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 DV, Dhavale A, Desai H, Mane DN, Raut SK, Dhingra G, Sardesai U, Saoji S, Rohra M, Shinde VG, 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 CJ, Mereu M, Okunola OM, Cao J, Prisinzano TE, Mazier S, Kopajtic T, Shi L, Katz JL, Tanda G, Newman AH (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 KC, Reith ME (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.
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.