Modafinil acid (code name CRL-40467), also known as modafinilic acid or modafinil carboxylate, is one of the two major metabolites of modafinil – the other being modafinil sulfone.[1] Modafinil acid is also a metabolite of the modafinil prodrug, adrafinil, and the (R)-(–)-enantiomer is a metabolite of armodafinil, the (R)-(–)-enantiomer of modafinil.[2] Between 30 - 60% of modafinil is converted to modafinil acid and its half life is roughly half that of modafinil (about 7 hours).[3] Modafinil acid seems to be inactive,[4] and similarly to modafinil sulfone, does not appear to contribute to the wakefulness-promoting/psychostimulant effects of modafinil.[5][6][7]
In the breakdown process of modafinil, modafinil is primarily hydrolyzed by an esterase or amidaseenzyme into modafinil acid.[8] The apparent clearance of modafinil acid is significantly higher than that of modafinil, following the hypothesis that metabolism increases the polarity and the clearance of modafinil.[9]
Referencesedit
^Dubey S, Ahi S, Reddy IM, Kaur T, Beotra A, Jain S (December 2009). "A novel study of screening and confirmation of modafinil, adrafinil and their metabolite modafinilic acid under EI-GC-MS and ESI-LC-MS-MS ionization". Indian Journal of Pharmacology. 41 (6): 278–283. doi:10.4103/0253-7613.59928. PMC2846503. PMID 20407560.
^Sousa A, Dinis-Oliveira RJ (2020). "Pharmacokinetic and pharmacodynamic of the cognitive enhancer modafinil: Relevant clinical and forensic aspects". Substance Abuse. 41 (2): 155–173. doi:10.1080/08897077.2019.1700584. PMID 31951804. S2CID 210709160.
^Wong YN, King SP, Simcoe D, Gorman S, Laughton W, McCormick GC, Grebow P (March 1999). "Open-label, single-dose pharmacokinetic study of modafinil tablets: influence of age and gender in normal subjects". Journal of Clinical Pharmacology. 39 (3): 281–288. doi:10.1177/009127009903900312. PMID 10073328. S2CID 30258993.
^Wong YN, Wang L, Hartman L, Simcoe D, Chen Y, Laughton W, et al. (October 1998). "Comparison of the single-dose pharmacokinetics and tolerability of modafinil and dextroamphetamine administered alone or in combination in healthy male volunteers". Journal of Clinical Pharmacology. 38 (10): 971–978. doi:10.1002/j.1552-4604.1998.tb04395.x. PMID 9807980. S2CID 32857213.
^Schwertner HA, Kong SB (March 2005). "Determination of modafinil in plasma and urine by reversed phase high-performance liquid-chromatography". Journal of Pharmaceutical and Biomedical Analysis. 37 (3): 475–479. doi:10.1016/j.jpba.2004.11.014. PMID 15740906.
^Robertson P, Hellriegel ET (2003). "Clinical pharmacokinetic profile of modafinil". Clinical Pharmacokinetics. 42 (2): 123–137. doi:10.2165/00003088-200342020-00002. PMID 12537513. S2CID 1266677.
^Robertson P, Hellriegel ET, Arora S, Nelson M (January 2002). "Effect of modafinil on the pharmacokinetics of ethinyl estradiol and triazolam in healthy volunteers". Clinical Pharmacology and Therapeutics. 71 (1): 46–56. doi:10.1067/mcp.2002.121217. PMID 11823757. S2CID 21552865.
^Wu KH, Guo T, Deng CH, Guan Z, Li L, Zhou TY, Lu W (November 2012). "Population pharmacokinetics of modafinil acid and estimation of the metabolic conversion of modafinil into modafinil acid in 5 major ethnic groups of China". Acta Pharmacologica Sinica. 33 (11): 1401–1408. doi:10.1038/aps.2012.124. PMC4011351. PMID 23103618.
^"Modafinil As A Physical Performance Enhancer". Retrieved 2017-02-22.
This drug article relating to the nervous system is a stub. You can help Wikipedia by expanding it.
modafinil, acid, code, name, 40467, also, known, modafinilic, acid, modafinil, carboxylate, major, metabolites, modafinil, other, being, modafinil, sulfone, also, metabolite, modafinil, prodrug, adrafinil, enantiomer, metabolite, armodafinil, enantiomer, modaf. Modafinil acid code name CRL 40467 also known as modafinilic acid or modafinil carboxylate is one of the two major metabolites of modafinil the other being modafinil sulfone 1 Modafinil acid is also a metabolite of the modafinil prodrug adrafinil and the R enantiomer is a metabolite of armodafinil the R enantiomer of modafinil 2 Between 30 60 of modafinil is converted to modafinil acid and its half life is roughly half that of modafinil about 7 hours 3 Modafinil acid seems to be inactive 4 and similarly to modafinil sulfone does not appear to contribute to the wakefulness promoting psychostimulant effects of modafinil 5 6 7 Modafinil acid NamesPreferred IUPAC name Diphenylmethanesulfinyl acetic acidOther names Modafinilic acid Modafinil carboxylate CRL 40467IdentifiersCAS Number 63547 24 0 Y3D model JSmol Interactive imageChemSpider 2342211ECHA InfoCard 100 219 633PubChem CID 3085267UNII 54N37HN7N4 YCompTox Dashboard EPA DTXSID60979768InChI InChI 1S C15H14O3S c16 14 17 11 19 18 15 12 7 3 1 4 8 12 13 9 5 2 6 10 13 h1 10 15H 11H2 H 16 17 Key QARQPIWTMBRJFX UHFFFAOYSA NSMILES C1 CC C C C1 C C2 CC CC C2 S O CC O OPropertiesChemical formula C 15H 14O 3SMolar mass 274 33 g mol 1Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox references In the breakdown process of modafinil modafinil is primarily hydrolyzed by an esterase or amidase enzyme into modafinil acid 8 The apparent clearance of modafinil acid is significantly higher than that of modafinil following the hypothesis that metabolism increases the polarity and the clearance of modafinil 9 References edit Dubey S Ahi S Reddy IM Kaur T Beotra A Jain S December 2009 A novel study of screening and confirmation of modafinil adrafinil and their metabolite modafinilic acid under EI GC MS and ESI LC MS MS ionization Indian Journal of Pharmacology 41 6 278 283 doi 10 4103 0253 7613 59928 PMC 2846503 PMID 20407560 Sousa A Dinis Oliveira RJ 2020 Pharmacokinetic and pharmacodynamic of the cognitive enhancer modafinil Relevant clinical and forensic aspects Substance Abuse 41 2 155 173 doi 10 1080 08897077 2019 1700584 PMID 31951804 S2CID 210709160 Wong YN King SP Simcoe D Gorman S Laughton W McCormick GC Grebow P March 1999 Open label single dose pharmacokinetic study of modafinil tablets influence of age and gender in normal subjects Journal of Clinical Pharmacology 39 3 281 288 doi 10 1177 009127009903900312 PMID 10073328 S2CID 30258993 Wong YN Wang L Hartman L Simcoe D Chen Y Laughton W et al October 1998 Comparison of the single dose pharmacokinetics and tolerability of modafinil and dextroamphetamine administered alone or in combination in healthy male volunteers Journal of Clinical Pharmacology 38 10 971 978 doi 10 1002 j 1552 4604 1998 tb04395 x PMID 9807980 S2CID 32857213 Schwertner HA Kong SB March 2005 Determination of modafinil in plasma and urine by reversed phase high performance liquid chromatography Journal of Pharmaceutical and Biomedical Analysis 37 3 475 479 doi 10 1016 j jpba 2004 11 014 PMID 15740906 Robertson P Hellriegel ET 2003 Clinical pharmacokinetic profile of modafinil Clinical Pharmacokinetics 42 2 123 137 doi 10 2165 00003088 200342020 00002 PMID 12537513 S2CID 1266677 Robertson P Hellriegel ET Arora S Nelson M January 2002 Effect of modafinil on the pharmacokinetics of ethinyl estradiol and triazolam in healthy volunteers Clinical Pharmacology and Therapeutics 71 1 46 56 doi 10 1067 mcp 2002 121217 PMID 11823757 S2CID 21552865 Wu KH Guo T Deng CH Guan Z Li L Zhou TY Lu W November 2012 Population pharmacokinetics of modafinil acid and estimation of the metabolic conversion of modafinil into modafinil acid in 5 major ethnic groups of China Acta Pharmacologica Sinica 33 11 1401 1408 doi 10 1038 aps 2012 124 PMC 4011351 PMID 23103618 Modafinil As A Physical Performance Enhancer Retrieved 2017 02 22 nbsp This drug article relating to the nervous system is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Modafinil acid amp oldid 1188104541, wikipedia, wiki, book, books, library,
