Analysis of the enantiomers of citalopram and its demethylated metabolites using chiral liquid chromatography

Kosel, Markus; Eap, Chin B.; Amey, M.; Baumann, Pierre

doi:10.1016/s0378-4347(98)00384-3

Cited by 70 publications

(49 citation statements)

References 8 publications

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“…The organic phase was removed and the remaining acid was washed with 0.5 ml n-heptane, and a 15-ml aliquot was injected onto the HPLC. The compounds were separated on a Zorbax SB C-18-column (75 ¥ 4.6 mm, particle size 3.5 mm) [17]. The mobile phase consisted of acetonitrile and ammonium acetate 50 mM pH 6.5, in the proportion 29 : 71 (v/v).…”

Section: Assay Of Total (S Plus R) Citalopram and Metabolitesmentioning

confidence: 99%

“…The volume of each fraction was reduced to about 100 ml in a vacuum centrifuge (Speed Vac SC 110 A; Savant Instruments) before injection onto a chiral HPLC column as described by Rochat et al [16]. The enantiomers were separated on a cyclobond I 2000 column (250 ¥ 4.6 mm) [17]. The mobile phase consisted of 22% acetonitrile and 88% aqueous triethylamine buffer 1%, adjusted to pH 6.2 with acetic acid (v/v 22 : 78).…”

Section: Chiral Assay Of Ct and Its Metabolitesmentioning

confidence: 99%

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Metabolism of citalopram enantiomers in CYP2C19/CYP2D6 phenotyped panels of healthy Swedes

Herrlin

Yasui‐Furukori

Tybring

et al. 2003

Brit J Clinical Pharma

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Aims To investigate pharmacokinetics of the enantiomers of citalopram (CT) and its metabolites desmethylcitalopram (DCT) and didesmethylcitalopram (DDCT) in Swedish healthy volunteers in relation to CYP2C19 and CYP2D6 geno-and phenotypes. Methods Racemic CT was given for seven days to panels with different genotypes and the following mephenytoin (Me) and debrisoquine (De) hydroxylation phenotypes: EM De /EM Me , PM De /EM Me , EM De /PM Me ( n = 6 in all groups), and one PM De / PM Me subject. Blood sampling was carried out during day 7, and all urine was collected for 12 h after the last dose of CT. Results The AUC of S-CT was significantly higher in the EM De /PM Me panel compared to the EM De /EM Me and PM De /EM Me panels ( P < 0.05), whereas the AUC of R-CT did not differ between the panels. Similar differences, although they did not reach statistical significance, were noted for S-DCT and R-DCT. The enantiomers of DDCT were not quantifiable in PM De, and there was no difference in DDCT enantiomer concentrations between the other two panels. A PM De /PM Me subject stopped taking CT after five days due to severe adverse effects. Based on two time points, this subject had a very long CT half-life of 95 h. The value of 1.0 for the S/R ratio of the CT trough in this subject was similar to the mean S/R CT trough ratio of the EM De /PM Me panel, but higher than the S/R CT ratio of the EM De /EM Me panel (0.56; 95% CI 0.49-0.63) and the PM De /EM Me panel (0.44; 95% CI 0.31-0.57). Thus the latter two phenotypes eliminated S-CT more rapidly via CYP2C19. An adverse effect described as an 'alcohol hangover' feeling was reported by one subject from each of the three panels. These individuals had the highest concentrations of both CT enantiomers. Conclusions The AUC of S-, but not R-(CT) was found to be significantly higher in PM of mephenytoin compared to EMs, PMs may need a lower dosage of CT.

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Section: Assay Of Total (S Plus R) Citalopram and Metabolitesmentioning

confidence: 99%

Section: Chiral Assay Of Ct and Its Metabolitesmentioning

confidence: 99%

Metabolism of citalopram enantiomers in CYP2C19/CYP2D6 phenotyped panels of healthy Swedes

Herrlin

Yasui‐Furukori

Tybring

et al. 2003

Brit J Clinical Pharma

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“…17 However, in order to quantitative analyses of the enantiomeric composition of citalopram, various analytical methods have been developed in recent years. [18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33][34] Most of them are involved in the employment of HPLC or supercritical fluid chromatography (SFC), equipped with chiral stationary phases. This study, presents a new, rapid, accurate, precise and the suitable analytical method for seperation of citalopram and the determination of enantiomeric purity of escitalopram with the chiral column composed of silica-based phenylcarbamated β-cyclodextrin (chiral CD-PH).…”

Section: Introductionmentioning

confidence: 99%

Development and Validation of a Chiral HPLC Method for Quantitative Analysis of Enantiomeric Escitalopram

Rahman

Haque

Rahman

et al. 2018

Dhaka Univ. J. Pharm. Sci

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ABSTRACT:In the present study a rapid, accurate and precise chiral HPLC method was developed and validated for enantiomeric separation of racemate citalopram and escitalopram according to the guidelines of United States of Pharmacopeia (USP) and International Conference on Harmonization (ICH). The chiral chromatographic separation was achieved with ammonium acetate/ ethanol/ 2-propanol/ methylene dichloride (100 : 150 : 70 : 30, v/v) at a flow rate of 0.5 ml/min using a chiral CD-PH column. The HPLC analyses were monitored at 254 nm. The method showed a good linearity with regression coefficient (r 2 ) of 0.998 in the range of 20.0-70.0 µg/ml for escitalopram. The detection limit (LOD), quantitation limit (LOQ) and average percentage of recovery for escitalopram were found to be 2.54, 7.68 µg/ml and 100.28% to 102.86%, respectively. The percentage of relative standard deviation (%RSD) for intra-and inter-day precision were found as 0.16% and 0.09%, respectively. The established method proved as reproducible with a %RSD value of less than 2 and having the robustness within specified limit. The present study also showed the enantiomeric purity or excess (%ee) of seven pharmaceutical preparations of escitalopram. Thus the proposed chiral method can be applied for the enantiomeric purity determination of escitalopram formulations.

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“…norepinephrine (NE) or dopamine (DA). Although DCIT and its immediate downstream metabolite DDCIT possess lesser serotonin reuptake inhibitory properties than citalopram, they retain considerable activity as SSRI, with some differences between their enantiomers (Kosel et al, 1998). Furthermore, their half-lives are measurably longer compared with citalopram (Sanchez and Hyttel, 1999).…”

Section: Introductionmentioning

confidence: 99%

“…With regard to the monitoring of (−)-(R) and (+)-(S) enantiomers of CIT and of their metabolites, different HPLC (Kosel et al, 1998;Rochat et al, 1995;Zheng et al, 2000) and CE stereoselective methods have been developed. To date, all these methods have dealt with the use of chiral chromatographic columns and none of them use an indirect method based on the derivatization with a chiral reagent.…”

Section: Introductionmentioning

confidence: 99%

Stereoselective determination of demethyl‐ and didemethyl‐citalopram in rat plasma and brain tissue by liquid chromatography with fluorescence detection using precolumn derivatization

Millán

Goicolea

Sánchez

et al. 2007

Biomedical Chromatography

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A rapid and sensitive HPLC enantioselective method with fluorescence detection was developed to determine (-)-(R) and (+)-(S) enantiomers of the metabolites of citalopram, demethyl- and didemethyl-citalopram in plasma and brain tissue. This assay involves pre-column chiral derivatization with (-)-(R)-1-(1-naphthyl)ethyl isocyanate followed by separation on a normal-phase silica column. The developed liquid-liquid extraction procedure permits quantitative determination of analytes with recoveries ranged between 81 and 88% with intra- and inter-day relative standard deviations less than 10.5%. Linearity was obtained over the concentration range 5-1000 ng/mL and 100-10,000 ng/g for spiked drug-free plasma and brain tissue, respectively, with detection limits lower than 2.1 ng/mL and 42.8 ng/g.

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Analysis of the enantiomers of citalopram and its demethylated metabolites using chiral liquid chromatography

Cited by 70 publications

References 8 publications

Metabolism of citalopram enantiomers in CYP2C19/CYP2D6 phenotyped panels of healthy Swedes

Metabolism of citalopram enantiomers in CYP2C19/CYP2D6 phenotyped panels of healthy Swedes

Development and Validation of a Chiral HPLC Method for Quantitative Analysis of Enantiomeric Escitalopram

Stereoselective determination of demethyl‐ and didemethyl‐citalopram in rat plasma and brain tissue by liquid chromatography with fluorescence detection using precolumn derivatization

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