Esmodafinil

Esmodafinil
	(S)-(+)-Modafinil
Clinical data
Other names	CRL-40983; (S)-Modafinil; S-Modafinil; (S)-(+)-Modafinil; (+)-Modafinil; NH-02D
Drug class	Atypical dopamine reuptake inhibitor; wakefulness-promoting agent
Pharmacokinetic data
Elimination half-life	3–5 hours
Identifiers
	IUPAC name 2-[(S)-benzhydrylsulfinyl]acetamide;
CAS Number	112111-47-4;
PubChem CID	11173366;
ChemSpider	9348458;
UNII	152JRG3T0U;
ChEBI	CHEBI:77591;
ChEMBL	ChEMBL1672355;
CompTox Dashboard (EPA)	DTXSID70457709 ;
ECHA InfoCard	100.234.492
Chemical and physical data
Formula	C15H15NO2S
Molar mass	273.35 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1=CC=C(C=C1)C(C2=CC=CC=C2)[S@@](=O)CC(=O)N;
	InChI 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;

Esmodafinil (also known as (S)-modafinil or (+)-modafinil; developmental code name CRL-40983) is the enantiopure (S)-(+)-enantiomer of modafinil. Unlike armodafinil ((R)-(–)-modafinil), esmodafinil has never been marketed on its own.^[3]

Esmodafinil is suspected to be less clinically useful for treating conditions that modafinil and armodafinil are marketed for, such as narcolepsy, shift work sleep disorder, and obstructive sleep apnea.^[4]

^ Cite error: The named reference SousaDinis-Oliveira2020 was invoked but never defined (see the help page).
^ Hersey M, Tanda G (2024). "Modafinil, an atypical CNS stimulant?". Pharmacological Advances in Central Nervous System Stimulants. Advances in Pharmacology. Vol. 99. pp. 287–326. doi:10.1016/bs.apha.2023.10.006. ISBN 978-0-443-21933-7. PMID 38467484.
^ "NCATS Inxight Drugs — MODAFINIL, (S)-". drugs.ncats.io. Retrieved 2023-06-28.
^ Tembe DV, Dhavale A, Desai H, Mane DN, Raut SK, Dhingra G, et al. (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: 514351. doi:10.1155/2011/514351. PMC 3135062. PMID 21766023.

[SousaDinis-Oliveira2020-1] Cite error: The named reference SousaDinis-Oliveira2020 was invoked but never defined (see the help page).

[HerseyTanda2024-2] Hersey M, Tanda G (2024). "Modafinil, an atypical CNS stimulant?". Pharmacological Advances in Central Nervous System Stimulants. Advances in Pharmacology. Vol. 99. pp. 287–326. doi:10.1016/bs.apha.2023.10.006. ISBN 978-0-443-21933-7. PMID 38467484.

[3] "NCATS Inxight Drugs — MODAFINIL, (S)-". drugs.ncats.io. Retrieved 2023-06-28.

[4] Tembe DV, Dhavale A, Desai H, Mane DN, Raut SK, Dhingra G, et al. (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: 514351. doi:10.1155/2011/514351. PMC 3135062. PMID 21766023.

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Esmodafinil

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