Modafinil acid: Difference between revisions

Modafinil acid
Names
	IUPAC name 2-Benzhydrylsulfinylacetic acid
	Other names Modafinilic acid; Modafinil carboxylate; CRL-40467
Identifiers
CAS Number	63547-24-0;
3D model (JSmol)	Interactive image;
ChemSpider	2342211;
ECHA InfoCard	100.219.633
PubChem CID	3085267;
CompTox Dashboard (EPA)	DTXSID60979768 ;
	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

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Revision as of 20:14, 26 January 2016

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 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

^ 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.
^ 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.
^ 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.
^ 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.
^ 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.

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[WongWang1998-1] 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.

[SchwertnerKong2005-2] 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.

[RobertsonHellriegel2003-3] 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.

[Robertson2002-4] 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.

[WuGuo2012-5] 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.

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-'''Modafinil acid''' (code name '''CRL-40467'''), also known as '''modafinilic acid''' or '''modafinil carboxylate''', is one of the two major circulating [[metabolite]]s 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 does not appear to possess the [[wakefulness-promoting agent|wakefulness-promoting]]/[[psychostimulant]] effects of modafinil.{{Citation needed|date=January 2015}}
+'''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,<ref name="WongWang1998">{{cite journal|last1=Wong|first1=Y. Nancy|last2=Wang|first2=Lixia|last3=Hartman|first3=Linda|last4=Simcoe|first4=Donna|last5=Chen|first5=Yusong|last6=Laughton|first6=Watson|last7=Eldon|first7=Richard|last8=Markland|first8=Colin|last9=Grebow|first9=Peter|title=Comparison of the Single-Dose Pharmacokinetics and Tolerability of Modafinil and Dextroamphetamine Administered Alone or in Combination in Healthy Male Volunteers|journal=The Journal of Clinical Pharmacology|volume=38|issue=10|year=1998|pages=971–978|issn=00912700|doi=10.1002/j.1552-4604.1998.tb04395.x}}</ref> and does not appear to contribute to the [[wakefulness-promoting agent|wakefulness-promoting]]/[[psychostimulant]] effects of modafinil.<ref name="SchwertnerKong2005">{{cite journal|last1=Schwertner|first1=Harvey A.|last2=Kong|first2=Suk Bin|title=Determination of modafinil in plasma and urine by reversed phase high-performance liquid-chromatography|journal=Journal of Pharmaceutical and Biomedical Analysis|volume=37|issue=3|year=2005|pages=475–479|issn=07317085|doi=10.1016/j.jpba.2004.11.014}}</ref><ref name="RobertsonHellriegel2003">{{cite journal|last1=Robertson|first1=Philmore|last2=Hellriegel|first2=Edward T.|title=Clinical Pharmacokinetic Profile of Modafinil|journal=Clinical Pharmacokinetics|volume=42|issue=2|year=2003|pages=123–137|issn=0312-5963|doi=10.2165/00003088-200342020-00002}}</ref><ref name="Robertson2002">{{cite journal|last1=Robertson|first1=P|title=Effect of modafinil on the pharmacokinetics of ethinyl estradiol and triazolam in healthy volunteers|journal=Clinical Pharmacology & Therapeutics|volume=71|issue=1|year=2002|pages=46–56|issn=00099236|doi=10.1067/mcp.2002.121217}}</ref>
 In the [[catabolism|breakdown]] process of modafinil, modafinil is primarily [[hydrolysis|hydrolyzed]] by an [[esterase]] or [[amidase]] [[enzyme]] into modafinil acid.<ref name="WuGuo2012">{{cite journal|last1=Wu|first1=Ke-hua|last2=Guo|first2=Tao|last3=Deng|first3=Chen-hui|last4=Guan|first4=Zheng|last5=Li|first5=Liang|last6=Zhou|first6=Tian-yan|last7=Lu|first7=Wei|title=Population pharmacokinetics of modafinil acid and estimation of the metabolic conversion of modafinil into modafinil acid in 5 major ethnic groups of China|journal=Acta Pharmacologica Sinica|volume=33|issue=11|year=2012|pages=1401–1408|issn=1671-4083|doi=10.1038/aps.2012.124}}</ref> The apparent [[clearance (medicine)|clearance]] of modafinil acid is significantly higher than that of modafinil, following the hypothesis that metabolism increases the [[polarity]] and the clearance of modafinil.