Modafinil acid

Modafinil acid

Names
IUPAC name 2-Benzhydrylsulfinylacetic acid
Other names Modafinilic acid; Modafinil carboxylate; CRL-40467
Identifiers
CAS Number	63547-24-0
3D model (Jmol)	Interactive image
ChemSpider	2342211
PubChem	3085267
UNII	54N37HN7N4
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

Modafinil acid (code name CRL-40467), also known as modafinilic acid or modafinil carboxylate, is the major metabolite of modafinil, and one of the two major metabolites of modafinil – the other being modafinil sulfone. 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. Modafinil acid seems to be inactive,^[1] and similarly to modafinil sulfone, does not appear to contribute to the wakefulness-promoting/psychostimulant effects of modafinil.^[2][3][4]

In the breakdown process of modafinil, modafinil is primarily hydrolyzed by an esterase or amidase enzyme into modafinil acid.^[5] 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.

References

1. Wong, Y. Nancy; Wang, Lixia; Hartman, Linda; Simcoe, Donna; Chen, Yusong; Laughton, Watson; Eldon, Richard; Markland, Colin; Grebow, Peter (1998). "Comparison of the Single-Dose Pharmacokinetics and Tolerability of Modafinil and Dextroamphetamine Administered Alone or in Combination in Healthy Male Volunteers". The Journal of Clinical Pharmacology. 38 (10): 971–978. doi:10.1002/j.1552-4604.1998.tb04395.x. ISSN 0091-2700.
2. Schwertner, Harvey A.; Kong, Suk Bin (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. ISSN 0731-7085.
3. Robertson, Philmore; Hellriegel, Edward T. (2003). "Clinical Pharmacokinetic Profile of Modafinil". Clinical Pharmacokinetics. 42 (2): 123–137. doi:10.2165/00003088-200342020-00002. ISSN 0312-5963.
4. Robertson, P (2002). "Effect of modafinil on the pharmacokinetics of ethinyl estradiol and triazolam in healthy volunteers". Clinical Pharmacology & Therapeutics. 71 (1): 46–56. doi:10.1067/mcp.2002.121217. ISSN 0009-9236.
5. Wu, Ke-hua; Guo, Tao; Deng, Chen-hui; Guan, Zheng; Li, Liang; Zhou, Tian-yan; Lu, Wei (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. ISSN 1671-4083.