug Information 2017. Bethesda, MD. 2017, p. 2448


For more Therapeutic Uses (Complete) data for Citalopram (16 total), please visit the HSDB record page.


4.3 Drug Warning

/BOXED WARNING/ SUICIDALITY AND ANTIDEPRESSANT DRUGS. Antidepressants increased the risk compared to placebo of suicidal thinking and behavior (suicidality) in children, adolescents, and young adults in short-term studies of major depressive disorder (MDD) and other psychiatric disorders. Anyone considering the use of citalopram or any other antidepressant in a child, adolescent, or young adult must balance this risk with the clinical need. Short-term studies did not show an increase in the risk of suicidality with antidepressants compared to placebo in adults beyond age 24; there was a reduction in risk with antidepressants compared to placebo in adults aged 65 and older. Depression and certain other psychiatric disorders are themselves associated with increases in the risk of suicide. Patients of all ages who are started on antidepressant therapy should be monitored appropriately and observed closely for clinical worsening, suicidality, or unusual changes in behavior. Families and caregivers should be advised of the need for close observation and communication with the prescriber. Citalopram is not approved for use in pediatric patients.

NIH; DailyMed. Current Medication Information Citalopram Tablet, Film Coated (Updated: June 14, 2017). Available from, as of February 9, 2018: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=6daeb45c-451d-b135-bf8f-2d6dff4b6b01


It is recommended that citalopram should not be used in patients with congenital long QT syndrome, bradycardia, hypokalemia or hypomagnesemia, recent acute myocardial infarction, or uncompensated heart failure. Citalopram should also not be used in patients who are taking other drugs that prolong the QTc interval. Such drugs include Class 1A (e.g., quinidine, procainamide) or Class III (e.g., amiodarone, sotalol) antiarrhythmic medications, antipsychotic medications (e.g., chlorpromazine, thioridazine), antibiotics (e.g., gatifloxacin, moxifloxacin), or any other class of medications known to prolong the QTc interval (e.g., pentamidine, levomethadyl acetate, methadone).

NIH; DailyMed. Current Medication Information Citalopram Tablet, Film Coated (Updated: June 14, 2017). Available from, as of February 9, 2018: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=6daeb45c-451d-b135-bf8f-2d6dff4b6b01


The citalopram dose should be limited in certain populations. The maximum dose should be limited ... in patients who are CYP2C19 poor metabolizers or those patients who may be taking concomitant cimetidine or another CYP2C19 inhibitor, since higher citalopram exposures would be expected. The maximum dose should also be limited ... in patients with hepatic impairment and in patients who are greater than 60 years of age because of expected higher exposures.

NIH; DailyMed. Current Medication Information Citalopram Tablet, Film Coated (Updated: June 14, 2017). Available from, as of February 9, 2018: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=6daeb45c-451d-b135-bf8f-2d6dff4b6b01


The development of a potentially life-threatening serotonin syndrome has been reported with selective norepinephrine-reuptake inhibitors (SNRIs) and serotonin-reuptake inhibitors (SSRIs), including citalopram tablets, alone but particularly with concomitant use of other serotonergic drugs (including triptans, tricyclic antidepressants, fentanyl, lithium, tramadol, tryptophan, buspirone, amphetamines, and St. John's Wort) and with drugs that impair metabolism of serotonin (in particular, MAOIs, both those intended to treat psychiatric disorders and also others, such as linezolid and intravenous methylene blue). Serotonin syndrome symptoms may include mental status changes (e.g., agitation, hallucinations, delirium, and coma), autonomic instability (e.g., tachycardia, labile blood pressure, dizziness, diaphoresis, flushing, hyperthermia), neuromuscular symptoms (e.g., tremor, rigidity, myoclonus, hyperreflexia, incoordination), seizures and/or gastrointestinal symptoms (e.g., nausea, vomiting, diarrhea). Patients should be monitored for the emergence of serotonin syndrome.

NIH; DailyMed. Current Medication Information Citalopram Tablet, Film Coated (Updated: June 14, 2017). Available from, as of February 9, 2018: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=6daeb45c-451d-b135-bf8f-2d6dff4b6b01


For more Drug Warnings (Complete) data for Citalopram (49 total), please visit the HSDB record page.


4.4 Drug Indication

For the treatment of depression, as indicated by the FDA label. Off-label indications include but are not limited to: treatment of sexual dysfunction, post-stroke behavioural changes, ethanol abuse, obsessive-compulsive disorder (OCD) in children, and diabetic neuropathy,,,,,,,.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Citalopram belongs to a class of antidepressants known as selective serotonin reuptake inhibitors (SSRIs). It has been found to relieve or manage symptoms of depression, anxiety, eating disorders and obsessive-compulsive disorder among other mood disorders. The antidepressant, anti-anxiety, and other actions of citalopram are linked to its inhibition of CNS central uptake of serotonin. Serotonergic abnormalities have been reported in patients with mood disorders. Behavioral and neuropsychological of effects of serotonin include the regulation of mood, perception, reward, anger, aggression, appetite, memory, sexuality, and attention, as examples. The onset of action for depression is approximately 1 to 4 weeks. The complete response may take 8-12 weeks after initiation of citalopram. In vitro studies demonstrate that citalopram is a strong and selective inhibitor of neuronal serotonin reuptake and has weak effects on norepinephrine and dopamine central reuptake. The chronic administration of citalopram has been shown to downregulate central norepinephrine receptors, similar to other drugs effective in the treatment of major depressive disorder. Citalopram does not inhibit monoamine oxidase.


5.2 MeSH Pharmacological Classification

Selective Serotonin Reuptake Inhibitors

Compounds that specifically inhibit the reuptake of serotonin in the brain. (See all compounds classified as Selective Serotonin Reuptake Inhibitors.)


Antidepressive Agents, Second-Generation

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.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
CITALOPRAM
5.3.2 FDA UNII
0DHU5B8D6V
5.3.3 Pharmacological Classes
Serotonin Uptake Inhibitors [MoA]; Serotonin Reuptake Inhibitor [EPC]
5.4 ATC Code

N06AB04

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355


N - Nervous system

N06 - Psychoanaleptics

N06A - Antidepressants

N06AB - Selective serotonin reuptake inhibitors

N06AB04 - Citalopram


5.5 Absorption, Distribution and Excretion

Absorption

Rapidly and well absorbed from the GI tract. Peak plasma concentrations occur within 4 hours of a single orally administered dose. Bioavailability is 80% following oral administration. Food does not affect absorption.


Route of Elimination

12-23% of an oral dose of citalopram is found unchanged in the urine, while 10% of the dose is found in the faeces.


Volume of Distribution

12 L/kg Citalopram is highly lipophilic and likely widely distributed throughout the body, including the blood-brain-barrier. However, its metabolite, _demethylcitalopram_ does not penetrate the blood-brain-barrier well.


Clearance

The systemic clearance of citalopram is 330 mL/min, with approximately 20% renal clearance.


Like other selective serotonin-reuptake inhibitors, citalopram is a highly lipophilic compound that appears to be rapidly and well absorbed from the GI tract following oral administration. Following a single 40-mg oral dose of citalopram as a tablet, the manufacturer states that peak plasma concentrations averaging approximately 44 ng/mL occur at about 4 hours.

American Society of Health-System Pharmacists 2017; Drug Information 2017. Bethesda, MD. 2017, p. 2460


The absolute bioavailability of citalopram is approximately 80% relative to an IV dose. The oral tablets and solution of citalopram reportedly are bioequivalent. Food does not substantially affect the absorption of citalopram.

American Society of Health-System Pharmacists 2017; Drug Information 2017. Bethesda, MD. 2017, p. 2460


Distribution of citalopram and its metabolites into human body tissues and fluids has not been fully characterized. However, limited pharmacokinetic data suggest that the drug, which is highly lipophilic, is widely distributed in body tissues.

American Society of Health-System Pharmacists 2017; Drug Information 2017. Bethesda, MD. 2017, p. 2460


/MILK/ /The purpose of the study was/ to characterize milk/plasma (M/P) ratio and infant dose, for citalopram and demethylcitalopram, in breast-feeding women taking citalopram for the treatment of depression, and to determine the plasma concentration and effects of these drugs in their infants. Seven women (mean age 30.6 years) taking citalopram (median dose 0.36 mg/kg/day) and their infants (mean age 4.1 months) were studied. Citalopram and demethylcitalopram in plasma and milk were measured by high-performance liquid chromatography over a 24 hr dose interval. Infant exposure was estimated (two separate methods) as the product of milk production rate and drug concentration in milk, normalized to body weight and expressed as a percentage of the weight-adjusted maternal dose. Mean M/PAUC values of 1.8 (range 1.2-3) and 1.8 (range 1.0-2.5) were calculated for citalopram and demethylcitalopram, respectively. The mean maximum concentrations of citalopram and demethylcitalopram in milk were 154 (95% CI, 102-207) ug/L and 50 (23-77) ug/L. Depending on the method of calculation, mean infant exposure was 3.2 or 3.7% for citalopram and 1.2 or 1.4% for demethylcitalopram. Citalopram (2.0, 2.3 and 2.3 ug/L) was detected in three of the seven infants. Demethylcitalopram (2.2 and 2.2 ug/L was detected in plasma from two of the same infants. ... The mean combined dose of citalopram and demethylcitalopram (4.4-5.1% as citalopram equivalents) transmitted to infants via breast milk is below the 10% notional level of concern. ...

PMID:10971311 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2014979 Rampono J et al; Br J Clin Pharmacol 50 (3): 263-8 (2000)


For more Absorption, Distribution and Excretion (Complete) data for Citalopram (14 total), please visit the HSDB record page.


5.6 Metabolism/Metabolites

Citalopram is metabolized mainly in the liver via N-demethylation to its main metabolite, _demethylcitalopram_ by CYP2C19 and CYP3A4. Other metabolites include _didemethylcitalopram_ via CYP2D6 metabolism, and _citalopram N-oxide_ via monoamine oxidase enzymes and aldehyde oxidase. It is a deaminated propionic acid derivative. After a single dose of citalopram, peak blood concentrations occur at approximately 4 hours. This drug in is found mainly unchanged in the plasma as citalopram. Cytochrome P450 (CYP) 3A4 and 2C19 isozymes appear to be heavily involved in producing _demethylcitalopram_. Demethylcitalopram appears to be further N-demethylated by CYP2D6 to didemethylcitalopram. Citalopram metabolites exert little pharmacologic activity in comparison to the parent drug and are not likely to contribute to the clinical effect of citalopram.


In a 2002 study, 11 women took citalopram (20-40 mg/day) during pregnancy; 10 throughtout gestation and 1 starting at 20 weeks' gestation. The mean ratio of two metabolites was significantly higher during pregnancy than at 2 months postdelivery, indicating induction of the CYP2D6 isoenzyme. The trough plasma concentration of citalopram, desmethylcitalopram, and didesmethylcitalopram in the normal new borns were 64%, 66%, and 68% of the maternal concentrations, respectively.

Briggs, G.G., Freeman, R.K., Yaffee, S.J.; Drugs in Pregancy and Lactation Tenth Edition. Wolters Kluwer/Lippincott Williams & Wilkins, Philadelphia, PA. 2015, p. 282


The antidepressant citalopram (CT), a selective serotonin uptake inhibitor, was given in its labelled form, 14(C)-CT, as a single oral dose in 50 mL aqueous solution (0.1 mmol/30 uCi/1.1 MBq) to four healthy male volunteers. Concentrations of radioactivity in whole blood and plasma were similar. ... The HPLC profile of urinary components showed that besides the known metabolites of citalopram, three glucuronides were present. The relative amounts of CT and its metabolites in urine collected for 7 days were: CT (26 %), N-demethyl-CT (DCT, 19%), N,N-didemethyl-CT (DDCT,9%), the N-oxide (7%), the quaternary ammonium glucuronide of CT (CT-GLN, 14%), the N-glucuronide of DDCT (DDCT-GLN, 6%), and the glucuronide of the acid metabolite (CT-acid-GLN, 12%) formed by N,N-dimethyl deamination of CT. CT-GLN was isolated using preparative chromatography and identified by LC-MS-MS and NMR. DDCT-GLN and CT-acid-GLN were identified by LC-MS. This study shows that protracted renal excretion represents the major route of elimination, with a small fraction voided with feces. A considerable portion of the urinary excreted dose consists of N-glucuronides of CT and DDCT together with the O-acyl glucuronide of CT-acid.

PMID:10574684 Dalgaard L, Larsen C; Xenobiotica 29 (10): 1033-41 (1999)


This study was conducted to identify enzyme systems eventually catalyzing a local cerebral metab of citalopram. ... The metab of citalopram, of its enantiomers and demethylated metabolites was investigated in rat brain microsomes & in rat and human brain mitochondria. No cytochrome P-450 mediated transformation was observed in rat brain. ... In rat whole brain and in human frontal cortex, putamen, cerebellum & white matter of five brains monoamine oxidase activity was determined by the stereoselective measurement of the production of citalopram propionate. All substrates were metabolized by both forms of MAO, except in rat brain, where monoamine oxidase B activity could not be detected. Apparent Km and Vmax of S-citalopram biotransformation in human frontal cortex by monoamine oxidase B were found to be 266 uM & 6.0 pmol min/mg protein & by monoamine oxidase A 856 uM & 6.4 pmol min/mg protein, respectively. These Km values are in the same range as those for serotonin & dopamine metab by monoamine oxidases. ...

PMID:11840311 Kosel M, et al; Mol Psychiatry 7 (2): 181-8 (2002)


Citalopram ... is N-demethylated to N-desmethylcitalopram partially by CYP2C19 & partially by CYP3A4 & N-desmethylcitalopram is further N-demethylated by CYP2D6 to the likewise inactive metabolite di-desmethylcitalopram. The two metabolites are not active. ... In vitro citalopram does not inhibit CYP or does so only very moderately. A number of studies in healthy subjects and patients have confirmed, that this also holds true in vivo. Thus no change in pharmacokinetics or only very small changes were observed when citalopram was given with CYP1A2 substrates (clozapine & therophylline), CYP2C9 (warfarin), CYP2C19 (imipramine & mephenytoin), CYP2D6 (sparteine, imipramine & amitriptyline) and CYP3A4 (carbamazepine & triazolam). ...

PMID:11532381 Brosen K, Naranjo CA; Eur Neuropsychopharmacol 11 (4): 275-83 (2001)


For more Metabolism/Metabolites (Complete) data for Citalopram (7 total), please visit the HSDB record page.


Citalopram has known human metabolites that include Citalopram N-oxide and N-Desmethylcitalopram.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560


5.7 Biological Half-Life

About 35 hours.


The antidepressant citalopram (CT), a selective serotonin uptake inhibitor, was given in its labelled form, 14(C)-CT, as a single oral dose in 50 mL aqueous solution (0.1 mmol/30 uCi/1.1 MBq) to four healthy male volunteers. Concentrations of radioactivity in whole blood and plasma were similar. The respective pharmacokinetic parameters were: ... half life = 90.2+/-22.5 and 79.5 +/- 14.9 hr respectively. ...

PMID:10574684 Dalgaard L, Larsen C; Xenobiotica 29 (10): 1033-41 (1999)


The elimination half-life of citalopram averages approximately 35 hours in adults with normal renal and hepatic function.

American Society of Health-System Pharmacists 2017; Drug Information 2017. Bethesda, MD. 2017, p. 2460


5.8 Mechanism of Action

The mechanism of action of citalopram results from its inhibition of CNS neuronal reuptake of serotonin (5-HT). The molecular target for citalopram is the serotonin transporter (solute carrier family 6 member 4, _SLC6A4_), inhibiting its serotonin reuptake in the synaptic cleft. Citalopram binds with significantly less affinity to histamine, acetylcholine, and norepinephrine receptors than tricyclic antidepressant drugs. This drug has no or neglible affinity for _5-HT1A_, _5-HT2A_, _dopamine D_1 and _D2_, _1-_, _2_-, and_ adrenergic_, _histamine H1_, _gamma-aminobutyric acid_ (GABA), _muscarinic_, _cholinergic_, and _benzodiazepine_ receptors. Antagonism of _muscarinic_, _histaminergic_, and _adrenergic receptors_ is thought to be associated with several anticholinergic, sedative, and cardiovascular effects of other psychotropic drugs.


/In/ whole-cell patch clamp recording of heterologous HERG-mediated currents in transfected mammalian cells ... citalopram blocks HERG with an IC(50) of 3.97 uM. This is slightly less potent than fluoxetine in /the same/ system (IC(50) of 1.50 uM). In isolated guinea pig ventricular cardiomyocytes, citalopram inhibited L-type calcium current (I(Ca,L)). The voltage dependence of I(Ca,L) inactivation in the presence of 100 uM citalopram was shifted significantly leftward. As a result, the I(Ca,L) 'window' in citalopram was found to be smaller & leftward-shifted compared to control. /These/ effects ... may help to explain citalopram's good cardiac safety profile, given its propensity to block HERG at excessive dosages. /Salt not specified/

PMID:11852052 Witchel HJ, et al; FEBS Lett 512 (1-3): 59-66 (2002)


The study was aimed to investigate the effects of the minimal effective doses of acute citalopram (5 mg/kg), (+/-)-8-hydroxydipropylaminotetralin HBr (8-OH-DPAT; 0.1 mg/kg), & their combined treatment on the rat open field & forced swimming behaviour & post-mortem monoamine content. The animals were prospectively divided into the vehicle- and para-chlorophenylalanine (p-CPA)-pretreated (350 mg/kg) groups. Acute citalopram (5 mg/kg), 8-OH-DPAT (0.1 mg/kg), or their combined treatment had no major effect on the rat open field & forced swimming behaviour. The post-mortem catecholamine content in four brain regions studied was unchanged in all treatment groups. The combined 8-OH-DPAT (0.1 mg/kg) & citalopram (5 mg/kg) treatment partially reversed the p-CPA-induced decr of serotonin (5-HT) and 5-hydroxy-indolacetic acid (5-HIAA) content. The present experiments demonstrate that the 5-HT1A receptors mediate some of the selective serotonin reuptake inhibitor-induced biochemical phenomena.

PMID:11817498 Pruus K, et al; Prog Neuropsychopharmacol Biol Psychiatry 26 (2): 227-32 (2002)


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08-Jan-2021
29-Aug-2024
KGS
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Quantity (KGS) & Unit rate (USD/KGS) over time

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