Enantioselective separation and determination of adrafinil and modafinil on Chiralcel OJ-H column in rat serum and urine using solid-phase extraction followed by HPLC

Biomedical Chromatography

Volumn 23, Issue 8, 2009, Pages 811-816

  Rao, R Nageswara ^a   Shinde, Dhananjay D ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Adrafinil; Chiralcel OJ H; Metabolite; Pharmacokinetics; Psychostimulants; Solid phase extraction

Indexed keywords

BIOMOLECULES; BODY FLUIDS; ENANTIOMERS; EXTRACTION; HEXANE; PHARMACOKINETICS; PHASE SEPARATION; RATS;

ADRAFINIL; CHIRALCEL OJ-H; ENANTIOSELECTIVE SEPARATION; MODAFINIL; PHOTO DIODES; PSYCHOSTIMULANTS; RAT SERUM; RAT URINE; SIMPLE++; SOLID-PHASE EXTRACTION;

METABOLITES;

ADRAFINIL; ALCOHOL; MODAFINIL;

ANIMAL EXPERIMENT; ARTICLE; DRUG BLOOD LEVEL; DRUG DETERMINATION; DRUG HALF LIFE; DRUG STRUCTURE; DRUG URINE LEVEL; ENANTIOMER; FLOW RATE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MAXIMUM PLASMA CONCENTRATION; NONHUMAN; PHASE SEPARATION; RAT; SEPARATION TECHNIQUE; SOLID PHASE EXTRACTION; TIME TO MAXIMUM PLASMA CONCENTRATION;

RATTUS;

EID: 70349481996     PISSN: 02693879     EISSN: 10990801     Source Type: Journal    
DOI: 10.1002/bmc.1190     Document Type: Article

References (27)

1. Abo M, Okubo A and Yamazaki S. Preparative asymmetric deoxygenation of alkyl aryl sulfoxides by Rhodobacter sphaeroides f.sp. denitrificans. Tetrahedron Asymmetry 1997; 8: 345.
2. Aboul-Enein HY and Wainer IW. The impact of stereochemistry on drug development and use. Chemical Analysis Series 1997; 142: 403.
3. Anonymous. FDA'S policy statement for the development of new stereoisomeric drugs. Chirality 1992; 4: 338.
4. Ariens EJ. Stereochemistry, a basis for sophisticated nonsense in pharmacokinetics and clinical pharmacology. European Journal of Clinical Pharmacology 1984; 26: 663.
5. Boyer P. Age et performance cognitives, plaintes mnesiques et attentionnelles au quotidien. Synapse spécial 'Vers une medecine des comportements', 1994; 1.
6. Carrea G, Redigolo B, Riva S, Colonna S, Gaggero N, Battistel E and Bianchi D. Effects of substrate structure on the enantioselectivity and stereochemical course of sulfoxidation catalyzed by cyclohexanone monooxygenase. Tetrahedron: Asymmetry 1992; 3: 1063.
7. Delini-Stula A and Hunn C. Effects of single and repeated treatment with antidepressants on apomorphine-induced yawning in the rat: the implication of alpha-1 adrenergic mechanisms in the D-2 receptor function. Psychopharmacology (Berlin) 1990; 101: 62.
8. Dewailly P, Durocher AM, Durot A, Bukowski JV, Frigard B, Herbin H, Lemaire P, Kohler F, Betrancourt JC and Lubin S. Adrafinil et ralentissement du sujet age institutionnalise: de la significativite statistique a la pertinence clinique (resultat d'une etude multicentrique en double aveugle versus placebo). Actualites Medicales Internationales Psychiatrie 1989; 6: 1.
9. DHHD, FDA and CDER. Guidance for Industry, Bioanalytical Method Validation. US Department of Health and Human Services, Food and Drug Administration, Center for Drug Evaluation and Research, May 2001.
10. Diwan PV, Chauhan AS, Sridevi S, Chalasani KB, Jain AK, Jain SK and Jain NK. Dendrimer-mediated transdermal delivery: enhanced bioavailability of indomethacin. Journal of Controlled Release 2003; 90: 335.
11. 2O/(R,R)-diphenylethane-1,2-diol complex: a versatile and highly enantioselective oxidation protocol. Journal of Organic Chemistry 1998; 63: 9392.
12. Duteil J., Rambert FA, Pessonnier J, Gombert R and Assous E. A possible-adrenergic mechanism for drug (CRL 40028)-induced hyperactivity. European Journal of Pharmacology 1979; 59: 121.
13. FDA. Guidance for industry, Q2B Validation of analytical procedures, methodology. Available from: http://www.fda.gov/cber/guidelines.htm, 1996.
14. Fontan, Fondarai J, Micas M and Albarede J-L. Interet de la psychometrie informatisee dans l'appreciation de l'activite d'Olmifon (adrafinil) on alertness and cognitive performance in elderly retirement home patients. Psychologie Medicale 1990; 22: 253.
15. Hascoet M and Bourin M. A new approach to the light/dark test procedure in mice. Pharmacology Biochemistry and Behavior 1998; 60: 645.
16. Israel L, Fondarai J, Lubin S, Salin B and Hugono R. L'Adrafinil (Olmifon) et patients ages ambulatoires. Efficacite, versus placebo, de l'Adrafinil sur l'eveil dans les activites de la vie quotidienne. Psychologie Medicale 1989; 21: 1235.
17. Jenner P and Testa B. The influence of stereochemical factors on drug disposition. Drug Metabolism Reviews 1973; 2: 117.
18. Kohler F and Lubin S. Etude en medecine generale de l'interet therapeutique d'Olmifon chez des malades presentant des symptomes precoces de vieillissement cerebral handicapant leur activite quotidiennne. Etude ouverte pragmatique chez 304 patients. Vie Medicale 1990; 2: 335.
19. Kusters E, Loux V, Schmid E and Floersheim Ph. Enantiomeric separation of chiral sulphoxides. Screening of cellulose-based sorbents with particular reference to cellulose tribenzoate. Journal of Chromatography A 1994; 666: 421.
20. Matlin SA, Tiritan EM, Crawford EJ, Cass QB and Boyd DR. HPLC with carbohydrate carbamate chiral phases: influence of chiral phase structure on enantioselectivity. Chirality 1994; 6: 135.
21. Milhaud CL and Klein MJ. The effect of adrafinil on the nocturnal activity of the rhesus monkey. Journal of Pharmacology 1985; 16: 372.
22. Okamoto Y, Kawashima M and Hatada K. Chromatographic resolution. XI. Controlled chiral recognition of cellulose triphenylcarbamate derivatives supported on silica gel. Journal of Chromatography A 1986; 363: 173.
23. 2 catalyzed by (salen) Mn (III) complexes. Tetrahedron Letters 1992; 33: 7111.
24. Rao RN, Shinde DD and Talluri MVNK. Development and validation of a reversed phase liquid chromatographic method for separation and determination of related-substances of modafinil in bulk drugs. Talanta 2007; 73: 407.
25. Rao RN, Shinde DD, Talluri MVNK and Agawane SB. LC-ESI-MS determination and pharmacokinetics of adrafinil in rats. Journal of Chromatography B 2008; 873: 119-123.
26. Superchi S and Rosini C. Catalytic asymmetric oxidation of aryl methyl sulfides mediated by a (S,S)-1,2-diphenylethan-1,2-diol/titanium/water complex. Tetrahedron Asymmetry 1997; 8: 349.
27. Yamanoi Y and Imamoto T. Preparation of enantiopure 2,2,5,5-tetramethyl-3,4-hexanediol and its use in catalytic enantioselective oxidation of sulfides to sulfoxides. Journal of Organic Chemistry 1997; 62: 8560.