Esmodafinil

(S)-(+)-modafinil
Names
IUPAC name
2-[(S)-benzhydrylsulfinyl]acetamide
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.234.492
EC Number
  • 807-091-3
UNII
  • InChI=1S/C15H15NO2S/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,(H2,16,17)/t19-/m0/s1
    Key: YFGHCGITMMYXAQ-IBGZPJMESA-N
  • C1=CC=C(C=C1)C(C2=CC=CC=C2)[S@@](=O)CC(=O)N
Properties
C15H15NO2S
Molar mass 273.35 g·mol−1
Hazards
GHS labelling:[1]
GHS07: Exclamation mark
Warning
H302
P264, P270, P301+P317, P330, P501
Related compounds
Related compounds
 Modafinil, Armodafinil
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Esmodafinil (also known as (S)-modafinil or (+)-Modafinil) is the enantiopure isolation of the (S) enantiomer of modafinil. Unlike armodafinil, esmodafinil has never been marketed on its own.[2]

Esmodafinil is suspected to be less clinically useful for treating conditions that modafinil and armodafinil are marketed for, such as narcolepsy, sleep-shift work disorder, and obstructive sleep apnea.[3]

Pharmacology

Pharmacokinetics

Esmodafinil possesses a substantially shorter half life (3-5 hours) compared to armodafinil (10-13 hours).[4]

Pharmacodynamics

Esmodafinil has a 3 times lower affinity for the dopamine transporter compared to armodafinil.[4] Both enantiomers of modafinil preferentially bind to the dopamine transporter in an inward facing conformation.[4][5]

Preclinical research

Esmodafinil has been researched for the treatment of cocaine addiction.[4][5] Like armodafinil, esmodafinil attenuates the effects of cocaine by occupying the dopamine transporter.[5] While doing so, esmodafinil increases dopamine in the nucleus accumbens to a lesser extent than cocaine.[4] However, the short half-life of esmodafinil has been cited as reason to investigate armodafinil as a cocaine addiction treatment instead.[4]

Analysis in biological samples

Modafinil is considered a stimulant doping agent and as such is prohibited by World Anti-Doping Agency in sports competitions.[6] The validated methods are researched to separately quantify modafinil enantiomers in the real samples.[7]

References

  1. ↑ "(S)-Modafinil". pubchem.ncbi.nlm.nih.gov.
  2. ↑ "NCATS Inxight Drugs — MODAFINIL, (S)-". drugs.ncats.io. Retrieved 2023-06-28.
  3. ↑ Tembe, D. V.; Dhavale, A.; Desai, H.; Mane, D. N.; Raut, S. K.; Dhingra, G.; Sardesai, U.; Saoji, S.; Rohra, M.; Shinde, V. G.; Padsalge, M.; Paliwal, A.; Abbasi, K.; Devnani, P.; Papinwar, S. (2011-06-01). "Armodafinil versus Modafinil in Patients of Excessive Sleepiness Associated with Shift Work Sleep Disorder: A Randomized Double Blind Multicentric Clinical Trial". Neurology Research International. 2011: e514351. doi:10.1155/2011/514351. ISSN 2090-1852. PMC 3135062. PMID 21766023.
  4. 1 2 3 4 5 6 Loland, Claus J.; Mereu, Maddalena; Okunola, Oluyomi M.; Cao, Jianjing; Prisinzano, Thomas E.; Mazier, Sonia; Kopajtic, Theresa; Shi, Lei; Katz, Jonathan L.; Tanda, Gianluigi; Newman, Amy Hauck (September 2012). "R-Modafinil (Armodafinil): A Unique Dopamine Uptake Inhibitor and Potential Medication for Psychostimulant Abuse". Biological Psychiatry. 72 (5): 405–413. doi:10.1016/j.biopsych.2012.03.022. PMC 3413742. PMID 22537794.
  5. 1 2 3 Schmitt, Kyle C.; Reith, Maarten E. A. (2011). "The atypical stimulant and nootropic modafinil interacts with the dopamine transporter in a different manner than classical cocaine-like inhibitors". PLOS ONE. 6 (10): e25790. Bibcode:2011PLoSO...625790S. doi:10.1371/journal.pone.0025790. ISSN 1932-6203. PMC 3197159. PMID 22043293.
  6. ↑ "The Prohibited List".
  7. ↑ Harvanová M, Gondová T (May 2017). "New enantioselective LC method development and validation for the assay of modafinil". J Pharm Biomed Anal. 138: 267–271. doi:10.1016/j.jpba.2017.02.028. PMID 28231529. S2CID 43492396.
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