Jump to content

Modafinil acid: Difference between revisions

Add links
From Wikipedia, the free encyclopedia
Browse history interactively
← Previous editNext edit →
Content deleted Content added
VisualWikitext
fix mistake
R-enantiomer armodafinil
Line 20: Line 20:
| StdInChIKey = QARQPIWTMBRJFX-UHFFFAOYSA-N
| StdInChIKey = QARQPIWTMBRJFX-UHFFFAOYSA-N
| ChemSpiderID = 2342211
| ChemSpiderID = 2342211
}}
}}


| Section2 = {{Chembox Properties
| Section2 = {{Chembox Properties
Line 30: Line 30:
| BoilingPt =
| BoilingPt =
| Solubility =
| Solubility =
}}
}}


| Section3 = {{Chembox Hazards
| Section3 = {{Chembox Hazards
Line 36: Line 36:
| FlashPt =
| FlashPt =
| AutoignitionPt =
| AutoignitionPt =
}}
}}
}}
}}


'''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]]. 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=0091-2700|doi=10.1002/j.1552-4604.1998.tb04395.x|pmid=9807980|s2cid=32857213}}</ref> and similarly to modafinil sulfone, 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=0731-7085|doi=10.1016/j.jpba.2004.11.014|url=https://zenodo.org/record/1259161|pmid=15740906}}</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|pmid=12537513|s2cid=1266677}}</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=0009-9236|doi=10.1067/mcp.2002.121217|pmid=11823757|url=https://semanticscholar.org/paper/1fed41650acdb5c9b2a88d730936aebfe91e716f}}</ref>
'''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]].<ref>{{Cite journal|last=Dubey|first=S.|last2=Ahi|first2=S.|last3=Reddy|first3=I. M.|last4=Kaur|first4=T.|last5=Beotra|first5=A.|last6=Jain|first6=S.|date=|title=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|url=https://pubmed.ncbi.nlm.nih.gov/20407560/|journal=Indian Journal of Pharmacology|volume=41|issue=6|pages=278–283|doi=10.4103/0253-7613.59928|issn=1998-3751|pmc=2846503|pmid=20407560}}</ref><ref>{{Cite web|title=Ultimate Modafinil Guide 2021|url=https://modapills.co.uk/ultimate-modafinil-guide-2021/|url-status=live|access-date=2021-11-04|website=Nootropics UK - Modafinil UK|language=en-US}}</ref> 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.<ref>{{Cite journal|last=Sousa|first=Ana|last2=Dinis-Oliveira|first2=Ricardo Jorge|date=2020|title=Pharmacokinetic and pharmacodynamic of the cognitive enhancer modafinil: Relevant clinical and forensic aspects|url=https://pubmed.ncbi.nlm.nih.gov/31951804/|journal=Substance Abuse|volume=41|issue=2|pages=155–173|doi=10.1080/08897077.2019.1700584|issn=1547-0164|pmid=31951804}}</ref> 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=0091-2700|doi=10.1002/j.1552-4604.1998.tb04395.x|pmid=9807980|s2cid=32857213}}</ref> and similarly to modafinil sulfone, 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=0731-7085|doi=10.1016/j.jpba.2004.11.014|url=https://zenodo.org/record/1259161|pmid=15740906}}</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|pmid=12537513|s2cid=1266677}}</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=0009-9236|doi=10.1067/mcp.2002.121217|pmid=11823757|url=https://semanticscholar.org/paper/1fed41650acdb5c9b2a88d730936aebfe91e716f}}</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|pmid=23103618|pmc=4011351}}</ref> The apparent [[clearance (medicine)|clearance]] of modafinil acid is significantly higher than that of modafinil, following the hypothesis that metabolism increases the [[Chemical polarity|polarity]] and the clearance of modafinil.<ref>{{Cite web|url=http://www.brainsupplements.co.uk/modafinil-physical-performance-enhancer/|title=Modafinil As A Physical Performance Enhancer|language=en-US|access-date=2017-02-22}}</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|pmid=23103618|pmc=4011351}}</ref> The apparent [[clearance (medicine)|clearance]] of modafinil acid is significantly higher than that of modafinil, following the hypothesis that metabolism increases the [[Chemical polarity|polarity]] and the clearance of modafinil.<ref>{{Cite web|url=http://www.brainsupplements.co.uk/modafinil-physical-performance-enhancer/|title=Modafinil As A Physical Performance Enhancer|language=en-US|access-date=2017-02-22}}</ref>
Line 49: Line 49:
[[Category:Human drug metabolites]]
[[Category:Human drug metabolites]]
[[Category:Sulfoxides]]
[[Category:Sulfoxides]]



{{nervous-system-drug-stub}}
{{nervous-system-drug-stub}}

Revision as of 20:04, 4 November 2021

Modafinil acid
Names
Preferred IUPAC name
(Diphenylmethanesulfinyl)acetic acid
Other names
Modafinilic acid; Modafinil carboxylate; CRL-40467
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.219.633 Edit this at Wikidata
UNII
  • 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
  • C1=CC=C(C=C1)C(C2=CC=CC=C2)S(=O)CC(=O)O
Properties
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).

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] 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 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

  1. ^ Dubey, S.; Ahi, S.; Reddy, I. M.; Kaur, T.; Beotra, A.; Jain, S. "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. ISSN 1998-3751. PMC 2846503. PMID 20407560.{{cite journal}}: CS1 maint: unflagged free DOI (link)
  2. ^ "Ultimate Modafinil Guide 2021". Nootropics UK - Modafinil UK. Retrieved 2021-11-04.{{cite web}}: CS1 maint: url-status (link)
  3. ^ Sousa, Ana; Dinis-Oliveira, Ricardo Jorge (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. ISSN 1547-0164. PMID 31951804.
  4. ^ 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. PMID 9807980. S2CID 32857213.
  5. ^ 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. PMID 15740906.
  6. ^ 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. PMID 12537513. S2CID 1266677.
  7. ^ 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. PMID 11823757.
  8. ^ 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. PMC 4011351. PMID 23103618.
  9. ^ "Modafinil As A Physical Performance Enhancer". Retrieved 2017-02-22.
Stub icon

This drug article relating to the nervous system is a stub. You can help Wikipedia by expanding it.

Retrieved from "https://en.wikipedia.org/w/index.php?title=Modafinil_acid&oldid=1053589121"