(S)-Oxazepam

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

What is the (S)-Oxazepam?

The molecule (S)-Oxazepam presents a molecular formula of C15H11ClN2O2 and its IUPAC name is (3S)-7-chloro-3-hydroxy-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one.

(S)-Oxazepam is a molecule in the class of organic compounds known as benzodiazepines. Benzodiazepines are a class of psychoactive drugs whose core chemical structure is a fusion of a benzene ring and a diazepine ring. (S)-Oxazepam is a member of the subgroup of benzodiazepines known as short-acting drugs. Short-acting benzodiazepines have a relatively short half-life in the body, meaning that they are metabolized and eliminated more quickly than long-acting benzodiazepines. The short half-life of (S)-oxazepam is approximately 4-15 hours..

Benzodiazepines are typically used to treat anxiety, insomnia, and seizures. (S)-Oxazepam is approved for use in the treatment of anxiety and insomnia in many countries. In the United States, (S)-oxazepam is not currently approved for use in treating anxiety or insomnia, but is approved for use as an anticonvulsant..

The mechanism of action of benzodiazepines is not completely understood, but it considered that they work by binding to and activating the GABA-A receptor. The GABA-A receptor is a protein in the brain that is responsible for mediating the effects of the neurotransmitter GABA. When benzodiazepines bind to and activate the GABA-A receptor, they increase the effects of GABA, leading to a decrease in neuronal activity and a feeling of calmness and relaxation..

(S)-Oxazepam is a relatively safe and well-tolerated drug. The most common side effects of (S)-oxazepam include drowsiness, dizziness, and lightheadedness. More serious side effects are rare, but can include difficulty breathing, confusion, and depression. As with all benzodiazepines, there is a risk of abuse, dependence, and addiction. Benzodiazepines should be used with caution in people with a history of substance abuse..

3D structure

Cartesian coordinates

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

2D drawing

 

(S)-Oxazepam ADIMAYPTOBDMTL-HNNXBMFYSA-N chemical compound 2D structure molecule svg
(S)-Oxazepam

 

Molecule descriptors

 
IUPAC name(3S)-7-chloro-3-hydroxy-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one
InChI codeInChI=1S/C15H11ClN2O2/c16-10-6-7-12-11(8-10)13(9-4-2-1-3-5-9)18-15(20)14(19)17-12/h1-8,15,20H,(H,17,19)/t15-/m0/s1
InChI KeyADIMAYPTOBDMTL-HNNXBMFYSA-N
SMILESO=C1Nc2ccc(Cl)cc2C(c2ccccc2)=N[C@H]1O

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.

  • (3S)-7-Chloro-1,3-dihydro-3-hydroxy-5-phenyl-2H-1,4-benzodiazepin-2-one
  • (S)-Oxazepam
  • 2H-1,4-Benzodiazepin-2-one, 7-chloro-1,3-dihydro-3-hydroxy-5-phenyl-, (3S)-
  • 40762-00-3
  • 7RM38L3JWY
  • D-Oxazepam
  • Oxazepam, (S)-
  • S-Oxazepam

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC575
  • UNII-7RM38L3JWY
  • CHEMBL1743322
  • SCHEMBL528376

Physico-Chemical properties

IUPAC name(3S)-7-chloro-3-hydroxy-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one
Molecular formulaC15H11ClN2O2
Molecular weight286.713
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity84.21
LogP2.0
Topological polar surface area61.7

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.