Modafinil acid

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][2] 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.[3] Between 30 - 60% of modafinil is converted to modafinil acid and its half life is roughly half that of modafinil (about 7 hours).[4] Modafinil acid seems to be inactive,[5] and similarly to modafinil sulfone, does not appear to contribute to the wakefulness-promoting/psychostimulant effects of modafinil.[6][7][8]

Modafinil acid
Names
Preferred IUPAC name
(Diphenylmethanesulfinyl)acetic acid
Other names
Modafinilic acid; Modafinil carboxylate; CRL-40467
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.219.633
PubChem CID
UNII
InChI
  • 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-N
SMILES
  • C1=CC=C(C=C1)C(C2=CC=CC=C2)S(=O)CC(=O)O
Properties
Chemical formula
 C15H14O3S
Molar mass 274.33 g·mol−1
Except 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.[9] 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.[10]

References
  1. 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.
  2. "Ultimate Modafinil Guide 2021". Nootropics UK - Modafinil UK. Retrieved 2021-11-04.{{cite web}}: CS1 maint: url-status (link)
  3. 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.
  4. 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.
  5. 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.
  6. 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.
  7. 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.
  8. 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.
  9. 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.
  10. "Modafinil As A Physical Performance Enhancer". Retrieved 2017-02-22.
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