Esmodafinil
-(%2B)-modafinil.svg) (S)-(+)-modafinil
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| Names | |
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| IUPAC name
2-[(S)-benzhydrylsulfinyl]acetamide
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| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.234.492 |
| EC Number |
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PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C15H15NO2S | |
| Molar mass | 273.35 g·mol−1 |
| Hazards | |
| GHS labelling:[1] | |
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| Warning | |
| H302 | |
| P264, P270, P301+P317, P330, P501 | |
| Related compounds | |
Related compounds
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Modafinil, Armodafinil |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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[edit]
Pharmacokinetics[edit]
Esmodafinil possesses a substantially shorter half life (3–5 hours) compared to armodafinil (10–13 hours).[4]
Pharmacodynamics[edit]
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[edit]
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[edit]
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[edit]
- ^ "(S)-Modafinil". pubchem.ncbi.nlm.nih.gov.
- ^ "NCATS Inxight Drugs — MODAFINIL, (S)-". drugs.ncats.io. Retrieved 2023-06-28.
- ^ 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.
- ^ a b c d e f 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.
- ^ a b c 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.
- ^ "The Prohibited List".
- ^ 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.