Armodafinil

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Armodafinil are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Armodafinil?

The molecule Armodafinil presents a molecular formula of C15H15NO2S and its IUPAC name is 2-[(R)-benzhydrylsulfinyl]acetamide.

Armodafinil is a molecule of the central nervous system stimulant class of drugs. Armodafinil is the enantiopure modafinil molecule, which means it is composed of only one isomer of modafinil. Armodafinil is a wakefulness-promoting drug (or eugeroic) used to treat excessive daytime sleepiness (EDS) in adults. It is thought to work by inhibiting the reuptake of dopamine, a neurotransmitter that plays a role in wakefulness. Armodafinil is a Schedule IV controlled substance in the United States..

Armodafinil was first approved by the FDA in 2007 for the treatment of EDS in adults. It is now also approved for the treatment of shift work sleep disorder (SWSD) and obstructive sleep apnea/hypopnea syndrome (OSAHS). Armodafinil is marketed under the brand name Nuvigil in the United States..

The most common side effects of armodafinil include headache, nausea, nervousness, and insomnia. Armodafinil is not recommended for use in children..

Armodafinil is a wakefulness-promoting drug used to treat excessive daytime sleepiness in adults. Armodafinil is a eugeroic, or wakefulness-promoting drug, and is used to treat excessive daytime sleepiness (EDS) in adults. Armodafinil is the enantiopure modafinil molecule, which means it is composed of only one isomer of modafinil. Armodafinil is a Schedule IV controlled substance in the United States..

Armodafinil was first approved by the FDA in 2007 for the treatment of EDS in adults. It is now also approved for the treatment of shift work sleep disorder (SWSD) and obstructive sleep apnea/hypopnea syndrome (OSAHS). Armodafinil is marketed under the brand name Nuvigil in the United States..

The most common side effects of armodafinil include headache, nausea, nervousness, and insomnia. Armodafinil is not recommended for use in children..

Armodafinil is a wakefulness-promoting drug used to treat excessive daytime sleepiness in adults. Armodafinil is a eugeroic, or wakefulness-promoting drug, and is used to treat excessive daytime sleepiness (EDS) in adults. Armodafinil is the enantiopure modafinil molecule, which means it is composed of only one isomer of modafinil. Armodafinil is a Schedule IV controlled substance in the United States..

Armodafinil was first approved by the FDA in 2007 for the treatment of EDS in adults. It is now also approved for the treatment of shift work sleep disorder (SWSD) and obstructive sleep apnea/hypopnea syndrome (OSAHS). Armodafinil is marketed under the brand name Nuvigil in the United States..

The most common side effects of armodafinil include headache, nausea, nervousness, and insomnia. Armodafinil is not recommended for use in children..

3D structure

Cartesian coordinates

Geometry of Armodafinil in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Armodafinil YFGHCGITMMYXAQ-LJQANCHMSA-N chemical compound 2D structure molecule svg
Armodafinil

 

Molecule descriptors

 
IUPAC name2-[(R)-benzhydrylsulfinyl]acetamide
InChI codeInChI=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-/m1/s1
InChI KeyYFGHCGITMMYXAQ-LJQANCHMSA-N
SMILESNC(=O)C[S@@](=O)C(c1ccccc1)c1ccccc1

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (-) modafinil
  • (-)-(R)-modafinil
  • (-)-2-((R)-(Diphenylmethyl)sulfinyl)acetamide
  • (-)-2-[(r)-(diphenylmethyl)sulfinyl]acetamide
  • (-)-2R-[(Diphenylmethyl)sulfinyl]acetamide
  • (-)-Modafinil
  • (R)-(-)-Modafinil
  • (R)-Modafinil
  • 112111-43-0
  • 2-[(R)-(Diphenylmethyl)sulfinyl]acetamide
  • 2-[(r)-benzhydrylsulfinyl]acetamide
  • ACETAMIDE, 2-((R)-(DIPHENYLMETHYL)SULFINYL)-
  • AT22562
  • Acetamide, 2-((diphenylmethyl)sulfinyl)-, (-)-
  • Armodafinil
  • Armodafinil (USAN/INN)
  • BDBM50336892
  • CCG-230228
  • CEP 10953
  • CEP-10952
  • CEP-10953
  • CRL 40982
  • CRL-40982
  • CS-0665
  • D03215
  • DB06413
  • HY-15201
  • Modafinil, (r)-
  • NSC 751850
  • NSC 758711
  • NSC-751850
  • NSC-758711
  • Nuvigil
  • Q418913
  • R-(-)-Modafinil
  • S4645
  • V63XWA605I
  • armodafinilo
  • armodafinilum
  • l-Modafinil

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC6156
  • UNII-V63XWA605I
  • AKOS030211019
  • DTXSID90920667
  • CHEMBL1201192
  • CHEBI:77590
  • SCHEMBL34489

Physico-Chemical properties

IUPAC name2-[(R)-benzhydrylsulfinyl]acetamide
Molecular formulaC15H15NO2S
Molecular weight273.35
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity76.69
LogP3.6
Topological polar surface area79.4

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.